Southshorehomefinder.com Search Results

$8,625,000

Legacy estate set prominently on one of the highest Osterville bluffs delivers classic waterfront expectations with a superior dock and substantial dynamic views from the Vineyard to Hyannisport. The grand yesteryear home constructed in 1920 conveys the qualities of that oceanfront era, with higher ceilings, multiple great rooms, and the character of hidden porches, exclusive balconies, and romantic patios. Curving stone walls, terraced rock feature gardens, and stone patios complement the entire grounds. Across the river from your 200 feet of waterfront is Long Beach, a pristine barrier stretch of powdery white sand and privacy. The dock enjoys some of the deepest water of any house on this stretch, allowing for multiple boats and other recreational craft. The quaint conclusion to this fairytale setting is a larger detached apartment over the garage. The square footage of 9,011, seven bedrooms and seven-and-a-half bathrooms speak for themselves. This treasure is waiting for you.

7 Beds ⋅ 8 Baths ⋅ 73543017 MLS

Legacy estate set prominently on one of the highest Osterville bluffs delivers classic waterfront expectations with a superior dock and substantial dynamic views from the Vineyard to Hyannisport. The grand yesteryear home constructed in 1920 conveys the qualities of that oceanfront era, with higher ceilings, multiple great rooms, and the character of hidden porches, exclusive balconies, and romantic patios. Curving stone walls, terraced rock feature gardens, and stone patios complement the entire grounds. Across the river from your 200 feet of waterfront is Long Beach, a pristine barrier stretch of powdery white sand and privacy. The dock enjoys some of the deepest water of any house on this stretch, allowing for multiple boats and other recreational craft. The quaint conclusion to this fairytale setting is a larger detached apartment over the garage. The square footage of 9,011, seven bedrooms and seven-and-a-half bathrooms speak for themselves. This treasure is waiting for you.

63 Main Street, Barnstable

Listing courtesy of Listing Agent: Christa Zevitas from Listing Office: .

$8,500,000

A rare and truly exceptional offering in the heart of downtown Portsmouth—this one-of-a-kind property includes a luxury penthouse residence, a second residential unit, and two commercial storefronts, all offered in its entirety. Built in 2008 and meticulously maintained, the property blends modern construction, upscale amenities, and timeless interior style in an unbeatable downtown location. The main entrance on State Street opens to a foyer with elevator access to both residences and the lower level. A four-car garage is accessed from the rear of the foyer, while two ground-level storefronts with premier State Street frontage flank the entrance. Both retail spaces are leased to established tenants, with one at-will and one under lease. The second floor features a spacious three-bedroom, four-bath garden-style residence with an open-concept floor plan, hardwood floors, gas fireplaces, and three en suite bedrooms. The third and fourth floors comprise a stunning two-story penthouse offering four bedrooms and six baths, including four en suite bedrooms plus a fifth en suite office or guest suite. The expansive main living level showcases a chef’s kitchen with island, casual and formal dining areas, private office, mudroom, and rich cognac-toned wide-pine floors. Expansive decks span all three residential levels, each oriented toward the quiet, sun-filled, south-facing Court Street side. Additional highlights include secure private elevator access to each residence, four deeded garage parking spaces with additional storage, and a finished lower level ideal for a fitness room, wine storage, or flexible use space.Condominium conversion potential presents a rare investment or legacy ownership opportunity. Enjoy the many benefits of New Hampshire living, including no state income or sales tax, close proximity to the scenic coastlines and beaches of NH and Maine, and convenient access to 4 regional and international airports in less than one hour.

8 Beds ⋅ 12 Baths ⋅ 5085575 MLS

A rare and truly exceptional offering in the heart of downtown Portsmouth—this one-of-a-kind property includes a luxury penthouse residence, a second residential unit, and two commercial storefronts, all offered in its entirety. Built in 2008 and meticulously maintained, the property blends modern construction, upscale amenities, and timeless interior style in an unbeatable downtown location. The main entrance on State Street opens to a foyer with elevator access to both residences and the lower level. A four-car garage is accessed from the rear of the foyer, while two ground-level storefronts with premier State Street frontage flank the entrance. Both retail spaces are leased to established tenants, with one at-will and one under lease. The second floor features a spacious three-bedroom, four-bath garden-style residence with an open-concept floor plan, hardwood floors, gas fireplaces, and three en suite bedrooms. The third and fourth floors comprise a stunning two-story penthouse offering four bedrooms and six baths, including four en suite bedrooms plus a fifth en suite office or guest suite. The expansive main living level showcases a chef’s kitchen with island, casual and formal dining areas, private office, mudroom, and rich cognac-toned wide-pine floors. Expansive decks span all three residential levels, each oriented toward the quiet, sun-filled, south-facing Court Street side. Additional highlights include secure private elevator access to each residence, four deeded garage parking spaces with additional storage, and a finished lower level ideal for a fitness room, wine storage, or flexible use space.Condominium conversion potential presents a rare investment or legacy ownership opportunity. Enjoy the many benefits of New Hampshire living, including no state income or sales tax, close proximity to the scenic coastlines and beaches of NH and Maine, and convenient access to 4 regional and international airports in less than one hour.

58 State St, Portsmouth

Listing courtesy of Jennifer Madden from Gibson Sotheby's International Realty. ()

$8,475,000

Back Bay Single Family Brownstone on Marlborough Street - Designed for the buyer who values privacy and operational ease. Pull into three radiantly heated brownstone parking spaces, step inside, and let the elevator carry you from the parlor hosting floor to the rooftop terrace. Entertaining starts in the custom kitchen with integrated appliances, moves through formal dining and living rooms, then out to the private garden patio for open air evenings. Later, take the elevator up to the top floor family and media room, then step onto the rooftop terrace for open sky and distance from the street below. The entire third floor is devoted to the primary suite with dressing room, sitting room or office, and a radiant heated marble clad bath. A guest or au pair suite with wet bar keeps separation when you need it. Four bedrooms, three gas fireplaces, two wet bars, walnut built ins, and chevron floors finish the interiors. Private showings by request only.

4 Beds ⋅ 7 Baths ⋅ 73479490 MLS

Back Bay Single Family Brownstone on Marlborough Street - Designed for the buyer who values privacy and operational ease. Pull into three radiantly heated brownstone parking spaces, step inside, and let the elevator carry you from the parlor hosting floor to the rooftop terrace. Entertaining starts in the custom kitchen with integrated appliances, moves through formal dining and living rooms, then out to the private garden patio for open air evenings. Later, take the elevator up to the top floor family and media room, then step onto the rooftop terrace for open sky and distance from the street below. The entire third floor is devoted to the primary suite with dressing room, sitting room or office, and a radiant heated marble clad bath. A guest or au pair suite with wet bar keeps separation when you need it. Four bedrooms, three gas fireplaces, two wet bars, walnut built ins, and chevron floors finish the interiors. Private showings by request only.

352 Marlborough St, Boston

Listing courtesy of Listing Agent: Michael Carucci from Listing Office: Serhant.

$8,450,000

Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling details & European windows that flood the interiors w/ natural light.The Chef's Kitchen is highlighted by natural stone countertops,a dramatic stone backsplash & custom stone hood, premium appliances with column refrigerator & freezer all set flush to the cabinets. Luxurious living and entertaining spaces flow seamlessly to the outdoor oasis featuring a sparkling pool, spa, & private 1.6 property w/an irrigation system Belgium block trimmed driveway The magnificent primary suite is a private retreat, complete w/ a custom rift oak cathedral ceiling & a covered balcony w/ glass & wood railings overlooking the property.The 2nd level features 5 BRs w/ensuite baths. The 6th BR Suite is privately in the LL where there is a large FR & Gym.Additional amenities include natural gas, city water, Visual Comfort luxury lighting throughout, integrated recessed lighting, & countless custom features that elevate every room.This is a rare opportunity to own a newly built, architecturally stunning estate where exceptional design and refined living come together beautifully. Ready for move in Summer 2026

6 Beds ⋅ 8 Baths ⋅ 24190641 MLS

Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling details & European windows that flood the interiors w/ natural light.The Chef's Kitchen is highlighted by natural stone countertops,a dramatic stone backsplash & custom stone hood, premium appliances with column refrigerator & freezer all set flush to the cabinets. Luxurious living and entertaining spaces flow seamlessly to the outdoor oasis featuring a sparkling pool, spa, & private 1.6 property w/an irrigation system Belgium block trimmed driveway The magnificent primary suite is a private retreat, complete w/ a custom rift oak cathedral ceiling & a covered balcony w/ glass & wood railings overlooking the property.The 2nd level features 5 BRs w/ensuite baths. The 6th BR Suite is privately in the LL where there is a large FR & Gym.Additional amenities include natural gas, city water, Visual Comfort luxury lighting throughout, integrated recessed lighting, & countless custom features that elevate every room.This is a rare opportunity to own a newly built, architecturally stunning estate where exceptional design and refined living come together beautifully. Ready for move in Summer 2026

10 Beltas Farm Ln, Westport

Listing courtesy of Linda Skolnick from Coldwell Banker Realty. (203) 246-0088 (203) 227-8424

$8,300,000

Sited privately in Lincoln Center on 6.25A park like grounds, this rare architectural estate seamlessly blends history, modernism and sustainability. Originally built in the 1860 as a Victorian manor, the home was reimagined in 1950 introducing the Bauhaus principles of clean lines, functional design and indoor-outdoor harmony. Today, after a meticulous LEED-certified restoration, the residence stands as both a preserved landmark and a showcase of modern luxury. Expansive glass walls, dramatic overhangs, and a sculptural spiral staircase define interiors that flow with light and openness. A kitchen with recycled glass and quartz countertops, professional-grade appliances and radiant-heated stone floors anchors the home. Five spacious bedrooms, spa-inspired baths and flexible living spaces include a library, office, music room, recreation room and wine cellar, offering comfort and versatility.

5 Beds ⋅ 10 Baths ⋅ 73471157 MLS

Sited privately in Lincoln Center on 6.25A park like grounds, this rare architectural estate seamlessly blends history, modernism and sustainability. Originally built in the 1860 as a Victorian manor, the home was reimagined in 1950 introducing the Bauhaus principles of clean lines, functional design and indoor-outdoor harmony. Today, after a meticulous LEED-certified restoration, the residence stands as both a preserved landmark and a showcase of modern luxury. Expansive glass walls, dramatic overhangs, and a sculptural spiral staircase define interiors that flow with light and openness. A kitchen with recycled glass and quartz countertops, professional-grade appliances and radiant-heated stone floors anchors the home. Five spacious bedrooms, spa-inspired baths and flexible living spaces include a library, office, music room, recreation room and wine cellar, offering comfort and versatility.

23 Bedford Rd, Lincoln

Listing courtesy of Listing Agent: Salem Coughlin Group from Listing Office: Compass.

$8,250,000

190 Brookwood Lane is set in one of New Canaan's most unique and desirable residential settings - a bucolic landscape of rolling meadows, mature woodlands, and gently flowing streams set on just over 3 acres of quintessential New England beauty. Situated in the heart of New Canaan, the property offers a peaceful and established neighborhood setting where quiet roads, mature trees, and estate-scale properties create an atmosphere increasingly difficult to replicate. This extraordinary proposed residence blends timeless New England architecture with refined modern living. Designed by Tanner White Architects as the quintessential New Canaan colonial with gracious proportions and exceptional scale, the home is envisioned with approximately 7,500 square feet across the first and second floors, including expansive entertaining spaces, dramatic 10-foot ceilings on the main level, generously scaled bedrooms, and seamless indoor-outdoor living throughout. The proposed floor plan includes 6 bedrooms, 8 bathrooms, 3-car garage, and pool with the opportunity to finish attic and lower-level spaces for more than 10,000 total square feet. The oversized homesite provides exceptional flexibility for estate level outdoor amenities while maintaining tremendous privacy and natural beauty.

6 Beds ⋅ 8 Baths ⋅ 24184237 MLS

190 Brookwood Lane is set in one of New Canaan's most unique and desirable residential settings - a bucolic landscape of rolling meadows, mature woodlands, and gently flowing streams set on just over 3 acres of quintessential New England beauty. Situated in the heart of New Canaan, the property offers a peaceful and established neighborhood setting where quiet roads, mature trees, and estate-scale properties create an atmosphere increasingly difficult to replicate. This extraordinary proposed residence blends timeless New England architecture with refined modern living. Designed by Tanner White Architects as the quintessential New Canaan colonial with gracious proportions and exceptional scale, the home is envisioned with approximately 7,500 square feet across the first and second floors, including expansive entertaining spaces, dramatic 10-foot ceilings on the main level, generously scaled bedrooms, and seamless indoor-outdoor living throughout. The proposed floor plan includes 6 bedrooms, 8 bathrooms, 3-car garage, and pool with the opportunity to finish attic and lower-level spaces for more than 10,000 total square feet. The oversized homesite provides exceptional flexibility for estate level outdoor amenities while maintaining tremendous privacy and natural beauty.

190 Brookwood Ln, New Canaan

Listing courtesy of James Hoffman from Houlihan Lawrence. (203) 517-8105 (203) 869-0700

$8,250,000

A rare offering in back-country Greenwich, this timeless estate is set on 3.58 exquisitely landscaped and gated acres, masterfully blending classic architecture with contemporary luxury. Designed for both grand-scale entertaining and intimate everyday living, the residence offers a sun-filled interior with soaring ceilings, custom millwork, and modern, bespoke finishes throughout. The grand foyer of this center hall colonial sets the tone for elegant, refined living. The gourmet marble kitchen opens to a multi-exposure family room with sweeping views of the manicured yard, pool, and fully equipped outdoor kitchen. The grounds are equally captivating, with a tranquil koi pond enhancing the natural beauty of the landscape. The luxurious primary suite with sitting area, spa-inspired bath, and three walk-in closets is among five second-level bedroom suites, each offering exceptional privacy and comfort. A versatile second-level suite with private entrance currently functions as a private gym but can effortlessly serve as an au pair suite or guest quarters. The thoughtfully executed lower level is fit with a theater, bar, wine cellar, and recreation spaces. The pool house extends the living experience with two additional bedrooms and two full baths-set amidst expansive patios and a lush, tree-lined lawn. Located just minutes from town, schools, and 45 minutes to Manhattan, this meticulously designed compound offers a rare blend of serenity, sophistication, and convenience.

6 Beds ⋅ 9 Baths ⋅ 24169340 MLS

A rare offering in back-country Greenwich, this timeless estate is set on 3.58 exquisitely landscaped and gated acres, masterfully blending classic architecture with contemporary luxury. Designed for both grand-scale entertaining and intimate everyday living, the residence offers a sun-filled interior with soaring ceilings, custom millwork, and modern, bespoke finishes throughout. The grand foyer of this center hall colonial sets the tone for elegant, refined living. The gourmet marble kitchen opens to a multi-exposure family room with sweeping views of the manicured yard, pool, and fully equipped outdoor kitchen. The grounds are equally captivating, with a tranquil koi pond enhancing the natural beauty of the landscape. The luxurious primary suite with sitting area, spa-inspired bath, and three walk-in closets is among five second-level bedroom suites, each offering exceptional privacy and comfort. A versatile second-level suite with private entrance currently functions as a private gym but can effortlessly serve as an au pair suite or guest quarters. The thoughtfully executed lower level is fit with a theater, bar, wine cellar, and recreation spaces. The pool house extends the living experience with two additional bedrooms and two full baths-set amidst expansive patios and a lush, tree-lined lawn. Located just minutes from town, schools, and 45 minutes to Manhattan, this meticulously designed compound offers a rare blend of serenity, sophistication, and convenience.

34 Carrington Dr, Greenwich

Listing courtesy of Carissa Larriuz from Houlihan Lawrence. (203) 914-5218 (203) 869-0700

$8,200,000

Set on over 1.2 acres with a 1.62-acre experience via a neighboring easement, this exceptional Chestnut Hill estate offers a tranquil oasis on one of the area’s most coveted and secluded streets. Originally built in 1900 and thoughtfully renovated over time, the residence spans more than 9,300 square feet with six bedrooms, six full bathrooms, and three half bathrooms. Its richly detailed living spaces were designed for both elegant entertaining and everyday comfort. Gracious formal rooms, soaring ceilings, and exquisite millwork overlook beautifully landscaped grounds featuring a heated, in-ground pool, a basketball court, and ample parking. Once home to Alvan T. Fuller, the 50th Governor of Massachusetts, the property carries remarkable historic provenance. The grounds were originally designed by Frederick Law Olmsted, further contributing to the property’s timeless character. This is a rare opportunity to own a historic estate of this scale in an unbeatable location.

6 Beds ⋅ 9 Baths ⋅ 73526856 MLS

Set on over 1.2 acres with a 1.62-acre experience via a neighboring easement, this exceptional Chestnut Hill estate offers a tranquil oasis on one of the area’s most coveted and secluded streets. Originally built in 1900 and thoughtfully renovated over time, the residence spans more than 9,300 square feet with six bedrooms, six full bathrooms, and three half bathrooms. Its richly detailed living spaces were designed for both elegant entertaining and everyday comfort. Gracious formal rooms, soaring ceilings, and exquisite millwork overlook beautifully landscaped grounds featuring a heated, in-ground pool, a basketball court, and ample parking. Once home to Alvan T. Fuller, the 50th Governor of Massachusetts, the property carries remarkable historic provenance. The grounds were originally designed by Frederick Law Olmsted, further contributing to the property’s timeless character. This is a rare opportunity to own a historic estate of this scale in an unbeatable location.

40 Singletree Rd, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$8,200,000

Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in its surroundings while still just a short drive to Stratton Mountain Resort and the Stratton Helipad. Step into an open-concept haven where elegance meets comfort. Framed by soaring timber beam ceilings, the main living area echoes the grandeur of the mountains while preserving the warmth and intimacy of a true retreat. Natural materials, handcrafted details, and thoughtful design choices create a home that feels warm, timeless and deeply personal. The estate preserves uninterrupted views across the landscape—ensuring that natural beauty remains the focal point from every vantage point.The grand stone fireplace anchors the living area, drawing the eye to soaring ceilings and expansive windows that frame breathtaking mountain ridges. Sunlight floods the space, highlighting the harmonious blend of natural textures and refined finishes.The gourmet kitchen blends beauty and function with custom wood cabinetry, hand-carved artistic accents, a welcoming breakfast bar, and an expansive island designed for conversation, connection, and effortless entertaining. Every space in this residence has been intentionally designed with a keen eye to detail. While every room blends effortlessly with the home’s elevated rustic feel, each one remains extremely unique. Offering six en-suite bedroom in the main residence and 2 bedroom2.5 bath guest quarters. Main Residence with extraordinary gathering rooms and multiple suites, 5 bay barn, guest quarters, pond, miles of maintained trails for mountain biking and winter activities,

6 Beds ⋅ 10 Baths ⋅ 5076041 MLS

Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in its surroundings while still just a short drive to Stratton Mountain Resort and the Stratton Helipad. Step into an open-concept haven where elegance meets comfort. Framed by soaring timber beam ceilings, the main living area echoes the grandeur of the mountains while preserving the warmth and intimacy of a true retreat. Natural materials, handcrafted details, and thoughtful design choices create a home that feels warm, timeless and deeply personal. The estate preserves uninterrupted views across the landscape—ensuring that natural beauty remains the focal point from every vantage point.The grand stone fireplace anchors the living area, drawing the eye to soaring ceilings and expansive windows that frame breathtaking mountain ridges. Sunlight floods the space, highlighting the harmonious blend of natural textures and refined finishes.The gourmet kitchen blends beauty and function with custom wood cabinetry, hand-carved artistic accents, a welcoming breakfast bar, and an expansive island designed for conversation, connection, and effortless entertaining. Every space in this residence has been intentionally designed with a keen eye to detail. While every room blends effortlessly with the home’s elevated rustic feel, each one remains extremely unique. Offering six en-suite bedroom in the main residence and 2 bedroom2.5 bath guest quarters. Main Residence with extraordinary gathering rooms and multiple suites, 5 bay barn, guest quarters, pond, miles of maintained trails for mountain biking and winter activities,

557 Trager Rd, Jamaica

Listing courtesy of Kim Morgan-Wohler from Wohler Realty Group. ()

$8,000,000

Elegant single family home set on a landscaped European garden on Marlborough St. Renovated to the finest standards while keeping the quintessential Back Bay details, this home boasts 5 BR's, 3 full & 2 half baths.There is a gourmet chef's kitchen & family room on the lower level that lead out to a private patio, hot tub & direct to 2 full sized parking spaces. The main level showcases a fireplaced formal living room & dining room w/ a butler's pantry, perfect for hosting family & friends. Up one flight to the 2nd floor on an original classic staircase, you will enter the sumptuous primary suite w/ fireplace. It spans the entire floor, complete with a huge spa bathroom w/ a large soaking tub. A custom walk in closet is not to be missed. The remaining four BR's are on the upper floors & are spacious & versatile for home office & guests. Two more full baths service these BR's. A beautiful stained glass skylight crowns the top of this fabulous home. Central AC rounds out this showpiece!

5 Beds ⋅ 5 Baths ⋅ 73492678 MLS

Elegant single family home set on a landscaped European garden on Marlborough St. Renovated to the finest standards while keeping the quintessential Back Bay details, this home boasts 5 BR's, 3 full & 2 half baths.There is a gourmet chef's kitchen & family room on the lower level that lead out to a private patio, hot tub & direct to 2 full sized parking spaces. The main level showcases a fireplaced formal living room & dining room w/ a butler's pantry, perfect for hosting family & friends. Up one flight to the 2nd floor on an original classic staircase, you will enter the sumptuous primary suite w/ fireplace. It spans the entire floor, complete with a huge spa bathroom w/ a large soaking tub. A custom walk in closet is not to be missed. The remaining four BR's are on the upper floors & are spacious & versatile for home office & guests. Two more full baths service these BR's. A beautiful stained glass skylight crowns the top of this fabulous home. Central AC rounds out this showpiece!

340 Marlborough St, Boston

Listing courtesy of Listing Agent: Lisa Merriman Barth from Listing Office: Barth Real Estate.

$7,995,000

Nestled amid beautifully landscaped grounds, this exceptional 7,500± square foot residence captures breathtaking views over West Bay and Eel River. A private sandy beach and deep-water dock provide effortless access to Nantucket Sound, creating a rare combination of serenity and seafaring adventure. Inside, the five-bedroom home blends refined architecture with inviting coastal warmth. A dramatic two-story great room opens to an expanse of windows that frame the water, seamlessly connecting the interior to the surrounding natural beauty. The thoughtfully designed main level includes a chef's kitchen adjoining a sun-filled sitting room, elegant dining room, gracious living room, and handsome home office. The first-floor primary suite offers a peaceful retreat with water views, while a second primary suite and three additional bedrooms complete the upper level. A captivating tower room provides a 360-degree vantage point for enjoying sweeping sunsets and the ever-changing coastal landscape. The finished lower level extends the living space with a recreation area, wet bar, and kitchenette, ideal for casual gatherings or guest overflow. A two-car garage, expansive outdoor terrace and lush gardens complement the home's elegant yet relaxed design. Privately positioned, yet moments from Osterville's charming village center, this remarkable estate epitomizes luxurious waterfront living on Cape Cod. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

5 Beds ⋅ 6 Baths ⋅ 22505080 MLS

Nestled amid beautifully landscaped grounds, this exceptional 7,500± square foot residence captures breathtaking views over West Bay and Eel River. A private sandy beach and deep-water dock provide effortless access to Nantucket Sound, creating a rare combination of serenity and seafaring adventure. Inside, the five-bedroom home blends refined architecture with inviting coastal warmth. A dramatic two-story great room opens to an expanse of windows that frame the water, seamlessly connecting the interior to the surrounding natural beauty. The thoughtfully designed main level includes a chef's kitchen adjoining a sun-filled sitting room, elegant dining room, gracious living room, and handsome home office. The first-floor primary suite offers a peaceful retreat with water views, while a second primary suite and three additional bedrooms complete the upper level. A captivating tower room provides a 360-degree vantage point for enjoying sweeping sunsets and the ever-changing coastal landscape. The finished lower level extends the living space with a recreation area, wet bar, and kitchenette, ideal for casual gatherings or guest overflow. A two-car garage, expansive outdoor terrace and lush gardens complement the home's elegant yet relaxed design. Privately positioned, yet moments from Osterville's charming village center, this remarkable estate epitomizes luxurious waterfront living on Cape Cod. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

168 Garrison Lane, Osterville

Listing courtesy of Listing Agent: Robert B Kinlin (rkinlin@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

$7,995,000

LEGACY COMPOUND WITH EXTRAORDINARY VIEWS // Pleasant Dreams is a spectacular one-of-a-kind family compound on perhaps one of the most desirable pieces of property on Cape Cod. This 2.5 acre estate boasts approximately 345 feet of saltwater frontage directly on Pleasant Bay with access to the Atlantic Ocean and showcases 180-degree breathtaking views of Pleasant Bay and beyond. This compound features 3 unique buildings. An approximately 7000 square foot main house, a guest cottage with pool and a boat house. This home contains the finest in craftsmanship and impeccable attention to detail. The large, open professional kitchen complete with top-of-the-line appliances, an oversized island and generous windows that overlook the bay makes this the natural centerpiece of the main house. Designed and professionally manicured landscaping with multi-level stone walls and gardens makes this property look magazine worthy. A truly unique family compound where memories will be created for a lifetime.

5 Beds ⋅ 7 Baths ⋅ 22601038 MLS

LEGACY COMPOUND WITH EXTRAORDINARY VIEWS // Pleasant Dreams is a spectacular one-of-a-kind family compound on perhaps one of the most desirable pieces of property on Cape Cod. This 2.5 acre estate boasts approximately 345 feet of saltwater frontage directly on Pleasant Bay with access to the Atlantic Ocean and showcases 180-degree breathtaking views of Pleasant Bay and beyond. This compound features 3 unique buildings. An approximately 7000 square foot main house, a guest cottage with pool and a boat house. This home contains the finest in craftsmanship and impeccable attention to detail. The large, open professional kitchen complete with top-of-the-line appliances, an oversized island and generous windows that overlook the bay makes this the natural centerpiece of the main house. Designed and professionally manicured landscaping with multi-level stone walls and gardens makes this property look magazine worthy. A truly unique family compound where memories will be created for a lifetime.

77 Towhee Lane, Orleans

Listing courtesy of Listing Agent: Chris Rhinesmith (chris.rhinesmith@compass.com) from Listing Office: Compass Massachusetts, LLC.

$7,995,000

Unprecedented opportunity to purchase two landmark, historic residences, situated side by side on Ridgefield's beloved Main St., which have been developed into an unparalleled lifestyle compound. This once in a lifetime sale includes the treasured Hawley House at 236 Main St. - Ridgefield's oldest home, on its original lot (5) which was built by the proprietors in 1713 for the Rev. Thomas Hawley, first pastor & town clerk. It also includes 250 Main St. - the iconic & brightly colored neighboring Gothic Revival Victorian, built Ca. 1826 by Hawley descendants. Working with Peter Coffin of DCA Architects & the Historic District Commission, the home underwent a meticulous full restoration & renovation, thoughtfully balancing historic preservation with modern luxury updates. Over $10M has been spent in top of the line improvements & designer appointments inside & out. Together, both homes span a pastoral 3.16 acres, juxtaposing sidewalks to vibrant downtown Ridgefield with rear privacy including 2 magnificent barns. 236 Main's "Red Barn," Ca. 1900 & renovated in 2012 features: 2,015 sf, indoor basketball court, home office/conference rm, arts & crafts studio, 1 full/2 half bths & 2 car garage. 250 Main's Pool/Carriage house includes: 3,684 sf, 1-2 BRs, 2 full/1 half bths, 2 fplcs, 2 car garage (2 Tesla chargers), gym with sauna, game room/bar, poker room, arcade, 30+ seat movie theater, plus kitchen/great room open to the heated, gunite, saltwater pool, spa & outdoor resort oasis.

8 Beds ⋅ 9 Baths ⋅ 24170626 MLS

Unprecedented opportunity to purchase two landmark, historic residences, situated side by side on Ridgefield's beloved Main St., which have been developed into an unparalleled lifestyle compound. This once in a lifetime sale includes the treasured Hawley House at 236 Main St. - Ridgefield's oldest home, on its original lot (5) which was built by the proprietors in 1713 for the Rev. Thomas Hawley, first pastor & town clerk. It also includes 250 Main St. - the iconic & brightly colored neighboring Gothic Revival Victorian, built Ca. 1826 by Hawley descendants. Working with Peter Coffin of DCA Architects & the Historic District Commission, the home underwent a meticulous full restoration & renovation, thoughtfully balancing historic preservation with modern luxury updates. Over $10M has been spent in top of the line improvements & designer appointments inside & out. Together, both homes span a pastoral 3.16 acres, juxtaposing sidewalks to vibrant downtown Ridgefield with rear privacy including 2 magnificent barns. 236 Main's "Red Barn," Ca. 1900 & renovated in 2012 features: 2,015 sf, indoor basketball court, home office/conference rm, arts & crafts studio, 1 full/2 half bths & 2 car garage. 250 Main's Pool/Carriage house includes: 3,684 sf, 1-2 BRs, 2 full/1 half bths, 2 fplcs, 2 car garage (2 Tesla chargers), gym with sauna, game room/bar, poker room, arcade, 30+ seat movie theater, plus kitchen/great room open to the heated, gunite, saltwater pool, spa & outdoor resort oasis.

236 & 250 Main St, Ridgefield

Listing courtesy of Laura Ancona from William Pitt Sotheby's Int'l. (203) 733-7053 (203) 438-9531

$7,995,000

Pleasant Dreams is a spectacular one-of-a-kind family compound on perhaps one of the most desirable pieces of property on Cape Cod. This 2.5 acre estate boasts approximately 345 feet of saltwater frontage directly on Pleasant Bay with access to the Atlantic Ocean and showcases 180-degree breathtaking views of Pleasant Bay and beyond. This compound features 3 unique buildings. An approximately 7000 square foot main house, a guest cottage with pool and a boat house. This home contains the finest in craftsmanship and impeccable attention to detail. The large, open professional kitchen complete with top-of-the-line appliances, an oversized island and generous windows that overlook the bay makes this the natural centerpiece of the main house. Designed and professionally manicured landscaping with multi-level stone walls and gardens makes this property look magazine worthy. A truly unique family compound where memories will be created for a lifetime.

5 Beds ⋅ 7 Baths ⋅ 73493011 MLS

Pleasant Dreams is a spectacular one-of-a-kind family compound on perhaps one of the most desirable pieces of property on Cape Cod. This 2.5 acre estate boasts approximately 345 feet of saltwater frontage directly on Pleasant Bay with access to the Atlantic Ocean and showcases 180-degree breathtaking views of Pleasant Bay and beyond. This compound features 3 unique buildings. An approximately 7000 square foot main house, a guest cottage with pool and a boat house. This home contains the finest in craftsmanship and impeccable attention to detail. The large, open professional kitchen complete with top-of-the-line appliances, an oversized island and generous windows that overlook the bay makes this the natural centerpiece of the main house. Designed and professionally manicured landscaping with multi-level stone walls and gardens makes this property look magazine worthy. A truly unique family compound where memories will be created for a lifetime.

77 Towhee Lane, Orleans

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$7,995,000

Nestled amid beautifully landscaped grounds, this exceptional 7,500± square foot residence captures breathtaking views over West Bay and Eel River. A private sandy beach and deep-water dock provide effortless access to Nantucket Sound, creating a rare combination of serenity and seafaring adventure. Inside, the five-bedroom home blends refined architecture with inviting coastal warmth. A dramatic two-story great room opens to an expanse of windows that frame the water, seamlessly connecting the interior to the surrounding natural beauty. The thoughtfully designed main level includes a chef's kitchen adjoining a sun-filled sitting room, elegant dining room, gracious living room, and handsome home office. The first-floor primary suite offers a peaceful retreat with water views, while a second primary suite and three additional bedrooms complete the upper level. A captivating tower room provides a 360-degree vantage point for enjoying sweeping sunsets and the ever-changing coastal landscape. The finished lower level extends the living space with a recreation area, wet bar, and kitchenette, ideal for casual gatherings or guest overflow. A two-car garage, expansive outdoor terrace and lush gardens complement the home's elegant yet relaxed design. Privately positioned, yet moments from Osterville's charming village center, this remarkable estate epitomizes luxurious waterfront living on Cape Cod. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

5 Beds ⋅ 6 Baths ⋅ 73441700 MLS

Nestled amid beautifully landscaped grounds, this exceptional 7,500± square foot residence captures breathtaking views over West Bay and Eel River. A private sandy beach and deep-water dock provide effortless access to Nantucket Sound, creating a rare combination of serenity and seafaring adventure. Inside, the five-bedroom home blends refined architecture with inviting coastal warmth. A dramatic two-story great room opens to an expanse of windows that frame the water, seamlessly connecting the interior to the surrounding natural beauty. The thoughtfully designed main level includes a chef's kitchen adjoining a sun-filled sitting room, elegant dining room, gracious living room, and handsome home office. The first-floor primary suite offers a peaceful retreat with water views, while a second primary suite and three additional bedrooms complete the upper level. A captivating tower room provides a 360-degree vantage point for enjoying sweeping sunsets and the ever-changing coastal landscape. The finished lower level extends the living space with a recreation area, wet bar, and kitchenette, ideal for casual gatherings or guest overflow. A two-car garage, expansive outdoor terrace and lush gardens complement the home's elegant yet relaxed design. Privately positioned, yet moments from Osterville's charming village center, this remarkable estate epitomizes luxurious waterfront living on Cape Cod. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

168 Garrison Ln, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$7,990,000

Build your coastal dream home on a rare, full acre* property along one of Compo Beach's most coveted cul-de-sacs, where opportunities of this caliber seldom become available. Ideally positioned just across from Longshore and moments from the shoreline, this extraordinary setting places Westport's most treasured amenities at your fingertips: golf, tennis, swimming, boating, beaches, playgrounds, fine dining, and more. To be custom built by Coastal Luxury Homes, Fairfield County's foremost luxury builder, this distinguished residence will offer three beautifully finished levels defined by unrivaled quality and meticulous craftsmanship. Expansive walls of glass will bathe the interiors in natural light, showcase the magnificent grounds, and create a seamless connection to the outdoors. Exquisite millwork, natural stone, refined finishes, a curated selection of top-tier appliances, and generous allowances will elevate every space, while the sumptuous primary suite will serve as a private, resort-inspired retreat. Thoughtfully tailored to your every wish with room for a pool, this remarkable home will reflect your personal style and vision for sophisticated coastal living.

6 Beds ⋅ 8 Baths ⋅ 24194541 MLS

Build your coastal dream home on a rare, full acre* property along one of Compo Beach's most coveted cul-de-sacs, where opportunities of this caliber seldom become available. Ideally positioned just across from Longshore and moments from the shoreline, this extraordinary setting places Westport's most treasured amenities at your fingertips: golf, tennis, swimming, boating, beaches, playgrounds, fine dining, and more. To be custom built by Coastal Luxury Homes, Fairfield County's foremost luxury builder, this distinguished residence will offer three beautifully finished levels defined by unrivaled quality and meticulous craftsmanship. Expansive walls of glass will bathe the interiors in natural light, showcase the magnificent grounds, and create a seamless connection to the outdoors. Exquisite millwork, natural stone, refined finishes, a curated selection of top-tier appliances, and generous allowances will elevate every space, while the sumptuous primary suite will serve as a private, resort-inspired retreat. Thoughtfully tailored to your every wish with room for a pool, this remarkable home will reflect your personal style and vision for sophisticated coastal living.

4a Compo Pkwy, Westport

Listing courtesy of Jaclyn Picarillo from Higgins Group Bedford Square. (203) 981-5012 (203) 226-0300

$7,985,000

Introducing 12 Beltas Farm Lane, an extraordinary new construction estate in Westport, Connecticut, set within Beltas Farm-one of Westport's newest and most distinctive luxury enclaves. Once part of a 23-acre working family farm, this special setting has been thoughtfully transformed into an intimate collection of exceptional residences, with nearly five acres preserved as open space. The result is something increasingly rare in Westport: beautiful open views, a sense of space and privacy, and an enclave of significant luxury homes. Offered at $7,895,000 and built by Fairfield County Contractors, known for exceptional quality and craftsmanship, this remarkable new Westport home encompasses more than 9,000 square feet of sophisticated living space. A handsome wood roof introduces timeless architecture and the exceptional level of finish found throughout. Designed for today's luxury lifestyle, the residence features six ensuite bedrooms and beautifully proportioned living and entertaining spaces filled with natural light and oriented to capture the property's open views. A wine cellar adds another layer to the home's exceptional entertaining spaces, while the thoughtful floor plan balances impressive scale with comfortable everyday living. Outside, a stunning pool and spa create a private resort experience surrounded by the beauty and openness of the Beltas Farm setting. What distinguishes 12 Beltas Farm Lane is not simply the caliber of the new construction, but the rarity

6 Beds ⋅ 6 Baths ⋅ 24205532 MLS

Introducing 12 Beltas Farm Lane, an extraordinary new construction estate in Westport, Connecticut, set within Beltas Farm-one of Westport's newest and most distinctive luxury enclaves. Once part of a 23-acre working family farm, this special setting has been thoughtfully transformed into an intimate collection of exceptional residences, with nearly five acres preserved as open space. The result is something increasingly rare in Westport: beautiful open views, a sense of space and privacy, and an enclave of significant luxury homes. Offered at $7,895,000 and built by Fairfield County Contractors, known for exceptional quality and craftsmanship, this remarkable new Westport home encompasses more than 9,000 square feet of sophisticated living space. A handsome wood roof introduces timeless architecture and the exceptional level of finish found throughout. Designed for today's luxury lifestyle, the residence features six ensuite bedrooms and beautifully proportioned living and entertaining spaces filled with natural light and oriented to capture the property's open views. A wine cellar adds another layer to the home's exceptional entertaining spaces, while the thoughtful floor plan balances impressive scale with comfortable everyday living. Outside, a stunning pool and spa create a private resort experience surrounded by the beauty and openness of the Beltas Farm setting. What distinguishes 12 Beltas Farm Lane is not simply the caliber of the new construction, but the rarity

12 Beltas Farm Ln, Westport

Listing courtesy of Judy Michaelis from Coldwell Banker Realty. (203) 247-5000 (203) 227-8424

$7,950,000

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed home by Morgan Studio, a husband-and-wife-led boutique design firm. Created for effortless indoor-outdoor living, the residence features soaring ceilings, a flowing floor plan, oversized windows, and exceptional materials and finishes throughout. A private interior courtyard, envisioned as an edible garden, anchors the home and connects seamlessly to the cathedral-ceiling great room with a wood-burning fireplace and a 20' x 40' heated gunite pool. The chef's kitchen features a Patagonia Tiffany stone island, breakfast nook, and butler's pantry. Private bedroom suites occupy separate wings, including a spa-inspired primary suite with a circular skylit shower and wall-to-wall travertine. A bright lower level with 10-foot ceilings provides generous recreation and entertaining space. A custom furniture package is available upon request for a truly turnkey offering. Conveniently located near Crocker Drive with easy access to South Beach, bike paths, Katama, and downtown Edgartown. A refined interpretation of the Vineyard summer house, thoughtfully designed for relaxed coastal living.

4 Beds ⋅ 5 Baths ⋅ 22603541 MLS

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed home by Morgan Studio, a husband-and-wife-led boutique design firm. Created for effortless indoor-outdoor living, the residence features soaring ceilings, a flowing floor plan, oversized windows, and exceptional materials and finishes throughout. A private interior courtyard, envisioned as an edible garden, anchors the home and connects seamlessly to the cathedral-ceiling great room with a wood-burning fireplace and a 20' x 40' heated gunite pool. The chef's kitchen features a Patagonia Tiffany stone island, breakfast nook, and butler's pantry. Private bedroom suites occupy separate wings, including a spa-inspired primary suite with a circular skylit shower and wall-to-wall travertine. A bright lower level with 10-foot ceilings provides generous recreation and entertaining space. A custom furniture package is available upon request for a truly turnkey offering. Conveniently located near Crocker Drive with easy access to South Beach, bike paths, Katama, and downtown Edgartown. A refined interpretation of the Vineyard summer house, thoughtfully designed for relaxed coastal living.

2 Lexington Avenue, Edgartown

Listing courtesy of Listing Agent: Peyton Wallace (peyton@studiorealty.com) from Listing Office: Studio Realty LLC.

$7,950,000

Nestled in the highly coveted enclave of Acoaxet and Westport Harbor, this magnificent coastal estate at 169 Atlantic Ave offers the pinnacle of New England waterfront living. Meticulously reimagined from top to bottom, this home underwent a complete, high-end remodel completed in 2021. Sited flawlessly to maximize panoramic views of the open Atlantic Ocean, sandy shorelines, and the Elizabeth Islands, this property seamlessly blends classic Shingle-style architecture with unparalleled private luxury.

5 Beds ⋅ 6 Baths ⋅ 73543062 MLS

Nestled in the highly coveted enclave of Acoaxet and Westport Harbor, this magnificent coastal estate at 169 Atlantic Ave offers the pinnacle of New England waterfront living. Meticulously reimagined from top to bottom, this home underwent a complete, high-end remodel completed in 2021. Sited flawlessly to maximize panoramic views of the open Atlantic Ocean, sandy shorelines, and the Elizabeth Islands, this property seamlessly blends classic Shingle-style architecture with unparalleled private luxury.

169 Atlantic Avenue, Westport

Listing courtesy of Listing Agent: Kirk Schryver Team from Listing Office: Compass.

$7,950,000

Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the home's historic integrity while introducing refined, livable spaces. Interiors by acclaimed designer Katie Ridder bring a fresh yet classic sensibility, blending color, texture, and bespoke detail throughout. The main residence offers 7 bedrooms and 6 full baths, anchored by five fireplaces that add warmth and character across its gracious living spaces. A classic carriage house offers a fully equipped 2-bedroom, 1-bath guest residence with its own kitchen, providing exceptional flexibility-ideal for extended stays, in-law living, or a private home office retreat. The grounds, designed by renowned landscape architect Janice Parker, are a true highlight-lush, structured, and beautifully layered for year-round interest. An in-ground saltwater pool completes the estate-like setting, creating a private retreat perfect for both entertaining and quiet enjoyment. Rich in history and elevated by a world-class design team, 16 East Trail offers a rare opportunity to own a piece of Darien's architectural legacy-seamlessly tailored for modern living.

9 Beds ⋅ 10 Baths ⋅ 24168537 MLS

Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the home's historic integrity while introducing refined, livable spaces. Interiors by acclaimed designer Katie Ridder bring a fresh yet classic sensibility, blending color, texture, and bespoke detail throughout. The main residence offers 7 bedrooms and 6 full baths, anchored by five fireplaces that add warmth and character across its gracious living spaces. A classic carriage house offers a fully equipped 2-bedroom, 1-bath guest residence with its own kitchen, providing exceptional flexibility-ideal for extended stays, in-law living, or a private home office retreat. The grounds, designed by renowned landscape architect Janice Parker, are a true highlight-lush, structured, and beautifully layered for year-round interest. An in-ground saltwater pool completes the estate-like setting, creating a private retreat perfect for both entertaining and quiet enjoyment. Rich in history and elevated by a world-class design team, 16 East Trail offers a rare opportunity to own a piece of Darien's architectural legacy-seamlessly tailored for modern living.

16 E Trail, Darien

Listing courtesy of Ashley Dineen from Compass Connecticut, LLC. (203) 253-9616 (203) 423-3100

$7,950,000

New Construction BY Ritzzo Development a premier builder! Situated on a country road among luxury estates, this 8,050 sq. ft., to be built new construction strikes the perfect balance of secluded privacy and commanding views. The 8.18 acre lot is bordered by state forest on 3 sides. The welcoming front porch sets a sophisticated tone, leading into an interior defined by 5" white oak flooring, Pella windows and doors with exquisite craftsmanship throughout. The heart of the home is a chef's kitchen with custom white oak cabinetry paired with professional Sub-Zero/Wolf appliances, an inviting island, and a sun-drenched breakfast room. Dramatic architecture defines the family room, where exposed beams complement a soaring vaulted ceiling and a striking wood-burning hearth. The residence offers six en-suite bedrooms. The expansive primary retreat is a true standout, boasting dual bathroom suites and matching, dual walk-in closets. Functional luxury continues with a main-level guest suite, a dedicated home office, and two powder rooms on the main level. Personal gym in the lower level. Outdoor highlights include a premium granite patio with built in barbeque overlooking a stunning 18x36 in-ground gunite pool. For peace of mind the electric service is buried with 400-amp service, with a dedicated EV charger, plus a fully equipped Generac 26KW auto transfer generator. This is a rare opportunity to start the year in a home designed for ultimate style, comfort and sophistication

6 Beds ⋅ 8 Baths ⋅ 24166431 MLS

New Construction BY Ritzzo Development a premier builder! Situated on a country road among luxury estates, this 8,050 sq. ft., to be built new construction strikes the perfect balance of secluded privacy and commanding views. The 8.18 acre lot is bordered by state forest on 3 sides. The welcoming front porch sets a sophisticated tone, leading into an interior defined by 5" white oak flooring, Pella windows and doors with exquisite craftsmanship throughout. The heart of the home is a chef's kitchen with custom white oak cabinetry paired with professional Sub-Zero/Wolf appliances, an inviting island, and a sun-drenched breakfast room. Dramatic architecture defines the family room, where exposed beams complement a soaring vaulted ceiling and a striking wood-burning hearth. The residence offers six en-suite bedrooms. The expansive primary retreat is a true standout, boasting dual bathroom suites and matching, dual walk-in closets. Functional luxury continues with a main-level guest suite, a dedicated home office, and two powder rooms on the main level. Personal gym in the lower level. Outdoor highlights include a premium granite patio with built in barbeque overlooking a stunning 18x36 in-ground gunite pool. For peace of mind the electric service is buried with 400-amp service, with a dedicated EV charger, plus a fully equipped Generac 26KW auto transfer generator. This is a rare opportunity to start the year in a home designed for ultimate style, comfort and sophistication

197 A Tinker Hill Rd, Washington

Listing courtesy of Sharon Wyant McGuire from William Pitt Sotheby's Int'l. (203) 417-2925 (860) 868-6600

$7,950,000

A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the Vineyard. The property, located on a private way in the historic Hatch Road neighborhood, is a short distance to downtown Vineyard Haven and the West Chop Club. The home, built in 1900, was the summer residence of Leland and Carol Powers who named their estate ''The Mooring.'' Enjoy the magnificent views and sounds from the wrap-around porch: spectacular sunrise over East Chop; tell time by the passing ferries; see youngsters learn the art of sailing from the Yacht Club; see the Black Dog tall ships raise their sails in front of you; watch family members and guests enjoy lawn games, and swimming.

5 Beds ⋅ 3 Baths ⋅ 73476753 MLS

A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the Vineyard. The property, located on a private way in the historic Hatch Road neighborhood, is a short distance to downtown Vineyard Haven and the West Chop Club. The home, built in 1900, was the summer residence of Leland and Carol Powers who named their estate ''The Mooring.'' Enjoy the magnificent views and sounds from the wrap-around porch: spectacular sunrise over East Chop; tell time by the passing ferries; see youngsters learn the art of sailing from the Yacht Club; see the Black Dog tall ships raise their sails in front of you; watch family members and guests enjoy lawn games, and swimming.

33 Goethals Way, Tisbury

Listing courtesy of Listing Agent: Buder Team from Listing Office: Sandpiper Realty, Inc..

$7,926,000

Set within Westport's most prestigious private estate enclave, surrounded by grand coastal estates and quintessential antique treasures, this exceptional Greens Farms 2+ acre* new construction offering is poised to become one of Fairfield County's most coveted addresses. Perfectly positioned, moments from beaches, downtown boutiques, vibrant dining scene, and just an express train to Manhattan, the property offers a rare blend of privacy, convenience, and timeless sophistication. Fully customizable and designed to fit your lifestyle and desired scale, this masterfully built residence will feature bespoke craftsmanship, rich stone, curated designer finishes, advanced smart home technology, and world-class amenities tailored entirely to your vision. Expansive grounds offer tranquil space for a private resort-style setting with endless possibilities for outdoor living and recreation. Walk the property with us and the Coastal Luxury Homes team and begin designing your dream estate.

6 Beds ⋅ 7 Baths ⋅ 24177287 MLS

Set within Westport's most prestigious private estate enclave, surrounded by grand coastal estates and quintessential antique treasures, this exceptional Greens Farms 2+ acre* new construction offering is poised to become one of Fairfield County's most coveted addresses. Perfectly positioned, moments from beaches, downtown boutiques, vibrant dining scene, and just an express train to Manhattan, the property offers a rare blend of privacy, convenience, and timeless sophistication. Fully customizable and designed to fit your lifestyle and desired scale, this masterfully built residence will feature bespoke craftsmanship, rich stone, curated designer finishes, advanced smart home technology, and world-class amenities tailored entirely to your vision. Expansive grounds offer tranquil space for a private resort-style setting with endless possibilities for outdoor living and recreation. Walk the property with us and the Coastal Luxury Homes team and begin designing your dream estate.

Clapboard Hill Rd Unit (New Build), Westport

Listing courtesy of Brett Lieberman from The Riverside Realty Group. (203) 216-2515 (203) 226-8300

$7,900,000

Spectacular waterfront property located in the exclusive village of Daniels Island inside of the resort community of New Seabury. This stately property sits high above Popponesset Bay which allows for panoramic views of the bay and distant views of Nantucket Sound. Highlights of this 6 bedroom home include an open first floor plan with water views from almost every room, great room with vaulted ceiling and fireplace, chef's kitchen with double Wolf gas range and oversized kitchen island, secluded 2nd floor Primary Suite with his & her baths/sitting area and private balcony that overlooks the heated pool, raised hot tub & Popponesset Bay. Other features of this property include separate guest/nanny quarters, home office, additional first floor bedroom and 2 additional bedrooms with shared bath upstairs using its own private staircase, 2 car garage and private dock located on the bay. The property is walking distance to the marina and a short drive to the shops, restaurants in New Seabury, The Country Club at New Seabury and the stores at Mashpee Commons.

6 Beds ⋅ 7 Baths ⋅ 22604537 MLS

Spectacular waterfront property located in the exclusive village of Daniels Island inside of the resort community of New Seabury. This stately property sits high above Popponesset Bay which allows for panoramic views of the bay and distant views of Nantucket Sound. Highlights of this 6 bedroom home include an open first floor plan with water views from almost every room, great room with vaulted ceiling and fireplace, chef's kitchen with double Wolf gas range and oversized kitchen island, secluded 2nd floor Primary Suite with his & her baths/sitting area and private balcony that overlooks the heated pool, raised hot tub & Popponesset Bay. Other features of this property include separate guest/nanny quarters, home office, additional first floor bedroom and 2 additional bedrooms with shared bath upstairs using its own private staircase, 2 car garage and private dock located on the bay. The property is walking distance to the marina and a short drive to the shops, restaurants in New Seabury, The Country Club at New Seabury and the stores at Mashpee Commons.

141 Daniels Island Road, Mashpee

Listing courtesy of Listing Agent: Mark A Thompson (Mark@newseaburyre.com) from Listing Office: New Seabury Sotheby's International Realty.

$7,900,000

A truly rare offering on the shores of Winter Harbor, this remarkable 20 acre property presents a once-in-a-generation opportunity to own one of the most extraordinary waterfront estates in Wolfeboro. Comprised of one distinct 20-acre parcels, the property captures the very essence of lakeside New England living. On the lake side of North Main Street, an antique seasonal cottage overlooks the sparkling waters of Lake Winnipesaukee, where breathtaking sunsets paint the sky above Winter Harbor each evening. Sandy waterfront, sweeping views, and the tranquil setting create an idyllic retreat to enjoy today while envisioning what tomorrow may bring. The existing home offers an opportunity for restoration or redevelopment, while the gently sloping terrain provides exceptional flexibility for future plans, including the potential for walkout lower levels designed to maximize both views and indoor-outdoor living. Whether your vision is a private family compound, or a multigenerational retreat, or a thoughtfully designed development opportunity, the rare combination of substantial acreage, waterfront, and lake views offers possibilities that are nearly impossible to replicate in today's market. This is a property meant to be cherished, shaped by its next steward, and enjoyed for generations to come. Adding to its appeal is the location itself. Welcome to Wolfeboro, often regarded as one of New England's most charming villages. Here, you'll find the perfect balance of peace and privacy while remaining just minutes from the vibrant downtown, with its boutique shops, restaurants, marinas, and year-round community events.

5 Beds ⋅ 1 Baths ⋅ 5095851 MLS

A truly rare offering on the shores of Winter Harbor, this remarkable 20 acre property presents a once-in-a-generation opportunity to own one of the most extraordinary waterfront estates in Wolfeboro. Comprised of one distinct 20-acre parcels, the property captures the very essence of lakeside New England living. On the lake side of North Main Street, an antique seasonal cottage overlooks the sparkling waters of Lake Winnipesaukee, where breathtaking sunsets paint the sky above Winter Harbor each evening. Sandy waterfront, sweeping views, and the tranquil setting create an idyllic retreat to enjoy today while envisioning what tomorrow may bring. The existing home offers an opportunity for restoration or redevelopment, while the gently sloping terrain provides exceptional flexibility for future plans, including the potential for walkout lower levels designed to maximize both views and indoor-outdoor living. Whether your vision is a private family compound, or a multigenerational retreat, or a thoughtfully designed development opportunity, the rare combination of substantial acreage, waterfront, and lake views offers possibilities that are nearly impossible to replicate in today's market. This is a property meant to be cherished, shaped by its next steward, and enjoyed for generations to come. Adding to its appeal is the location itself. Welcome to Wolfeboro, often regarded as one of New England's most charming villages. Here, you'll find the perfect balance of peace and privacy while remaining just minutes from the vibrant downtown, with its boutique shops, restaurants, marinas, and year-round community events.

606 N Main St, Wolfeboro

Listing courtesy of Lobin Frizzell from KW Coastal and Lakes & Mountains Realty/Meredith. ()

$7,900,000

Set along one of Back Bay's most picturesque tree-lined streets, this distinguished single-family residence pairs timeless architectural elegance with thoughtfully updated interiors and modern amenities. Grand living spaces are defined by soaring ceilings, oversized bay windows, elegant custom built-ins, handsome fireplaces, and abundant natural light. The beautifully renovated kitchen features custom cabinetry, top-of-the-line appliances, and a spacious butler's pantry designed for effortless entertaining. Crowning the home is a spectacular roof deck with sweeping views of the Back Bay skyline and city beyond. Recent improvements include updated HVAC systems and lighting throughout. Additional amenities include an elevator servicing all floors, a wine room, and a versatile lower level with kitchenette and full bath, ideally suited for a guest suite. Complete with an outdoor patio and 2 full parking spaces, this residence offers a rare opportunity in Boston's most coveted neighborhood.

4 Beds ⋅ 6 Baths ⋅ 73536744 MLS

Set along one of Back Bay's most picturesque tree-lined streets, this distinguished single-family residence pairs timeless architectural elegance with thoughtfully updated interiors and modern amenities. Grand living spaces are defined by soaring ceilings, oversized bay windows, elegant custom built-ins, handsome fireplaces, and abundant natural light. The beautifully renovated kitchen features custom cabinetry, top-of-the-line appliances, and a spacious butler's pantry designed for effortless entertaining. Crowning the home is a spectacular roof deck with sweeping views of the Back Bay skyline and city beyond. Recent improvements include updated HVAC systems and lighting throughout. Additional amenities include an elevator servicing all floors, a wine room, and a versatile lower level with kitchenette and full bath, ideally suited for a guest suite. Complete with an outdoor patio and 2 full parking spaces, this residence offers a rare opportunity in Boston's most coveted neighborhood.

122 Marlborough Street, Boston

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.

$7,900,000

Introducing a one-of-a-kind gem in Darien: the historic Eliaseph Whitney House, originally built in 1770, nestled on an expansive 4.12-acre parcel- one of the largest of its kind in town. This iconic property effortlessly blends centuries-old charm with modern-day functionality. Step inside to discover timeless details like wood-beamed ceilings and floors, multiple fireplaces, a cozy den and library, all complemented by bright, open living spaces with a kitchen family room space built for today's lifestyle. Two garage spaces offer room for six cars and incredible storage. The surprises don't stop indoors-step outside into meticulously maintained grounds showcasing a gorgeous pool, landscaping, split rail fences, and charming stone walls that evoke a sense of storybook elegance. A sprawling, incredible field offers endless opportunities for recreation or relaxation, and the potential to divide the property into two lots opens the door to even more possibilities. Adding to the allure is a stunning barn-style guest house, built in 2008, offering two bedrooms and endless possibilities. Whether it's a private retreat for guests, a party barn, or a multi-generational living space, this addition enhances the property's versatility. This is more than a home - it's a rare opportunity to own a piece of Darien's history, surrounded by natural beauty, modern comforts, and limitless potential. A true treasure, this iconic home is a generational opportunity awaiting you!

7 Beds ⋅ 9 Baths ⋅ 24165104 MLS

Introducing a one-of-a-kind gem in Darien: the historic Eliaseph Whitney House, originally built in 1770, nestled on an expansive 4.12-acre parcel- one of the largest of its kind in town. This iconic property effortlessly blends centuries-old charm with modern-day functionality. Step inside to discover timeless details like wood-beamed ceilings and floors, multiple fireplaces, a cozy den and library, all complemented by bright, open living spaces with a kitchen family room space built for today's lifestyle. Two garage spaces offer room for six cars and incredible storage. The surprises don't stop indoors-step outside into meticulously maintained grounds showcasing a gorgeous pool, landscaping, split rail fences, and charming stone walls that evoke a sense of storybook elegance. A sprawling, incredible field offers endless opportunities for recreation or relaxation, and the potential to divide the property into two lots opens the door to even more possibilities. Adding to the allure is a stunning barn-style guest house, built in 2008, offering two bedrooms and endless possibilities. Whether it's a private retreat for guests, a party barn, or a multi-generational living space, this addition enhances the property's versatility. This is more than a home - it's a rare opportunity to own a piece of Darien's history, surrounded by natural beauty, modern comforts, and limitless potential. A true treasure, this iconic home is a generational opportunity awaiting you!

246 Brookside Rd, Darien

Listing courtesy of Keiley Fuller from Compass Connecticut, LLC. (203) 858-4609 (203) 423-3100

$7,900,000

140 Acres of Rare Opportunity in Kensington, NH. Discover an extraordinary property offering a truly rare opportunity in one of southern New Hampshire’s most desirable locations. Just 4 miles from I-95, this remarkable parcel combines privacy, convenience, and scale - only 50 minutes to Boston, 20 minutes to the beaches, and a short drive to Exeter and Portsmouth. The land features rolling pastures, wooded areas, three serene ponds, four professionally maintained orchards with apple, peach, and plum trees, a picturesque bridge, and up to 80 acres of open fields. Over a mile of paved road winds through the property, providing excellent access throughout. All underground utilities are in place, adding valuable infrastructure for future use and development. A 5,000+ sq. ft. post-and-beam barn, guest or caretaker cottage, and chicken coop are already on site, creating a versatile framework for agricultural, equestrian, recreational, or future vision-based use. The existing main house offers potential for renovation, replacement, or a custom rebuild, allowing the next owner to shape the property to suit their needs. This is a rare chance to own a substantial and highly versatile piece of Kensington with exceptional location, scale, and long-term potential.

3 Beds ⋅ 3 Baths ⋅ 5081944 MLS

140 Acres of Rare Opportunity in Kensington, NH. Discover an extraordinary property offering a truly rare opportunity in one of southern New Hampshire’s most desirable locations. Just 4 miles from I-95, this remarkable parcel combines privacy, convenience, and scale - only 50 minutes to Boston, 20 minutes to the beaches, and a short drive to Exeter and Portsmouth. The land features rolling pastures, wooded areas, three serene ponds, four professionally maintained orchards with apple, peach, and plum trees, a picturesque bridge, and up to 80 acres of open fields. Over a mile of paved road winds through the property, providing excellent access throughout. All underground utilities are in place, adding valuable infrastructure for future use and development. A 5,000+ sq. ft. post-and-beam barn, guest or caretaker cottage, and chicken coop are already on site, creating a versatile framework for agricultural, equestrian, recreational, or future vision-based use. The existing main house offers potential for renovation, replacement, or a custom rebuild, allowing the next owner to shape the property to suit their needs. This is a rare chance to own a substantial and highly versatile piece of Kensington with exceptional location, scale, and long-term potential.

14 Bartlett Rd, Kensington

Listing courtesy of Kevin Kneeland from Compass New England, LLC. ()

$7,900,000

Introducing Butternut Brook House; a Majestic, Luxurious Country Estate commanding stunning 360-degree views of the Litchfield Hills. Representing a masterful fusion of absolute privacy, consummate sophistication and breathtaking natural beauty, this legacy property spans over 36 pristine acres of rolling countryside. The palatial main residence encompasses an impressive 13,056 square feet, including a recently appointed lower level. Accommodations are lavish, with seven principal bedrooms, each distinguished by its own fireplace and six & a half sumptuous baths. Inside, discover character-filled living spaces designed for grand entertaining and intimate repose. A spacious open plan kitchen / dining / family room flows into the formal Dining Room with custom millwork adjoining the elegant Living Room and screened porch. Luxury amenities abound, including an elevator to all 4 levels, a serene spa, dedicated billiards room and a timeless wood-paneled library/study. The second floor hosts dual primary suites and four supplementary bedrooms, while the third floor is home to a dedicated bunk room and a state-of-the-art home theater. The finished lower level is an entertainer's dream, offering a spacious recreation room, climate-controlled wine cellar, wet bar, two additional fireplaces, gym area and a half bath. The estate's auxiliary structures elevate the property to a luxurious, multifaceted estate and gathering complex.

7 Beds ⋅ 8 Baths ⋅ 24155364 MLS

Introducing Butternut Brook House; a Majestic, Luxurious Country Estate commanding stunning 360-degree views of the Litchfield Hills. Representing a masterful fusion of absolute privacy, consummate sophistication and breathtaking natural beauty, this legacy property spans over 36 pristine acres of rolling countryside. The palatial main residence encompasses an impressive 13,056 square feet, including a recently appointed lower level. Accommodations are lavish, with seven principal bedrooms, each distinguished by its own fireplace and six & a half sumptuous baths. Inside, discover character-filled living spaces designed for grand entertaining and intimate repose. A spacious open plan kitchen / dining / family room flows into the formal Dining Room with custom millwork adjoining the elegant Living Room and screened porch. Luxury amenities abound, including an elevator to all 4 levels, a serene spa, dedicated billiards room and a timeless wood-paneled library/study. The second floor hosts dual primary suites and four supplementary bedrooms, while the third floor is home to a dedicated bunk room and a state-of-the-art home theater. The finished lower level is an entertainer's dream, offering a spacious recreation room, climate-controlled wine cellar, wet bar, two additional fireplaces, gym area and a half bath. The estate's auxiliary structures elevate the property to a luxurious, multifaceted estate and gathering complex.

19 Seherr Thoss Dr, Litchfield

Listing courtesy of Alan O'Doherty from William Pitt Sotheby's Int'l. (917) 993-3483 (860) 927-1141

$7,850,000

This classic New England home in Katama offers a refined blend of timeless architecture and modern comfort, set on a spacious, beautifully landscaped lot. The main house features three well-appointed bedrooms, including a light-filled primary suite and inviting guest rooms designed for comfort and privacy. The open-concept living area is ideal for entertaining, highlighted by a cozy fireplace and large windows overlooking the manicured grounds. French doors lead to a deck perfect for outdoor dining and relaxation. A state-of-the-art media room with plush seating and a large screen provides the ultimate space for movie nights or game days, with a wine cellar just steps away. The carriage house includes a three-car garage with a spacious one-bedroom apartment above. Located beside Sheriff’s Meadow Conservation land with public access to Katama Bay, and just minutes to South Beach and downtown Edgartown.

4 Beds ⋅ 6 Baths ⋅ 73504170 MLS

This classic New England home in Katama offers a refined blend of timeless architecture and modern comfort, set on a spacious, beautifully landscaped lot. The main house features three well-appointed bedrooms, including a light-filled primary suite and inviting guest rooms designed for comfort and privacy. The open-concept living area is ideal for entertaining, highlighted by a cozy fireplace and large windows overlooking the manicured grounds. French doors lead to a deck perfect for outdoor dining and relaxation. A state-of-the-art media room with plush seating and a large screen provides the ultimate space for movie nights or game days, with a wine cellar just steps away. The carriage house includes a three-car garage with a spacious one-bedroom apartment above. Located beside Sheriff’s Meadow Conservation land with public access to Katama Bay, and just minutes to South Beach and downtown Edgartown.

24 Katama Bay View Road, Edgartown

Listing courtesy of Listing Agent: Thomas Wallace from Listing Office: Wallace & Co. Sotheby's International Realty.