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$4,045,500
4 Beds 4 Baths 22601594 MLS
Tucked within the gated enclave of Oyster Harbors, 93 Oyster Way blends timeless coastal elegance with modern luxury. Designed for both everyday living and entertaining, the home offers sun-filled interiors with vaulted ceilings and rich hardwood floors. Formal living and dining rooms provide inviting gathering spaces with serene backyard views. At the heart of the home, the chef's kitchen features custom wood cabinetry, granite countertops, a large center island, and premium Wolf and Sub-Zero appliances. An adjacent breakfast nook enhances the kitchen's functionality, with direct access to the family room and screened porch for seamless indoor-outdoor living. The primary suite offers a private retreat with dual walk-in closets, patio access, and a spa-like bath with soaking tub and walk-in shower. Additional bedrooms, en-suite baths, and a home office add flexibility. A finished lower level includes a gym, office, wine cellar, and ample storage. Outdoors, a brick patio and stone wall frame a yard with room for a pool. Complete with deeded beach and dock rights, generator, irrigation, and expansion potential, this is Oyster Harbors living at its finest.

93 Oyster Way, Osterville

Listing courtesy of Listing Agent: Kelly Crosby (kcrosby@landvest.com) from Listing Office: LandVest, Inc..

$4,045,500
4 Beds 4 Baths 73504181 MLS
Tucked within the gated enclave of Oyster Harbors, 93 Oyster Way blends coastal elegance with modern luxury. Sunlit interiors feature vaulted ceilings, hardwood floors, and inviting living and dining spaces overlooking a private backyard. The chef’s kitchen offers custom cabinetry, granite countertops, a large island, and premium Wolf and Sub-Zero appliances, opening to a family room and screened porch for seamless indoor-outdoor living.The primary suite is a serene retreat with dual walk-in closets, patio access, and a spa-like bath with soaking tub and walk-in shower. Additional bedrooms, en-suite baths, and a home office provide comfort and flexibility.A finished lower level includes a gym, office, and storage. Outdoors, a brick patio and stone wall frame a yard with room for a pool. Expansion potential is already in place for a second floor with 10-foot ceilings, offering a rare opportunity to grow within Oyster Harbors.

93 Oyster Way, Barnstable

Listing courtesy of Listing Agent: Kelly Powers Crosby from Listing Office: LandVest, Inc..

$4,000,000
4 Beds 3 Baths 24205297 MLS
A rare Shorehame Association lot with unobstructed Long Island Sound sight lines offered as an amazing opportunity to build new or reimagine the existing residence in one of Old Greenwich's most sought after waterfront settings. The .28 acre property sits within a private association that includes sandy beach access, a boat launch ramp for paddle boarding, kayaking and boating and a large communal waterfront lawn. The current home features a large living room with direct Sound views, a formal dining room, a kitchen and family room opening to a stone patio facing Long Island Sound, and a primary bedroom suite with private bath. Three additional bedrooms and full bath occupy the upper level, sharing the same water views. Gas heating, central air conditioning and an attached 2-car garage are in place. A beautiful and serene location in a private waterfront association, Long Island Sound views and steps to Tod's Point - all within minutes of the Old Greenwich train station, Old Greenwich shops and dining and schools.

14 Shoreham Club Rd, Greenwich

Listing courtesy of Catherine Aaron from Berkshire Hathaway NE Prop.. (917) 887-3138 (203) 869-0500

$4,000,000
5 Beds 6 Baths 24178727 MLS
Welcome to a property where a collector's garden of Japanese maples, rhododendrons, and azaleas - in every shade from gold to crimson to blush pink - announces something extraordinary before you've even reached the front door. A circular drive leads to this classic New England white Colonial, set on nearly three and a half acres on prestigious Turtle Back Road, where grounds shaped with the care of a private arboretum unfold: flagstone terraces, fieldstone walls, and specimen plantings set against a canopy of mature trees. From its copper roof to its storied gardens, every element of this five-bedroom, six-bath New Canaan property feels distinctive. With nearly 5,200 square feet of living space, the home offers generous accommodations while maintaining real warmth and character. Positioned to embrace its surroundings, sun-filled interiors and tranquil views from nearly every room create a seamless connection between indoors and out. Whether entertaining on a grand scale or savoring the simple pleasures of everyday life, the property offers a rare sense of space, comfort, and retreat. Just minutes from the heart of New Canaan, this exceptional home provides easy access to downtown amenities, award-winning schools, parks, and Metro-North - while feeling worlds away from it all. Seldom does a property offer such a rare combination of privacy, beauty, and one of Fairfield County's most sought-after addresses.

248 Turtle Back Rd, New Canaan

Listing courtesy of John Dunn from Compass Connecticut, LLC. (203) 388-5353 (203) 442-6626

$4,000,000
6 Beds 8 Baths 5106236 MLS
Perched high above the rolling hills of New Boston, where panoramic mountain views stretch for miles and privacy is absolute, lies one of New Hampshire's most extraordinary and coveted estates. A true legacy property, this architectural masterpiece is tucked away on 9 pristine acres, offering an unparalleled blend of luxury, serenity, and resort style living. Spanning more than 15,000 square feet, with an additional 5,000 square feet of newly completed living space finished this year, this remarkable residence was designed without compromise. Every space has been thoughtfully curated to deliver an exceptional living experience, whether hosting elegant gatherings or enjoying peaceful moments surrounded by nature. The estate features 6 luxurious bedrooms, 8 beautifully appointed bathrooms, 3 full kitchens, multiple laundry rooms, and an impressive 8 bay garage, effortlessly accommodating multi-generational living, extended guests, or grand-scale entertaining. Resort caliber amenities rival those of a five star retreat. Enjoy both indoor and outdoor heated saltwater pools, a stunning newly constructed pool house, an expansive entertainment lounge, a home gym, a private movie theater, and a spa-inspired sauna with a walk-in shower adjoining the indoor pool creating your own year-round wellness retreat. From sunrise over the mountains to evenings spent under the stars, every inch of this estate was crafted to inspire. Adding to its exceptional versatility is a bonus townhouse-style guest house, complete with additional bedrooms and bathrooms, its own private parking, a separate entrance, and a private yard offering an ideal space for extended family, guests, or additional living accommodations. This is truly a must-see in person to fully appreciate the magnificent craftsmanship, scale, privacy, and what this extraordinary estate has to offer. Broker interest.

104 Foxberry Dr, New Boston

Listing courtesy of Thomas A Svoleantopoulos from AmeraBay. ()

$4,000,000
5 Beds 4 Baths 73542491 MLS
A private estate spanning 11 spectacular acres, this distinguished 1912 residence offers timeless character and exceptional privacy in one of the Boston area's most coveted settings. The five-BR home features 4,500+ square feet of beautifully maintained living space blending classic architectural details with modern comfort. Grand living and dining rooms, a sun-drenched conservatory, and an intimate library create a sophisticated backdrop for entertaining. Center island chef's kitchen and FP'd family room. Period details include custom millwork, French doors, a spacious butler’s pantry and multiple fireplaces. Expansive porches and patios overlook lush gardens and sweeping grounds, leading to a tucked-away pool. An oversized 3-car carriage house with loft adds further versatility. This rare offering includes a separate buildable lot, providing an opportunity for expansion or legacy compound. Minutes to the commuter rail, major routes, and premier shopping. An irreplaceable opportunity.

157 Grove Street, Westwood

Listing courtesy of Listing Agent: Bell Property Partners from Listing Office: Compass.

$4,000,000
4 Beds 4 Baths 24182872 MLS
This exquisite Frank Lloyd Wright Usonian-inspired lakefront home offers a rare opportunity on the serene shores of Lake Waramaug. Known for its pristine waters, natural beauty, and timeless appeal, Lake Waramaug is one of Connecticut's most beautiful and well-preserved natural lakes. Set in the charming village of New Preston, the to-be-built residence is presented by Viridian Custom Homes and Lindal Cedar Homes, with a masterful design by Aris Georges, a leading authority on Frank Lloyd Wright's design principles. Finishes by Kathleen Goodwin Interiors reflect a sophisticated blend of Connecticut and New York City design sensibilities. This 4-bedroom, 3.5-bath, 3,285 SF home features airy rooms, dramatic ceiling heights, organic materials, broad roof overhangs, abundant natural light, and a seamless connection to the land. Set on 1.85 acres with 500 ft of private waterfront and dock rights, the property offers spectacular westerly views. A rare opportunity to create a modern lakefront retreat that blends architectural elegance, natural beauty, and timeless Wright-inspired design.

31a June Rd, Washington

Listing courtesy of Jonathan Cape from William Pitt Sotheby's Int'l. (914) 486-1234 (203) 438-9531

$3,999,999
5 Beds 6 Baths 22604445 MLS
Tucked away in one of South Orleans' most coveted coastal enclaves, 135-137 Portanimicut Road offers a rare opportunity to experience the Cape exactly as it was meant to be—surrounded by natural beauty, close to the water, and with room to gather. Comprised of two distinct residences, this exceptional property offers an effortless sense of togetherness while preserving the privacy that makes a true family compound so desirable. Thoughtfully suited for extended family and guests, the homes provide inviting spaces to come together and comfortable retreats of their own—perfect for summer escapes, weekends with friends, and generations of family traditions. Direct access to Pleasant Bay makes boating, kayaking, and paddleboarding part of everyday life, while the peaceful South Orleans setting captures the relaxed rhythm of coastal living. More than simply two homes, this is a rare opportunity to create a lasting Cape Cod legacy—a place for family, friends, and memories for generations to come. The property is held in condominium ownership. Buyers and/or their agents are encouraged to verify all listing information.

135-137 Portanimicut Road, Orleans

Listing courtesy of Listing Agent: Justin M Blair (JBlair@MonomoyRC.com) from Listing Office: Monomoy Properties Group LLC.

$3,999,999
6 Beds 6 Baths 73568425 MLS
Tucked at the end of a desirable cul-de-sac in Chestnut Hill, this classic shingle-style residence offers four beautifully finished levels of living with a timeless traditional design. Hardwood floors, gracious room proportions, and a warm, inviting floor plan create a home equally suited for everyday living and entertaining.Featuring 6 bedrooms and 6 full bathrooms, the residence offers exceptional flexibility for family, guests, home offices, and additional living spaces. The finished walk-out lower level adds another dimension of usable space with direct access outdoors, while the three-car garage provides both convenience and ample storage.Beautifully landscaped grounds enhance the home’s curb appeal and sense of privacy, with the property set on approximately 25,000 square feet of land. Combining substantial living space, classic New England architecture, and a sought-after Chestnut Hill cul-de-sac location, this is a special opportunity to enjoy comfort, scale, and timeless character.

31 Kesseler Way, Newton

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.

$3,999,999
5 Beds 6 Baths 22601395 MLS
This beautiful Coastal New England / Nantucket-style home overlooks scenic West Dennis Beach and is abutted by Uncle Stephen's Pond. Custom built in 2016 by Pecoy Signature Homes, the residence spreads 5-bedrooms and 5.5 baths over 4,834 square feet of thoughtfully designed living space, with natural light and water views throughout. A gracious entry introduces an expansive open-concept layout where scale and sophistication meet effortless livability. The main level features a stunning great room, private office, mudroom, laundry, and multiple dining areas, all centered around a showpiece chef's kitchen. Appointed with an oversized quartz island, custom cabinetry, a vented NXR range, wet bar, and a generous walk-in pantry, the space is ideal. The main-level primary suite offers a serene retreat, complete with a spacious walk-in closet and a spa-like en suite bath. Upstairs, three well-appointed en suite bedrooms provide comfort and privacy for family and guests, complemented by an additional living area. The third-floor loft serves as a sophisticated lounge with wet bar, opening to a private deck. The houses on Uncle Stephens Rd share a private ocean beach (pictured).

10 Uncle Stephens Road, West Dennis

Listing courtesy of Listing Agent: Christopher F Bowser (cbowser@jackconway.com) from Listing Office: Jack Conway.

$3,999,999
5 Beds 6 Baths 73496678 MLS
This beautiful Coastal New England / Nantucket-style shingle home overlooks scenic W. Dennis Beach and is abutted by Uncle Stephen’s Pond. Custom built in 2016 by Pecoy Signature Homes, the residence spreads 5-bedrooms and 5.5 baths over 4,834 square feet of thoughtfully designed living space, with natural light and water views showcased throughout. A gracious entry introduces an expansive open-concept layout. The main level features a stunning great room, private office, mudroom, laundry, and multiple dining areas, all centered around a showpiece chef’s kitchen. Appointed with an oversized quartz island, custom cabinetry, a vented NXR range, wet bar, and a generous walk-in pantry. The main-level primary suite offers an ensuite. Three ensuite bedrooms are located on the 2nd level the third-floor loft serves as a sophisticated lounge with wet bar, opening to a private deck with panoramic ocean views. The houses on Uncle Stephens share a private ocean beach (pictured).

10 Uncle Stephens Rd, Dennis

Listing courtesy of Listing Agent: Chris Bowser from Listing Office: Conway - Mattapoisett.

$3,999,999
6 Beds 4 Baths 24128777 MLS
Subdivision Potential! One of the Largest Land Parcels in Bethel - Over 61 Acres! A rare opportunity for investors, developers, and visionaries to own more than 61 acres in the highly sought-after Codfish Hill area. This former farmland, once a thriving homestead, offers a unique combination of development potential and the charm of an existing colonial farmhouse with multiple outbuildings. The property includes an oversized 3-bay garage/barn with a full second level, and a nearly 4,500 sq. ft. farmhouse filled with character and possibility. Inside, you'll find a grand great room with a soaring floor-to-ceiling stone fireplace featuring French doors leading to an expansive deck-perfect for entertaining. The home features 5 bedrooms (potentially 6), 3.5 baths, and 3 stone fireplaces, including a first-floor primary suite with separate office/nursery, its own fireplace and spa-like bath, plus a walk-out lower-level in-law suite with private entrance, stone fireplace, and separate laundry hookups. This is truly a diamond in the rough-whether you're looking to restore the farmhouse to its former glory or envisioning a subdivision project on one of the largest parcels left in Bethel. Opportunities like this are few and far between-don't miss it! Buyer use due diligence in possible subdivision and zoning requirements per town of Bethel. Property is part of an estate and sold as-is and subject to probate approval.

62 Codfish Hill Rd, Bethel

Listing courtesy of Rich Lechthaler from Great Estates, CT. (203) 707-8242 (203) 200-7030

$3,999,500
5 Beds 5 Baths 73528794 MLS
Envision a carefree lifestyle in this exquisitely crafted, top-quality home with elevator to every floor. Extensively redesigned and practically rebuilt in 2007, no expense was spared in a complete reimagining of the home. Expansive rooms with custom installations, imported finishes and details, formal and informal tastefully created spaces - this home presents an oasis for modern living. Floor to ceiling window installations allow tremendous light to stream into every corner. Features include hand-tooled kitchen and bathroom cabinetry, top-of-the-line windows and doors, a primary suite with private deck and two large walk-in closets, a media room with radiant heated floor, and a barbecue great room leading out to a fantastic entertaining space, beneath a handsome custom-built pergola. A stunning landscape design impresses with gorgeous flowering perennials and mature trees, as well as a sweeping view of lush green lawn, surrounded by professionally manicured planting beds and bushes.

73 Countryside Road, Newton

Listing courtesy of Listing Agent: Brenda van der Merwe from Listing Office: Hammond Residential Real Estate.

$3,999,500
3 Beds 5 Baths 24174562 MLS
Rarely does a property offer frontage on both Long Island Sound and Pine Creek. Positioned along a naturally elevated stretch of Fairfield Beach framed by protective dunes, the property enjoys a broad sandy beach at both high and low tide. Located within a residential section of Fairfield Beach away from many public beach access points, the setting offers a unique combination of beach, creek, and open water frontage. Across the street, the South Pine Creek frontage offers water views, sunsets, a detached two-car garage, and remnants of a former dock, offering potential boating opportunities subject to due diligence and approvals. Designed by renowned architect Jack Franzen and featured in Westport Magazine, the home reflects timeless neoclassical design. The thoughtful floor plan places the primary suite on the first floor, while the main living level is elevated above to maximize light and views. A sweeping staircase and interior elevator lead to open-concept living spaces overlooking Long Island Sound. An in-ground spa completes this exceptional waterfront offering. Agent/Owner Related Owner/Broker. Agents: Additional information is available in the disclosure section. Ask about the extremely low cost and transferable flood insurance policy.

1681 Fairfield Beach Rd, Fairfield

Listing courtesy of Stephanie Barnes from William Raveis Real Estate. (203) 368-8754 (203) 426-3429

$3,999,000
6 Beds 6 Baths 73576242 MLS
Experience exceptional waterfront living in Quincy's prestigious Merrymount neighborhood. This impeccably maintained brick estate offers approximately 7,100 square feet of luxurious living space with 6 bedrooms and 4 full and 2 half bathrooms, showcasing breathtaking panoramic views of Boston Harbor and the Boston skyline from nearly every room. Designed to maximize its extraordinary setting, the home features expansive sun-filled living spaces, oversized picture windows, and an updated chef's kitchen that seamlessly flows into gracious gathering areas—perfect for both everyday living and entertaining. A private in-law apartment with its own entrance provides exceptional flexibility for multigenerational living, guests, or an au pair suite. Step outside to an unrivaled waterfront oasis. The expansive stone patio is designed for entertaining with a custom wood-fired pizza oven, built-in grilling station, fire pit, and multiple seating areas overlooking the harbor. Enjoy direct water access via your private seawall, offering a rare opportunity to experience the waterfront lifestyle—launch a kayak or paddleboard, or simply relax while taking in spectacular sunsets and ever-changing harbor views. Blending timeless brick construction, meticulous craftsmanship, and one of Merrymount's most coveted waterfront locations, this extraordinary residence offers an unmatched combination of luxury, privacy, and coastal elegance just minutes from Boston

128 Shore Ave, Quincy

Listing courtesy of Listing Agent: Shaughnessy & Cochran Group from Listing Office: Coldwell Banker Realty - Boston.

$3,999,000
5 Beds 8 Baths 5108480 MLS
Old Mill on Haystack Mountain is a mountain residence designed for the next chapter of family life, set on 3.58 acres within the gates of The Hermitage Club with views of the Haystack trails. With over 6,000 square feet of finished living space, the home offers the scale and flexibility to comfortably accommodate children, grandchildren, friends, and extended family while still providing a sense of privacy. The five-bedroom layout includes both a first-floor primary suite and a second-floor primary suite, along with generous gathering spaces and a finished lower level designed for recreation, entertaining, and guests. At the heart of the home is a dramatic two-story great room with soaring ceilings, wood tongue-and-groove detailing, and a wood-burning fireplace. Ten-inch wide-plank white oak flooring carries through the main living areas, complementing the custom chef’s kitchen with high-end cabinetry, a 48-inch Wolf range, and a 48-inch Sub-Zero refrigerator. Substantial windows bring in natural light and frame the mountain setting, while the lower level continues the home’s impressive scale with 10-foot ceilings, a gas fireplace, and additional space to gather and unwind. Radiant heat, a heat-pump system, and air conditioning provide year-round comfort, and upscale finishes throughout reinforce the home’s refined modern mountain aesthetic. For families who already understand the appeal of Haystack and The Hermitage Club lifestyle, Old Mill offers something increasingly difficult to find: substantial new construction without the years typically required to secure land, design, permit, and build from the ground up. The home is scheduled to be ready for Winter 2027, with an early purchaser having the opportunity to personalize selected finishes. Thoughtfully designed for the way families gather in Vermont today, Old Mill on Haystack Mountain offers the space, comfort, and setting to enjoy the mountain for years to come.

5 Old Mill Xing, Wilmington

Listing courtesy of Betsy Wadsworth from Four Seasons Sotheby's Int'l Realty. ()

$3,999,000
6 Beds 7 Baths 73564446 MLS
A rare diamond in a perfect setting. Totally NEW CONSTRUCTION in highly requested Follen Hill neighborhood. While the thoughtful design and impeccable craftsmanship are evident throughout the home and landscaping, the striking clean lines blend timeless character with contemporary comfort. Your first steps are into the grand 2-story foyer. The WOW factor begins! What could be more valuable to a home than the excellent addition of an INTERIOR ELEVATOR gliding from the lower level to the first and second floors. There are 10-ft ceilings throughout the first floor and stunning windows. With an additional spectacular walk-in pantry, the 25 -ft open concept kitchen flows into a take-your-breath-away 25-ft fireplaced family room—a perfect arrangement for great entertaining events. A welcoming porch, stunning deck, and stepdown patio offer outdoor joys. A much-requested elegant first floor guest bedroom suite could also be a study/office. Magnificent is the word for the prime bedroom with oversized dressing room and stunning bathroom accoutrements. There are 3 other ensuite bedrooms on this level as well as a full laundry room. The walk-out lower level hosts the 6th bedroom, full bath, and recreation space. Completing the well-planned layout is an attached 3-car tandem garage. There is still time to choose some finishing selections. Your search for perfection in style, function, and comfort is over.

19 Richard Road, Lexington

Listing courtesy of Listing Agent: Judith Alexander from Listing Office: Barrett Sotheby's International Realty.

$3,999,000
5 Beds 8 Baths 73562442 MLS
At the end of a quiet cul-de-sac sits a residence where grand scale, thoughtful design and inviting spaces come together on more than two acres. Welcome to 373 Caterina Heights. Offering over 8,400 sq. ft., this meticulously maintained home is impressive and grand yet designed to feel warm and welcoming throughout. The oversized foyer sets the tone from the moment you walk in. On one side - a handsome office with custom built-ins and wet bar creating a distinguished workspace; to the other side boasting a sunken living room flowing to the formal dining room. The foyer then leads to the main living areas which are equally impressive. The beautifully appointed kitchen features a large island, Wolf appliances and Sub-Zero refrigeration and connects to a sunroom for all seasons (with heating & cooling) providing an exceptional place to relax while overlooking the private grounds and in-ground pool/hot tub area. And speaking of exceptional...a great room with soaring vaulted ceilings, custom cabinetry and a dramatic stone fireplace for you to enjoy. Walls of windows frame views of the expansive backyard, while an overlook from the second-floor landing adds to the room’s architectural presence. Two staircases enhance the home’s thoughtful flow, while multiple living areas provide room to gather as well as space to retreat. Five bedrooms each enjoy the privacy of an en-suite bath, including two primary suites - one on each floor - giving the new owner many options. The fifth bedroom upstairs offers privacy and includes its own sitting area, creating an ideal retreat for guests, extended family, teens or an au pair suite while the upstairs den with a full closet offers the flexibility of a sixth bedroom. The lower level boasts approximately 1,000 sq. ft. of possibility with marble flooring, a second kitchen area with Sub-Zero refrigeration, full bath and generous storage. Complete with a three-car garage and owned solar panels, this extraordinary property offers a rare combination of space, privacy and timeless appeal—all within an established and desirable neighborhood. A home created not simply to impress but to be enjoyed. Make your appointment today and judge for yourself. This home speaks for itself.

373 Caterina Hts, Concord

Listing courtesy of Listing Agent: Team Sonia Rollins & Associates from Listing Office: EXIT Premier Real Estate.

$3,999,000
3 Beds 3 Baths 5102855 MLS
Spanning the full width of Melody Island, 2 Melody Island is a truly remarkable and one-of-a-kind Lake Winnipesaukee retreat. With approximately 315 feet of waterfront on both sides of the island, the property offers the rare opportunity to enjoy beautiful sunrises from one shoreline and spectacular long-range sunset views from the other. The property’s diverse shoreline features multiple swimming areas, including sandy beaches and a naturally formed submerged stone terrace. This distinctive in-water gathering area provides a wonderful place for swimmers to stand, sit, and relax while surrounded by the lake (an especially memorable feature for family and friends of all ages). The main residence offers three bedrooms and a spacious, open-concept living area centered around a beautiful stone fireplace. Expansive lake views bring the beauty of Winnipesaukee indoors, while comfortable gathering spaces create an inviting setting for entertaining, relaxing, and making lasting memories. A separate bunkhouse provides additional privacy and flexibility for guests, complete with its own bathroom, laundry facilities, and generous sleeping accommodations. Together, the main house and bunkhouse offer ample space to welcome extended family and friends while allowing everyone to enjoy a sense of privacy. Conveniently located just a 5 minute boat ride from Wolfeboro, Melody Island offers close proximity to shopping, dining, coffee shops, and town docks adding to the ease and enjoyment of island living. With its extraordinary shoreline, sunrise-to-sunset views, 2 Melody Island is a rare and unforgettable retreat that captures the very best of Lake Winnipesaukee island living.

2 Melody Is, Wolfeboro

Listing courtesy of Jen McCullough from Maxfield Real Estate/Wolfeboro. ()

$3,999,000
6 Beds 9 Baths 24173869 MLS
This exceptional residence, one of Sharon's most historic properties, occupies much of the original 1812 Georgian mansion, home to a notable family, including William F. Buckley, Jr., for over a century. The layout is spacious & flexible, offering multiple options for purchase: 1) purchase in its current layout as a spacious, 6-bedroom residence, 2) divide the current 6-bedroom residence into two spacious 3-bedroom residences, 3) additionally acquire the north wing to recreate a more complete version of the original mansion for use as an expansive single-family residence, a family compound, or separate residences for rental income. The current 6,716 sq ft home has been thoughtfully restored & offers 6 bedrooms with primary suites on both levels, 7 full baths, and 2 powder rooms. The kitchen opens to a stunning library & informal dining area, complemented by formal living & dining rooms, a family room, office, gym, den, laundry room and 7 fireplaces. At the center of the home, a dramatic three-story 1250 sq foot glass atrium (the 1,250 sq ft is not included in the 6,716 sq ft) - enclosing the 1929 courtyard - creates a year-round living space that brings light & openness into the core of the home. This is estate living with the ease of a managed community. Enjoy beautifully maintained grounds with specimen trees & beautiful plantings. Amenities include: junior Olympic-sized heated pool, pool house, tennis court & separate paddle/pickle courts and more. More info below.

1 Great Elm Dr, Sharon

Listing courtesy of Ann Stettner from Neil Charles Real Estate. (917) 660-3266 (845) 266-8374

$3,999,000
6 Beds 8 Baths 73481956 MLS
Set on a beautifully landscaped one-acre lot, this exceptional new construction home offers the prestige of the estate side of town with a rare sense of privacy and space. Spanning over 7,100 sq ft, the residence features 6 beds, 7.5 baths, and refined craftsmanship throughout. The chef’s kitchen includes top-of-the-line appliances, an oversized island, and a working pantry, opening to a sun-filled family room overlooking the expansive, private yard. The acre setting offers outstanding potential for a pool, sports court, & outdoor living. The main level features a first-floor en suite bedroom & formal dining room. Upstairs, the primary suite offers a spa-like bath & generous walk-in closet. Each bedroom is thoughtfully designed w/ an en suite bath. A finished lower level provides flexible space for a gym or media room. Complete with a 3-car garage, custom millwork, & designer finishes, this home offers a rare blend of elegance & convenience minutes from top rated schools & town center.

8 Crestview Road, Needham

Listing courtesy of Listing Agent: Connor Gillen from Listing Office: Keller Williams Realty.

$3,999,000
5 Beds 9 Baths 73322653 MLS
Discover the epitome of luxury at this exquisite waterfront estate, a haven of tranquility and elegance. Built in 2002 and meticulously renovated, this stunning home offers unmatched comfort and privacy on 4.32 acres. With prime waterfront access and breathtaking views, this expansive 16-room residence features 5 spacious bedrooms and 9 baths including steam shower. The interior boasts two elegant primary suites with gas fireplaces, expansive walk-in closets, and deep hydro-massaging tubs. The masterfully crafted kitchen is equipped with top-line appliances, custom cabinets and granite countertops. The lower level includes hobby and pool table rooms, a kitchenette, an entertainment center and substantial storage. Outdoors, enjoy a stunning heated saltwater pool, oversized hot tub, waterfalls, multilevel stone terrace, outdoor shower, cabana with full bath and a built-in cooking area.This waterfront estate is more than just a home; it's a lifestyle.

26 Walkerwoods Dr, Harwich

Listing courtesy of Listing Agent: Karen Lopez from Listing Office: Great Estates Realty, Inc..

$3,998,000
5 Beds 6 Baths 24142076 MLS
WHERE THE WORLD FALLS AWAY 227 acres. 227 years. At East Hill Road's summit, East Hill Farm is a fully realized estate where infrastructure, land, and possibility are complete and in place. The 1798 Thomas Shepard House-museum-quality restoration featuring 5 bedrooms, 5.5 baths, 5 fireplaces, original King's board floors, hand-blown glass windows-awaits your vision for kitchens and baths. Modern additions: radiant heat, elevator, sun-filled library, luminous sunroom overlooking formal gardens and 4-acre spring-fed pond. The 227 acres aren't just land-they're composition. Meadow unfolding to pond positioned where morning & evening light catch it. Mature forest giving way to unbroken views. Trails looping you gently home by blue hour. Stone walls, pool, tennis court, greenhouse. Magnificent 3,550sf hand-hewn barn moved here. Northern land borders State Forest; southern abuts conservation land-permanent privacy. Guest house (6,668sf): 4 residences replete with possibilities-multigenerational living, art studios, writing spaces, media rooms, yoga, creative sanctuary. Cathedral ceilings, fireplaces, soaring light. The quiet money cannot buy: depth of silence settling at dusk, Milky Way stretching clear across valley, no light pollution. Architecture, land, and sky speaking the same language. Where hosting feels like breathing, completely natural. 5 families in 227 years. You'll be 5th. 5 min to dining, 20 min to Great Barrington, 2.5 hrs to Boston/NYC. Complete and irrepla

764 E Hill Rd, New Marlborough

Listing courtesy of Karen Climo from William Pitt Sotheby's Int'l. (203) 644-1470 (203) 644-1470

$3,998,000
5 Beds 6 Baths 73451336 MLS
East Hill Farm offers 227 acres of protected quiet, anchored by the elegant 1798 Thomas Shepard House. A private hilltop world.Main house: Georgian-Federal; 5 BR, 5.5 BA, ~5,000 SF; 5 fireplaces; unusually high ceilings, wide-board floors, antique glass, rooms that hold the light, views that connect. Graceful, welcoming.A complete estate that also can be a working-farm or equine property: barns + outbuildings, pastures, private trails + roads, 4+ acre pond, gardens + orchard, pool, pool house, greenhouse, tennis.A vast former Arabian horse barn, now guest compound, or for you to reimagine. Preserved with rigor, lived in with joy, and rooted in the land and history that defines the Berkshires. One of the most complete and intact agricultural landscapes remaining in Southern Berkshire County, has no true comparable. Read the history. Experience East Hill Farm. Reach out.

764 East Hill Road, New Marlboro

Listing courtesy of Listing Agent: Chapin Fish from Listing Office: William Pitt Sotheby's International Realty.

$3,997,000
3 Beds 4 Baths 24151511 MLS
Welcome to Greystone, a masterpiece of modern architecture. Bordered by a protected wildlife area, this 4500 sf smart home offers peace and privacy. The main level features an open living room, dining area and kitchen, den, office, half bath, laundry room and primary bedroom suite. Two ensuite bedrooms and a rooftop deck comprise the upper level. The lower level affords access to the backyard and has finished space for a gym or home office as well as a rough-in for a full bath. The kitchen boasts a 10' x 4' island and large walk-in pantry and is well appointed with Wolf and Sub-Zero appliances. An expansive white limestone wrap-around deck and spacious lawn---with an irrigation system---are perfect for relaxing or entertaining. The attached two-car garage is heated. White oak radiant-heated flooring complements the oak Unilux windows and exterior doors. Interior pocket doors and custom cabinetry continue the sleek contemporary look. Kitchen and bathroom countertops are quartzite, some with waterfall edging. Bathrooms feature limestone floors and unique tadelakt plaster walls. Designed with energy efficiency in mind, Greystone uses a geothermal system for heating and cooling. Smart home technology includes programmable LED lighting, motorized shades, security system, and wiring for audio and AI systems. A whole-house generator connects automatically during power outages.

314 Ferry Rd, Old Lyme

Listing courtesy of Karen Amlong Lee from Coldwell Banker Realty. (860) 575-6574 (203) 245-4700

$3,995,000
5 Beds 4 Baths 73575977 MLS
A rare opportunity for new construction in Hingham’s coveted Crow Point, where refined design and coastal living come together just steps from the harbor. Thoughtfully conceived for its setting, this custom five-bedroom residence offers nearly 4,000 square feet of beautifully proportioned living space with harbor and ocean views and deeded private beach rights. The main level unfolds with an elegant balance of open gathering spaces and more intimate rooms, including a dramatic coffered-ceiling living room with fireplace, a beautifully appointed kitchen centered around an oversized island, walk-in pantry, sunlit morning room, formal dining room and private study. French doors and expansive windows draw the outdoors in, while a porch and patio extend the living space beyond the home. Upstairs, the primary suite is a serene retreat with a spa-inspired bath, generous walk-in closets and private balcony. Four additional bedrooms, three full baths, a second-floor lounge and dedicated laundry provide exceptional flexibility for family and guests. Hardwood floors, custom millwork and carefully considered finishes lend a timeless quality throughout. An attached two-car garage and thoughtfully designed mudroom complete the home. Set within one of Hingham’s most desirable coastal neighborhoods, moments from Hingham Yacht Club, the harbor, downtown Hingham and commuter routes to Boston, 119 Downer Avenue presents a rare opportunity to enjoy newly built luxury in an established seaside community.

119 Downer Ave, Hingham

Listing courtesy of Listing Agent: Kevin Lewis from Listing Office: Coldwell Banker Realty - Hingham.

$3,995,000
5 Beds 5 Baths 73574564 MLS
Beautifully Renovated Beacon Hill sun-drenched single-family brownstone is gracefully situated on a quiet, tree-lined street just moments from the Boston Common and the boutiques and dining of Charles Street. Featuring 5 bedrooms and 5 full baths the main level offers an elegant, open-concept living and dining area designed for refined entertaining, complemented by a thoughtfully appointed chef’s kitchen featuring premium stainless-steel appliances and gas cooking. On the second floor, the serene primary suite is anchored by a stately fireplace and enhanced by dual closets and a well-appointed en-suite bath. A spacious front-facing room across the hall provides exceptional flexibility as a family room, office, or additional bedroom. The third floor hosts two generously proportioned bedrooms, including a rear-facing suite with a beautifully updated en-suite bath. Crowning the home, the sunlit fourth floor offers a private retreat ideal for an au pair or guests, complete with a full kitchen, expansive bedroom, full bath, and inviting living area. Skylights flood the space with natural light, while sliding glass doors open to a private balcony showcasing captivating views of the Back Bay skyline. Truly an elegant Home. Open Houses Saturday 9/12 from 12-1:30 & and Sunday 9/13 from 1-2.

54 Brimmer St, Boston

Listing courtesy of Listing Agent: Judy Pagano from Listing Office: Gibson Sotheby's International Realty.

$3,995,000
5 Beds 6 Baths 73573659 MLS
Nestled in one of the area's most coveted neighborhoods with a seamless commute to Boston, this exceptional residence offers the perfect balance of luxury, privacy, and convenience. Thoughtfully gut-renovated with the finest materials and craftsmanship, the home showcases an open-concept floor plan designed for both elegant entertaining and everyday living. Expansive windows flood the interiors with natural light, creating bright, inviting spaces even on the gloomiest days. At the heart of the home is a stunning designer kitchen complemented by a fully equipped catering butler's pantry. A spacious three-car garage and custom mudroom provide exceptional functionality for modern living. Flexible living spaces include two private offices, while generously sized bedrooms each enjoy their own dedicated bathrooms. The finished walkout lower level is bathed in natural light and offers abundant additional and flexible living space. Professionally landscaped grounds provide remarkable privacy .

39 Fairbanks Ave, Wellesley

Listing courtesy of Listing Agent: Donahue Maley and Burns Team from Listing Office: Compass.

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