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$7,750,000
6 Beds ⋅ 7 Baths ⋅ 73574746 MLS
An entire South End brownstone. One remarkable home. A truly distinctive opportunity in a market defined largely by condominium living, this offering presents the chance to own an entire classic bow-front brownstone on one of the South End’s most beautiful & coveted tree-lined streets. Currently configured as two meticulously renovated residences, a penthouse triplex & garden duplex, the property has been transformed to near-new construction standards, bringing together timeless architecture, tailored interiors & exceptional flexibility under one roof. For those seeking the scale, privacy & permanence of a true townhome, the property offers the opportunity to combine both residences into one substantial single-family home, with conversion plans available for review. The existing configuration also provides immediate flexibility for multigenerational living, extended family, guests, an au pair or the ability to occupy one residence while generating income from the other. The approximately 2,518 SF penthouse triplex offers 3+ beds & 3.5 baths across three beautifully considered levels. Soaring ceilings, abundant natural light, custom millwork, gas fireplaces & refined finishes define the interiors, while a designer kitchen with custom cabinetry & high-end appliances anchors the main entertaining level. A private balcony extends from the kitchen, while an expansive private roof deck offers Boston skyline views, a built-in grill, integrated sound & fire pit. The approximately 1,802 SF garden duplex offers 2 beds & 2.5 baths across two generous levels, with beautifully proportioned living & dining spaces, a gas fireplace, custom cabinetry, integrated storage & curated finishes throughout. The living space opens directly to a substantial private patio for seamless indoor-outdoor living. Together, the residences provide approximately 4,320 SF of finished interior space, private outdoor living at both the garden & rooftop levels & 2 direct-access parking spaces. Moments from acclaimed dining, cafés, parks, SoWa, boutiques, galleries & premier private schools, this is a rare opportunity to move beyond the traditional condo & own an entire South End brownstone, ready to live beautifully today or become one extraordinary home for the future.

189 W Brookline St, Boston

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.
$7,750,000
5 Beds ⋅ 6 Baths ⋅ 73467958 MLS
Set on 180 feet of beachfront, this rare and highly coveted Marblehead Neck estate offers an extraordinary blend of privacy, scale, and coastal prestige. Encompassing nearly 2-acres of irreplaceable shoreline, the property presents a once-in-a-generation opportunity to reimagine a legacy retreat in one of North Shore’s most exclusive enclaves. This 5 bedroom, 5.5 bath residence captures sweeping ocean vistas, awe-inspiring sunrises, and gentle sea breezes, providing an unparalleled setting for refined coastal living with private beach ownership. Whether the current home is meticulously restored or the site is transformed into a bespoke modern masterpiece, the land itself represents the ultimate in luxury. Expansive and rich with possibility, this estate is a lifestyle investment offering the rare freedom to design a beachfront vision that will endure for generations. For those seeking a premier waterfront acquisition, this property stands as a hallmark of North Shore excellence.

349 Ocean Avenue, Marblehead

Listing courtesy of Listing Agent: Judith Toner from Listing Office: The Proper Nest Real Estate.
$7,725,000
7 Beds ⋅ 13 Baths ⋅ 24164249 MLS
Exquisite Nantucket-style country estate magnificently sited on seven sprawling acres in Redding, CT's coveted Umpawaug neighborhood. Comprised of three extraordinary residences, this masterfully crafted 2008 HOBI award-winning compound offers 13,904 sf of carefully constructed living space with meticulous architectural details, effortlessly balancing timeless elegance with modern function. The main residence greets with a sweeping two story entry bathed in natural light, flanked by gracious formal living & dining rooms with fireplaces. The heart of the home, a chef's kitchen with custom cabinetry, high-end appliances, butler's pantry & French doors to an expansive terrace, seamlessly integrated with spectacular grounds. Additional main-level highlights include great room & study with fireplaces, steps from a serene covered porch; mudroom, full bath, & attached three-car garage. Upstairs, a primary suite sanctuary with fireplace, sitting room with wet bar, dressing room with custom cabinetry & spa-like bath with soaking tub & steam shower. Completing the 2nd floor, four additional bedrooms featuring en-suite baths & walk-in closets, family room and laundry. On the 3rd level, 2nd office, gym, half bath & ample storage. Elevator to wine cellar, home theater, billiards room & walkout au pair suite; commercial grade utilities & generator. Award-winning pool house, carriage house with in-law suite, heated gunite pool, spa & manicured grounds complete a remarkable legacy property.

206 Umpawaug Rd, Redding

Listing courtesy of Lauren Parr from Houlihan Lawrence. (347) 852-2599 (203) 438-0455
$7,595,000
5 Beds ⋅ 7 Baths ⋅ 22505128 MLS
Waterfront Perfection on Buzzards Bay North Falmouth. At the tip of a private peninsula, this exceptional Cape Cod estate embodies the essence of elegant coastal living. Set on 1.07 acres with sweeping views of Buzzards Bay, the residence combines timeless architecture, refined craftsmanship, and every amenity for a luxurious seaside lifestyle. Built by renowned Osterville builder Polhemus Savery, the home offers five en suite bedrooms, including a first-floor primary suite and three additional bedrooms upstairs, plus a separate guest or nanny suite above the garage—ideal for extended stays. A comfortable second-floor family room provides a casual space for gathering. The light-filled, south-facing living areas are designed to capture the beauty of the Bay. The open-concept kitchen and living room invite effortless entertaining, while the formal dining room offers an intimate setting overlooking the water. French doors lead to a covered porch and patio area that frame the saltwater system pool, spa and pool house, all just steps from your private beach, over 250 feet of water frontage, perfect for launching kayaks, paddle boards, sunfish sailboats and more. Additional features include hardwood floors, central air conditioning, custom built-ins, a private study, and so much more. Outdoors, enjoy both sunrise and sunset vistas, a heated pool, and direct water access for all your coastal pursuits. Residents may also join the nearby Wild Harbor Yacht Club, offering sailing, swimming, and a vibrant seaside community. A rare offering, out of the flood zone, in pristine condition, this estate represents the pinnacle of Cape Cod waterfront livingprivate, polished, and perfectly positioned on Buzzards Bay.

40 Point Road, North Falmouth

Listing courtesy of Listing Agent: Kerrie A Marzot (kerrie.marzot@sothebys.realty) from Listing Office: Sotheby's International Realty.
$7,595,000
5 Beds ⋅ 6 Baths ⋅ 73442362 MLS
At the tip of a private peninsula, this exceptional Cape Cod estate embodies the essence of elegant coastal living. Set on 1.07 acres with sweeping views of Buzzards Bay, the residence combines timeless architecture, refined craftsmanship, and every amenity for a luxurious seaside lifestyle. Built by renowned Osterville builder Polhemus Savery, the home offers five en suite bedrooms, including a first-floor primary suite and three additional bedrooms upstairs, plus a separate guest or nanny suite above the garage—ideal for extended stays. A comfortable second-floor family room provides a casual space for gathering.The light-filled, south-facing living areas are designed to capture the beauty of Buzzards Bay. With roughly 250 feet of water frontage it is ideal for swimming, launching paddle boards and kayaks. Not to be missed!

40 Point Rd, Falmouth

Listing courtesy of Listing Agent: Kerrie Marzot from Listing Office: Sotheby's International Realty.
$7,550,000
6 Beds ⋅ 9 Baths ⋅ 73511372 MLS
Designed for elevated everyday living and effortless entertaining, this exceptional residence at 132 Country Drive in Weston offers the perfect blend of luxury, comfort, and convenience. Set in one of Weston’s most desirable neighborhoods—known for its top-ranked schools and peaceful surroundings—the home is just minutes from Boston and major commuter routes. Inside, an oversized chef’s kitchen with a large center island and walk-in pantry anchors the open-concept layout. Expansive living and dining spaces are filled with natural light, creating an inviting atmosphere throughout. Upstairs, four spacious bedrooms each feature en-suite baths and custom closets, including a luxurious primary suite with a private deck, spa-like bath, and walk-in closet. The lower level is designed for entertaining and wellness, complete with a second living area, home theater, golf simulator, gym, sauna, and more. Outdoors, the walk-out backyard offers a fire pit, dining space, and room for a future pool.

132 Country Drive, Weston

Listing courtesy of Listing Agent: Simon Collaborative Group from Listing Office: Gibson Sotheby's International Realty.
$7,500,000
25 Beds ⋅ 13 Baths ⋅ 22604481 MLS
A strategic coastal acquisition opportunity for developers, hospitality groups and commercial investors in Dennis Port's established resort district. Situated across the street from the beach, this nearly one-acre property combines significant site area, approximately 50 existing parking spaces, a substantial commercial building previously operated as a 180-seat restaurant with a transferable liquor license and multiple residential structures. Located within the Chase Avenue Hotel Resort Area, the property benefits from a zoning framework designed to accommodate significant hospitality investment. Qualifying hotel development may reach up to 4½ stories or 50 feet. Chase Avenue is an active hospitality corridor surrounded by oceanfront resorts, vacation properties, beaches and established dining destinations. This concentration provides a built-in visitor base and places the property within one of Cape Cod's most recognizable resort settings. Whether envisioned as a boutique resort, hotel-condominium development, signature hospitality concept, restaurant revival, or adaptive-reuse project, this site offers substantial potential in a proven coastal destination.

88-94 Chase Avenue, Dennis Port

Listing courtesy of Listing Agent: Paul McCormick (paul.mccormick@gibsonsir.com) from Listing Office: Gibson Sotheby's International Realty.
$7,500,000
3 Beds ⋅ 6 Baths ⋅ 22602282 MLS
Nestled along the sparkling shores of North Bay in the heart of Osterville, this exceptional Waterfront Estate delivers timeless beauty and relaxed elegance. Wake each morning to sweeping water views and ocean breezes, step onto your boat from the Substantial Dock, (complete with 30 Amp power outlets and fresh water). Featuring a Primary Suite and Guest Suite both on the 1st Floor, the residence is thoughtfully designed to blend coastal charm with modern comfort, with sun-filled living spaces, expansive windows, and seamless indoor-outdoor flow perfect for entertaining or quiet seaside relaxation. Waterfront Chef's Kitchen with Cathedral Ceiling, Living Rooms, Dens, separate living quarters complete with a Kitchen over the 3-Bay Garage. Step outside to your private waterfront oasis, where launching a kayak at sunrise, enjoying afternoon boating on North Bay, or taking sunset walks with the dog, every day feels like a vacation. Located just moments from Osterville Village's boutiques, restaurants, and marinas, this rare offering combines serenity, sophistication, and the quintessential Cape Cod lifestyle in one unforgettable waterfront setting.

46 Great Bay Road, Osterville

Listing courtesy of Listing Agent: Chuck Tuttle (chuck@chucktuttlehomes.com) from Listing Office: William Raveis Real Estate & Home Services.
$7,500,000
4 Beds ⋅ 5 Baths ⋅ 24165467 MLS
This is not simply waterfront living. This is a waterfront lifestyle unlike any other. Tucked within the coveted enclave of Sachem's Head, this extraordinary estate commands direct Long Island Sound frontage with unobstructed harbor views and breathtaking sunsets. Masterfully crafted in 2003 and transformed by the current owners with uncompromising quality, the 6,000 SF+ residence is defined by Dramatic walls of glass framing endless water views from virtually every room offering seamless indoor-outdoor living. You will be immediately wowed by the jaw dropping great room with an incredible fireplace & soaring ceiling. At the heart of the home lies a stunning Poliform kitchen, the pinnacle of modern luxury, thoughtfully appointed with premium appliances and designed to delight the most discerning chef. Oversized dining area that effortlessly steps right onto the expansive Ipe deck for additional outdoor waterfront entertaining. The all glass-enclosed family room overlooks the sound as well as the heated saltwater pool. Upstairs, a dramatic suspended gallery leads to an octagonal office and private outdoor captain's walk with endless vistas. The primary suite is a sanctuary with panoramic water views, balcony, fireplace, custom closets, and a spa-inspired bath with oversized shower and infrared sauna. A separate wing offers three en-suite bedrooms with stunning new baths and custom bunks for additional guests. Exceptional boating amenities include a permanent pier of concrete

620 Colonial Rd, Guilford

Listing courtesy of Susan Santoro from William Pitt Sotheby's Int'l. (203) 605-5297 (203) 453-2533
$7,500,000
3 Beds ⋅ 6 Baths ⋅ 73520995 MLS
Nestled along the sparkling shores of North Bay in the heart of Osterville, this exceptional Waterfront Estate delivers timeless beauty and relaxed elegance. Wake each morning to sweeping water views and ocean breezes, step onto your boat from the Substantial Dock. Featuring a Primary Suite and Guest Suite both on the 1st Floor, the residence is thoughtfully designed to blend coastal charm with modern comfort, with sun-filled living spaces, expansive windows, and seamless indoor-outdoor flow perfect for entertaining or quiet seaside relaxation. Waterfront Chef's Kitchen with Cathedral Ceiling, Living Rooms, Dens, separate living quarters complete with a Kitchen over the 3-Bay Garage. Step outside to your private waterfront oasis, where launching a kayak at sunrise, enjoying afternoon boating on North Bay, or taking sunset walks with the dog, every day feels like a vacation. Located just moments from Osterville Village's boutiques, restaurants, and marinas.

46 Great Bay Rd, Barnstable

Listing courtesy of Listing Agent: Chuck Tuttle from Listing Office: William Raveis R.E. & Home Services.
$7,500,000
5 Beds ⋅ 8 Baths ⋅ 73498221 MLS
Welcome to 75 Hancock Street Beacon Hill, a beautifully renovated townhouse with elevator that epitomizes luxury living in one of Boston's most prestigious neighborhoods. This 24' wide six-level residence features 5 spacious bedrooms, 5 full bathrooms, and 3 half bathrooms, including a private au pair suite. The state-of-the-art kitchen, complete with a butler’s pantry, opens to a cozy family room and a stunning private garden adorned with stone pavers and a gas fireplace—perfect for outdoor gatherings. The elegant parlor level is ideal for entertaining, boasting a full wet bar and access to an inviting outdoor deck and patio. Additional highlights include opulent marble baths, restored fireplaces, a dedicated laundry room, and a top-level entertaining space with soaring ceilings and another wet bar. The basement is finished and designed for ample dry storage and gym with high ceilings. Meticulously designed with the finest craftsmanship, this exceptional home is a true Beacon Hill gem

75 Hancock St, Boston

Listing courtesy of Listing Agent: Rodney Scott from Listing Office: Engel & Volkers Boston.
$7,500,000
6 Beds ⋅ 8 Baths ⋅ 73487838 MLS
A rare find in Brookline, this property offers privacy and tranquility on a secluded lot adjacent to Sargent Estates. Spanning three finished levels plus a lower level, the home features 6 bedrooms and 6 full and 2 half baths, with meticulous craftsmanship and striking architectural details throughout. A grand rotunda entry leads to a chef’s kitchen, expansive living and dining rooms, family room, and mudroom. The second floor includes three bedroom suites, each with its own bath, plus two office spaces. The third floor offers two additional bedroom suites, while the lower level includes a sixth suite, gym, large family room, and laundry. Surrounded by mature landscaping and set well back from the street, the property boasts a pool, hot tub, sauna, outdoor fireplace, pizza oven, and full outdoor kitchen—an exceptional setting for both relaxation and entertaining. Not to be missed!

1 Chestnut Place, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
$7,500,000
5 Beds ⋅ 7 Baths ⋅ 73486301 MLS
Nestled within Seven Gates Farm, one of Martha’s Vineyard’s most storied and scenic communities, this 26.5-acre estate features a beautifully renovated farmhouse blending modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property also includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench overlooking Vineyard Sound and the Elizabeth Islands. Located just steps from Gray’s Beach and dock, this is among the most picturesque settings in Seven Gates Farm. The community includes 45 homesites across 1,600 acres, with 1,000 acres of protected conservation land, open fields, woodlands, ponds, and miles of trails. Residents enjoy exclusive access to 1.5 miles of private beach, two piers, and tennis courts. An extraordinary opportunity to be part of a community dedicated to preserving the island’s natural beauty.

85 North Reservoir Road, West Tisbury

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
$7,499,999
4 Beds ⋅ 5 Baths ⋅ 73566967 MLS
Experience the vibrant energy of maritime life paired with the serenity of coastal living. Set within the coveted enclave of Saquatucket Bluffs with private association beach rights, this sophisticated residence has been meticulously renovated to strike a flawless balance between architectural elegance and coastal warmth. A classic front porch provides a graceful welcome, leading into a vaulted living room bathed in natural light. The layout emphasizes effortless indoor-outdoor living, with water views from nearly every room and direct access to the exterior. The main level features a dedicated office and a versatile ensuite, while the second floor serves as a sanctuary featuring dual balconies and two additional guest ensuites. The heart of the home is the chef's kitchen, outfitted with a center island, spacious pantry, and a breakfast nook designed to frame panoramic views of boats navigating the harbor. Entertaining is elevated by a dedicated bar with a wine fridge and a seamless flow to the large deck. Outside, professionally landscaped grounds host a harbor-view pool. Moments from downtown Harwich Port, this home offers a refined lifestyle and a premier waterfront connection.

18 Saquatucket Point, Harwich

Listing courtesy of Listing Agent: Sandra Tanco from Listing Office: Kinlin Grover Compass.
$7,499,999
4 Beds ⋅ 6 Baths ⋅ 22603923 MLS
Experience the vibrant energy of maritime life paired with the serenity of coastal living. Set within the coveted enclave of Saquatucket Bluffs with private association beach rights, this sophisticated residence has been meticulously renovated to strike a flawless balance between architectural elegance and coastal warmth. A classic front porch provides a graceful welcome, leading into a vaulted living room bathed in natural light. The layout emphasizes effortless indoor-outdoor living, with water views from nearly every room and direct access to the exterior. The main level features a dedicated office and a versatile ensuite, while the second floor serves as a sanctuary featuring dual balconies and two additional guest ensuites. The heart of the home is the chef's kitchen, outfitted with a center island, spacious pantry, and a breakfast nook designed to frame panoramic views of boats navigating the harbor. Entertaining is elevated by a dedicated bar with a wine fridge and a seamless flow to the large deck. Outside, professionally landscaped grounds host a harbor-view pool. Moments from downtown Harwich Port, this home offers a refined lifestyle and a premier waterfront connection.

18 Saquatucket Point, Harwich Port

Listing courtesy of Listing Agent: Sandra Tanco (sandra.tanco@compass.com) from Listing Office: Kinlin Grover Compass.
$7,499,000
6 Beds ⋅ 10 Baths ⋅ 24184383 MLS
NEW CONSTRUCTION - Set on a quiet cul-de-sac just minutes from the heart of New Canaan, this custom-built estate by renowned builder V&A Construction reflects the superior craftsmanship, attention to detail and refined finishes for which the company is known. Currently in the final stages of construction, the home is designed for both everyday living and effortless entertaining. A gracious floor plan features ceilings exceeding 10 feet, two staircases, an elevator serving multiple floors, six spacious ensuite bedrooms, 10 bathrooms, two laundry rooms, imported European windows and doors, wide-plank white oak floors throughout and a Brava premium composite slate roof. At the center of the home is a spectacular chef's kitchen appointed with Sub-Zero and Wolf appliances, dual dishwashers, custom cabinetry and a large island. The space opens seamlessly to the family room, formal living and dining rooms, a grand private office and outdoor living areas. The private backyard is designed for resort-style living with a 20' x 50' heated Gunite pool featuring a sun shelf and integrated spa, a well-equipped outdoor kitchen, covered porch, expansive patios and professionally designed landscaping framed by mature plantings.

46 Norholt Dr, New Canaan

Listing courtesy of Katherine Kuras from BHHS Darien/New Canaan. (203) 524-3352 (203) 655-5114
$7,499,000
8 Beds ⋅ 12 Baths ⋅ 73474238 MLS
Located in the highly sought-after Stevens Farm neighborhood of Westwood, this gated estate is set on 3.48 acres of beautifully landscaped grounds and was designed by noted architect Patrick Ahearn. The foyer, with its dramatic three-story atrium, leads to French doors opening on a 70’ terrace overlooking a spectacular pool and cabana. Formal living and dining rooms flow seamlessly off the atrium. The striking new chef’s kitchen adjoins the family room, casual dining room, and a separate terrace. A mahogany-paneled study with lounge and wet bar is ideal for private conferences. The residence offers 8+ en-suite bedrooms, including a grand primary suite with dual baths and a 20’x25’ walk-in closet. Two guest suites provide flexibility, each with a private entrance. The lower level includes a gym, sauna, steam, changing rooms, playroom, theater, wine cellar, and billiard room. Close to Rte 128/95 and top-rated schools.

18 Longmeadow Drive, Westwood

Listing courtesy of Listing Agent: John Boyle from Listing Office: LandVest, Inc..
$7,498,000
4 Beds ⋅ 4 Baths ⋅ 5085295 MLS
"Days End" is a magnificent waterfront estate situated on 2.08 acres in Straws Point. Known for its grand history and record-breaking sales of $18.5M and $25M, Straws Point is an exclusive coastal enclave representing the pinnacle of luxury in a tax-free haven. This coastal New England property is defined by its access to a private beach with panoramic, unobstructed ocean views of the Atlantic and the vibrant, ever-changing tidal marsh, emphasizing the desirable land and magical setting. Perfect for entertaining with family and friends, the floorplan is anchored by a magnificent great room providing 3 grand French doors leading to the terrace and a formal dining room perfect for large-scale hosting. The interior highlights include an impressive curved staircase, 5 fireplaces, a stately paneled library, a chef’s kitchen offering top appliances and an octagon English conservatory surrounded by glass with views of the tidal marsh and Rock Beach. The spectacular outdoor space is bordered by stone walls and includes an expansive stone patio, a screen porch, a wrap-around covered porch, professionally designed gardens, sweeping lawns, and a Bocci court, with the significant acreage offering incredible potential for expansion (ADU, multi-generational compound). Accessed via a private road, 6 Wildwood Lane ensures a level of seclusion, distinction, and prestige to be cherished for generations. Enjoy a short walk (about 1/10th of a mile) to Jenness Beach. Under the main photo, please click on the virtual tour links for the virtual tours.

6 Wildwood Ln, Rye

Listing courtesy of Lauren Stone from Carey Giampa, LLC/Rye. (Cell: 603-944-1368)
$7,495,000
5 Beds ⋅ 8 Baths ⋅ 24194488 MLS
Exceptional, new 2027 construction showcases an architecturally stunning in-town Colonial on .72 acres with pool, private yard and resort-style amenities close to world-class shops, restaurants and Schools. Expertly built by acclaimed Sonny Anand/AR Luxury Homes, this sunlit residence reflects their signature blend of sophisticated design, superior craftsmanship and outstanding architectural detail. Seamless indoor-outdoor living unfolds across a covered terrace with fireplace, Phantom screens, heaters; outdoor kitchen and lower level wellness center with gym, cold plunge and sauna. Standout features include elevator, three fireplaces, office, chef's dream kitchen, butler's pantry, stylish formal rooms, family room, primary suite with deck and four en-suite bedrooms. Still time to customize.

64 Hillside Rd, Greenwich

Listing courtesy of Amanda Bates from Houlihan Lawrence. (203) 536-1195 (203) 869-0700
$7,450,000
5 Beds ⋅ 6 Baths ⋅ 73575249 MLS
Renovated Venetian Gothic beauty located on a much sought after South End Square – Rutland Square designed in the 19-Century around an English-style central garden park. This beautiful low stoop single family developed with a 4-story glass extension is comprised of 5 bedrooms (4 on the top two levels – a rare find), 4 bathrooms and 2 powder rooms, open concept kitchen flows naturally to the living/dining room, expansive family room, sitting room and separate library & office. Distinguishing features include 3 gas fireplaces, custom cabinetry & millwork, wired for home audio/surround sound, custom closets (tremendous amount of storage), designer/custom window treatments & rugs, 2 wet bars, high ceilings, 2 laundry locations, deck off the kitchen, roof deck, patio and direct access parking for 2 cars.

21 Rutland Sq, Boston

Listing courtesy of Listing Agent: Sprogis Neale Doherty Team from Listing Office: Sprogis & Neale Real Estate.
$7,400,000
6 Beds ⋅ 8 Baths ⋅ 24205691 MLS
Set on a plateau with panoramic, protected views, West Wind Hill is a masterfully crafted estate spanning 391 acres that straddles the Connecticut and New York border. Reached by a private, gated drive that winds past old stonewalls, open meadow, and a serene pond, the property offers a level of privacy rarely found within two hours of New York City. The stone-and-shingle residence was built with singular attention to craft: the architect camped on site before construction began to orient the home for the finest light and views in every season, and the estate's stonework, including a 20-foot great room fireplace, was quarried directly from the hilltop on which the house sits. Reclaimed chestnut floors, hand-detailed millwork, and banks of French doors and windows run throughout the roughly 8,919-square-foot residence, which includes six bedrooms, a paneled library, a chef's kitchen with its own massive stone hearth, a billiard room, a media room, and a wine cellar with tasting room. The primary suite occupies a private wing of the main level. A stone-and-gunite pool and pool house with full kitchen, plus two stone barns, complete the grounds, which also include hiking trails, open meadows, and a pond.

33 Nodine Pasture Rd, Kent

Listing courtesy of Stephen Pener from William Pitt Sotheby's Int'l. (203) 470-0393 (860) 927-1141
$7,400,000
6 Beds ⋅ 7 Baths ⋅ 24141938 MLS
This magical light-filled New England 7,945 s.f. "cottage" takes full advantage of its private waterfront location overlooking LIS and a wildlife estuary. Sited in a private community on 1.27 acres with 300' of water frontage provides panoramic water views of sunrises and sunsets from most rooms. A heated swimming pool, two beaches and mooring rights guarantee outdoor pleasures. There is also room for a tennis court. The house was expanded from its original 1912 footprint and fully renovated over 3 years (1987-1990) with the best curated materials including Tischler high impact windows throughout. French doors in the 18' ceilinged living room, dining room and family room all open to a flagstone terrace. The 6+ bedrooms, all but one with ensuite bathrooms, can be accessed by elevator or front and back stairs. There is also a separate handicapped accessible apartment. The impressive, newly renovated kitchen with table sitting up to eight is equipped with top of the line appliances. Privacy, gracious living space and endless recreation possibilities make this special property an ideal retreat. Check floor plans for more details.

84 Johnsons Point Rd, Branford

Listing courtesy of Margaret Muir from William Pitt Sotheby's Int'l. (203) 415-9187 (203) 245-6700
$7,400,000
7 Beds ⋅ 7 Baths ⋅ 24144503 MLS
Another Day in Paradise! Timeless grandeur, architectural mastery, and opportunity define this exceptional plantation-style colonial set on 39.23 acres bordered by 100+ acres of protected forestland-a rare opportunity for stately country living in a singular setting.For the sportsman, pristine woodlands and abundant wildlife offer boundless opportunities for hunting, hiking, and connecting with nature. The residence-a nod to Antebellum architecture-presents grand columns, symmetrical facades, a 97-foot wraparound veranda, and ornate interior design. Every detail has been thoughtfully curated for comfort and quality.Your journey begins with the breathtaking grand foyer flanked by dual staircases and crowned by a soaring domed ceiling artfully decorated with colorful rosettes. Exemplary features include seven fireplaces, an elegant banquet-worthy formal dining room, a chef's kitchen with top-grade appliances, a spacious fireplaced breakfast room, a dazzling sun-filled family room, and two home offices.The exquisite primary suite is a luxurious haven featuring its own artfully adorned domed ceiling, sitting room, and wall-of-glass French doors open to a private balcony with views of the in-ground pool and woodlands. The sumptuous marble bath is a spa-like sanctuary. An invaluable addition to this amazing property is the finished studio over the six-car drive-through garage providing flexible living space. All this and so much more awaits in this extraordinary estate!

63 Turney Rd, Redding

Listing courtesy of Roni Agress from William Pitt Sotheby's Int'l. (203) 733-2656 (203) 438-9531
$7,350,000
6 Beds ⋅ 7 Baths ⋅ 24152219 MLS
Set behind gates on over four exquisitely landscaped acres in Westport's coveted Beachside enclave, 69 Beachside Avenue is a private coastal estate offering a rare blend of scale, privacy, and resort-style living just moments from the shoreline. A long, gracious approach leads to a timeless residence defined by exceptional craftsmanship and sun-filled interiors. Expansive living spaces feature soaring ceilings, seamless flow, and walls of glass that frame the estate's serene, park-like setting-ideal for both grand entertaining and everyday living. At the center of the home, a chef's kitchen opens to elegant formal and informal spaces, creating an effortless environment for hosting. Each room is thoughtfully appointed with high-end finishes, bespoke details, and a refined sense of understated luxury, now fully realized with a newly completed primary bath designed as a private, spa-like retreat. Outdoors, the property transforms into a true resort experience, with a stunning pool and spa, spacious terraces, and a full Har-Tru tennis court set amid rolling lawns and mature plantings, offering exceptional privacy and tranquility. Perfectly positioned near Westport's beaches, Longshore Club, and vibrant downtown, this property also offers the rare advantage of direct access to Greens Farms Academy, a feature shared by only a select few homes. This property is where luxury, land, and lifestyle come together in one of Westport's most prestigious addresses.

69 Beachside Ave, Westport

Listing courtesy of John Raus from Berkshire Hathaway NE Prop.. (203) 253-0635 (203) 227-5117
$7,252,000
4 Beds ⋅ 8 Baths ⋅ 24175287 MLS
Commandingly sited above the Aspetuck River, this exceptional 9,600+ sq ft cut stone manor offers sweeping views of a 40 acre horse farm and an estate setting rarely available. A long, stately driveway sets a grand first impression, opening to a large courtyard framed by manicured boxwoods. As you enter the home, a grand hall and great room with a dramatic view of the outdoor waterfall establishes the scale and craftsmanship found throughout. The custom kitchen blends beauty and function with a SubZero armoire style refrigerator and freezer, double Viking gas range, and dual Fisher & Paykel dishwashers. A separate full caterer's kitchen-with additional refrigeration, dishwasher, and oven-supports effortless entertaining. Sun filled formal rooms, a richly detailed library, and a stunning river view sunroom showcase the home's craftsmanship. Wide plank cherry floors, solid cherry doors, and a custom wet bar with soapstone counters, built-in entertainment center, and tin ceiling add warmth and character. An elevator services all three levels. Six fireplaces, a walk-in wine room, and a media room with stadium seating elevate the lifestyle experience. A private caretaker/au pair apartment with its own entrance provides flexibility. With 6 garages, expansive lawns, and complete privacy-yet only 65 miles from NYC-this residence delivers an extraordinary blend of beauty and serenity.

7 Equestrian Ridge Rd, Newtown

Listing courtesy of Mary Ann Hebert from BHGRE Gaetano Marra Homes. (203) 592-0186 (203) 758-1300
$7,250,000
6 Beds ⋅ 8 Baths ⋅ 73575775 MLS
Perched on a private, picturesque lot in Waban, this classic colonial with a 3-car garage showcases timeless elegance & craftsmanship. Extensive millwork, curved archways, oversized windows, and 2 fireplaces add warmth & character, while formal living & dining spaces invite intimate gatherings. A gracious foyer and sweeping staircase welcome guests to a French-inspired interior. At the heart of the home is a kitchen anchored by a striking La Cornue range, with custom cabinetry, butler’s pantry, and dedicated coffee station. Upstairs, the primary suite features a grand walk-in closet with island, oversized double shower, and soaking tub alcove. A large & bright laundry room and 4 add’l en-suite bedrooms complete the 2nd floor. The lower level offers a glass-enclosed gym, media room ideal for theater or golf simulator, family room with wet bar, powder room, and en-suite guest bedroom. Surrounded by mature trees, the flat backyard offers room for a pool and create a private outdoor oasis.

101 Alban Road, Newton

Listing courtesy of Listing Agent: Ilene Solomon from Listing Office: Coldwell Banker Realty - Newton.
$7,250,000
6 Beds ⋅ 6 Baths ⋅ 22602281 MLS
This exquisite custom-built home in the coveted New Seabury community offers a rare blend of natural beauty and modern luxury. Perched perfectly to capture panoramic views of Nantucket Sound, the residence boasts a pristine sandy beach right outside your door, providing the ultimate waterfront lifestyle. Inside, the open-concept layout is thoughtfully designed, showcasing a gourmet kitchen with premium appliances, a stunning quartz island, and bespoke cabinetry. The sun-drenched living room features soaring ceilings, a statement stone fireplace, and expansive glass doors that seamlessly connect to the outdoor oasis. The primary suite is a sanctuary, complete with a spa-inspired marble bath, a generous walk-in closet, and a private deck to savor sunrise views over the water. The finished lower level offers versatile space, perfect for a media room, home gym, or guest quarters. Outdoors, the heated pool, bluestone patio, and professionally landscaped gardens create an unparalleled setting for relaxation or entertaining. Approved permits are in place for an 1,800 sq. ft. guest house, offering endless possibilities for multi-generational living, guests, or staff. With direct beach access and breathtaking ocean vistas from nearly every room, this home embodies the essence of Cape Cod luxury.

50 Coastline Drive, Mashpee

Listing courtesy of Listing Agent: Paul E Grover (paul@paulgrover.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
$7,250,000
7 Beds ⋅ 11 Baths ⋅ 22502682 MLS
Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and casual seating area at one end and a full second kitchen with custom built-in grill and dining area at the other, all enclosed by retractable screens for effortless seasonal enjoyment. Tucked away on the main level, the primary suite offers a private sanctuary, with its own fireplace, luxurious spa-like bath, and refined home office. The comfort and sophistication continue on the second level with four generously proportioned en-suite bedrooms and an inviting sitting room. Designed for comfort and connection, the finished lower level offers a wine cellar, media room, game room, and fitness space. This lavish interior flows effortlessly to an equally impressive exterior, where lush landscaping surrounds a resort-style pool framed by expansive lounging areas-perfect for everything from quiet afternoons to grand entertaining. Completing this offering is a beautiful two-bedroom guest house providing privacy and comfort for visiting guests. Set within a prestigious gated enclave with coveted beach and dock rights, this remarkable estate is the perfect fusion of architectural sophistication and everyday warmth - an extraordinary offering in one of Cape Cod's most prestigious settings. 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.

440 Grand Island Drive, Osterville

Listing courtesy of Listing Agent: Robert B Kinlin (rkinlin@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
$7,250,000
5 Beds ⋅ 5 Baths ⋅ 73548621 MLS
Impeccably renovated Shingle Style estate perched on Monument Street a mile from Concord Center. Wind up the oak & beech adorned drive to a granite cobbled courtyard connecting the main 5 BR house and classic New England Barn w/ 2 BR apartment. Gracious & flowing interior design defined by high ceilings, tall windows, generous hallways, & hearty custom millwork. Chef's kitchen w/ hand-crafted cabinetry, wood fireplace, wetbar, prep area, pantry & breakfast nook. A spacious sunken family room, elegant living room & dining room offer balance for large gatherings and the daily calm. 2nd floor primary suite w/ sitting room & walk-in closets. Updated baths. Lower level wine cellar, sauna & storage. Post-and-beam barn w/ a large 2-story space for your studio, basketball court & parties. Heated billiard room, 3 car garage & 2BR apartment. Wander the gardens, rolling lawn and old growth trees, all newly professionally landscaped w/ resurfaced tennis court & direct access to Estabrook Woods.

819 & 825 Monument Street, Concord

Listing courtesy of Listing Agent: Abby White from Listing Office: LandVest, Inc., Concord.
$7,250,000
5 Beds ⋅ 5 Baths ⋅ 24177235 MLS
Introducing: Katsura. It might surprise you to learn that the ultimate lake wilderness retreat you've been searching for in Maine, Vermont, or Montana is actually hidden right here in the foothills of Connecticut. Perfectly positioned just over two hours from NYC, Katsura Lodge is a masterclass in privacy, offering a rare opportunity to truly escape into nature. Set at the end of a gated, long private crushed stone driveway, this 118-acre unspoiled woodland sanctuary offers approximately a mile of pristine frontage on Winchester Lake. It is the ultimate luxury camp. A place to unplug, exhale, and reconnect with family and friends. Offering over 5,000 square feet of sophisticated living space, this custom built, 5 bedroom contemporary residence integrates beautifully with its surroundings. Exceptional craftsmanship including heart pine and stone floors, custom cherry cabinetry, and soaring cathedral ceilings creates an elevated, warm aesthetic. In the great room, an impressive double-height fireplace, crafted from stones sourced directly from the property, anchors the space, while a cozy windowed reading nook invites quiet afternoons. Seemingly endless Albertini sliding glass doors erase the line between indoors and out, framing captivating views of the manicured grounds and the water. The home is designed for seamless entertaining on any scale. A gourmet chef's kitchen features top-of-the-line appliances, an adjoining wet bar, and a spacious wine cellar.

841 Winchester Rd, Norfolk

Listing courtesy of Lenore Mallett from William Pitt Sotheby's Int'l. (203) 209-1777 (860) 435-2400

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