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$5,195,000
8 Beds ⋅ 9 Baths ⋅ 24182442 MLS
West Winds is one of Washington's most extraordinary country estates, offering an unparalleled combination of privacy, natural beauty, recreation, and equestrian amenities. A long, winding drive meanders through expansive meadows and orchards, culminating at a remarkable 10,000+ square-foot barn-style residence. Meticulously crafted using reclaimed beams and siding from a 19th-century Dutch barn, the home blends authentic historic character with modern comfort and scale. Set on 62 acres across 4 separate parcels, the property enjoys over 1,000 feet of frontage along the Bantam River, with sweeping views across the water to the mountains beyond (including iconic Mt. Tom). Outdoor amenities are exceptional, highlighted by a spectacular infinity-edge pool surrounded by stone terraces and walls, a private pond for fishing and winter skating, and direct access to miles of protected land trust trails ideal for hiking, biking, horseback riding, and exploring the surrounding countryside. For equestrian enthusiasts, West Winds offers a rare opportunity to ride directly from the property onto adjacent trail networks that follow the scenic Bantam River. The horse facility includes 4 stalls, tack area, and paddocks creating a turnkey setup for both recreational and serious riders. The heart of the home is the renovated eat-in kitchen, ideally positioned between the dramatic vaulted great room and the expansive media/game room.

56 W Morris Rd, Washington

Listing courtesy of Stacey Matthews from W. Raveis Lifestyles Realty. (203) 671-9067 (860) 868-0511
$5,190,000
4 Beds ⋅ 7 Baths ⋅ 24170471 MLS
Set beyond stone walls and a landscaped entrance, 48 Old Farm Road is a newly completed Wilton residence blending timeless New England architecture with a bright, refined modern interior. The open central hall makes an immediate impression with pale oak floors, abundant natural light and a striking staircase with black metal balusters. Generously proportioned living spaces feature custom millwork, expansive windows and seamless flow for everyday living and entertaining. The kitchen opens to the main gathering areas and overlooks the rear grounds. Spacious bedrooms include vaulted ceilings, large windows and beautifully finished baths with stone surfaces, frameless glass showers and thoughtfully selected fixtures. An elevator adds convenience between levels, while the three-car garage, broad driveway and multiple covered outdoor areas enhance daily function. Mature trees, open lawn, stonework and a private setting create the feel of a composed country property. An approved proposed pool is shown on the property survey, and the detached 2000 sq. ft. accessory building may be converted into a pool house, $620 per foot plus the pool. Served by Wilton Public Schools and convenient to Wilton Center, local amenities and Metro-North service to New York City.

48 Old Farm Rd, Wilton

Listing courtesy of Kevin O'Brien from O'Brien Premier Properties. (203) 943-9586 (203) 822-2524
$5,150,000
4 Beds ⋅ 5 Baths ⋅ 73573266 MLS
An elegant English-inspired Gothic Revival residence in Brookline’s coveted Fisher Hill neighborhood, distinguished by steep slate roofs, dramatic gables and arched architectural and copper details. Designed for Mrs. Harold Hammond by noted architects Kilham, Hopkins & Greeley, whose work also includes the Devotion School (Florida Ruffin Ridley School) and Brookline High School (source: Brookline Preservation Commission), this stately home offers 5,744 sq. ft. of living space across four finished levels, with 4 bedrooms, 3 full and 2 half baths, 5 fireplaces and an attached 2-car garage.The main level features a welcoming kitchen with convenient side entry, dining room with fireplace, gracious living room with fireplace, a light-filled sunroom overlooking the serene garden, two offices and powder room. The exceptional walk-out garden level is designed for both everyday living and entertaining, anchored by a dramatic two-story family room with fireplace, custom built-in bookcases, wet bar, floor-to-ceiling windows and French doors opening to a stone patio and private backyard. A wine cellar and lounge, exercise room, powder room and direct garage access complete this level.Upstairs, the generously scaled primary suite features a fireplace, walk-in closet and private outdoor balcony. Two additional bedrooms, a full bath and laundry complete the second floor. The finished top floor offers two spacious and versatile rooms—ideal for bedrooms, offices, hobbies or recreation—along with a full bath and abundant storage.Set on .35 acres, the beautifully landscaped private grounds offer mature specimen trees, stone walls, lawns and peaceful spaces for outdoor dining, entertaining and play. Meticulously maintained and thoughtfully updated over the years, the home combines period character with comfortable, move-in-ready living and exceptional storage throughout.A quiet and secluded setting on a tree-lined street, yet remarkably convenient to Washington Square, Cleveland Circle, schools, parks, public transportation (C & D lines), shopping and Boston.

67 Hyslop Rd, Brookline

Listing courtesy of Listing Agent: Ingvild Brown from Listing Office: Keller Williams Realty.
$5,150,000
8 Beds ⋅ 8 Baths ⋅ 5089880 MLS
Bringing generations together in a place that inspires connection, adventure, celebration, work and stewardship, Moosewalk Lane is a purpose built multigenerational family compound. Created over two decades and set on 384 private acres in Vermont's Green Mountains, Moosewalk Lane is offered fully furnished and equipped. Anchored by a 10,062 square foot timber frame home, guest house, writer's cabin, equipment barn, and miles of private trails, Moosewalk provides a true sense of place where comfort, privacy, and recreation exist in equal measure. Designed for year round living and entertaining, the compound comfortably accommodates extended family, friends, and guests with eight bedrooms, seven full baths, a dramatic two story great room, a chef's kitchen with Viking appliances and an Italian wood fired pizza oven, a library, media and game room, fitness space, six garage bays, and thoughtfully designed gathering places both inside and out. Just beyond the backyard, Broadway, the property's original logging road turned trailhead, provides direct access to the balance of the 384 acre property and four season recreation. Ride horses through open meadows, hike, snowshoe, or explore miles of private woodland trails, produce maple syrup from your own gravity fed sugarbush, enjoy direct access to Vermont's VAST trail system, or retreat to the writer's cabin overlooking the Connecticut River Valley. Historic stone walls, managed hardwood forests, abundant wildlife, and protected Current Use acreage reflect more than ownership, they reflect stewardship. Thoughtfully created for extended family, private retreats, entertaining, or simply escaping the pace of everyday life, Moosewalk offers something increasingly rare: a place where time slows, memories are made, meals are shared, and life is measured by moments well spent.

3800 Weston Andover Rd, Andover

Listing courtesy of Steve Stettler from Four Seasons Sotheby's Int'l Realty. (steve.stettler@fourseasonssir.com)
$5,100,000
10 Beds ⋅ 10 Baths ⋅ 5101885 MLS
Location, Location, Location. Representing the pinnacle of Stratton Mountain trailside living, 15 Sawmill is a generational property where unrivaled ski-in/ski-out access creates one of Stratton's most exceptional legacy offerings. This is one of the few homes located along the trail - one you admire and wish was yours when you ski by it all winter season! Perfectly positioned directly on the ski trails with effortless access, this remarkable opportunity is an open palate for the next owner. This rare property delivers an unparalleled lifestyle designed to be treasured for generations. This 10 bedroom 9.5 bath residence (with 7 ensuite bedrooms), offers an expansive floor plan thoughtfully crafted for entertaining, family gatherings, & private retreats. An open concept great room is anchored by a commanding stone fireplace, walls of glass facing the trails and a kitchen design featuring an oversized island and dining area. Designed to comfortably accommodate family & guests alike, the residence features an exceptional ski room that opens up to the trailside for ease of trail access! A large family/game room is perfect for watching the game after a day on the slopes or cozying up to watch a movie. Expansive deck - perfect for spring apres ski and summer mornings. The oversized garage provides ample space for vehicles, recreational equipment, & seasonal storage. The scale & thoughtful layout, make this an ideal retreat for multiple generations to gather under one roof. This is more than a residence. It's a rare opportunity to establish your family legacy in one of Stratton Mountain's most coveted locations, where effortless slope side living define the ultimate mountain lifestyle.There are very few Stratton Mountain Resort residences that enjoy direct access to the Wanderer Trail. Convenience abounds. A priceless legacy property. Rare Indeed.

15 Sawmill Rd, Stratton

Listing courtesy of Kim Morgan-Wohler from Wohler Realty Group. ()
$5,100,000
3 Beds ⋅ 7 Baths ⋅ 73511019 MLS
Situated on a lovely street, this very special five story townhome has it all. There are three plus bedrooms with potential for more as the top floor with an open floor plan and sunny balcony offers great flexibility. Wonderful entertaining space and formal rooms with beautiful proportions and architectural details add to the charm. A door from the living room opens out to an extraordinary deck with a balustrade. The bright, eat-in kitchen with large windows looks out on the inviting garden. Amenities include a finished basement with a garden room and lots of storage.

52 Pinckney St, Boston

Listing courtesy of Listing Agent: Sally T. Brewster from Listing Office: Brewster & Berkowitz R. E..
$5,000,000
4 Beds ⋅ 4 Baths ⋅ 22604591 MLS
This stately waterfront home sits at the end of a private cul-de-sac on a secluded 1.89 acre wooded lot with stunning views of Little Pleasant Bay. The homeowners association privileges include: tennis, pickle ball, bocci, a landing on Pilgrim Lake, and a shared deep-water DOCK for boating access to Pleasant Bay and the Atlantic. Entering the central hall from the large covered entry porch reveals an excellent view of the bay through the living room's bank of windows. The breakfast table, adjoining the generous size kitchen, also offers water views, while the adjacent great room features a formal dinning area, radiant heated floors, a large fireplace, and French doors leading to a spacious deck with spectacular views. The home boasts two primary bedrooms with water views on both the first and second floors, the latter en-suite with walk-in closet. The upper floor has two more bedrooms, a large office, an exercise room, and a laundry room. The partially finished lower level has a second fireplace, a sleep-in bonus room, and a workshop. This is truly a distinctive Cape Cod retreat, situated in a special setting and lovingly cared for by these original owners.

46 Thayer Lane, Orleans

Listing courtesy of Listing Agent: Chester Crabtree, III (ccrabtree@cireab.com) from Listing Office: Christie's International Real Estate Atlantic Brokerage.
$5,000,000
4 Beds ⋅ 4 Baths ⋅ 73571790 MLS
There are beautiful homes on Cape Cod, and then there are properties whose scale, setting and presence place them in a category entirely on their own. Privately set at the end of a quiet North Truro cul-de-sac, 8 Schardt Way is one of those rare gems—a Chatham-like estate in scale and sophistication, surrounded by the untamed beauty of the Outer Cape and just minutes from Provincetown. Built by Cape Associates in 2009, the four-bedroom, three-and-one-half-bath residence offers an impressive 5,824 square feet of living space on approximately 3.7 private acres. Elevated above its surroundings, the home captures sweeping views toward Provincetown and Cape Cod Bay from almost every room—expansive skies, changing light and unforgettable sunsets become part of everyday life. Adding to the extraordinary nature of this offering is 6 Schardt Way, an adjacent vacant, buildable parcel of approximately 1.1 acres, creating a combined setting of approximately 4.8 acres and providing additional privacy, flexibility and a rare opportunity to control more of the surrounding landscape.Enhancing its future potential, 6 Schardt Way has an engineered Title V plan designed for a five-bedroom residence, along with a test well, offering an exceptional opportunity to further develop the property as an expanded estate, guest residence or multigenerational family compound. The residence was created on a scale rarely encountered on the Outer Cape. Generous living and entertaining spaces invite a house filled with family and friends, while the expansive grounds provide the extraordinary feeling of having your own world within one of Cape Cod's most treasured landscapes. This is a property that gives purpose to coming home—where summer weekends become traditions, children and grandchildren return year after year, friends gather around the pool, and spectacular Cape sunsets remind you exactly why you chose to be here. A saltwater in-ground pool creates a private resort-like setting, while a heated three-bay garage, heated driveway track, radiant basement floors, 30kW Kohler automatic generator and extensive recent mechanical upgrades provide exceptional year-round comfort. The primary suite offers its own private sanctuary, highlighted by a BainUltra ThermoMasseur bath. There is a certain feeling that comes with owning a property of this significance—a sense of arrival, permanence and belonging. A place worthy of what you have accomplished.

8 Schardt Way, Truro

Listing courtesy of Listing Agent: The Beach Buoys from Listing Office: Gibson Sotheby's International Realty.
$5,000,000
6 Beds ⋅ 5 Baths ⋅ 73571780 MLS
Maplemere is one of Lexington’s truly distinctive properties, with origins dating to the early 19th century. The architectural character, historic barn, and carriage house preserve a tangible connection to Lexington’s agricultural past. Set on 1.7 acres in the coveted Meriam Hill neighborhood and directly abutting 27 acres of conservation land, Maplemere enjoys an extraordinary sense of privacy, permanence, and protected natural beauty. Mature landscaping and expansive grounds create a rare feeling of seclusion while remaining close to the character and community of Lexington. Inside, gracious living spaces are designed for both sophisticated entertaining and comfortable family life, all anchored by a magnificent family room that invites gathering. A large wrap-around porch, partially screened-in, extends the living spaces outdoors, creating beautiful settings for dining, entertaining, and enjoying the landscape throughout the seasons. The main level is thoughtfully designed for modern living, with a private second main bedroom offering the rare convenience of first-floor living. Two dedicated home offices provide elegant spaces for work or study, while a handsome library offers a quiet retreat for reading and conversation. Upstairs, the primary suite offers a particularly special vantage point, overlooking the protected conservation land and opening to a private walk-out balcony. Four additional bedrooms provide generous accommodations for family and guests, complemented by a fitness room. The grounds unfold as a private retreat, with a beautiful swimming pool and pool house at the heart of summer living. The surrounding conservation land provides a peaceful backdrop and protected views, while mature trees and gardens create an atmosphere of timeless beauty. There is a rare sense of continuity at Maplemere. The land that once supported a historic Lexington farm now provides the backdrop for an extraordinary modern lifestyle. A landmark property, Maplemere offers something increasingly difficult to find: enduring land, exceptional privacy, and a home thoughtfully designed for generations of living. Ideally situated just blocks from Lexington Center, this location offers exceptional proximity to top-rated schools and major commuter routes.

42 Adams Street, Lexington

Listing courtesy of Listing Agent: Andrea Jackson from Listing Office: Barrett Sotheby's International Realty.
$5,000,000
4 Beds ⋅ 4 Baths ⋅ 22604413 MLS
There are beautiful homes on Cape Cod, and then there are properties whose scale, setting and presence place them in a category entirely on their own. Privately set at the end of a quiet North Truro cul-de-sac, 8 Schardt Way is one of those rare gems—a Chatham-like estate in scale and sophistication, surrounded by the untamed beauty of the Outer Cape and just minutes from Provincetown. Built by Cape Associates in 2009, the four-bedroom, three-and-one-half-bath residence offers an impressive 5,824 square feet of living space on approximately 3.7 private acres. Elevated above its surroundings, the home captures sweeping views toward Provincetown and Cape Cod Bay from almost every room—expansive skies, changing light and unforgettable sunsets become part of everyday life. Adding to the extraordinary nature of this offering is 6 Schardt Way, an adjacent vacant, buildable parcel of approximately 1.1 acres, creating a combined setting of approximately 4.8 acres and providing additional privacy, flexibility and a rare opportunity to control more of the surrounding landscape. Enhancing its future potential, 6 Schardt Way has an engineered Title V plan designed for a five-bedroom residence, along with a test well, offering an exceptional opportunity to further develop the property as an expanded estate, guest residence or multigenerational family compound. The residence was created on a scale rarely encountered on the Outer Cape. Generous living and entertaining spaces invite a house filled with family and friends, while the expansive grounds provide the extraordinary feeling of having your own world within one of Cape Cod's most treasured landscapes. This is a property that gives purpose to coming home—where summer weekends become traditions, children and grandchildren return year after year, friends gather around the pool, and spectacular Cape sunsets remind you exactly why you chose to be here. A saltwater in-ground pool creates a private resort-like setting, while a heated three-bay garage, heated driveway track, radiant basement floors, 30kW Kohler automatic generator and extensive recent mechanical upgrades provide exceptional year-round comfort. The primary suite offers its own private sanctuary, highlighted by a BainUltra ThermoMasseur bath. There is a certain feeling that comes with owning a property of this significance—a sense of arrival, permanence and belonging. A place worthy of what you have accomplished, yet perhaps even more meaningful for what comes next. More than a home, 8 Schardt Way is a family gathering place, a private retreat and a legacy to carry forward—a remarkable opportunity to make one of the Outer Cape's truly singular properties your own.

8 Schardt Way, North Truro

Listing courtesy of Listing Agent: The Beach Buoys (TheBBTeam@Gibsonsir.com) from Listing Office: Gibson Sotheby's International Realty.
$5,000,000
3 Beds ⋅ 3 Baths ⋅ 24192754 MLS
Some properties are defined by the house that sits on them. Others are defined by the land itself...by history, landscape and a sense of beauty that simply cannot be created. This is such a place. Owned and farmed by the same family for 200 years, this remarkable 16 Acre piece sitting on the Hammonassett River is the last piece of the original farm to be sold. With over 1500 ft. bordering the river, the property unfolds across open hay fields, tidal marshes and expansive river views. The landscape changes with the seasons and the light, grasses moving with the wind and water reflecting the ever changing sky...a landscape that is both bucolic and breathtaking. This is an exceptional setting for a distinctive country residence, a private retreat or a place to enjoy a quieter chapter of life. An existing, well appointed, three bedroom ranch home sits on the property and enjoys the same remarkable views. Comfortable as it stands, the home could ultimately serve as a guest house, artist's studio or private office. The property offers the potential for more than one lot, but with generations of family ownership, the sellers have hopes to see the land remain intact, so no soil testing has been undertaken for subdivision. A survey is available and buyers considering additional development should conduct their own due diligence. After two centuries in the same family, this is a rare opportunity to become the next steward of an extraordinary Connecticut landscape.

118 River Rd, Madison

Listing courtesy of Judy Dannemann from William Raveis Real Estate. (203) 675-8944 (203) 318-3570
$5,000,000
6 Beds ⋅ 7 Baths ⋅ 73478835 MLS
Step inside this recently constructed Victorian style home to discover an exquisite and majestic estate that has been meticulously built to seamlessly blend modern convenience with timeless elegance, perfectly tailored to fit the needs of today’s lifestyle. Nestled within highly desirable Merriam Hill and offering a prime location only steps to the town center and on one of the most historic sites in Lexington, 16 Meriam Street is sited on the very spot where Samuel Adams exclaimed to John Hancock upon hearing the first shots of the revolution, “Oh what a glorious morning for America!” The exterior and surrounding gardens are captivating with professionally landscaped grounds, stone walls, and specialty plantings. Whether hosting a grand soiree or an intimate family gathering, this home elevates your entertaining endeavors to new heights. The heart of the home opens with the stunning chef’s kitchen with professional grade, high end appliances including the 48” True double door refrigerator/freezer and Wolf 60” gas range. The chef is sure to appreciate the granite countertops with quartz accents, a rounded center island, a breakfast bar topped with custom artistic glass by Thinkglass, a custom designed backsplash, and a spacious informal dining area overlooking the backyard entertainment haven, easily accessible from both the kitchen and gazebo. The primary suite is a sanctuary, featuring a gas fireplace with a quartz surround and double French doors to a private balcony with Ipe flooring overlooking the backyard. A huge walk-in closet offers a window seat, a curved hanging area, and custom built-ins to provide the ultimate organization. The spa-like primary bathroom features an additional gas fireplace, and a dual sink vanity with a glass countertop and glass vessel sinks. Retreat to the secluded third level with two additional bedrooms, a full bathroom, perfect to use as a teen/au pair suite. Enjoy the home theater with 110” screen, high-definition Sony projector, and 7.1 surround sound system for an immersive cinematic experience. Slate tile flooring flows throughout the rest of the lower level, complete with a game room, home gym, and mudroom. Venture outdoors to find your very own private resort. The huge bluestone patio offers lots of space for outdoor enjoyment, including the barbecue station and a granite-topped breakfast bar. The heated saltwater lap pool glistens in the backdrop with its infinity waterfall, a welcome retreat on hot summer days.

16 Meriam St, Lexington

Listing courtesy of Listing Agent: Danielle Fleming from Listing Office: MA Properties.
$5,000,000
4 Beds ⋅ 2 Baths ⋅ 24148801 MLS
Originally established in the mid-1700s as a livestock farm, Deans Mill Farm has been beautifully restored & transformed into one of CT's most charming destinations. This small home serves as a full-time Airbnb or could house live-in help. Over 70 acres of pristine countryside in Stonington, property now operates as an event venue! The Main House offers 5-Bedroom (bed & breakfast), Dragonfly Equestrian Center has 18-stalls, Indoor/Outdoor riding ring, round pen, Multiple Buildings, wash stalls, trainer's apartment, hiking/horse trails & Dragonfly Disc Golf (NEW PRO SHOP!). Deans Mill Farm is ideal for weddings, parties, and special events. Guests may book individual rooms or reserve the entire property for privacy. The Farmhouse accommodates intimate indoor gatherings of up to 50 guests, while outdoor tented celebrations can host up to 250 guests with multiple picturesque backdrops. Whether you continue the existing business or make this amazing estate your home, the possibilities are endless. Picture the equestrian center as a unique indoor wedding venue, cocktail hour alongside the stalls, & private events where you live and entertain on-site. The equestrian center features a lovely living space above with a private deck-perfect for an owner, manager, or VIP guest. The main estate functions as both an Airbnb and bridal suite. The beer garden hosts music every Thursday & Sunday, offering food, beer, and lively charm that adds to its income potential.

1189 Pequot Trl, Stonington

Listing courtesy of Linda O'Hara from William Raveis Real Estate. (860) 209-7044 (860) 388-3936
$5,000,000
5 Beds ⋅ 7 Baths ⋅ 24148794 MLS
Originally built in the mid-1700s as a livestock farm, Deans Mill Farm has been beautifully restored & transformed into one of Ct's most charming destinations. Over 70 acres of pristine countryside in Stonington, property now operates as an event venue & 5-room bed & breakfast. It shares the grounds with Dragonfly Equestrian Center, stalls, Indoor/Outdoor riding ring, round pen, Multiple Buildings, wash stalls, trainer's apartment , hiking/horse trails & Dragonfly Disc Golf (NEW PRO SHOP)! Deans Mill Farm is ideal for weddings, parties, and special events. Guests may book individual rooms or reserve the entire property for privacy. The Farmhouse accommodates intimate indoor gatherings of up to 50 guests, while outdoor tented celebrations can host up to 250 guests with multiple picturesque backdrops. Whether you continue the existing business or make this amazing estate your home, the possibilities are endless. Picture the equestrian center as a unique indoor wedding venue, cocktail hour alongside the stalls, & private events where you live and entertain on-site. The equestrian center features a lovely living space above with a private deck-perfect for an owner, manager, or VIP guest. A small home serves as a full-time Airbnb or could house live-in help. The main estate functions as both an Airbnb and bridal suite. The beer garden hosts music every Thursday & Sunday, offering food, beer, and lively charm that adds to its income potential.

1189 Pequot Trl, Stonington

Listing courtesy of Linda O'Hara from William Raveis Real Estate. (860) 209-7044 (860) 388-3936
$4,999,999
6 Beds ⋅ 8 Baths ⋅ 24206656 MLS
THIS IS THE ONE YOU'VE BEEN WAITING FOR! Under constuction very close to completion. Brand new construction opportunity by highly regarded Lecher Development, on a prime, quiet in-town cul-de-sac. This exceptional luxury home offers 8000 + SF of high quality finishes, light-filled, living space across four finished levels. Highlights include: Gourmet Kitchen: A state-of-the-art kitchen featuring a large center island, premium stainless steel appliances, and an open layout that flows seamlessly into the family room with a fireplace and French doors leading to a covered porch. Flexible Main-Level Living: The first floor includes a private main floor space that can serve as a home office or sixth bedroom, complete with a full bath. Finished Third Floor: Ideal for a second office, playroom, guest suite, or au pair quarters. Spacious Lower Level: Featuring 10-foot ceilings, full bath, plenty of options to crate the perfect gym, media room, playroom, or additional recreation space. Generous Ceiling Heights: 9-foot ceilings on the main and second floors enhance the home's open, airy feel. Additional amenities include a 24-kW generator, five-zone heating and cooling, town water and gas. Set on a level property with a designated pool site, this home combines luxury, comfort, and customization in an unbeatable location. Don't miss the opportunity to make this exceptional property your dream home

19 Orchard Ln, New Canaan

Listing courtesy of Hannelore Kaplan from William Raveis Real Estate. (914) 450-3880 (203) 966-3555
$4,999,500
6 Beds ⋅ 9 Baths ⋅ 73573665 MLS
One of 13 estates in Dover’s magnificent Snow’s Hill neighborhood, 5 Hamlin’s Crossing includes 3.2+ impeccably manicured acres overlooking & abutting gorgeous conservation land. Privacy, timeless finish/craftsmanship, brilliant entertaining spaces & outstanding value distinguish this extraordinary property. Dover Land Conservation Trust manages 138 acres of trails adjacent to the neighborhood. Stunning stone walls outline the 2-tiered front lawn & the generous circular drive creates a dramatic approach. Exhale & enjoy the unequaled peace & privacy Snow’s Hill residents enjoy. French-inspired architecture, incl. multiple brick porticos & pretty dormered windows, reveals a home built with no detail spared. Inside, a 2-story foyer w/marble floors & sensational dome ceiling is anchored by a dramatic curved staircase. Windows everywhere provide abundant direct views of the backyard & pool. Magnificent. Richly lined w/custom bookshelves, the home office includes a FP & generous seating area. Multigenerational households take note: the west wing offers a rare 1st-floor 4-room primary suite, effortlessly accommodating family or long-term guests. Dedicated billiard room w/deluxe bar & egress to the side-yard putting green is a playful, beloved gathering spot. Beautiful sunken LR & enormous FR w/cathedral ceiling & custom architectural beams are the main gathering spaces. Designed for holidays & family parties, the open-concept kitchen/FR is where everyone gathers. Eat-in dining area w/island & peninsula seating + comfortable built-in window seat accommodates the crowd. This is the heart of the home. Priceless. Royal formal DR, mudroom off spotless 4-car garage & 2 half BRs complete the main level. 2nd level is accessed by 1 of 2 staircases & connected by wide hallways & elegant catwalk. West side includes a 2nd primary suite w/rich, spacious bath, 2 WICs, dressing room & bonus custom closet. 4 ensuite BRs w/spotless hardwood floors, generous laundry room w/awesome storage & folding spaces + media room w/Savant AV projector/screen ideal for family movie nights & game days complete the 2nd level. Glorious sun-splashed deck is steps from the saltwater pool. Insta-worthy slide & waterfall + fully equipped pool house w/bath, full kitchen & laundry make end-of-year parties & cocktail hours effortless. Expensive recent improvements incl. high-efficiency gas furnaces, Tesla Power wall/solar panels, Crestron lighting system & extensive landscaping/hardscaping.

5 Hamlins Crossing, Dover

Listing courtesy of Listing Agent: The Bauman Group from Listing Office: Gibson Sotheby's International Realty.
$4,999,000
6 Beds ⋅ 8 Baths ⋅ 73555707 MLS
Nature Lovers Paradise on the Charles River! Stunning in every season, each element of this spectacular property is crafted to maximize your enjoyment and access to the great outdoors. Reimagined by renowned architect Patrick Ahern, the exterior boasts a flat grassy backyard and stone patios with unobstructed views. Inside, a gracious and flexible floor plan is filled with light and views from myriad windows, French doors, and private balconies. First floor living with exquisite primary bedroom suite, a great room, expansive living room, dining and updated kitchen w/ light-filled breakfast room, an add’l bedroom suite and choice of offices complete the main floor. Upstairs, 4 more ensuite bedrooms, including a 2nd primary suite option. Large walk-out finished LL w/ bar, gym & media room. 3 car garage and flat courtyard driveway off protected cul de sac within minutes of extensive Wellesley Trails and Town Center. A notch above the rest. Bring your hiking shoes, kayaks, lounge chairs and lawn games!

12 Winding River Cir, Wellesley

Listing courtesy of Listing Agent: Christine Lawrence from Listing Office: Rutledge Properties.
$4,999,000
5 Beds ⋅ 7 Baths ⋅ 5098585 MLS
A breathtaking country estate seamlessly integrated into the Vermont landscape, this exceptional two-residence compound offers refined living less than two miles from Stowe Mountain Resort and just minutes to the charm of Stowe Village. Masterfully re-imagined, the property blends timeless design with superior craftsmanship and luxurious comfort. The main residence spans over 10,000 square feet of beautifully finished interiors, complemented by a separate guest house—each designed to elevate daily living and effortless entertaining. A meticulous renovation showcases the highest quality materials and artisan-level detailing throughout, including custom millwork, wide-plank flooring, finely crafted cabinetry, and premium appliances. Every space reflects an uncompromising commitment to excellence. Outside, a tiered, dry-laid stone patio sets the stage for unforgettable outdoor living, featuring a hot tub, dining terraces, and panoramic mountain views. A tranquil pond enhances the natural beauty and serenity of the setting. This is a rare opportunity to own a legacy estate in one of Vermont’s most sought-after locations—crafted with extraordinary care for generations to come.

235 Lower Sanborn Rd, Stowe

Listing courtesy of Smith Macdonald Group from Coldwell Banker Carlson Real Estate. ()
$4,999,000
5 Beds ⋅ 5 Baths ⋅ 5095734 MLS
Welcome to one of Okemo’s most distinctive properties, an iconic SKI-ON, SKI-OFF Tennessee log-style home set directly on the Moon Shadow ski trail within Solitude Village. Offered fully furnished and turnkey, this home is ready for enjoyment. Its exceptional rental performance provides an opportunity to offset substantial ownership costs and meaningfully reduce the effective cost of owning a premier slopeside retreat. With direct trail access, panoramic views, and a proven rental history, this is a rare opportunity to combine an extraordinary Okemo lifestyle with compelling ownership economics. Panoramic mountain views stretch across the Okemo Valley, while authentic log construction, broad-hewn timbers, wide chinking, reclaimed wood floors, and exceptional stonework create an unmistakable sense of place. Seven wood-burning fireplaces add warmth throughout, and soaring ceilings and expansive windows frame the breathtaking views. Designed for both grand entertaining and intimate retreats, the home features five bedrooms and four and a half baths, including three private en-suites. Separate guest quarters with a private entrance, great room, and fireplace provide an ideal space for visitors. The primary suite is a true escape, highlighted by a soaking tub perfectly positioned to capture the view. The gourmet kitchen blends rustic character with refined finishes, featuring high-end appliances, honed granite countertops, a wood-burning fireplace, large island, and commercial-style ice maker. Dual washers and dryers add convenience for owners and guests. Living spaces flow effortlessly to a spacious deck and elevated stone patio with an oversized hot tub overlooking the trail, an ideal setting for après-ski relaxation. A large game room offers gaming tables and pinball machines, while additional gathering spaces include a billiards loft. A well-appointed ski room with boot warmers and abundant storage keeps gear organized. ROFR

62 Moon Shadow Dr, Ludlow

Listing courtesy of Sarah N Sheehan from William Raveis Real Estate Vermont Properties. (Off: 802-228-8877)
$4,999,000
5 Beds ⋅ 9 Baths ⋅ 24146882 MLS
A rare offering, this Gambrel shingle-style estate is a sanctuary on over 15 acres with a lake and separate building lot-ideal for equestrian pursuits or a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered ceilings elevate the space. At the heart of the home, a stunning marble kitchen outfitted with Subzero and Wolf appliances, a breakfast nook, and butler's pantry opens to a soaring two-story family room as well as formal dining and living rooms for effortless entertaining. A main level bedroom suite is ideal for guests. Two private offices and well appointed mudroom enhance everyday functionality, while four fireplaces add warmth to the home. Upstairs, a spectacular primary suite with balcony, and 3 additional ensuite bedrooms are accompanied by a spacious bonus room with adjoining craft room. Intricate millwork and custom built-ins enrich every inch of this special home, reflecting its master craftsmanship. Wraparound covered patios overlook the saltwater Gunite pool, while an outdoor kitchen and fire pit invites alfresco dining. Pool house with kitchenette, laundry, 2 baths, rec room with balcony is perfect for guests. Five garage bays for the car enthusiast. The property offers unmatched luxury. Quite simply, there is nothing else like it.

294 Maple Rd, Easton

Listing courtesy of Linda Toscano from Coldwell Banker Realty. (203) 520-7899 (203) 245-4700
$4,998,500
4 Beds ⋅ 5 Baths ⋅ 73520842 MLS
Nestled on a private 0.92-acre lot in the prestigious Chestnut Hill neighborhood, this exceptional custom-designed Mid-Century Modern ranch, inspired by the timeless architecture of Frank Lloyd Wright, offers a rare blend of sophistication, privacy, and seamless indoor-outdoor living. Thoughtfully designed with gracious proportions and walls of glass, the home is filled with natural light and overlooks beautifully landscaped grounds. A spectacular four-season breakfast room with four skylights complements the chef’s kitchen featuring top-of-the-line appliances, three ovens, two dishwashers, and custom cabinetry. The luxurious primary suite serves as a private sanctuary with dual showers and vanities, smart toilets, separate dressing areas, a soaking tub, and an attached office/library. The versatile lower level offers excellent potential for an in-law suite. Sliding glass doors line the rear of the home, opening to a serene outdoor retreat with an elegant patio and heated pool. Superb

9 Singletree Rd, Brookline

Listing courtesy of Listing Agent: Deborah M. Gordon from Listing Office: Coldwell Banker Realty - Brookline.
$4,998,000
6 Beds ⋅ 6 Baths ⋅ 73501987 MLS
Elegance, sophistication & incredible architectural craftsmanship highlight this exquisite home, walkable to both Newton Centre & Newtonville. This contemporary colonial offers over 6900 sqft of luxurious living with 6 bedrooms & 6 full baths. The sunsplashed main level offers a formal dining, living room, office/bedroom with a 2 sided fireplace & full bath. The spacious chef's kitchen features Wolf & Subzero appliances, 2 dishwashers & 2 sinks, an island that seats 5 as well as a separate breakfast & sitting area. The inviting oversized family room with vaulted ceilings & fireplace lead out to a patio & private yard featuring an in ground pool & spa perfect for hours of entertaining. The 2nd level offers an gorgeous primary suite with a spa like bathroom & 2 walk in closets. Three additional generously sized en suite bedrooms & laundry complete this level. The finished lower level includes a spacious great room, wet bar, 2 mudrooms, bedroom, bathroom & elevator. A true masterpiece!

136 Beaumont Ave, Newton

Listing courtesy of Listing Agent: The Jeff Groper Group from Listing Office: Coldwell Banker Realty - Newton.
$4,995,700
4 Beds ⋅ 5 Baths ⋅ 24176377 MLS
Come walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul de sac in Long Lots. Peace, quiet, and the highest quality custom home spec'd to your wishlist by Coastal Luxury Homes is yours at 22 Dawn Drive. Go bigger/smaller, add an in-law suite or extra bedroom, an art studio, include a pool/spa, pickle court... let's discuss all the possibilities. Square footage and specs can vary, but the standard of excellence does not. Coastal Luxury Homes is the premier Fairfield County bespoke builder.

22 Dawn Dr, Westport

Listing courtesy of Jaclyn Picarillo from Higgins Group Bedford Square. (203) 981-5012 (203) 226-0300
$4,995,000
5 Beds ⋅ 6 Baths ⋅ 22604593 MLS
The ultimate Chatham compound! Set high on a bluff with views of Hardings Beach and Nantucket Sound, this impressive property features a 4,100+ sqft main house, oversized two-car garage with private guest suite above, and a resort-style backyard with an expansive patio and pool. Inside, ten-foot ceilings, custom built-ins, abundant natural light, and generous living spaces set the tone. The grand family room opens directly to the backyard, while the adjacent kitchen offers top-of-the-line appliances, soaring ceilings, outdoor access, and a spacious dining area. A formal dining room, living room, first-floor primary suite, guest bedroom, full bath, powder room, and laundry provide easy one-level living. Upstairs, a second primary suite features a sitting area, walk-in closet, and private deck overlooking Nantucket Sound. Two additional bedrooms, a sitting room, and a full bath complete the second floor. The heated garage is topped by a private guest suite with coffee bar, full bath, and sitting area. Outside, enjoy a deck, patio, fire pit, multiple gathering areas, and large pool. Deeded access to the private neighborhood path to Hardings Beach is less than 1/10 mile away.

65 Harbor View Road, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith (chris.rhinesmith@compass.com) from Listing Office: Compass Massachusetts, LLC.
$4,995,000
5 Beds ⋅ 5 Baths ⋅ 24195094 MLS
1716 Shippan Avenue represents a rare opportunity to own a legacy estate on 1.01 acres in Stamford's sought-after Shippan neighborhood. This distinguished Tudor home is comprised of approximately 6,000 square feet of timeless architectural character, sophisticated modern updates, and a thoughtfully designed 2016 renovation by Granoff Architects. With 5 bedrooms, 3 full and 2 half baths, the home is rich in detail, including original stained glass, oak paneling, unique solid oak arched interior doors, and three wood-burning fireplaces. Custom millwork, a Vermont slate roof, and new Marvin windows throughout further showcase the home's exceptional craftsmanship. The beautifully updated second-floor bathrooms feature custom cabinetry, bookmatched marble showers and countertops, and heated floors. In addition to generous living and entertaining spaces, the home also includes a finished lower level, a third-floor loft with water views (currently used as a home gym), and a charming attached greenhouse. Outside, a 40' x 20' gunite pool and spa, expansive patio, and mature gardenscape create a picturesque private oasis. Exceptionally private, the expansive grounds made up of 2 parcels provide an idyllic backdrop for sun-filled summer days, evenings spent poolside, and memorable gatherings with family and friends. Enjoy Shippan's waterfront community minutes away from the Stamford Yacht Club, local dining, and the express train to Manhattan.

1716 Shippan Ave, Stamford

Listing courtesy of Amanda Spatola from Houlihan Lawrence. (203) 273-8615 (203) 655-8238
$4,995,000
6 Beds ⋅ 9 Baths ⋅ 73574370 MLS
This impressive residence offers an elevated lifestyle in one of Needham’s most coveted estate neighborhoods. Set gracefully on more than an acre of beautifully landscaped grounds, the property combines timeless elegance with an exceptional array of amenities designed for both everyday living & grand-scale entertaining. An abundance of natural light fills the thoughtfully designed interiors, creating a warm & welcoming atmosphere throughout. Spacious living areas flow effortlessly from one room to the next, offering refined finishes, generous proportions & a seamless connection to the spectacular outdoors. The true centerpiece is the extraordinary manicured yard, crafted for relaxation and entertaining. A sparkling swimming pool & spa complemented by a charming pool house, screened in porch & sports court all surrounded by mature landscaping & lush greenery creates a resort-like setting. This remarkable property offers privacy, sophistication & an unparalleled staycation experience - all in a prestigious setting close to top schools, commuter routes & town. Fabulous opportunity!!

99 Country Way, Needham

Listing courtesy of Listing Agent: The Lara & Chelsea Collaborative from Listing Office: Coldwell Banker Realty - Wellesley.
$4,995,000
3 Beds ⋅ 3 Baths ⋅ 73566298 MLS
Waterfront home with Deep-Water dock on Popponessett Island, within our New Seabury Resort! Rare opportunity to own an exceptional contemporary with sweeping views of Nantucket Sound & Popponesset Creek. Thoughtfully designed to showcase this spectacular setting, the sun-filled open floor plan features a dramatic floor-to-ceiling wall of glass that frames the breathtaking water views. The large kitchen flows seamlessly into the living room w/a wood-burning FP. The dining area with multiple sliders opens to a spacious deck perfect for outdoor dining, entertaining or taking in the ever-changing scenery. In addition, there is a primary bedroom w/private bath, plus a bedroom and bath. The lower level features a bedroom, bath, den & home office offering flexible living space for family and guests. The generous family room with a bar area has direct access to a waterfront patio and a lush lawn ideal for all your summer gatherings. This home is located at the end of a quiet cul-de-sac surrounded by water. Enjoy easy access to a sandy ocean beach on Nantucket Sound, spend the day boating to Martha's Vineyard, kayaking or simply relax taking in the cool summer breezes & endless water views.

145 Popponesset Island Rd, Mashpee

Listing courtesy of Listing Agent: Dorothy Oosterman from Listing Office: New Seabury Sotheby's International Realty.
$4,995,000
5 Beds ⋅ 7 Baths ⋅ 5105868 MLS
A rare opportunity awaits at this exceptional Dorset Hollow estate, privately situated at the end of exclusive Marcia Lane. Perched high on Dorset Mountain across 16.74 acres, the property captures breathtaking long-range views of Owls Head, Equinox Mountain, and beyond. Built in 2005 by renowned craftspeople, this 7,451-square-foot, five-bedroom, seven-bath estate has undergone a multimillion-dollar renovation, creating an updated, turnkey retreat. Improvements include a new kitchen addition with locally sourced Danby marble and high-end cabinetry, a remodeled primary suite, and comprehensive renovations to the interior, exterior, and grounds. The home offers seamless indoor-outdoor living, flowing onto a wraparound porch and stone patio with an outdoor kitchen. Stone walkways lead to a large lap pool with a diving rock, a ball field, manicured gardens, wildflower meadows, an apple orchard, and an English garden with a fountain and marble bench. Year-round amenities include three wood-burning fireplaces, multiple gathering rooms, a gym, a theater with surround sound and a large wood-burning fireplace, and a hot tub with spectacular views. Speakers serve the first floor, porch, and pool area. The impressive Bensonwood timber-frame barn features an indoor pickleball court and basketball and a full game room. A separate heated equipment barn with power and internet offers space for equipment storage, a woodworking shop, or other uses. Smart-home upgrades include indoor and outdoor lighting controls, thermostats, and a security system with cameras. Wired and wireless internet extends throughout the property, and a full-estate 80 kW generator provides added reliability. Refined finishes include hand-nailed wide-plank pine floors, crown molding, wainscoting, slate, marble, cherry wood, handmade wrought iron, and locally sourced materials. The grand primary suite showcases dramatic Bensonwood timber framing, creating a warm private retreat.

440 Marcia Ln, Dorset

Listing courtesy of David A Halligan from Four Seasons Sotheby's Int'l Realty. ()
$4,995,000
5 Beds ⋅ 4 Baths ⋅ 73563718 MLS
A rare waterfront offering in Sherborn, gracefully set along the shores of picturesque Farm Pond. Privately sited amid mature trees and lush grounds, this classic New England residence offers an exceptional setting of secluded, natural beauty, and timeless character. Direct Farm Pond frontage includes your own beach, creating a truly special opportunity for swimming, kayaking, paddleboarding, or simply enjoying peaceful days at the water’s edge. A sparkling saltwater pool provides an additional destination for summer entertaining, while expansive lawns, mature landscaping, and wooded surroundings create a serene sense of tranquility. The residence offers the warmth and enduring appeal of classic architecture, thoughtfully complemented by its extraordinary natural setting. From the landscaped grounds to the sweeping pond views, every element invites a more relaxed way of living. A singular opportunity to embrace exclusive waterfront living and quintessential New England beauty less than 25 miles from Boston. Located within the highly regarded Dover-Sherborn Regional School District, consistently ranked among the top 5 school districts in the Commonwealth.

112 Farm Rd, Sherborn

Listing courtesy of Listing Agent: The Berkowitz Team from Listing Office: Keller Williams Boston MetroWest.
$4,995,000
3 Beds ⋅ 3 Baths ⋅ 22603892 MLS
Waterfront home with Deep-Water dock on Popponessett Island, within New Seabury! Rare opportunity to own an exceptional contemporary with sweeping views of Nantucket Sound & Popponesset Creek. Thoughtfully designed to showcase this spectacular setting, the sun-filled open floor plan features a dramatic floor-to-ceiling wall of glass that frames the breathtaking water views. The large kitchen flows seamlessly into the living room w/a wood-burning FP. The dining area with multiple sliders opens to a spacious deck perfect for outdoor dining, entertaining or taking in the ever-changing scenery. In addition, there is a primary bedroom w/private bath, plus a bedroom and bath. The lower level features a bedroom, bath, den & home office offering flexible living space for family and guests. The generous family room with a bar area has direct access to a waterfront patio and a lush lawn ideal for all your summer gatherings. This home is located at the end of a quiet cul-de-sac surrounded by water. Enjoy easy access to a sandy ocean beach on Nantucket Sound, spend the day boating to Martha's Vineyard, kayaking or simply relax taking in the cool summer breezes & endless water views.

145 Popponesset Island Road, Mashpee

Listing courtesy of Listing Agent: Dorothy M Oosterman (dorothy@newseaburyre.com) from Listing Office: New Seabury Sotheby's International Realty.

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