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$5,900,000
7 Beds ⋅ 8 Baths ⋅ 24194285 MLS
Set behind private gates in Westport's prestigious Red Coat estate area, this extraordinary luxury residence offers the utmost in privacy and sophisticated design. Thoughtfully conceived with elegant architecture, exceptional proportions, soaring 10-foot ceilings on the main level, 9-foot ceilings on the second floor and finished lower level, and light-filled interiors, the home blends sophisticated style with effortless everyday living. A stunning custom kitchen appointed with premium Thermador appliances anchors the home, flowing seamlessly into beautifully designed living and entertaining spaces. Superior materials, custom millwork, and bespoke finishes define every room, while 6 ensuite bedrooms in the main residence provide exceptional comfort. Elevator-ready! Walk-up attic offers added possibilities. Outdoors, beautifully landscaped grounds create a private resort setting featuring a spectacular saltwater pool and spa. A separate 550-square-foot guest/pool house/ADU offers ideal accommodations for guests, wellness, or entertaining, while the expansive property provides ample room for a future tennis or sport court. A rare offering in one of Westport's most coveted and prestigious locations, it's just minutes from Westport's bustling downtown, sunny beaches, and award-winning schools. This remarkable estate combines thoughtful design and an unparalleled lifestyle defined by privacy, bespoke design and high-end amenities. Still time to customize. Floor plans available

22 Cavalry Rd, Westport

Listing courtesy of Cyd Hamer from William Pitt Sotheby's Int'l. (917) 744-5089 (203) 227-1246
$5,900,000
6 Beds ⋅ 8 Baths ⋅ 22602789 MLS
The newest release within a private gated enclave in South Chatham's emerging luxury corridor, 50 Sylvan Way is a bespoke custom estate minutes from the Cape's most iconic downtowns, beaches, and dining, yet removed enough to feel like a world apart. Thirteen rooms across over 6,000 square feet of living space sited on 1.635 bucolic acres -- a sanctuary setting with the scale and usability to match. A first-floor primary wing. Three-car garage. Every bedroom ensuite. An open-concept great room with soaring ceilings anchors the floorplan, while a fully finished basement provides a complete auxiliary level for guests and entertaining -- a depth of program rarely found at this price point. Outside, a pool and integrated jacuzzi anchor the aquatic experience, framed by a dramatic firewall feature and wraparound deck purpose-built for outdoor living at scale. A property conceived for generational use, with the flexibility to customize finishes to suit your vision. Constructed by R.A. Martin -- among the most trusted names in Chatham custom construction -- 50 Sylvan Way is a singular proposition in the Chatham marketplace.

50 Sylvan Way, South Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group (aschofield@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
$5,900,000
6 Beds ⋅ 3 Baths ⋅ 22600002 MLS
There was a time before antique homes were ''rehabilitated'' or ''renovated.'' Discover this untouched jewel, sparkling quietly in Provincetown's coveted east end Commercial Street neighborhood of Captain's homes, boathouses, beach cottages and sandy lanes.There is still one of those hard to find gems remaining, an untouched sprawling home, once several residences in one on a large parcel of land with a private, enclosed rear garden, home to a two story Carriage House and a broad front yard.This unassuming but elegant expanded antique Cape sits comfortably back from Commercial Street with a view to the bay.The main house offers 11 rooms, period correct with pantry, closets, nooks, crannies, double doors, gorgeous wood flooring, original staircases and details at every turn, a surprise of antiquity with every glance paid. The bonus Carriage House in the back garden is ripe for conversion to a spacious artist's studio, home office, writing studio or gracious guest quarters. You won't be disappointed if you are a connoisseur of classic Cape Cod style and New England architecture. Secure this untouched masterpiece today to preserve it for generations to come.

580 Commercial Street, Provincetown

Listing courtesy of Listing Agent: Stephen M Briscoe (StephenMBriscoe@gmail.com) from Listing Office: SeasCape Realty, Inc..
$5,900,000
4 Beds ⋅ 5 Baths ⋅ 22603274 MLS
Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and additions in several directions in this very private location of North Chatham...Choice of 3 primary bedrooms with attached baths... Views over Chatham Harbor and beyond.......Beach and boating just an easy walk away. Or swim and relax in your own backyard in the heated Gunite pool....House has been very well maintained by the current owner who has been here for over 36 years and completed a new roof, many new windows, new bedroom addition, newer family room addition and more......All information here has not been independently verified and buyer should do his/her own due diligence by checking with their attorney, and zoning and building rules and by laws, etc.. Assessment numbers subject to change with new Fiscal Year.

95 Cotchpinicut Road, Chatham

Listing courtesy of Listing Agent: John B Burke (john.burke@raveis.com) from Listing Office: William Raveis Real Estate & Home Services.
$5,900,000
7 Beds ⋅ 5 Baths ⋅ 22602646 MLS
There is a town at the end of Martha's Vineyard. The road narrows, the houses thin, and the light changes. This is Aquinnah; the westernmost town, clay cliffs, a lighthouse, and one of the smallest year-round populations on the Vineyard. Compound-scale offerings rarely come to market here. 19 Locust Lane is one of them. Nearly 17 acres high above Vineyard Sound, with open water views to the Elizabeth Islands. A custom Dutch Colonial main residence and separate guest house, both built in 2005. Cedar shake. Stone walls. Built to belong to the landscape, not compete with it. Inside: over 6,000 square feet across six bedrooms. Wide-plank floors, an open-plan dining room, and a gourmet kitchen with a Tuscan oven. At its center, a great room with cathedral ceiling, cedar trusses, and a floor-to-ceiling stone fireplace, facing the ridgeline and water beyond. Room to host, with the flexibility of two living spaces. Aquinnah has kept its character. This is the place that lets you stay there.

19 Locust Lane, Aquinnah

Listing courtesy of Listing Agent: Kimberly Biggs (kimberly.biggs@exprealty.com) from Listing Office: eXp Realty, LLC.
$5,900,000
7 Beds ⋅ 9 Baths ⋅ 5101271 MLS
NIRVANA, a rare sanctuary set against majestic panoramic VIEWS. Experience the SERENE SECLUSION, a breathtaking tapestry of vibrant southern NH's mountains, in sought after TAX HAVEN New Hampshire, and nearby enchanting seacoast/lakes, Boston's allure, and airports are just a short journey away. Atop this spectacular hilltop 15.36 private acres a view estate flourishes, marrying international flair with architectural finesse. Every corner narrates a tale of considerable design and detail. The illuminated meandering driveway crests to a HEAVENLY reach for the stars PANORAMIC views and a Porte Cochere arrival. Step inside the expansive 3 story foyer, abounding with VIEWS and natures magnificence. Created for memories, a peaceful sanctuary for SHARING every moment, here is a celebration of life and a living oasis. For those who seek solace, the 1st floor primary suite offers an private retreat. UNWIND year round in the IDYLLIC island get away with INDOOR HEATED POOL, HOT TUB plus a TIKI BAR. Enjoy the expansive view balcony, and at night sit by the FIREPIT to enjoy the haven of STARRY NIGHTS. There are 7 bedrooms and 9 bathrooms....ideal for entertaining friends and family (every bedroom has private bathroom access on each of the 3 floors). A media room is prepared on the 2nd floor; ADD the GOLF SIMULATOR or MUSIC STUDIO in the walkout lower level. The 2nd circular driveway in the rear provides abundant parking and direct access for your automobile COLLECTION, and the oversized 6 car garage can accommodate even more treasures. Live life, and work from a private estate with A NEW VIEW EVERY DAY! Schedule your private tour of 94 FOXBERRY DRIVE. VISit today!

94 Foxberry Dr, New Boston

Listing courtesy of Marianna M Vis from Four Seasons Sotheby's Int'l Realty. ()
$5,900,000
4 Beds ⋅ 5 Baths ⋅ 73544856 MLS
Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and rooms and additions in several directions in this very private location of North Chatham....Choice of three primary bedrooms with attached baths... Views over Chatham Harbor and beyond.......Beach and boating just an easy walk away. Or swim and relax in your own backyard in the heated Gunite pool...Property has been very well maintained by the current owner who has been here for over 36 years and completed a new roof, many new windows, new bedroom addition, newer family room addition and more.....All information here has not been independently verified and buyer should do his/her own due diligence by checking with their attorney, and zoning and building rules and by laws, etc....Assessment numbers subject to change with new Fiscal Year.

95 Cotchpinicut, Chatham

Listing courtesy of Listing Agent: John Burke from Listing Office: William Raveis Chatham.
$5,900,000
3 Beds ⋅ 4 Baths ⋅ 5097197 MLS
Originally built circa 1815 Federal, Strawbery Court is one of Portsmouth's most distinctive residences, ideally positioned in the heart of Portsmouth's Historic South End. Long known as the beloved Strawbery Court Restaurant, the property was thoughtfully reimagined as an exceptional private residence. Expanded by renowned builder Peter Kasnet, the home beautifully blends nearly two centuries of history with refined modern living. Overlooking a picturesque city park beside the iconic Strawbery Banke Museum, the residence is moments from Prescott Park, the Piscataqua River waterfront, acclaimed restaurants, boutique shopping, galleries, theaters, and marinas. Few homes offer such an extraordinary combination of history, location, and lifestyle. Offering approximately 3,100 square feet, the residence features three bedrooms, three-and-one-half baths, two private offices, six working fireplaces (five gas and one wood-burning), radiant heated bathroom floors, a heated driveway, and a beautifully enclosed brick courtyard, creating an uncommon sense of privacy in the heart of downtown Portsmouth. A landmark residence that reflects the rich architectural heritage, enduring character, and exceptional lifestyle of Portsmouth's Historic South End. Mixed Use Zoning.

20 Atkinson St, Portsmouth

Listing courtesy of Tony Jalbert from Tate & Foss Sotheby's International Rlty. ()
$5,900,000
6 Beds ⋅ 8 Baths ⋅ 73533378 MLS
The newest release within a private gated enclave in South Chatham's emerging luxury corridor, 50 Sylvan Way is a bespoke custom estate minutes from the Cape's most iconic downtowns, beaches, and dining, yet removed enough to feel like a world apart. Thirteen rooms across over 6000 square feet of living space sited on 1.635 bucolic acres. A first-floor primary wing. Three-car garage. Every bedroom ensuite. An open-concept great room with soaring ceilings anchors the floor-plan, while a fully finished basement provides a complete auxiliary level for guests and entertaining — a depth of program rarely found. Outside, a pool and integrated jacuzzi anchor the aquatic experience, framed by a dramatic firewall feature and wraparound deck purpose-built for outdoor living at scale. Constructed by R.A. Martin — among the most trusted names in Chatham construction — the property offers a rare opportunity to customize finishes to suit. A singular proposition in the Chatham marketplace!

50 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$5,900,000
7 Beds ⋅ 5 Baths ⋅ 73526631 MLS
There is a town at the end of Martha's Vineyard. The road narrows, the houses thin, and the light changes. This is Aquinnah; the westernmost town, clay cliffs, a lighthouse, and one of the smallest year-round populations on the Vineyard. Compound-scale offerings rarely come to market here. 19 Locust Lane is one of them. Nearly 17 acres high above Vineyard Sound, with open water views to the Elizabeth Islands. A custom Dutch Colonial main residence and separate guest house, both built in 2005. Cedar shake. Stone walls. Built to belong to the landscape, not compete with it. Inside: over 6,000 square feet across six bedrooms. Wide-plank floors, an open-plan dining room, and a gourmet kitchen with a Tuscan oven. At its center, a great room with cathedral ceiling, cedar trusses, and a floor-to-ceiling stone fireplace, facing the ridgeline and water beyond. Room to host, with the flexibility of two living spaces. Aquinnah has kept its character. This is the place that lets you stay there.

19 Locust Ln, Aquinnah

Listing courtesy of Listing Agent: Creatini Group from Listing Office: eXp Realty LLC - Corporate Office.
$5,900,000
4 Beds ⋅ 4 Baths ⋅ 24165905 MLS
Welcome to your waterfront hidden gem! A once in a lifetime opportunity on the Connecticut River featuring 381 feet of direct waterfront, private two boat dock, private horseshoe bay and panoramic north facing views up the river. This modern Contemporary private estate features 5,600+ square feet of living space! Open floor plan, stunning water views from every room! The living room features cozy fireplace, floor to ceiling windows and opens to a 750 square foot inviting deck ideal for relaxing, entertaining, soaking in the hot tub, peaceful sunsets or simply taking in the ever-changing river views. A lower level 750 square foot patio overlooks landscaped grounds, gardens and new stone fire pit area. The chef's kitchen is a dream featuring an oversized granite island, high-end stainless-steel appliances, custom cabinetry, wet bar, wine chiller that invites both gourmet cooking and effortless hosting. Designed for comfort, the home offers multiple luxurious bedroom suites each with sweeping views, spa like bathrooms, walk in closets, hardwood floors and high ceilings. It is perfect for an in-law bedroom or an au pair suite. Spacious additional bedrooms with views, entertainment room, private office with views, a loft, 4.5 bathrooms. A 5-car garage provides ample space for cars, outdoor lawn equipment or storage. A luxury lifestyle experience unlike any other on the Connecticut shoreline.

12 Rocky Point Rd, Old Saybrook

Listing courtesy of Sharon Linder from Berkshire Hathaway NE Prop.. (860) 460-8862 (860) 388-3411
$5,895,000
6 Beds ⋅ 5 Baths ⋅ 24196978 MLS
A truly exceptional private estate, this country compound set on more than three private acres, blends timeless character, refined design, and modern luxury. Anchored by a beautifully preserved 1932 main residence and an extraordinary 2,300-square-foot poolside entertainment barn, the property is designed for both everyday living and effortless entertaining. The main residence offers five bedrooms and three full baths, including a luxurious primary suite with spa-like bath, expansive walk-in closet, and private deck overlooking the grounds. Gracious formal living and dining rooms complement a chef's kitchen opening to the family room and breakfast area. A finished lower level provides additional living and entertaining space. The poolside barn is a destination unto itself, with a dramatic Great room, wet bar and kitchenette, private gym, home office, full bath, and outdoor shower. Expansive lawns, perennial gardens, multiple outdoor fireplaces, a spectacular swimming pool, and gracious dining veranda complete the grounds. Distinct living and entertaining spaces flow effortlessly together, creating an experience like no other.

474 Brookside Rd, New Canaan

Listing courtesy of Christine Saxe from Compass Connecticut, LLC. (203) 273-1548 (203) 442-6626
$5,895,000
4 Beds ⋅ 6 Baths ⋅ 24166955 MLS
Everything stays on the other side. That is what people here say about the footbridge. You cross it, and whatever you were carrying does not come with you. Compo Mill Cove is a gated private peninsula of nineteen homes on Long Island Sound, and no car has come out here since 1903. It is the reason the loudest thing you hear most mornings is the tide turning under the bridge. Everyone in this town is trying to buy quiet. Out here it is structural. This is the one with the water in every room: 5,567 SF of Brooke Girty-designed shingle style, built in 2008 and laid out so the Sound is never more than a glance away. Century-old reclaimed French oak floors. A three-story Nautilus stair through the center of the house. Five fireplaces. A Viking and SubZero kitchen. A primary suite with its own fireplace, dual walk-ins and a balcony above the water. Four bedrooms, generously scaled, plus a full third floor for guests, a studio or an office. Then the part you actually live in. A screened porch for the mornings. A Brazilian hardwood deck and hot tub for the evenings. Your own sandy beach with a kayak pulled up on it, held by a Race Coastal-engineered bulkhead. A private gate opening into the protected shoreline and woodland of Sherwood Island State Park. Green's Farms station minutes away, Manhattan about an hour. Nineteen homes. There will not be a twentieth. Your car is 150 feet away. You will not want it.

46 Compo Mill Cv, Westport

Listing courtesy of Evangela Brock from Douglas Elliman of Connecticut. (203) 253-2356 (203) 622-4900
$5,895,000
7 Beds ⋅ 9 Baths ⋅ 73384674 MLS
Tucked away on one of Southborough’s most coveted cul-de-sacs, 14 Lovers Lane is a breathtaking custom-built estate that redefines luxury living. Crafted with the highest standards and attention to detail, the home showcases timeless architectural design and exquisite millwork throughout. From the grand foyer with soaring ceilings to the richly appointed formal rooms, every space is thoughtfully curated to impress and inspire. The heart of the home is a spectacular chef’s kitchen with top-of-the-line appliances, custom cabinetry, and a sunlit breakfast nook overlooking the grounds. The adjoining family room—with its stone fireplace and coffered ceiling—invites connection and relaxation. Outside, the grounds offer a tranquil and elegant backdrop for everyday living, with a bluestone patio, outdoor kitchen, and covered veranda that seamlessly extend the living space into nature. Each detail is thoughtfully chosen to enhance comfort, functionality, and timeless design.

14 Lovers Lane, Southborough

Listing courtesy of Listing Agent: Gina Anderson from Listing Office: MGS Group Real Estate LTD.
$5,890,000
4 Beds ⋅ 5 Baths ⋅ 5108166 MLS
Set gracefully within the dunes, this exceptional Seabrook residence offers a rare sense of privacy, beauty, and connection to the Atlantic. One of only a select few homes in Seabrook with a private, water-facing pool, the property is moments from the beach, reached by a path that winds naturally through the dunes. Remarkably private and not located in a flood zone, it offers an uncommon combination of tranquility and true oceanfront living. Spanning three thoughtfully designed levels, the contemporary home is defined by natural light, refined finishes, and sweeping views that unfold from nearly every room. From sunrise over the water to evenings spent gathered around the pool, the home is designed to make the most of its extraordinary setting. Created equally for intimate family life and effortless entertaining, the beautifully finished lower level opens to an exceptional outdoor environment. A private saltwater pool, parking for 9 with 3 in the garage, softly illuminated landscaping, and direct beach access create an idyllic setting for long summer days, celebrations, and unhurried time with family and friends across generations. From every level, expansive entertaining spaces frame uninterrupted Atlantic views stretching from Nubble Light to Cape Ann, beautifully framed by the surrounding dunes. The result is a home that feels both deeply connected to its natural surroundings and effortlessly suited to modern coastal living. A rare opportunity to experience the Atlantic not simply as a view, but as a way of life.

126 Ocean Blvd, Seabrook

Listing courtesy of Caleb DeVries from Engel & Volkers Portsmouth. (Phone: 603-937-7784)
$5,875,000
3 Beds ⋅ 4 Baths ⋅ 5099532 MLS
Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame home. Outside, perennial gardens give way to open pasture suitable for a few horses or sheep, woodland trails for riding, hiking, cross-country skiing, and snowshoeing and direct access to the GMHA trail system. Built in 2015, the three-bedroom residence is defined by soaring spaces, exposed fir beams, walls of glass, and craftsmanship that feels substantial without being formal. Nearly every principal room is oriented toward the eastern views, bringing the surrounding mountains and changing Vermont landscape into daily life. The main level is equally comfortable for quiet everyday living or a houseful of guests, with an open kitchen, dining area, and dramatic great room centered around a floor-to-ceiling double-sided stone fireplace. A more intimate sitting room, screened porch, expansive deck, and primary suite are also located on this floor. Upstairs are a loft office, two en suite guest bedrooms, and a media room. The walk-out lower level adds a gym, infrared sauna, workshop, and temperature-controlled wine room with capacity for approximately 1,000 bottles. An 18.5 kW solar array supports near net-zero living, while a three-bay garage accommodates vehicles, sporting equipment, and the gear that comes with an active Vermont life. Just minutes from Woodstock Village, 16 miles from Killington Resort, and 26 miles from Okemo Mountain Resort.

115 Eastman Rd, Woodstock

Listing courtesy of T Story Jenks from LandVest, Inc/Woodstock. ()
$5,850,000
5 Beds ⋅ 6 Baths ⋅ 22601111 MLS
This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

15 Windy Hill Way, Chatham

Listing courtesy of Listing Agent: Timothy P Bailey (timbailey1@verizon.net) from Listing Office: John C Ricotta & Assoc..
$5,850,000
5 Beds ⋅ 6 Baths ⋅ 73495151 MLS
This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

15 Windy Hill Way, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..
$5,844,000
8 Beds ⋅ 8 Baths ⋅ 5104275 MLS
Rare Stowe Offering: Extraordinary mountain estate Estate + Buildable Lot on Edson Hill. Discover a once-in-a-lifetime opportunity in Stowe—Eden, a stunning 22± acre estate paired with an adjacent 3.98-acre buildable lot on exclusive Edson Hill. Eden offers 8 bedrooms, 8 baths, a gourmet chef’s kitchen, vaulted ceilings, and multiple spaces for entertaining, including a great room, sunroom with stone fireplace, and a lower-level wellness retreat with twin spas, sauna, steam shower, and game room. Outdoor living is elevated with twin ponds, tennis court, heated pool, hot tubs, and exquisite gardens—all with breathtaking views of Mount Mansfield and the Worcester Range. The adjacent lot provides a rare chance to expand or build anew. Surrounded by multi-million dollar homes one of Stowe's most exclusive streets. It features mature trees, municipal water, approved wastewater and driveway permits, direct access to Wiessner Woods’ trails, streams, and sugarhouse—and extraordinary views that mirror those from the main estate. Just minutes from Stowe Mountain Resort and some of the area's best dining, this combined offering delivers unparalleled mountain lifestyle, seclusion, and potential.

740-2 Edson Hill Rd, Stowe

Listing courtesy of The Nancy Jenkins Team from Nancy Jenkins Real Estate. ()
$5,800,000
7 Beds ⋅ 9 Baths ⋅ 73536264 MLS
Set on a beautifully flat lot in one of Wellesley’s most desirable neighborhoods, this exceptional Colonial offers a rare combination of luxury, space, and timeless design. Located in a special community with a picturesque meadow at its center, providing a peaceful setting. Featuring 7 bedrooms, 7 full and 2 half bathrooms, this thoughtfully designed home offers flexibility for today’s lifestyle. The stunning chef’s kitchen features a center island, top-of-the-line appliances, custom cabinetry, and separate walk-in pantry. Spacious living areas, elegant formal rooms, high ceilings, natural light, and beautiful finishes create an inviting atmosphere. The luxurious primary suite offers a private retreat, while the generous secondary bedrooms provide comfort for family and guests. Multiple spaces allow for work, recreation, and entertaining. The expansive backyard is ideal for outdoor enjoyment, conveniently located near Wellesley’s top-rated schools, town center, train, and major routes.

45 Longmeadow Rd, Wellesley

Listing courtesy of Listing Agent: Lisa Sewall from Listing Office: Coldwell Banker Realty - Wellesley.
$5,800,000
6 Beds ⋅ 9 Baths ⋅ 73525014 MLS
Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. Association located dock on Lake Tashmoo!

31 Lambert's Cove Rd., Tisbury

Listing courtesy of Listing Agent: Idalyn Macchia Gilstad from Listing Office: Wallace & Co. Sotheby's International Realty.
$5,800,000
10 Beds ⋅ 3 Baths ⋅ 73490272 MLS
The iconic Hooper-Lee-Nichols House, built c.1685 and recognized as the second-oldest home in Cambridge, now seeks its next chapter. The three-story Georgian structure is distinguished by its central chimney and balanced proportions. Set on an expansive 18,012± sq. ft parcel, the house is sited well back from the street with a detached carriage house/garage accessed from Kennedy Road. Today it stands as the headquarters of History Cambridge and though it is currently configured for office use, future owners will have the opportunity to reimagine the interiors as a grand private home. The property is protected by historic preservation measures ensuring its integrity for generations to come. An easement held by the Massachusetts Historical Commission safeguards important interior features, while its location within the Old Cambridge Historic District safeguards the exterior. The Hooper-Lee-Nichols House is an invitation to stewardship—an opportunity to carry forward a 340-year legacy.

159 Brattle Street, Cambridge

Listing courtesy of Listing Agent: Monahan Barker Team from Listing Office: LandVest, Inc., Ipswich.
$5,800,000
4 Beds ⋅ 8 Baths ⋅ 5070706 MLS
“Tansy Hill Farm” is the quintessential Stowe, Vermont breathtaking, timeless, and meticulously crafted home. This exceptional farmhouse was designed and built by the current owners with an uncompromising eye for quality and detail. Offering over 8000 sq. ft. of beautifully appointed living space, the floor plan is both expansive and exceptionally functional. The main level features a grand living room with French doors opening to a gracious stone patio; an inviting library warmed by a gas fireplace; and a gourmet kitchen overlooking the circular cobblestone drive. The adjoining dining area, also with a gas fireplace, leads seamlessly into a stunning four-season sunroom equipped with a built-in gas grill. A spa-like primary suite with vaulted ceilings and office. A second bedroom offers vaulted ceilings and an extraordinary architectural centerpiece: a partial 20-foot faux oak tree with custom walnut stairs. Second floor offers 2 more spacious bedrooms complete with baths, a comfortable/family area with 1/2 bath, dining table and built in sleeping area. A spiral staircase leading to view the property completes the second floor. Finished basement with exercise room and hot tub. Three car attached garage. Charming one bedroom 2 bath cottage, a 4 stall barn complete with fully fenced area for your animals. Pole barn for equipment and toys. Over 28 acres of fields, woods, ponds and completely private bordering Sterling Brook!!

64 Needle Leaf Ln, Stowe

Listing courtesy of Angela Dodge from Pall Spera Company Realtors-Morrisville. (Phone: 802-279-8670)
$5,795,000
5 Beds ⋅ 6 Baths ⋅ 73569858 MLS
Sophisticated Katama Retreat with Pool and Custom Finishes - Tucked at the end of a lightly traveled road, this modern farmhouse blends sophisticated design, generous living spaces, and exceptional backyard privacy. Thoughtfully customized by the owners in collaboration with the builder, the home features distinctive design details and elevated finishes throughout. A dramatic wall of glass fills the open-concept great room with natural light and connects seamlessly to the outdoor entertaining areas. Spacious living and dining spaces are anchored by a gas fireplace and custom built-ins. The chef’s kitchen features marble countertops, commercial-style stainless and integrated appliances, an oversized center island, beverage refrigerator, and sliding glass panels opening to a poolside bar. A luxurious first-floor primary suite, private office, laundry area, and powder room complete the main level. The home offers five bedrooms and four-and-one-half baths, including a second en suite primary bedroom upstairs. Two additional upper-level bedrooms share a well-designed Jack-and-Jill bath. The finished lower level includes a fifth bedroom, full bath, and expansive game/media room with pool and ping-pong tables, providing flexible space for guests and recreation. Outside, the property becomes a private resort-style retreat with a heated 16-by-38-foot gunite saltwater pool and generous sun shelf. An expansive bluestone patio offers multiple lounge and dining areas, a fire table, and a separate wood-burning fire pit. Manicured grounds, thoughtful landscaping, broad lawn areas, and an enclosed outdoor shower complete the setting. With a strong rental income history, the property offers compelling potential for personal enjoyment and investment. Offered turnkey with indoor and outdoor furnishings for immediate enjoyment or continued rental use.

37 Plain Field Way, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$5,775,000
4 Beds ⋅ 4 Baths ⋅ 24179508 MLS
Where Architectural Inspiration Meets the Majesty of the Connecticut River. Perched majestically on 15.22 acres along the eastern bank of the Connecticut River, 89 River Road offers a rare convergence of architectural pedigree, natural beauty, privacy, and fully realized lifestyle design. Designed, owned, and meticulously crafted by one of America's leading architects, this 12,836-square-foot, three bedroom compound, completed in 2018, was conceived to inspire creativity, wellness, and a connection to the outdoors. Protected by parkland, Nature Conservancy, and Land Trust preserves, the heart of the home is defined by extensive, floor-to-ceiling glass walls that command uninterrupted, panoramic vistas of the Connecticut River while a scenic jeep road offers direct access to Chapman Creek and the River beyond. A seamless flow connects the breathtaking entertaining and living areas with a variety of outdoor decks and terraces. The estate offers a rare sanctuary designed to fuel both the mind and the body. It features an unparalleled suite of dedicated, professional- grade spaces that defy the ordinary. The Creative Hub: Fulfill your creative inspirations in one of four dedicated studios: a sky-lit art studio, a sky-lit writing/drawing studio, a fabrication studio, and a fully equipped woodworking shop.

89 River Rd, East Haddam

Listing courtesy of Colette Harron from William Pitt Sotheby's Int'l. (860) 304-2391 (860) 767-7488
$5,750,000
5 Beds ⋅ 5 Baths ⋅ 22601572 MLS
Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham, complete with deeded boat house! Encompassing over 4,000 square feet, this exceptional 5 Bdrm, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings and thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat with tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for family and guests. A walk-out lower level expands living space with an entertainment room and full bath. Features include new HVAC w/natural gas heat, Central A/C, outside shower, well-irrigation, spacious deck, yard with pool potential, and private stairs to the water. Beautifully sited on 1.83 acres of pastoral grounds, you'll enjoy over 230 feet of frontage on one of the most desirable boating waterways in Chatham, with deep water access to Nantucket Sound. This exceptional property just off the Chatham Loop offers both privacy and a picturesque natural setting only minutes to Town.

70 Judges Way, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski (lori@cireab.com) from Listing Office: Christie's International Real Estate Atlantic Brokerage.
$5,750,000
4 Beds ⋅ 5 Baths ⋅ 24177449 MLS
Your new fully custom near beach luxury residence is ready for you now... Introducing "White Birch", a masterfully executed collaboration between Fairfield County's premier Architect, Builder, & Designer, sets a new benchmark for bespoke coastal living and the effortless estate lifestyle. Every detail has been thoughtfully curated, every finish intentionally elevated, every inch built with specific intention and the highest level of craftsmanship. Completed in 2025 with gunite pool, hot tub, full outdoor kitchen, new patio & shower with changing stall - no expense was spared. Inspired by the world's finest hotels & surpassing that quality on 3 floors of living space: sophisticated & timeless rooms designed for quiet family time or large scale entertaining, peaceful reading nooks, 4 ensuite Bedrooms which includes the luxurious Primary w/balcony, fireplace, walk-in closets, and spa-caliber bathroom with soaking tub & steam shower; media/playroom with vaulted ceilings and full bath with sauna. Timeless paneling, rich ceiling details, organic textures & fabrics, and harmonious natural stone accents create an atmosphere of understated refinement and enduring beauty. Engineered with advanced smart home technology, commercial grade WiFi, & soundproof insulation ensures a seamless at-home experience. Set within the multi-million-dollar enclave of Fairfield Beach and just a stone's throw to the expansive LIS shoreline, this irresistible residence embodies the art of living beautiful

69 Birch Rd, Fairfield

Listing courtesy of Jaclyn Picarillo from Higgins Group Bedford Square. (203) 981-5012 (203) 226-0300
$5,750,000
6 Beds ⋅ 8 Baths ⋅ 73513932 MLS
Exquisitely crafted shingle-style home by Concord's Six Point Builders in the heart of Nashawtuc Hill, with direct access to miles of walking trails. The open first floor showcases custom millwork, a spacious gourmet eat-in kitchen with oversized island and the finest appliances. The family room is anchored by a stone fireplace overlooking the impeccably landscaped backyard, deck, and terraces . A screened porch , a stunning dining room, and the spacious living room provide perfect gathering spaces for family and friends. Upstairs offers five spacious en-suite bedrooms, including a luxurious primary suite with spa-like bath & a Jack & Jill walk-in dressing room/closet, plus an enormous laundry room with built in cabinetry. 2 private home offices add versatility on the first and second floor. The high-end walk-out lower level impresses with wine cellar, bar, billiards area, second LG washer & dryer, and guest suite. Experience the pinnacle of Concord living on iconic Nashawtuc Hill!

343 Nashawtuc Rd, Concord

Listing courtesy of Listing Agent: Kim Patenaude and Rory Fivek Real Estate Group from Listing Office: Barrett Sotheby's International Realty.
$5,750,000
5 Beds ⋅ 8 Baths ⋅ 73513467 MLS
Nestled in one of Needham’s most coveted neighborhoods, this custom-built shingled colonial exudes timeless elegance and exceptional quality. Set on a parklike 1.24-acre lot with a stately circular drive, the home offers unmatched curb appeal and an idyllic retreat. The main level features a gourmet kitchen with a massive island, a sunlit breakfast room overlooking the backyard, an executive office with rich woodwork, and expansive living, dining, and family rooms ideal for relaxing or entertaining. Upstairs, the primary suite includes a sitting room and dream closet, while four additional ensuite bedrooms, a secondary office/homework room, and a laundry room provide ample space and functionality. A graceful staircase, secondary back staircase, and elevator offer effortless access. The finished lower level features a spacious family room, gym, luxurious movie theater, and European-inspired stone wine cellar. Outside, enjoy a custom basketball court and meticulously landscaped yard.

50 Oxbow Rd, Needham

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.
$5,750,000
5 Beds ⋅ 5 Baths ⋅ 73506909 MLS
Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham. Encompassing over 4,000 sqft, this exceptional 5-bedroom, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings & thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat w/tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for guests. A walk-out lower level expands living space with an entertainment room and full bath. New HVAC w/natural gas heat, Central A/C, outside shower, well-irrigation, spacious deck, yard with pool potential, and private stairs to the water. Beautifully sited on 1.83 acres of pastoral grounds, you'll enjoy over 230 feet of frontage on one of the most desirable boating waterways in Chatham PLUS deeded rights to a boat house steps away!

70 Judges Way, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.

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