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$4,440,000
10 Beds ⋅ 10 Baths ⋅ 73582544 MLS
Court Street has long been known to mark the dividing line where the center ends and the West End begins. At its rise stands the Revere Guest House, an award-winning Provincetown inn shaped by nearly two centuries of life by the sea. Built circa 1830 as a sea captain's home, 14 Court Street carries its history quietly, with the scale, irregularities and intimate details of a place assembled through time rather than conceived all at once. Today, ten rooms unfold throughout the property alongside private living quarters. A brick courtyard gathers around a fire pit, while gardens, porches and a separate breakfast cottage create spaces to discover. For more than half a century, the Revere has welcomed travelers through its doors. Commercial Street and the harbor are moments away, yet the property sits above the movement of town, with water views that offer a quiet reminder of its connection to the sea. Few properties can tell the story of Provincetown without saying very much at all. 14 Court Street has been doing so for nearly two hundred years. The Revere Guest House now awaits its next chapter.

14 Court Street, Provincetown

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

$4,395,000
4 Beds ⋅ 6 Baths ⋅ 73580323 MLS
Truly one of kind property nestled in renowned Hunnewell Estates with horses and cows with the feel of Vermont yet close to Wellesley Center. 3 acres of a private sanctuary surrounded by conservation land and trails.. Incredible opportunity in Wellesley to have gardens, fruit trees, chickens... Gorgeous outdoor space with fire pits, zen waterfall, vegetable gardens with hand hewn raised beds from trees on the property. Orchard with 30 fruit and nut trees, 10 sugar maples for maple sugaring, herb garden, fragrance garden and chicken coop with run. Over 7200 sq ft of living on 3 levels. First floor main bedroom with full bath and double walk-in closets. Spa-glass conservatory off the main bedroom with built-in hot tub. Both a library and 2nd office off the main bedroom each with custom woodwork and built-ins. Large fireplaced living room with French doors along entire rear. Dining room perfect size for entertaining. Custom kitchen with large island and show stopping gorgeous stone fireplace that opens to the family room. Mudroom and laundry room complete the first floor. Perfect guest suite over the garage. Second level consists of and additional 2 large beds with walk-in closets and full bath. Lower level with large game room including a wet bar and media area. Additional playroom plus 2 more rooms with bath perfect for guests. 3 car garage. A must see!

150 Pond Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.

$4,395,000
4 Beds ⋅ 3 Baths ⋅ 73576832 MLS
Exceptional four bedroom single family located in the heart of the South End! Victorian double parlor level with pocket doors plaster moldings, wood casings, & marble mantels. A beautiful entertaining space & intimate den with home theater & wet-bar. The kitchen, dining & living level has an open floor plan with convenient half bath & wet-bar. The custom Venegas design kitchen is a cook's delight! Finished with an oversized island, quartzite counters, Sub-Zero, Wolf appliances & great storage. The primary suite is an oasis. The spacious bedroom connects seamlessly through the spa style bath with glass enclosed shower, double vanity to the dressing room with laundry & office. A full staircase continues to the amazing roof-deck with 360 degree city views! Lower entrance with easy access for bikes & strollers. Two additional spacious bedrooms & full bath with laundry. Garden level family room with kitchenette & office leads to a beautiful private patio. Control 4 A/V, central a/c & more.

112 Appleton Street, Boston

Listing courtesy of Listing Agent: Sprogis Neale Doherty Team from Listing Office: Sprogis & Neale Real Estate.

$4,395,000
3 Beds ⋅ 6 Baths ⋅ 73572956 MLS
Set along 163 feet of Lagoon frontage with its own sandy beach, 267 Barnes Road offers a fresh, contemporary take on waterfront living in Oak Bluffs. Set on 1.25 acres, the 4,046-square-foot home balances privacy with comfortable spaces for entertaining or relaxing. Oversized windows bring Lagoon views into nearly every room. The main level features soaring ceilings, a wood-burning fireplace, wet bar, and an eat-in kitchen opening to a sunny patio. A separate two-room wing with full bath and private deck offers flexible space for an office, den, studio, or guest accommodations. Upstairs, the primary suite includes a fireplace, walk-in closets, ensuite bath, and Lagoon-facing deck. Two additional ensuite bedrooms open to a wraparound deck and 3-season porch. The refinished 2,000-square-foot walk-out lower level includes a full bath, laundry, and space for a gym, media room, or additional living area. Offered fully furnished, this waterfront retreat is ready to enjoy. Whether you are hosting a full house or savoring a quiet weekend, the Lagoon becomes your backdrop: sunrise coffees, afternoon swims, and sunset gatherings right at the water’s edge.

267 Barnes Road, Oak Bluffs

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$4,388,000
5 Beds ⋅ 7 Baths ⋅ 73475892 MLS
Elegant Custom Estate on 1.8 Acres in Weston! This stunning 8,000+ sq ft Colonial sits on a beautifully landscaped, level 1.8-acre lot with a private drive and circular entry. Inside, a grand foyer with a sweeping staircase opens to formal living and dining rooms with soaring ceilings, crown moldings, and French doors. The gourmet kitchen with marble countertops, super high-end & branded appliances flows into a spacious family room and sunroom, both with fireplaces. A luxurious first-floor primary suite offers a spa-like bath, dual walk-in closets, private office, and gym. Residents and guests can unwind in the spacious private theater, perfect for an immersive entertainment experience. The expansive finished basement offers an additional comfortable living area, ideal for recreation, relaxation, or extended guest stays.Outdoors, enjoy a bluestone patio with built-in grill and fire pit, plus a resort-style pool with waterfall spa, surrounded by elegant stonework. Very near to schools.

568 Wellesley St, Weston

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.

$4,375,000
5 Beds ⋅ 7 Baths ⋅ 73570598 MLS
Set on coveted Mashpee Neck, this spectacular waterfront home seamlessly pairs classic Cape Cod architecture with modern luxury. Built in 2025, the residence showcases superlative quality and craftsmanship throughout, while a private deep-water dock delivers the best of coastal living with access to Nantucket Sound. Immediately upon entering, an open layout defines the light-filled living spaces, complete with beamed ceilings, hardwood floors, and custom millwork. The eat-in chef's kitchen is equipped with professional-grade appliances, stone countertops, and a butler's pantry, ideal for casual living or grand entertaining. In the adjacent living room, a gas fireplace and wet bar offer a refined ambience, while sliding glass doors open to a waterside deck for al fresco dining. Providing the utmost comfort and convenience, an expansive first-floor primary suite leaves nothing to be desired, complete with two walk-in closets, a private balcony, and a sumptuous bathroom. On the second level, four en suite bedrooms ensure well-appointed accommodations for family and friends. The finished lower level provides endless opportunities for entertainment, with a home theater, fitness room, bar, and sliding glass doors that open to a covered terrace with a built-in barbecue overlooking the water. Located minutes from Willowbend, Mashpee Commons, and Cotuit Village, this stunning waterfront home is ready to be enjoyed.

28 Quaker Run Road, Mashpee

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$4,350,000
4 Beds ⋅ 4 Baths ⋅ 73577841 MLS
Tucked away from the street amid mature trees in coveted Mid Cambridge, this 2023 free-standing residence is an architectural masterpiece and private sanctuary. Designed by Suzumori Architecture and built to Passive House standards, the home pairs sculptural modernism with exceptional comfort, efficiency, and wellness. Curved walls, soaring 12-ft ceilings, a dramatic white oak staircase, and full-height triple-pane windows flood the interiors with natural light while framing the extraordinary two-tier garden by Christie Dustman Co.—a secluded urban oasis of native plantings, custom stonework, trellises, and tranquil gathering spaces. The Scandinavian-inspired kitchen showcases a 10-ft quartzite island and artisan mosaic backsplash. The soaring primary suite features a jaw-dropping Zen luxe bath with floor-to-ceiling tile, curbless shower, and dual vanity. Complementing the primary suite are two additional bedrooms, a full bath, and a conveniently located laundry room, while a treetop studio with Juliet balcony provides a light-filled retreat for fitness, work, or creative pursuits. The finished lower level offers recreation space, guest accommodations, and a fourth bedroom with full bath. Enhanced by state-of-the-art smart-home technology, this one-of-a-kind residence delivers a holistic living experience where architecture, nature, and tranquility exist in perfect harmony.

12 Fayette Street (Rear), Cambridge

Listing courtesy of Listing Agent: Maggie Dee + Charles Cherney Team from Listing Office: Compass.

$4,350,000
6 Beds ⋅ 7 Baths ⋅ 73507578 MLS
Rare Oceanfront Queen Anne Victorian Estate | Beachhurst | Boston Skyline Views directly on the ocean just 11 miles from Boston, this magnificent shingle-style home offers an unparalleled oceanfront lifestyle. Featuring 6 bedrooms (4 ensuite), & multiple outdoor spaces, the home is designed for grand entertaining and relaxed coastal living. Wake to sweeping views of Boston's glittering skyline, harbor islands, and open sea from nearly every room. Direct access to Eisen Beach puts sand and surf at your doorstep. The chef's kitchen opens via French doors straight to the water, while the wraparound covered porch and pergola invite endless hours of coastal enjoyment. The original craftsmanship designed by Richard Morris Hunt shines with inlaid hardwood floors, hand-carved balusters, stained-glass entry doors, rich wood paneling & multiple ornate fireplaces. Swampscott's most iconic oceanfront home with green lawn, all just minutes from the commuter rail with direct service to Boston.

251 Puritan Road, Swampscott

Listing courtesy of Listing Agent: Beth Dickerson from Listing Office: Gibson Sotheby's International Realty.

$4,350,000
5 Beds ⋅ 7 Baths ⋅ 73488436 MLS
Welcome to Bay Pond Road, a private waterfront enclave in the heart of Powder Point. Make summer exceptional with views of boats sailing by, beautiful sunsets from a covered porch, and exclusive water access with a boat mooring. This gracious home is set on almost 1acre of beautifully landscaped level grounds offering ample opportunities for pool and guest house/ADU expansion. Extensively renovated in 2009 by a notable Boston architect, this 5 BR, 7 bath, 5800sf home combines understated elegance with refined modern living. An expansive first floor main suite offers 2 full baths, 2 walk-in closets and overlooks the English gardens. Generous light-filled rooms, marble kitchen and baths, 3 fireplaces, walls of French doors, and stone patios are all hallmarks of this property. Every element of this home, from the gas lanterns to the custom millwork was selected with intention. A rare opportunity for a new owner to create their own tradition of exceptional living in coveted Powder Point

39 Bay Pond Rd, Duxbury

Listing courtesy of Listing Agent: Suzanne Stevens from Listing Office: South Shore Sotheby's International Realty.

$4,299,000
5 Beds ⋅ 6 Baths ⋅ 73574948 MLS
Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully renovated, maintained and updated, blending classic architecture with modern comfort. This 5-bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and relaxed daily living. Water views serve as a serene backdrop to the large modern kitchen, where the natural light dapples and shines all day. It's what everyone craves: the bright, sunny, warm inviting hub of the home. There is an attached mudroom with custom lockers/cabinets, and radiant heat floors. A large family room is attached and is highlighted by a gas-burning fireplace. The expansive living and dining rooms offer plenty of space for more formal entertaining and big groups. One of our favorite features is the study, tucked off the living room and connected to a divine screened-in porch. The natural woodwork and handsome architecture harken to yesteryear while providing the perfect home office and a place to unwind when done working. A generous primary suite is a private retreat with a spacious bath and ample walk-in closets. There are 4 other ample bedrooms, 3 of which are connected to baths, and a second-floor laundry complete this floor. The basement has a huge media and game room, sauna, gym, wine cellar and direct access through a mudroom to a covered patio. Several curated outdoor dining and gathering areas invite entertaining, sunset dinners or quiet reading, overlooking the pond. There is also a full walk-up attic with great ceiling height, unfinished and waiting for your inspiration. An oversized two-car garage with soaring ceilings complete the must-haves. Kayak, skate, go fishing and enjoy life on the water in one of Winchester's most prized, quiet neighborhoods!

4 Dartmouth, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$4,295,000
7 Beds ⋅ 7 Baths ⋅ 73578127 MLS
Set on a landscaped, level lot in coveted West Newton Hill, this 1880 Victorian blends timeless architectural character with exceptional scale and comfort. Rich period details, soaring ceilings, generous proportions, and abundant natural light define the home. The sun-filled kitchen and family room, surrounded by windows on three sides, features a gas fireplace, oversized island, dining area, built-in office nook, and direct access to a bluestone patio and flat backyard. The main level also offers elegant formal living and dining rooms, a music room, mudroom, and 2 half baths. The 2nd floor includes a spacious primary suite with private office, deck, dressing room, and bath, plus three additional bedrooms, two full baths, and laundry. The third floor offers two bedrooms, a full bath, and family room. The finished lower level includes a guest bedroom, full bath, second laundry, storage, and flexible bonus space.

14 Winthrop St, Newton

Listing courtesy of Listing Agent: The Drucker Group from Listing Office: Compass.

$4,295,000
5 Beds ⋅ 7 Baths ⋅ 73574473 MLS
Why wait for new construction? Built in 2025, this Waban residence offers all the benefits of modern living in one of the most coveted locations on the same block as the recently built Zervas Elementary School and Richardson field and playground. Conveniently located with easy access to the heart of Waban Center, Newton Highlands and 4 Corners, as well as the the Windsor Club, and the MBTA Green Line (D), offering effortless access to Boston and beyond.Thoughtfully designed for today's lifestyle, the open-concept main level features a private office, elegant dining room, and a chef's kitchen showcasing custom cabinetry, top-of-the-line appliances, an oversized island, and a sun-drenched breakfast area with a beautiful built-in banquette. A spacious family room with fireplace flows seamlessly to a covered patio with outdoor kitchen, an entertainer's dream inside and out, complete with a large and private flat backyard. Upstairs, the luxurious primary suite impresses with two walk-in closets and a spa-inspired bath featuring a soaking tub, steam shower, and heated floors. Three additional ensuite bedrooms and a dedicated laundry room complete the second floor. A versatile third floor offers the ideal retreat for work or relaxation with another full bathroom, while the finished lower level provides a fifth bedroom, full bath, gym with built-in sauna, and media/playroom with space for every need. Solar panels are owned and included in the sale. Enjoy all the benefits of nearly new construction, in an established Waban location you'll love coming home to.

98 Beethoven Ave, Newton

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.

$4,295,000
4 Beds ⋅ 4 Baths ⋅ 73573613 MLS
BEACHFRONT LIVING AT ITS FINEST! Welcome to 41B Wingaersheek Road, a rare offering with 48 feet of private beachfront on one of Gloucester’s most coveted shorelines. Built by Honomobo, this beautifully designed modern modular home combines precision engineering with coastal luxury, connecting you effortlessly to the ocean. Built in Western Canada to withstand extreme temperatures, this property offers a sophisticated alternative to conventional construction, with the home factory-built in precision-fabricated modules and assembled on-site. The property features two beautifully appointed open-concept residences, each offering 2 bedrooms and 2 full baths, with a convenient lockout door providing ultimate flexibility to use the property as an expansive single-family featuring a versatile layout of 4 beds, 4 baths or as two independent units for a multi-family investment. Both residences feature sun-drenched living spaces, in-unit laundry, and sleek kitchens with quartz countertops, center islands, and stainless steel appliances. Outdoor living is thoughtfully designed with a spacious first-floor deck featuring both open and screened-in areas, perfect for enjoying the coastal setting in any season while the top floor deck takes full advantage of the location, offering unobstructed views of the private beach. The highly engineered building envelope pairs structural steel with wood framing to deliver incredible durability and a clean, modern aesthetic, while extensive closed-cell spray-foam insulation, high-efficiency heat-pump HVAC, and a heat-recovery ventilation (HRV) system provide year-round comfort and continuous fresh air. Designed for effortless seaside living, just step outside and follow your private path directly to the beach for a day of swimming or strolling the shoreline. Whether you envision a private family compound, a luxury vacation retreat, or a lucrative income-producing property, this meticulously executed home delivers a remarkable opportunity to own a premier piece of the Gloucester coastline.

41-B Wingaersheek Rd, Gloucester

Listing courtesy of Listing Agent: The Apex Team from Listing Office: Apex Realty Group, LLC.

$4,295,000
4 Beds ⋅ 4 Baths ⋅ 73542573 MLS
Experience the best of Magnolia waterfront living at 16 Hesperus Circle. Situated at the center of a truly private landscape with unobstructed, breathtaking views of the Atlantic, this exceptional residence offers over 4,000 square feet of living space with 4 bedrooms and 3.5 baths. A flowing open layout is designed to maximize natural light and showcase the spectacular coastal setting, creating an ideal space for both everyday living and entertaining. Step outside to a stunning infinity pool overlooking the water, where endless ocean vistas provide the backdrop for unforgettable gatherings and quiet moments alike. Enjoy the rare combination of privacy and convenience, with Magnolia Beach, downtown Magnolia's shops and restaurants, and all that Cape Ann has to offer just a short walk away. A remarkable opportunity to own a premier waterfront home in one of Gloucester's most coveted seaside neighborhoods.

16 Hesperus Circle, Gloucester

Listing courtesy of Listing Agent: Amanda Armstrong Group from Listing Office: Compass.

$4,295,000
4 Beds ⋅ 4 Baths ⋅ 73509923 MLS
This exceptional coastal retreat was designed to capture sweeping views of tidal salt marshes, natural vistas, and Nantucket Sound from nearly every room. Soaring ceilings & dramatic walls of glass fill the home with natural light and frame spectacular sunsets. Multiple sliders open to an expansive wraparound deck for effortless indoor-outdoor living. Chefs kitchen, dual living areas, and adjacent open dining create an exceptional setting for relaxing or entertaining. There's nearly 5,000 sq on three levels, with 4 bedrooms and 3.5 baths. The luxurious primary suite offers panoramic water and sunset views. A finished multi-room lower level includes family room and convenient kitchenette. Solar panels, generator, gas heat, Central A/C, outside shower, reclaimed wood floors & more. You'll enjoy a seasonal dock/catwalk on Bucks Creek for kayaking, paddle-boarding, or clamming from your own back yard - and the calm waters of Harding's Beach are a short stroll via sidewalk. Don't miss out!

38 Indian Trail, Chatham

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

$4,288,000
4 Beds ⋅ 4 Baths ⋅ 73574433 MLS
4 BEDROOMS, 3 FULL BATHS, 6442 SQUARE FEET.Situated on 2 acres of land with room to develop up to 6,000 more square feet onto the existing property, this is an unbelievable opportunity to be in the best location in Weston with the ability to expand — just a 15-minute commute to Boston. This renovated ranch-style estate is set in Weston's coveted South Side Golf Club neighborhood, bordering conservation land and scenic walking trails. Inside, the home offers light-filled, open living areas, dramatic high ceilings, and expansive windows throughout. A chef-caliber kitchen anchors the home with Wolf and Sub-Zero appliances, quartz counters, and custom cabinetry. The main level features a luxurious primary suite alongside two additional bedrooms, while the finished walkout lower level adds a guest/au pair suite, kitchenette, media room, and additional flexible living space.

80 Doublet Hill Rd, Weston

Listing courtesy of Listing Agent: William Montero from Listing Office: Gibson Sotheby's International Realty.

$4,275,000
4 Beds ⋅ 7 Baths ⋅ 73576629 MLS
Sited at the tip of one of the coveted West Dennis Fingers, this renovated waterfront home offers unobstructed, 180-degree water views that capture the feel of looking out from the deck of your private ship. Designed in an L-shape to ensure quiet, view-filled spaces, the home is a true private sanctuary at the water's edge where you can watch the sunrise, sunset & passing boats against the backdrop of Bass River & Nantucket Sound. Deep-water dockage includes a 72-foot dock on the protected lagoon side, plus a rare license & permit for a second dock on the river side. Extensive updates over the last five years feature new steel framing, a brand-new kitchen, refreshed baths, new wood floors, HVAC, whole-house generator and a custom seawall. The flexible floor plan offers primary suites on both the main & upper levels, plus a dedicated guest wing. Complete with a spacious two-car garage, seaside fire pit, and seamless ocean access, this is an extraordinary opportunity to establish your family's Cape Cod legacy.

18 Wendy Way, Dennis

Listing courtesy of Listing Agent: Katie Clancy from Listing Office: William Raveis Real Estate & Homes Services.

$4,250,000
6 Beds ⋅ 7 Baths ⋅ 73580905 MLS
Exquisitely renovated and restored in 2016, this architecturally significant fieldstone-faced attached single family marks the perfect confluence of historic charm, modern luxury, and a wildly desirable location in the heart of Brookline’s Washington Square area. Spanning more than 5700 sq ft of spectacular living space, this property serves as a master class in timeless craftsmanship and a showcase for beautifully curated fixtures and finishes. The main level, graced with 11’ ceilings, features an elegant entry foyer with a fireplace and built-in benches flanked by a spacious bay-front living room with diamond-paned glass detailing & an addl. fireplace. The dining room is an entertainer's paradise with bespoke built-in bar & coffee stations, a gas fireplace, and French doors to a professionally landscaped deck/oasis with irrigation. The open-plan kitchen is a true showstopper, outfitted with floor to ceiling cabinetry, marble countertops, premium appliances, a stone-capped island, and a luminous breakfast area. A sculptural central staircase with a multi-level modern glass chandelier leads to the second level, equipped with a luxe primary suite w/ a gas fireplace, marble bath w/ bidet, and multiple walk-in closets. This level also includes a spacious alternative primary suite equipped with a Murano glass chandelier, fireplace, built-in office, marble bath and laundry. Three more beautiful bedrooms or offices and a sleek modern bath comprise the third level. The sun-drenched top level aerie or art studio, currently used as a media / family room, features its own dedicated bath and triple walk-in closets. Downstairs, the well-appointed fully walkout garden level offers an expansive ensuite guest / in-law space; a play room or lounge; 1.5 renovated baths; an auxiliary laundry room or kitchenette w/ gym space; and ample storage. An enviable mud room boasts French doors and access to a professionally landscaped covered patio / dining area plus parking for 2-3 vehicles. Extensive infrastructure upgrades since 2016 include electric rewiring with 400amp service; five-zone HVAC with hydro air; gut renovations of the kitchen and five+ marble baths; repointing; basement remodeling; slate work; professional landscaping and irrigation; wiring for hi-speed Internet; mesh WiFi; Sonos sound system; & a new sewer line. Coveted location near top-tier shopping, dining, the C & D Green Lines; Longwood Medical; public & private schools. An exceptional opportunity.

362 Tappan St, Brookline

Listing courtesy of Listing Agent: Elisabeth Preis from Listing Office: Compass.

$4,250,000
3 Beds ⋅ 3 Baths ⋅ 73578367 MLS
Set on prized Chapoquoit Island - a private, gated community accessed by bridge in West Falmouth - this exceptional property stands as a showcase of classic New England architecture and relaxed coastal luxury. A rare opportunity to immediately enjoy the best of Cape Cod living, the residence was built to the highest standards in 2022 and delivers access to two association beaches, a dock, tennis/pickleball courts, and more. Lush gardens and mature trees set the stage upon approach, amidst the sounds of the ocean and a gentle sea breeze. Multiple outdoor living spaces are thoughtfully designed to capture the breathtaking surroundings, including a screened porch, stone patios, and a balcony. The interior layout emphasizes open spaces, natural light, and refined detail. Warm wide-plank wood flooring and crisp wainscoting run throughout the main living areas. Designed for effortless cooking and gathering, the kitchen features professional-grade appliances, a large stone island, and a custom mosaic tile backsplash. The first-floor primary suite offers comfort and convenience with a walk-in closet and a spa-inspired bath with double vanities and a soaking tub. On the second level, three guest bedrooms provide well-appointed accommodations for family and friends. A walk-out lower level complete with a sauna delivers extensive bonus space, currently configured as a rec room and fitness area. Whether spending warm summer days at the association beach, fishing off the pier, or paddling kayaks in the harbor, this exceptional home delivers a coveted lifestyle in one of Cape Cod's most desirable communities.

133 Associates Road, Falmouth

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$4,250,000
6 Beds ⋅ 8 Baths ⋅ 73577854 MLS
Welcome to 23 Stonefield Court, where timeless elegance meets everyday livability in one of Needham's most coveted neighborhoods. Set on a beautiful acre lot, this exceptional six-bedroom home offers space, style, and versatility for entertaining and everyday living.Inside, a sun-filled main floor unfolds through a gracious dining room, formal living room, and wood-paneled library, ideal for both quiet nights in and gatherings that spill from room to room. The gourmet kitchen, with two dishwashers, multiple ovens, refrigerator drawers, and a walk-in pantry, opens to a breakfast room and a vaulted family room anchored by a stone fireplace, with access to a bluestone patio and firepit for evenings outdoors.Upstairs, five bedrooms include a primary suite with vaulted ceilings, custom closets, and a marble bath, plus two additional en-suite bedrooms, three en-suite in all. The walkout lower level opens directly onto its own private stone patio and offers a sixth bedroom alongside a gym, theater, kitchenette, great room, full bath, and game room with its own fireplace, space built for however you want to use it.A separate carriage house adds exceptional flexibility as a private guest suite, in-law suite, or home office, complete with full bath, sitting area, and kitchenette, while five garage spaces in total handle the rest. All of this just minutes from the commuter rail and downtown Needham.23 Stonefield Court is more than a home, it is a place to gather, unwind, and settle in for the next chapter.

23 Stonefield Court, Needham

Listing courtesy of Listing Agent: Migdol Moore Team from Listing Office: Gibson Sotheby's International Realty.

$4,250,000
4 Beds ⋅ 5 Baths ⋅ 73576453 MLS
This exceptional Chatham residence blends coastal luxury with country farmhouse charm in the exclusive Stage Neck neighborhood. Sited on nearly an acre lot with a separate barn/out-building, this property allows for privacy, with easy access to the Chatham Loop and vibrant downtown life. Abundant curb appeal starts with the circular driveway, mature plantings, and covered mahogany farmer's porch. Step inside to a home created by one of the Cape's finest craftsmen; custom built with meticulous care and quality. The floor plan provides multiple living areas on two levels, combined with open living spaces today's Buyers are seeking. Four en-suite bedrooms including a wonderful primary on the first floor w/amazing walk-in closet. Bright, renovated granite and stainless kitchen w/breakfast bar, center island, butler's pantry, and wet bar. Spacious living room offers a slider to a deck overlooking the yard. The first floor also encompasses a dining room, office nook, and full laundry room. Three fireplaces, beautiful wood floors, custom crown moldings, built-ins, natural gas heat, Central A/C, outside shower, well-irrigation, 2-car garage, full basement, and so much more. The stunning lot includes a charming barn with many possibilities: workshop, artist studio, kayak storage, or park a tractor! Properties like this don’t come along very often; this is one-of-a-kind offering in a remarkable location. Whether you desire a Summer retreat or elegant year-round living, you will find it here at 22 Moonpenny Lane!

22 Moonpenny Ln, Chatham

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

$4,250,000
5 Beds ⋅ 8 Baths ⋅ 73568719 MLS
Welcome to 4 Sherburne Way, an extraordinary waterfront estate on Buzzards Bay. The journey begins with a drive through the Little Harbor Golf Club, under a lush canopy of trees, signaling your arrival at a retreat that offers a level of privacy rarely found on the South Coast. Beyond the stone pillars and gated entry, a stunning shingle-style residence awaits, complete with access to a shared tennis court. Inside, the home’s character unfolds with a grand foyer and a graceful turned staircase. The craftsmanship throughout is exceptional; the rich woodwork and architectural detail feel more like a sophisticated Beacon Hill estate than a typical beach house. The heart of the home is a soaring great room anchored by a fireplace and a formal dining area, flowing seamlessly into a chef’s kitchen. Outfitted with a Viking stove, Sub-Zero refrigeration, and a massive center island, this space is designed for both entertaining and quiet mornings. A casual sitting room and a spacious home office flank the main living area, offering versatile spaces for work or relaxation. The primary suite is also located on the main level, featuring a private fireplace, an expansive walk-in closet, and a spa-like ensuite bathroom with a soaking tub, double vanity, and bidet. Exterior doors lead directly to a large, covered porch, where a dedicated seating area and gas fireplace offer a perfect vantage point for the grounds. The second level is equally impressive, hosting a lounge area and three additional ensuite bedrooms. This floor also includes a self-contained living suite—perfect for guests or extended stays—featuring its own kitchen, living area, and full bath. The home’s most iconic architectural feature is the "tower room," designed to resemble a lighthouse. A ladder leads to an elevated lookout, providing breathtaking, panoramic water views that capture the true essence of this estate. The third level adds even more versatility with an additional seating area, full bath, and a wet bar. The outdoor living space is a masterpiece of stonework and natural beauty. Relax by the plunge pool or follow the path down to your own private beach. Whether you are launching a kayak, paddleboarding, or simply enjoying a swim, this is a rare opportunity to own a private coastal compound in an unmatched setting. Come live in a community where the landscape is treated with such reverence, surrounded by neighbors who truly value the stewardship and preservation of the natural world.

4 Sherburne Way, Wareham

Listing courtesy of Listing Agent: Shawn Costa from Listing Office: Compass.

$4,250,000
3 Beds ⋅ 4 Baths ⋅ 73552814 MLS
Exceptional waterfront estate offering breathtaking views from nearly every room and a private sandy beach. Lovingly owned by the same family for nearly three decades, this spectacular 3 bedroom, 3.5 bath residence offers three levels of beautifully designed living overlooking Crow's Pond. A grand foyer opens to a dramatic living room with soaring ceilings, a fireplace, walls of windows, and sweeping water views. Glass doors lead from the living room to a deck and patio overlooking the water, creating the perfect setting for entertaining or relaxing. The first floor also features a waterfront dining room, kitchen, spacious primary suite, wood-paneled den, powder room, laundry, and an attached two-car garage. A charming side porch provides yet another inviting outdoor retreat with spectacular water views. Upstairs, two guest bedrooms enjoy water views and share a full bath. The walkout lower level offers a family room, office, full bath, natural light, and excellent storage. Experience Cape Cod's finest waterfront living with boating, kayaking, swimming, and fishing right from your private sandy beach. Ideally located next to Eastward Ho! and a short drive to downtown Chatham.

600 Fox Hill Rd, Chatham

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

$4,200,000
3 Beds ⋅ 3 Baths ⋅ 73578788 MLS
Steeped in history this extraordinary antique estate presents a once-in-a-lifetime opportunity to own a remarkable piece of local heritage. Built circa 1694 and lovingly passed down through generations of the Holbrook family, this treasured property has never been offered for sale. Carefully preserved over the centuries, the residence retains much of its original character, including authentic paneling, exposed beams, plank flooring and countless period details that reflect its rich history and craftsmanship. Adding to the property's unique appeal is an extraordinary 3 story barn constructed prior to 1870 with approximately 12,000 square feet of space! This property is being offered as one complete package, including the historic home, barn and 22 acres. In addition to the main estate the acreage will include 4 buildable lots all with street frontage creating exceptional investment and development opportunities, or maintained as a private compound. Rarely does a property of this historical significance, scale and potential become available!!

69 Forest St, Sherborn

Listing courtesy of Listing Agent: Maryann Clancy from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$4,200,000
5 Beds ⋅ 5 Baths ⋅ 73570743 MLS
SET DIRECTLY on the Pleasant Bay estuary, 5 Kidd Way offers expansive water views, immediate deepwater boating access, and exceptional privacy on nearly 1.5 acres. This distinctive 5BR/5BA home spans three finished levels, with flexible living spaces designed to accommodate family and guests. The light-filled main level features open living and dining areas overlooking the water, a wood-burning fireplace, updated kitchen with quartz countertops and new appliances, and a spacious primary suite. Multi-level mahogany decks extend the living outdoors and provide an ideal setting for dining and entertaining. Additional bedroom suites and flexible spaces are located on the upper and lower levels, including private exterior access from the lower level. A separate heated and cooled guest cottage with full bath offers excellent possibilities for guests, a studio or home office, or potential ADU use. The 1.4+ acre setting provides room for a pool or additional accessory structure, subject to approvals. Enjoy private shoreline access for kayaking, paddleboarding, swimming, sailing, and boating. The existing deepwater mooring is available subject to Harbormaster approval.With a proven peak-season rental history approaching $100,000 per year, 5 Kidd Way offers an unusual combination of waterfront lifestyle, flexibility, and income potential—all just minutes from Orleans and Chatham. NOTE: A substantial addition and renovations have been completed at the property. These alterations are not yet reflected in public records, assessments, or estimated valuations.

5 Kidd Way, Orleans

Listing courtesy of Listing Agent: Frances Schofield from Listing Office: .

$4,200,000
5 Beds ⋅ 7 Baths ⋅ 73548853 MLS
Extraordinary Shingle Style estate set on one of Wayland’s most spectacular private settings. Positioned on a hill overlooking sweeping lawns, a winding drive leads to a circular motor court with generous parking. Blending classic style with relaxed comfort, a grand open-concept living space flows from a chef’s kitchen to a family room, “laptop lounge,” and billiard room with wet bar. Upstairs, the luxurious primary suite includes walk-in closets, fireplace, balcony, and gorgeous spa bath. A private one-bedroom guest apartment is located above the 3-car garage. The third floor offers space for recreation, media, or remote work. Additional highlights include a spacious home gym and a resort-style backyard with covered porch, expansive deck with outdoor kitchen and bar, fire pit, putting green, saltwater infinity-edge pool and spa, all surrounded by lush grounds and specimen plantings. This special retreat offers the benefit of top-rated schools and easy access to Boston.

226 Cochituate Rd, Wayland

Listing courtesy of Listing Agent: The Joni Shore Group from Listing Office: Douglas Elliman Real Estate - Wellesley.

$4,200,000
3 Beds ⋅ 3 Baths ⋅ 73515489 MLS
Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal showpiece set in Hardings Beach Hills, with sweeping views of the marsh and creek. Blending classic Cape vernacular with modern lines, the home showcases exceptional craftsmanship and architectural detail throughout. The open main level is anchored by an arched fireplace wall that flows into a dramatic two-story dining area and reading loft, both set off by a soaring wall of windows with water views. The chef’s kitchen offers bar seating, while a versatile bedroom or study, full bath and mudroom complete the floor. The primary suite is a quiet retreat, featuring a fireplace, built-in bookshelves, a window seat and a luminous stained-glass accent window. A second guest suite with vaulted ceilings completes the upper level. The walk-out lower level provides generous family space, custom built-ins, abundant storage and room for expansion. Outdoors, mature plantings, stonework, a large deck and a pergola.

30 Indian Trail, Chatham

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

$4,200,000
4 Beds ⋅ 5 Baths ⋅ 73500198 MLS
A remarkable waterfront setting meets exceptional craftsmanship on 1.55 acres along Cohasset’s Gulph River. Reimagined over two years as a forever home, this residence was comprehensively reconstructed by a respected local builder and expanded from the original foundation up, transforming a classic Cape into an elegant French Colonial while preserving meaningful pieces of its history. More than 5,700 SF of living space is framed by panoramic river and marsh views with walls of glass presenting spectacular sunrises and serene sunsets. The home's slopeside position creates an elevated setting overlooking the river and marsh while offering a private backyard oasis. Inside the home, wide-plank hickory floors, high-efficiency Andersen windows and doors, closed-cell insulation, three-zone HVAC and a high-performance hot water system reflect the same attention to quality found throughout. At the center of the home, the chef’s gourmet kitchen pairs professional-grade Viking appliances with leathered Brazilian quartzite, custom cabinetry, imported Moroccan tile and a commercial-grade hood trimmed in reclaimed 1800s barn beams. Open living and dining spaces flow to the waterside deck, while the living room’s gas fireplace features a handcrafted mantel of the original hand-sawn barn beam. The primary suite is a private retreat with a balcony, a walk-in closet, and a distinctive spa bath with a custom Turkish-spindle vanity, an oversized clawfoot soaking tub, and a Tadelakt-finished shower. Three additional bedrooms and two more full baths complete the second floor. The finished walkout lower level, with two sets of French doors, water views, full bath, and polished concrete floors, offers flexible space for a gym, recreation, guests and more. Outside, an expansive lawn offering endless possibilities leads toward the river with timeless views across the estuary and direct access to the water. A renovated barn adds exceptional versatility, including a heated and cooled second floor ideal for an office or studio. MoistureShield CoolDeck composite decking, a backup generator, and thoughtful efficiency upgrades complete this extraordinary Cohasset property, just a short walk to the Village, commuter rail, restaurants, and harbor.

392 S Main St, Cohasset

Listing courtesy of Listing Agent: Rosemary Sullivan from Listing Office: Conway - Hingham.

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