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$5,499,900
6 Beds ⋅ 8 Baths ⋅ 73555787 MLS
Introducing an extraordinary luxury estate to be constructed in Dedham’s prestigious Precinct One. Conceived as the signature residence within this exclusive offering, this exceptional home will showcase timeless architecture, expansive living spaces, and the highest level of craftsmanship. Planned to offer approximately 5,500–7,000 square feet of thoughtfully designed living space, the residence will feature grand entertaining areas, a designer kitchen, luxurious primary suite, private office, wellness and recreation spaces, and seamless indoor-outdoor living. Early purchasers may have the opportunity to personalize select finishes and design elements. Ideally located moments from Legacy Place, Dedham Country & Polo Club, private schools, commuter routes, and downtown Boston. Renderings are conceptual. Final plans, specifications, features, pricing, and finishes are subject to builder and purchaser selections.

265 Meadowbrook Road, Dedham

Listing courtesy of Listing Agent: Michael Musto from Listing Office: RE/MAX Distinct Advantage.
$5,499,900
5 Beds ⋅ 7 Baths ⋅ 73552370 MLS
Experience Newburyport’s most coveted waterfront lifestyles at Bartley’s Landing.By purchasing your home lot for $1,750,000 & engaging in a construction contract you will join an exclusive enclave of just 5 luxury residences along the Merrimack River.This exceptional new construction opportunity pairs timeless architecture, superior craftsmanship & thoughtful design with the ability to personalize your dream home alongside one of the area’s premier designer and construction teams.Enjoy year-round river activity where boats glide by, migratory birds gather, fish occasionally break the surface and the changing seasons create an ever-evolving backdrop.Owners enjoy access to the community boathouse and private dock, with slip space for boats up to 35 feet - making days on the water effortless.Rarely does a property come on the market combining exclusivity and connection to the river.Bartley’s Landing is year round luxury waterfront living at one of Newburyport’s most prestigious addresses.

570 Merrimac St, Newburyport

Listing courtesy of Listing Agent: Homes & Lifestyles Team from Listing Office: Gibson Sotheby's International Realty.
$5,499,000
4 Beds ⋅ 6 Baths ⋅ 73469087 MLS
Newly Refined with an Updated Design.Spectacular new construction in coveted World’s End by acclaimed design-build team White Oak Home and The Kerr Collective. This coastal residence offers the opportunity to personalize a thoughtfully designed custom home with harbor views and a private setting. Features include a dramatic great room with soaring ceilings, gas fireplace, and French doors to a rear patio for seamless indoor-outdoor living. The chef’s kitchen offers premium appliances, a 10-ft island, separate scullery, and elegant dining room with expansive windows. The first floor includes a bonus room with full bath, formal living room, and office. The second level features a luxurious primary suite with balcony and spa-style bath, three additional bedrooms, family room, and two full baths. Enjoy a 3-car garage, deeded beach rights, and a location steps to World’s End, minutes to Boston.

112 Martins Ln, Hingham

Listing courtesy of Listing Agent: Darleen Lannon from Listing Office: William Raveis R.E. & Home Services.
$5,497,000
5 Beds ⋅ 7 Baths ⋅ 73509134 MLS
Exceptional Luxury Living in Wellesley’s Generals Neighborhood. A rare opportunity for luxury buyers seeking exceptional craftsmanship, modern amenities, and a premier Wellesley location. Custom built in 2017, this 6,300+ SF Neoclassical Colonial in Wellesley’s coveted Generals neighborhood offers four elevator-served levels designed for sophisticated everyday living and effortless entertaining.Whole-house radiant heat, grain-matched white oak floors, bespoke millwork, and 9-foot ceilings—including the finished lower level—reflect a standard of construction rarely found. The chef’s kitchen features soapstone countertops, dual dishwashers, and a walk-in pantry, while five en-suite bedrooms provide exceptional privacy. The primary suite offers a spa-inspired bath and a serene retreat from the day.The lower level transforms into a destination of its own with a private executive office, home gym, wine storage, and Bowers & Wilkins Diamond cinema. Outdoors, enjoy a custom patio, fireplace, hot tub, and mature arborvitae creating a private setting for entertaining and relaxation. A two-car garage and dual EV chargers add everyday convenience.An exceptional choice for those relocating to Wellesley or moving up within town, with Morses Pond, Hardy Elementary, Linden Square, Wellesley Square, shopping, dining, and commuter rail all nearby.For buyers searching for a move-in-ready luxury home in Wellesley, 48 Marshall Road offers the rare combination of quality, location, privacy, and amenities that is difficult to replicate. Schedule your private tour today.

48 Marshall Rd, Wellesley

Listing courtesy of Listing Agent: Team Coyle from Listing Office: Compass.
$5,495,000
4 Beds ⋅ 5 Baths ⋅ 73526293 MLS
Set on 15.7 acres in the heart of Sherborn, The Grout Farm offers a rare blend of refined country living and thoughtfully developed equestrian amenities. The reimagined main residence features light-filled living spaces, a custom kitchen, updated systems, and warm modern finishes. The estate includes a detached 1-bedroom, 1-bath guest cottage, carriage barn connected to the main barn, and the Apple Barn with gym, storage, and flexible space designed for future equestrian use. Amenities include a large indoor arena, outdoor arena with specialized footing, drainage, and irrigation, 11 stalls, fenced paddocks, run-in sheds, automatic field waterers, and hacking paths throughout the property. Orchard, greenhouse, gardens, and open pasture complete this distinctive offering within one of New England’s most established equestrian communities, with exceptional access to Boston.

42 Washington St, Sherborn

Listing courtesy of Listing Agent: J. Stanley Edwards from Listing Office: LandVest, Inc., Concord.
$5,495,000
5 Beds ⋅ 8 Baths ⋅ 73514626 MLS
Perfectly situated in Pheasant Brook Estates, this remarkable property showcases Lexington's most premier landscape, offering a flawless blend of luxury, privacy and natural beauty. Surrounded by manicured grounds and serene private pond, this home spans over 9,000 square feet of thoughtfully designed living space. The main level showcases a harmonious, sun-drenched layout with clean architectural lines, expansive rooms and oversized windows seamlessly inviting the outdoors inside. Designed with balance and flow, every space feels both refined and welcoming. The second level features five spacious en-suite bedrooms, including a stunning primary suite with two-sided fireplace opening to a private home office, creating an ideal retreat. Each additional bedroom is graciously proportioned, offering comfort and privacy. Crafted to celebrate family, tranquility and connection to nature, this exceptional residence delivers a rare opportunity to own a truly luxurious and distinctive property.

16 Solomon Pierce Rd, Lexington

Listing courtesy of Listing Agent: Martha Sevigny from Listing Office: William Raveis R.E. & Home Services.
$5,495,000
4 Beds ⋅ 7 Baths ⋅ 73511241 MLS
This California Contemporary defines sophisticated living at its finest. Majestically nestled on 2 private, stunning acres in the coveted Weston Country Club neighborhood.The terraced grounds are accented with stone patios, a salt water pool and cabana. Soaring ceilings and an abundance of sunlight flood the multiple levels of thoughtfully designed living spaces. A dramatic family room has sweeping views of the magnificent rolling grounds while overlooking the open floor plan of the main entertainment level The bright and spacious kitchen with a prep pantry and breakfast room lead to the outside patios. The primary suite is adorned with a beautiful wood beamed ceiling and brick fireplace. Dual spa-like bathrooms are complemented by dual walk in closets. 3 en-suite bedrooms are situated in their own private enclaves. The lower level features a fabulous playroom, traditional media room and a brick wine cellar. Stone walls, a receiving court and 4 car garage complete this special home

44 Meadowbrook Road, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.
$5,495,000
2 Beds ⋅ 3 Baths ⋅ 73419421 MLS
Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape Cod. Whether you're looking to enjoy the existing home w/separate post & beam garage w/power & water, or build your dream estate, the possibilities are truly remarkable. Additional to the expansive waterfront, this property boasts access to an adjacent cove down a winding 10-foot path. The current home features wood floors, a 2-car garage, office & generous outdoor living areas. An expansive deck provides the perfect vantage point to take in the ever-changing coastal scenery & sea breezes.

99 Uncle Alberts Drive Ext, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.
$5,495,000
4 Beds ⋅ 4 Baths ⋅ 73391055 MLS
Development opportunities! Welcome to your private sanctuary—a breathtaking 5,898 sq. ft. custom contemporary estate nestled on a secluded 13.18-acre compound. In addition to the primary 4-acre lot, the property includes three additional parcels totaling 9.18 acres, offering unmatched privacy, expansion potential, or conservation opportunities. Designed with meticulous attention to detail, this four-bedroom, four-bathroom masterpiece seamlessly blends luxury and comfort. Exquisite custom stonework graces the interior and exterior, lending timeless elegance to the home’s modern aesthetic.Professionally landscaped grounds create a serene outdoor retreat, harmonizing architecture with nature. A spacious three-car garage offers ample storage and convenience, complementing the home’s thoughtful design. Whether hosting grand gatherings or enjoying the tranquility of its surroundings, this exceptional estate offers an unparalleled lifestyle in an extraordinary setting.

32-70 Lazell Street, Hingham

Listing courtesy of Listing Agent: Ashley Brennan from Listing Office: Gibson Sotheby's International Realty.
$5,490,000
4 Beds ⋅ 6 Baths ⋅ 73565201 MLS
Perched above Tiverton's coastline with sweeping views out to Fogland Beach, 10 High Hill Road is a newly built luxury home built by Hill and Harbor Design. This retreat spanning just over 5,000 square feet across a thoughtfully designed main residence and detached ADU. The 4-bedroom, 4.5-bath home showcases quality craftsmanship at every turn, with European white oak engineered flooring throughout and a chef's kitchen anchored by a Thermador appliance suite including a 48" gas range, panel-ready appliances, and a walnut island beneath waterfall quartzite countertops. The primary suite offers a spa-like marble bath with quartzite waterfall counters, a custom California Closets system, and Newport Brass fixtures. A coffered great room ceiling wrapped in natural grasscloth wallpaper anchors the main living space, warmed by a gas fireplace with a custom quartzite surround. Outside, a resort-style pool and outdoor shower are framed by professionally designed landscaping. Windows frame the water views from nearly every room, while a fully equipped one-bedroom ADU offers flexible space for guests, extended family, or a private studio. Premium finishes carry through every detail. Deeded mooring coveys with the property. Within walking distance to Fogland beach, restaurants, farm stands — making 10 High Hill Road coastal Rhode Island living at its finest.

10 High Hill Road, Tiverton

Listing courtesy of Listing Agent: Duckworth Prentice Group from Listing Office: Serhant.
$5,475,000
4 Beds ⋅ 6 Baths ⋅ 73387997 MLS
WORLD-CLASS BOSTON ARCHITECT designs a spectacular home incorporating the historic GREENOUGH BARN! 5,418 s.f. Of living space plus a 915 s.f heated and cooled garage/workshop designed for 3 car lifts/6 car storage! The barn frame was relocated from Carlisle conservation land! The barn was reimagined and will be reconstructed as a MODERN MASTERPIECE on one of the most dramatic lots ever offered for any Concord new construction. Surrounded on 3 SIDES BY CONCORD CONSERVATION LAND that is farmed for sunflower fields. Beyond the conservation land are open & UNDISTURBED VIEWS OF MINUTEMAN NATIONAL PARK in every direction. The main living space soars with 30'+ CEILINGS & MASSIVE GLASS WALLS. All 4 bedrooms are on the 1st floor of this one-of-a-kind home. 2nd floor features a media room & private home office. The house offers a 3 car garage significant enough for multiple car lifts. There is no comparable new home currently being built in Greater Boston! The lower level could be utilized for a playroom or additional recreation area. Designed to ENJOY THE LARGE SKY & SPECTACULAR SUNSET VIEWS! Rare Opportunity - permit approved!

241 Shadyside Avenue, Concord

Listing courtesy of Listing Agent: The Zur Attias Team from Listing Office: The Attias Group, LLC.
$5,395,000
6 Beds ⋅ 8 Baths ⋅ 73572478 MLS
Set on a private road at the end of a quiet cul de sac, 50 Willard offers exceptional privacy on 1.3 acres in one of Weston’s most desirable settings. This newly constructed 8,300+ sq ft home was designed for modern family living, with a light filled open floor plan, elegant family room, chef’s kitchen with oversized quartz waterfall island, breakfast area, butler’s pantry and wet bar. Four ensuite bedrooms upstairs include a serene primary suite with spa inspired bath and expansive walk in closet. The finished lower level features a gym, sauna, wine room, wet bar, theater and au pair suite. Beautifully landscaped grounds, generous patios and a three car garage create the perfect setting for entertaining, relaxing and family life. Just moments from Weston’s highly regarded schools, golf courses and walking trails, this 6 bed, 6.5 bath home combines new construction luxury with estate like privacy and easy access to Boston.

50 Willard, Weston

Listing courtesy of Listing Agent: Yassien Youssef from Listing Office: Compass.
$5,395,000
4 Beds ⋅ 3 Baths ⋅ 73544298 MLS
Nestled within the private waterfront enclave of Nyes Neck, one of the Upper Cape's most cherished coastal communities, 31 Sunset Point Road presents a rare opportunity to experience the timeless beauty of Buzzards Bay. Set high above the shoreline, this property commands sweeping panoramic views across the water, where ever-changing light, coastal breezes, and unforgettable sunsets shape the rhythm of each day. With direct beach access just steps away, the setting offers an exceptional blend of privacy, natural beauty, and coastal serenity. The four-bedroom residence has been lovingly maintained and is ready to be enjoyed immediately, offering comfortable living spaces, a first-floor primary suite, and walls of windows that keep the remarkable waterfront vistas front and center. While the home reflects a classic Cape aesthetic, its true distinction lies in the extraordinary site--one that offers the rare opportunity to enjoy today while envisioning the future. Life in Nyes Neck is defined by a deep connection to the water. Residents enjoy a private neighborhood beach, boating, swimming, kayaking, and the quiet rhythm of a close-knit waterfront community treasured by generations of Cape families. As the sun settles over Buzzards Bay each evening, it's easy to understand why opportunities on Sunset Point Road are so rarely available. Also available under a separate listing is the rare homesite at 0 Sunset Point Road, located directly across the street. Offering captivating water views and the opportunity to build a custom home in this highly sought-after waterfront enclave, it presents the unique chance to acquire one--or both--of these exceptional Nyes Neck properties. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

31 Sunset Point Rd, Falmouth

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .
$5,390,000
5 Beds ⋅ 6 Baths ⋅ 73507096 MLS
A rare opportunity on Cohasset Harbor now offered at a compelling new price. This stunning shingle-style estate offers extraordinary privacy on elevated land surrounded by 20 acres of salt marsh & woodland with sweeping harbor views. Meandering boardwalks lead to small islands, including one with a tidal dock for direct water access. Designed by Sally Weston & fully renovated, the home blends timeless architecture with modern comfort. A dramatic 2 story foyer opens to formal living & dining rooms each with fireplaces. The kitchen features a large island, baking room & banquette seating, flowing into a family room & sunroom filled with natural light. First-floor spaces include a unique octagonal bedroom, mudroom & potting kitchen. Upstairs the primary suite offers a private sitting area & a spa-like bath, alongside 3 bedrooms, a loft office & a deck overlooking the harbor. 3rd floor suite adds more living space with an additional full bath and room for guests or playroom. Amenities include tennis & bocce courts plus a three story barn perfect for boat storage, a car collection, indoor sports court or artist studio. Third floor of barn features a spacious totally renovated 4 room apartment perfect for generational living. Not in flood zone.

1-R Baileys Island Rd, Scituate

Listing courtesy of Listing Agent: Christine Powers from Listing Office: Coldwell Banker Realty - Cohasset.
$5,350,000
5 Beds ⋅ 8 Baths ⋅ 73573262 MLS
Set within Wellesley’s coveted Dana Hall neighborhood, this exceptional Colonial has been transformed into a secluded retreat where architecture, craftsmanship, and livability come together beautifully. Renovated by Flavin Architects and Ken Vona Construction, the home showcases an exacting level of design and detail. A gracious two-story foyer introduces interiors filled with natural light, while quarter-sawn oak floors lead to the formal dining room, where floor-to-ceiling windows and glass doors open to a secluded patio. A bright solarium and inviting screened-in porch offer additional spaces to unwind and take in the surrounding landscape.At the heart of the home, the Bulthaup kitchen features premium appliances, a butler’s pantry, double ovens, a full-size wine cooler, and an expansive island that flows into the family room with vaulted ceilings, custom built-ins, and a stone gas fireplace. Five bedrooms and six full baths include a serene primary suite with soaring ceilings, a spa-inspired bath, and a private balcony overlooking the grounds. The finished lower level provides a gym, playroom, wet bar, wine cellar, media room, full bath, and entertainment area. Meticulously landscaped grounds complete this distinctive residence, offering an extraordinary setting for both everyday living and entertaining.

55 Ridge Hill Farm Rd, Wellesley

Listing courtesy of Listing Agent: Debi Benoit from Listing Office: William Raveis R.E. & Home Services.
$5,300,000
6 Beds ⋅ 4 Baths ⋅ 73529550 MLS
Discover oceanfront quintessential island living in this newer constructed shingle style home, thoughtfully designed from the ground up to honor the storied architectural heritage of the New England coast while delivering every comfort the modern household demands. From the moment you arrive, the home's classic cedar-shingled façade and welcoming front porch communicate a sense of permanence and grace. It is a home that feels as though it has always belonged on this stretch of Plum Island shoreline. This home offers the most spectacular sunrises and sunsets. Waterviews are admired from every room. Every room tells the same story, thoughtful design, premium craft, and an abiding respect for the islands setting that surrounds it. The front and primary porches offer up a place for morning coffee, afternoon reading, and the simple pleasure of watching the world drift by at an island pace. Plum Island and this home is not just an address, it is a way of living a lifestyle.

4 35th St, Newbury

Listing courtesy of Listing Agent: Kristin Francoeur from Listing Office: Gibson Sotheby's International Realty.
$5,300,000
5 Beds ⋅ 4 Baths ⋅ 73493300 MLS
This historically significant townhouse was built in the Greek Revival style in 1834 by Asher Benjamin. The house was owned by Benjamin’s heirs until 1925 and was rented to the family of the well known landscape architect Arthur Shurcliff for many years. The home has five bedrooms, a beautiful living room with floor to ceiling windows and great light, a formal dining room, a deck, and a spacious kitchen looking out on a small garden. The home has had a number of updates over the years, including the addition of an exterior iron balcony. A lovely wide staircase winds through the lower four floors. This gem is one of the prettiest houses on Beacon Hill.

9 West Cedar St, Boston

Listing courtesy of Listing Agent: Sally T. Brewster from Listing Office: Brewster & Berkowitz R. E..
$5,295,000
4 Beds ⋅ 5 Baths ⋅ 73473408 MLS
Extraordinary and rarely offered, this private estate in the heart of historic Sandwich commands sweeping, panoramic views of Cape Cod Bay from nearly 19 acres of secluded land. A true legacy property, the setting offers unmatched privacy, rolling grounds, and endless possibilities in one of Cape Cod’s most coveted locations. The residence encompasses over 6,000 square feet and is designed to support both refined living and grand-scale entertaining, whether enjoyed as a seasonal retreat or year-round residence. Outdoor living is paramount, with a heated gunite pool, classic farmer’s porch, and widow’s walk serving as exceptional vantage points to take in the ever-changing bay views and coastal horizon. The property also features its own dedicated solar field, enhancing efficiency and sustainability. Rarely does an estate of this magnitude, acreage, and outlook become available—an exceptional opportunity to own a private sanctuary defined by space, serenity, and breathtaking water views

19 Cedarville Road, Sandwich

Listing courtesy of Listing Agent: Ashley Brennan from Listing Office: Gibson Sotheby's International Realty.
$5,250,000
4 Beds ⋅ 5 Baths ⋅ 73571701 MLS
Brand-new and sun-filled, this exceptional shingle-style Gambrel is privately set on nearly an acre of professionally landscaped, level grounds just off coveted Shore Road, less than a block from the ocean. A refined coastal retreat, the 4-bedroom, 4.5-bath residence pairs exceptional craftsmanship with effortless luxury and gracious indoor-outdoor living. Beautiful millwork and 9' ceilings define the first floor, anchored by a vaulted beam-ceiling primary suite with a spectacular spa-inspired bath. The generous eat-in kitchen and family room feature a dramatic shiplap-vaulted ceiling and open to a sun-drenched patio surrounding a heated plunge pool and oversize yard with unlimited potential. A second-floor deck overlooks the secluded grounds, while an additional primary en-suite and two bedrooms and two more baths complete the upper level. Stroll to Chatham Bars Inn, the Fish Pier and Main Street - an enviable setting where the best of Chatham is truly at your doorstep.

106 Barcliff Ave, Chatham

Listing courtesy of Listing Agent: Jill Boudreau from Listing Office: eXp Realty LLC - Corporate Office.
$5,250,000
4 Beds ⋅ 3 Baths ⋅ 1676996 MLS
Privately set along one of Brooklin's loveliest stretches of Blue Hill Bay, this extraordinary four-bedroom, three-full-bath residence represents a rare union of sophisticated architecture, uncompromising construction, and an extraordinary coastal setting. The interiors are distinguished by an understated elegance and an exceptional quality of craftsmanship. Rich hardwood flooring and radiant heat extend throughout the main level, complemented by a high-efficiency heating system. Custom-crafted woodwork lends distinction to every room, while expansive Andersen windows and sliding doors frame the ever-changing panorama of Blue Hill Bay. Architectural details are particularly compelling. Each bedroom enjoys its own water view, while a gracious sitting area overlooking the bay provides a vantage point from which to watch the rhythms of the coast. Lobstermen work their traps just offshore, while Cadillac Mountain rises majestically on the distant horizon. A beautifully appointed study/library offers a serene retreat, with views that invite lingering. Beyond the house, the setting is equally extraordinary. A broad waterfront deck overlooks a remarkable coastal ecosystem where deer, wild turkeys, river otters, and other native wildlife are frequent visitors. Perhaps the property's most prized feature is its rare private beach--an increasingly coveted amenity along Maine's coast. This exceptional stretch of shoreline offers direct access to deep water and some of the region's most celebrated fishing and lobster grounds. Whether launching a kayak, exploring the shoreline, swimming with the tide, or simply sitting at the water's edge as the day unfolds, this is a level of private coastal access few properties can claim. Rarely does a property combine architectural pedigree, enduring construction, privacy, and a highly prized private beach on Blue Hill Bay.

1197 Bay Rd, Brooklin

Listing courtesy of Keller Williams Realty.

$5,225,000
6 Beds ⋅ 4 Baths ⋅ 73472922 MLS
Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor shower, parking, and mini-split climate control; its upstairs bedroom enjoys views from Farm Pond to Nantucket Sound. Completing the property is the charming Lilac House, a fun open-concept bunk house with a full bath, water-view deck, and private outdoor shower. A wraparound porch captures sweeping ocean views, while beaches, shops, restaurants, Circuit Avenue, and the Harbor are moments away. An established rental history further enhances this rare opportunity in one of Oak Bluffs’ most iconic locations.

4 Canonicus Ave, Oak Bluffs

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$5,200,000
4 Beds ⋅ 5 Baths ⋅ 1671226 MLS
In one of the most extraordinary settings on Rockport Harbor, 1 Ship Street is a private harborfront enclave with two year-round residences, a private sandy beach, terraced gardens, and sweeping views across the harbor to Indian Island Lighthouse and beyond to Penobscot Bay and its islands. Offered for the first time since 1973, the property combines rare waterfront amenities, architectural distinction, and an intimate sense of privacy at the end of a dead-end street, all in the harbor Charles Kuralt once called ''the most perfect small harbor in America.'' The property comfortably sleeps up to eight guests and is especially well suited for family and guests with space to spread out and enjoy this quintessential coastal retreat. The main residence is a striking modern interpretation of a classic New England waterfront home, inspired by the owners' long admiration for renowned American architect Hugh Newell Jacobsen, with clean lines and light-filled interiors. The open main floor includes a vaulted living room with propane fireplace, a gourmet kitchen, and thoughtful custom details. The lower level offers two private bedroom suites, including a luxurious primary suite with a spa-like bath and sauna. At the water's edge, the year-round beach house, originally a 1940s boat-repair shop, provides additional accommodations with a full kitchen, two upstairs bedrooms, and one-and-a-half baths. The private sandy beach is an exceptional amenity on Rockport Harbor, creating a rare place for swimming, launching small watercraft, gathering by the water or beach fires. The Matthew Cunningham-designed grounds include terraced gardens, elegant stonework, mature plantings, and stone steps leading toward the shore. 1 Ship Street is a unique offering on Rockport Harbor in a design that honors coastal New England with fresh, sophisticated simplicity. Dead end road, absolutely no drive-bys.

1 Ship St, Rockport

Listing courtesy of LandVest, Inc..

$5,200,000
5 Beds ⋅ 4 Baths ⋅ 73534187 MLS
Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.

49 Gosnolds Way, Chilmark

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.
$5,195,000
3 Beds ⋅ 5 Baths ⋅ 1674352 MLS
More than 380 feet of frontage on Broad Cove and nearly five private acres create an extraordinary waterfront setting in the heart of Cumberland Foreside. Beyond a winding drive, the property reveals itself gradually, where mature trees frame the shoreline and the home settles naturally into the landscape. The experience here is defined by privacy, the quiet rhythm of the tides, and ever-changing water views from nearly every principal room. The property's size and configuration also present the potential to create a separate home site with water access. Designed to celebrate the landscape, the home unfolds through a series of beautifully proportioned spaces, each taking full advantage of the surrounding water and gardens. A dramatic two-story foyer, gracious living spaces, a vaulted sunroom wrapped in glass, and a beautifully appointed primary suite are all oriented toward the water, while rich millwork, warm hardwood floors, and carefully curated details create interiors that feel enduring and quietly refined. Bluestone terraces extend naturally toward the shoreline, inviting long summer evenings, effortless entertaining, or peaceful mornings overlooking the cove. Just minutes from Cumberland Center, Falmouth, Portland, yacht clubs, golf, and some of Maine's most treasured coastal destinations, this is a home of quiet beauty, where the landscape has always been the centerpiece.

26 Lanewood Rd, Cumberland

Listing courtesy of RE/MAX By The Bay.

$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
5 Beds ⋅ 6 Baths ⋅ 1673790 MLS
Thirteen Foreside Road is a classic Falmouth Foreside estate designed by revered Maine architect John Calvin Stevens. Built in 1925 as a summer residence and historically known as ''Fairways,'' the home is set on over 4 acres beside the Portland Country Club, with views across the Donald Ross-designed golf course toward Casco Bay. A long, winding, tree-lined gravel road creates a memorable sense of arrival, setting the tone for the property's old-world charm and quiet sense of seclusion. Thoughtfully updated by Palm Beach-based Stephanie Rae Interiors and Bloom Construction, the residence blends historic architectural character with a refined, modern sensibility. The home offers 5 bedrooms, 5 full bathrooms, and 1 half bathroom, including a first-floor bedroom suite and four additional bedrooms on the second level. Generous room proportions, wood floors, natural light, and a comfortable flow create a sense of ease throughout. The first floor includes a gracious living room with a wood-burning fireplace, a formal dining room with French doors, and a beautifully appointed kitchen centered around a marble island with a handmade butcher block. A butler's pantry adds function and style, while the four-season sunroom offers southern exposure and views across the fairways toward Casco Bay. Upstairs, the primary suite includes a soaking tub and walk-in closet, with additional bedrooms, baths, office space, and flexible bonus areas for guests, work, and everyday living. The former three-car garage has since been rebuilt into a finished office space and home gym. Outside, mature landscaping, wooded surroundings, and established grounds create a timeless setting in the heart of Falmouth Foreside. Just moments from Portland Country Club, Falmouth amenities, Route 1, and downtown Portland, Thirteen Foreside Road offers a rare combination of architectural pedigree, acreage, privacy, and convenience.

13 Foreside Rd, Falmouth

Listing courtesy of Legacy Properties Sotheby's International Realty.

$5,100,000
5 Beds ⋅ 4 Baths ⋅ 73578429 MLS
Welcome to 97 Oakmont, an extraordinary Montana-built log cabin retreat set on 80 private acres in Westminster. Combining exceptional craftsmanship, natural beauty, and unmatched privacy, this is the kind of property that rarely comes to market. The 5+ bedroom home showcases soaring log timbers, a dramatic fireplace, warm wood interiors, and expansive decks designed to take full advantage of the stunning surroundings. Nearly every room offers a view, including the beautifully positioned kitchen boasting Dakota mahogany granite countertops, overlooking the fields, meadows, and rolling landscape beyond. A second-floor office with water views provides a peaceful place to work, create, or simply enjoy the quiet. Outside, the property is just as impressive. Enjoy direct access to Croker Pond with your own private dock and views of the pond's two islands. Whether you're kayaking, fishing, paddleboarding, or simply enjoying a morning coffee by the water, the setting is nothing short of spectacular. The 80 acres offer a rare mix of open meadows, mature woods, and established trails for walking, hiking, exploring, and enjoying nature right outside your door. Organic fields free of chemical fertilizers, abundant wildlife, and a mature maple grove with maple syrup production potential create a property that feels both private and purposeful. The finished walk-out lower level includes a separate living area with direct access to a covered patio, creating a seamless connection to the outdoors and offering some of the property's most beautiful views. The lower garage allows you to park your snow mobile at the end of the day. While the setting feels worlds away, you're just minutes from everything Westminster has to offer, including local restaurants, shopping, Wachusett Mountain, golf, and year-round outdoor recreation. Route 2 and the Fitchburg commuter rail provide convenient access to Boston and surrounding communities.97 Oakmont is more than a home—it's a private New England estate offering waterfront living, extensive acreage, recreational opportunities, and the kind of peace and tranquility that is increasingly difficult to find. A truly rare opportunity.

97 Oakmont Ave, Westminster

Listing courtesy of Listing Agent: The Edwards Realty Team from Listing Office: Barrett Sotheby's International Realty.
$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 ⋅ 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.

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