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$5,995,000
4 Beds ⋅ 5 Baths ⋅ 73532630 MLS
Wing House Farm is an exceptional 12+ acre estate offering refined pastoral beauty and coastal country living. Abutting the 280+/- acre Destruction Brook Woods, the property enjoys direct access to scenic trails while remaining close to Village shops, marinas, beaches and dining. Rolling lawns, stone walls, split-rail fenced paddocks and established gardens define the picturesque landscape. At the heart of the estate is a meticulously renovated antique Colonial with elegant proportions and timeless charm. Equestrian amenities further distinguish the property, including a barn equipped with 4 box stalls, tack room and guest quarters. Perfectly sited between the barn and a detached 2 bay garage with loft space, the in-ground pool and spa add an inviting layer of leisure. A separate 2,100 sq ft guest cottage provides additional flexibility for family or guests.  A rare offering where historic character, equestrian amenities and coastal access converge along the South Coast.

111 Slades Corner Road, Dartmouth

Listing courtesy of Listing Agent: Team MCM from Listing Office: Gibson Sotheby's International Realty.
$5,995,000
5 Beds ⋅ 7 Baths ⋅ 73525277 MLS
New construction in one of Weston’s most exclusive neighborhoods, blending transitional design, exceptional craftsmanship, and state-of-the-art systems. This sun-filled home offers 5 bedrooms, 5 full and 2 half baths, 10’ ceilings, oversized windows, and curated finishes that offer scale and warmth. The chef’s kitchen features 36" refrigerator and a 36” freezer, double ovens, wine tower, and walk-in pantry, opening to an expansive family room with custom tray ceiling. The main level includes a private office, formal living and dining rooms, custom mudroom, and flexible first-floor primary or guest suite. Upstairs offers a second primary, three additional bedrooms, a lounge/game room, and laundry. The finished lower level with 11.5’ ceilings includes a second kitchen, theater, large entertaining space, and full bath. Set on 1.23 level acres with circular drive, patio, outdoor kitchen, pool potential, and 3-car garage, just minutes to town, top-ranked schools, and the commuter rail.

10 Hitching Post Lane, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
$5,995,000
5 Beds ⋅ 4 Baths ⋅ 1663704 MLS
Located directly on Scarborough Beach, one of Maine's most beautiful stretches of coastline, this is a rare opportunity to own in the sought after enclave of Prouts Neck. Originally built in 1960 with thoughtful updates over time, this classic coastal residence spans 3,029 square feet with 5 bedrooms, 3 ½ baths and private beachfront access. The southeast orientation features stunning sunrises over the ocean and sunlight throughout the day. Large picture windows and sliding doors open to a spacious beachfront deck, creating easy indoor-outdoor living. The property offers a private boardwalk for beach access with 144 feet of sandy beachfront on almost half an acre. With miles of gorgeous white sand beaches and dramatic rugged rocky coastline, Prouts Neck is an area of intense natural beauty. Steeped in history, the community is renowned as the setting for Winslow Homer's iconic seascapes. An exceptional offering of beachfront living in one of New England's most desirable summer communities.

25 Massacre Ln, Scarborough

Listing courtesy of Doris Homer Real Estate, Inc.. lcraig@proutsneckre.com
$5,995,000
9 Beds ⋅ 8 Baths ⋅ 1656043 MLS
Privately nestled on over 7 acres of dramatic, unspoiled waterfront, this extraordinary family compound commands breathtaking, panoramic views of Long Lake. A rare offering, the estate combines refined comfort, timeless architecture, and lakeside charm, creating a sanctuary designed for unforgettable gatherings and multigenerational enjoyment. At the heart of the property lies a magnificent main residence, meticulously crafted to maximize the natural beauty of its surroundings. Expansive windows and open-concept living spaces invite the outside in, capturing golden sunsets and the shimmering dance of light across the water. Tucked amidst the trees, whimsical guest suites, designed like luxurious tree houses, offer guests privacy and enchantment, while a spacious detached garage features an upper-level guest apartment perfect for extended stays. Adding to the magic is a beautifully preserved waterfront cottage, seemingly suspended above the lake. A nod to a bygone era, it has been lovingly updated while retaining it's charm. An elevated outdoor kitchen and lounge area is ideal for alfresco dining, cocktail hours, and summer soirées under the stars. Lobster bakes with Maine's finest catch or pizzas in the wood-burning oven are enjoyed at the lake's edge in the gazebo. No lakeside retreat would be complete without a boathouse, large enough to accommodate all the toys, tools, and vessels that define life on the water. Whether launching kayaks at dawn, cruising at sunset, or hosting lakeside events, this property is tailor-made for making memories. This is more than a home, it's a legacy estate, a setting for celebrating life's most treasured moments with friends and family, season after season, year after year.

224 Ledges Rd S, Naples

Listing courtesy of RE/MAX By The Bay.

$5,995,000
4 Beds ⋅ 4 Baths ⋅ 1661979 MLS
Situated amidst breathtaking granite landscapes and spanning 44.35 acres of preserved land in Lovell, Maine, this expertly designed lakefront retreat showcases the region's natural beauty. Created by the Boston firm Dimella Shaffer, the home features reclaimed wood, natural stone elements, and metal roofing. Inside, you'll find a chef's kitchen equipped with high-end appliances, an inviting elevated deck, and a bright, open-concept living area that boasts a double-sided stone fireplace and views of Lake Kezar. The main level includes a spacious primary suite filled with natural light, a luxurious bathroom, and an additional bedroom suite. A floating staircase leads to a family and game room on the lower level, which also houses two more guest bedrooms and a full bathroom. At the water's edge, there's a charming cottage with sliding doors that open to a dock and swim platform. Additional amenities include a security system and HVAC for comfort and peace of mind. Enjoy countless recreational activities in the picturesque landscape, just minutes away from the delightful community of Center Lovell. This is a unique opportunity for exceptional waterfront living in Western Maine.

242 Dragon Fly Rd, Lovell

Listing courtesy of Anne Erwin Sotheby's International Realty. 207-363-6640
$5,995,000
4 Beds ⋅ 8 Baths ⋅ 73508518 MLS
Quintessential Beacon Hill 4+ bedroom townhouse located just steps from Louisburg Square. 80 Pinckney Street is a dream-it offers a renovated open concept kitchen/living/family room, elegant formal entertaining spaces, and a truly exceptional garden & greenhouse. This tasteful home has an elegant entry foyer complemented by a dramatic staircase and a picturesque greenhouse drawing you in to see more! A formal dining room w/ fireplace has notable French Zuber wallcovering, the epitome of opulence. The gorgeous living room features another marble fireplace & floor to ceiling windows that overlook the home's lush garden w/ fountain. A nearby wetbar & powder room make this the ultimate floor for entertaining! A handsome library/den, sunny office, bdrm & 2 baths make up the 2nd fl. A luxurious primary suite features a bedroom, 2 ensuite baths & sitting room. 2 addt'l bdrms & 2 baths make up the top floor. Large, lush garden & greenhouse. Elevator, finished bsmt w/ multiple storage rooms.

80 Pinckney Street, Boston

Listing courtesy of Listing Agent: Rebecca Davis Tulman and Leslie Singleton Adam from Listing Office: Gibson Sotheby's International Realty.
$5,995,000
6 Beds ⋅ 6 Baths ⋅ 73499732 MLS
Set on a private lane within a five-home enclave, this 10,000+ SF estate is bordered by 7,000 acres of protected land in the Blue Hills Reservation, offering a level of privacy rarely found this close to Boston. Accessed by a stone bridge, the home unfolds across 20 thoughtfully designed rooms with 6 bedrooms and 6 bathrooms. A grand foyer leads to vaulted ceilings, a paneled library with fireplace, multiple living and recreation spaces, a home gym, and a dedicated home theater. The kitchen, equipped with premium appliances, opens seamlessly to a large family room anchored by a floor-to-ceiling stone fireplace. The primary suite features a five-piece bath, steam shower, and multiple walk-in closets. Set on 4+ acres, the grounds include a stone terrace with outdoor kitchen, fireplace, jacuzzi, and mature landscaping. A heated four-car garage, dual driveways, and circular motor court complete the offering. Not just a Milton home; an estate with a Milton address.

3 Stone Bridge Lane, Milton

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.
$5,995,000
8 Beds ⋅ 8 Baths ⋅ 73368530 MLS
Set on 1.23 acres of private waterfront looking out to Nahant’s iconic Egg Rock, this historic estate was built ca. 1890 by well-known builder Joseph T. Wilson, who constructed many of the North Shore’s grandest homes during the late 1800’s era of ‘summer cottages.’ The grandeur of the original mansion remains intact, its spectacular architecture and rich period detail preserved while incorporating 21st century updates to create a luxurious seaside compound. With eight bedrooms, six full and two half bathrooms, and 8,947 sf of living space on three levels, including a two and a half story great room opening to the oceanfront terrace and grounds, plaster ceilings with ornate medallions, tall Palladian windows, and elaborate woodwork throughout, this residence is built to a standard of craftsmanship and scale rarely found today. Ideally located 20 minutes from Logan Airport and downtown Boston, easily accessible to highways and commuter rail, this is an extraordinary property.

66 Ocean St, Nahant

Listing courtesy of Listing Agent: Amanda Armstrong Group from Listing Office: Compass.
$5,975,000
2 Beds ⋅ 5 Baths ⋅ 1672796 MLS
118 Wescott Battery is a spectacular waterfront estate in Castine, encompassing 40.3± acres, 915± feet of shorefront on the Bagaduce River, and stunning panoramic views. The main residence is an exceptional, custom-designed contemporary farmhouse with handsome proportions and a wraparound porch. Perfectly orientated to capture views of the water from every room, the main home's aesthetic blends contemporary and historic details in a pleasing combination. The formal living room is surrounded by doors and windows that open directly to the porch while exposed wood beams, wide-board wood floors, and a granite, wood-burning fireplace complement the surrounding natural landscape. There is a formal dining room with custom millwork and a charming 'game room' that could be an additional bedroom. The second floor of the home is dedicated entirely to the primary bedroom suite with a his/her bath, an office or sitting room, and good closet space. An in-law apartment over the garage and a substantial finished basement offer versatility. Accessed by a long, winding drive through open meadows dotted with small ponds, the bucolic landscape unfolds in rolling fields to the water, with mature trees and an apple orchard. A dock with ramp and float on the Bagaduce River completes this unique offering. The property contains the remnants of the historic habitat of Castine's namesake, Baron Saint-Castin and a portion of the property is subject to a Preservation and Conservation Easement held by the Castine Conservation Trust, Inc.

118 Wescott Battery, Castine

Listing courtesy of LandVest, Inc..

$5,950,000
5 Beds ⋅ 8 Baths ⋅ 73525098 MLS
Overlooking the golf course within the coveted gated community of Oyster Harbors, this exceptional residence combines timeless design with modern comforts in a beautifully crafted coastal setting. The home is defined by generous proportions, abundant natural light, and refined architectural detail throughout. The kitchen is tailored for both everyday living and entertaining, offering high-end appliances, expansive stone countertops, and a custom mahogany butler's pantry that provides additional prep and serving space. A secluded primary suite enjoys its own dedicated wing on the first floor, complete with a luxurious bathroom, two walk-in closets, and French doors that open to a private patio overlooking the swimming pool and gardens. Outdoor amenities take full advantage of the serene setting, with covered porches and a Gunite pool with limestone surround, all positioned to capture views of the 14th fairway. Ownership includes deeded beach access and passenger dock rights.

179 Pineleigh Path, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .
$5,950,000
4 Beds ⋅ 4 Baths ⋅ 73508634 MLS
Unique opportunity to have your dream home built in the heart of Fisher Hill! 11,338 sf level lot with foundation and plans for a 4 bedroom, 3.5 bath classic brick colonial home with 4,825 square feet of space (on 3 levels) and a 2 car detached garage with shed. Gourmet kitchen opens to the den, dining and living room. First floor covered porch and terrace, perfect for al fresco dining. Exceptional location, close to Fisher Hill Park, Runkle School, public transportation, shopping, dining, an easy commute to Boston, Longwood medical area and Cambridge. Modifications to the plans subject to review and approval. Buyer to verify all information. Photos are renderings.Also available as a lot with foundation for $2,950,000.

9 Willard Road, Brookline

Listing courtesy of Listing Agent: Celine Sellam from Listing Office: Coldwell Banker Realty - Brookline.
$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 recently retiled 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
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: .
$5,895,000
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.
$5,850,000
4 Beds ⋅ 5 Baths ⋅ 73522731 MLS
This beautiful and inviting four bedroom townhouse is situated on a highly desirable, quiet street just steps from Charles Street with all of its amenities.The first floor with its newly renovated kitchen, bordered by a forty foot garden with a fountain is ideal for cooking. There are quartz walls and counters, the finest appliances, a large Cornue stove, and a breakfast area. The large attractive dining room is perfect for conversation. The second floor has a thirty-eight foot double parlor with beautiful architectural details and is a wonderful entertaining area. There is a wet bar and a large sunny office. The spacious third floor primary suite with views to the gardens of Louisburg Square includes a sitting room. The fourth floor with three bedrooms and two bathrooms has a conveniently located laundry. There are 5 zones of heating and a/c. This is a must see!

13 West Cedar St, Boston

Listing courtesy of Listing Agent: Sally T. Brewster from Listing Office: Brewster & Berkowitz R. E..
$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..
$5,850,000
6 Beds ⋅ 7 Baths ⋅ 73466199 MLS
An elegant estate offering an opportunity to restore, renovate and reimagine a classic residence in a premier location. Introducing The Loring-Atherton House, an estate showcasing iconic Georgian Revival architecture located in the heart of Brookline’s Cottage Farm Historic District, a neighborhood celebrated for its architectural beauty, timeless character, and historical significance. Held by the same family for over half a century, this residence presents a once-in-a-generation opportunity to make this your perfect home and to become the next proud owner of one of Brookline’s most cherished addresses. This home currently features 6 beds & 6.5 baths across approx. 8326sf of finished living space sitting on a corner lot. Surrounded by elegant homes, tree-lined streets, across Mason Square Park and moments from the Longwood Medical Area, Fenway, Boston University, and some of the finest schools and green spaces in the region, the location is simply unmatched.

180 Ivy St, Brookline

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.
$5,849,000
5 Beds ⋅ 8 Baths ⋅ 73452478 MLS
BRAND NEW CONSTRUCTION just under one mile from historic Concord Center, with sidewalks leading all the way into town. Set on two private acres, 70 McCallar Lane offers the rare combination of timeless New England architecture, exceptional craftsmanship, and an unparalleled location. Designed for both elegant entertaining and comfortable everyday living, this 7,400+ square foot residence features beautifully proportioned living spaces, soaring 10-foot ceilings, expansive windows, custom millwork, and warm white oak floors throughout. The luxurious primary suite is a private retreat with a spa-inspired bath, while five en suite bedrooms provide exceptional comfort for family and guests. A home of remarkable quality in one of Concord's most sought-after locations—just moments from Concord Center's celebrated shops, restaurants, parks, and rich historic charm. Meet the Builder anytime and experience this exceptional home firsthand.

70 Mccallar Lane, Concord

Listing courtesy of Listing Agent: Jim J. D Agostine from Listing Office: Country Real Estate Inc..
$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.
$5,795,000
3 Beds ⋅ 4 Baths ⋅ 73553944 MLS
Stylish South Beach Retreat With Resort-Style Pool - Ideally located in the heart of Katama near South Beach, this stylish contemporary home offers the perfect blend of beach living and luxury amenities. Vaulted ceilings, a sleek linear fireplace, and a wall of 12-foot glass doors open the main living area to an expansive mahogany deck, creating seamless indoor-outdoor living. The gourmet kitchen, open dining area, and spacious living room are designed for effortless entertaining. The private primary suite features a balcony, two walk-in closets, and a spa-inspired bath. The walkout lower level includes a family room, two guest bedrooms, full bath, and laundry. Outside, enjoy a spectacular gunite pool with spa, waterfall, and fire feature, plus an outdoor cabana with bar, beverage refrigerators, and TV wall, along with a sunken firepit lounge. Offered furnished*, this turnkey Katama property is ideal for personal enjoyment or rental investment.

7 Katama Dr, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$5,790,000
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.
$5,750,000
6 Beds ⋅ 9 Baths ⋅ 1667521 MLS
East Bay is an exceptional coastal estate offering the perfect blend of a private summer retreat and a tranquil year-round residence. Set on more than five secluded acres with 430 feet of pristine, accessible waterfront, the property enjoys an elevated position above the scenic shoreline, where beautifully curated gardens and mature landscaping frame sweeping views across Penobscot Bay and its islands. The residence unfolds along a gently sloping bluff, capturing spectacular water vistas from nearly every room and outdoor living space. Originally built as a post-and-beam home around 2000, East Bay has been thoughtfully transformed over time. Its current design, inspired by the timeless coastal architecture of Royal Barry Wills, combines classic New England character with understated sophistication. Designed for both elegant entertaining and comfortable everyday living, the home offers a seamless balance of formal and informal spaces. Highlights include a first-floor primary suite with a private sitting room and office, multiple guest suites, inviting sitting rooms, a library, additional office spaces, a wine cellar, exercise room, updated mechanical systems, air conditioning, a generator, and a carport. The outdoor amenities are equally impressive. A heated swimming pool, hot tub, and sauna are perfectly positioned to maximize the breathtaking waterfront setting and views, while a custom-built staircase provides direct access to the property's private beach. Evoking the charm and grandeur of Islesboro's historic summer cottages, East Bay is a rare legacy property--an extraordinary expression of Maine's rugged coastal beauty, enduring craftsmanship, and timeless elegance. Explore the 3D tour and floor plans for a fully immersive experience of this remarkable estate.

866 Pendleton Point Rd, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

$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.
$5,695,000
5 Beds ⋅ 7 Baths ⋅ 73499334 MLS
Once in a lifetime opportunity to own in Wellesley's most coveted premier historic location, Pond Road. Featuring the finest custom craftsmanship throughout, professionally engineered mechanical systems, smart house and professionally designed ultra high end finishes. Over 9400 sq ft of living space on 3 floors. The floor plan everybody wants with a 1200 sq ft great room and over 10 foot ceilings. Oversized mudroom and pantry. First floor includes white oak herring bone hardwoods. 2nd floor ceilings 14-20 feet! An incredible main suite. All bedrooms en-suite with walk-in closets. Plus a 2nd floor lounge room or incredible guest suite. Lower level is unprecedented with 17 ft ceiling in 1/2 court basketball/ rec room (size of space also work for squash) with viewing room including wet bar. Theatre/media room with additional wet bar plus a gym with full bath including steam shower. Large flat yard. Close to Wellesley trails and town center.

196 Pond Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.
$5,650,000
6 Beds ⋅ 6 Baths ⋅ 73528133 MLS
Located within coveted Salten Point, this custom home captures sweeping views of Barnstable Harbor and Sandy Neck Beach. The open floor plan features mahogany millwork, walls of windows, and a living room with a grand stone fireplace and den. A chef’s kitchen boasts a marble island, Sub-Zero/Wolf appliances, and access to a screened-in dining porch. Outdoor amenities include a covered deck, pool, outdoor kitchen, and fire pit. An en suite guest bedroom completes the main level. Upstairs, the primary suite offers a private balcony, fireplace, and luxury bath with a soaking tub and walk-in shower, alongside three additional bedrooms (one en suite, two sharing a Jack-and-Jill bath). The lower level features built-in bunks, a TV area, and a fitness room. Equipped with a 2-car garage, top-of-the-line HVAC with air purification and dehumidification, and town sewer, the property includes deeded water access for swimming and kayaking, and is walking distance to Barnstable Village.

22 Kent Road, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .
$5,650,000
5 Beds ⋅ 6 Baths ⋅ 73507096 MLS
Set at the quiet edge of Cohasset Harbor, this shingle-style home offers rare 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 & spa-like bath, alongside 3 bedrooms, a loft office & a deck overlooking the harbor. 3rd floor suite adds more living space. Amenities include tennis & bocce courts plus a barn perfect for boat storage, a car collection, indoor sports court & a 1 bedroom apt. Not in flood zone.

1-R Baileys Island Rd, Scituate

Listing courtesy of Listing Agent: Christine Powers from Listing Office: Coldwell Banker Realty - Cohasset.
$5,627,000
9 Beds ⋅ 6 Baths ⋅ 73469901 MLS
Once-in-a-lifetime opportunity in Olde Chestnut Hill - this grand turn of the century victorian home is situated on almost 1 acre and offers mature trees and plantings, a large private back yard, and a separate 2+ car barn. Walking distance to many area amenities and public transportation, this elegant home is perfectly sighted away from the street and offers supreme privacy. Many restored historical details include a formal foyer with grand staircase, multiple fireplaces, and reclaimed hardwood flooring. Flooded with natural light this gracious home offers a large eat-in kitchen that overlooks the back yard, a banquet sized formal dining room, and a double parlor that is ideal for entertaining. The second floor of the home is complete with 4+ bedrooms, including a bright primary bedroom with en suite bath and study. The top floor boasts 3+ bedroom, large laundry room. Abundant storage throughout, partially finished basement, plus an outdoor covered loggia in the heart of Chestnut Hill

394 Hammond St, Newton

Listing courtesy of Listing Agent: Michael Harper from Listing Office: Coldwell Banker Realty - Boston.

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