Feature Properties

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.

$5,590,000

5 Beds ⋅ 6 Baths ⋅ 73476802 MLS

Welcome to Acres, an exceptional opportunity to create a legacy residence in Newburyport's coveted South End. Set on 2+ private acres in Newbury, this bespoke home will offer approximately 5800sqft of thoughtfully designed living - 5 beds, 5.5 baths, 3-car garage and option for a customized pool & pool house. Crafted by a highly regarded local builder, Acres will showcase exceptional custom millwork, bespoke materials & carefully curated stone & tile ensuring every space reflects both function & refined taste. The expansive first floor design is anchored by an open-concept kitchen & main living, highlighted by a dramatic wall of glass overlooking the private, backyard oasis. The cozy family room with fireplace offers a warm retreat. A primary suite to admire & a walkout lower level design allowing flexibility to tailor the layout to your lifestyle. Every detail is intentionally designed to deliver a timeless & elevated living experience, bringing every vision of luxury to life.

6 South Pond Street, Newburyport

Listing courtesy of Listing Agent: Kevin Fruh from Listing Office: Gibson Sotheby's International Realty.

$5,500,000

4 Beds ⋅ 4 Baths ⋅ 73555738 MLS

Tucked away on a private, no-through-traffic oceanfront way, this property enjoys a rare combination of tranquility, privacy, and stunning waterfront surroundings on Straitsmouth Point between Rockport’s legendary twin lighthouses on Thacher Island to the south; Sandy Bay and the Atlantic Ocean to the west and north and the rocky shoreline below. Every spacious room within the easy-flowing floor plan features an ocean view via massive windows and exudes a cozy, yet refined ambiance that meets today’s needs and desires for daily living and when entertaining. With 4 bedrooms – the primary suite has a massive closet - 3.5 baths and 4,000+ sf of air-conditioned living space, this spectacular residence with beautiful gardens, ample outdoor play spaces, palazzo-like covered patio, 2-car heated garage with a workshop, and substantial storage accommodates a multitude of must-haves as well as amenities you didn’t even know you wanted. A year-round property destined to become a generational treasure

5 Gap Head Rd, Rockport

Listing courtesy of Listing Agent: Ann Rick Gloucester Group from Listing Office: J. Barrett & Company.

$5,500,000

6 Beds ⋅ 7 Baths ⋅ 73534168 MLS

Elevated elegance awaits you at this new construction gambrel home with opportunity to customize. Over 7,400sqft of finished space on expansive 16.6k level lot which includes a separate cabana/lounge and office. The chef's kitchen featuring top of the line appliances, custom cabinetry, oversized island and walk in pantry. The second level has 4 ensuite bedrooms and baths. The primary bedroom has a spa bathroom with soaking tub and walk in closet. The lower level features a sitting area with a wet bar, bedroom and bonus spaces perfect for a movie theater, gym and wellness room. Leveled back yard with covered deck and built-in speakers perfect for outdoor gatherings. Perfectly located facing the park and short distance to middle schools and high school.

62 Country Club Rd, Newton

Listing courtesy of Listing Agent: Stephanie Lau from Listing Office: Bellafi Real Estate, Inc..

$5,500,000

7 Beds ⋅ 8 Baths ⋅ 73526522 MLS

True private resort living. Set on a private .73-acre lot in one of Lexington’s most coveted neighborhoods, This home offers over 10,500SF of curated living & entertaining space w/ 7 beds & 7.5 baths. Privately sited behind mature landscaping, this estate blends timeless architecture w/ resort-style amenities. Dramatic two-story foyer w/ arched windows, formal living & dining rooms, expansive open-concept kitchen/family room, oversized center island & professional-grade appliances. A luxurious primary suite w/ marble bath, soaking tub, oversized shower, boutique-style dressing room, changing area, shoe & accessory closets. Features include a private home office, custom theater, large game rooms, a gym, sauna, yoga room, pet washing station, a heated pool, full outdoor kitchen, fire pit lounge, basketball court, a mudroom w/ built-ins & attached 3-car garage. Expansive stone patios & mature fenced grounds.

28 Tyler Rd, Lexington

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.

$5,500,000

6 Beds ⋅ 7 Baths ⋅ 73492795 MLS

One of Hingham's most admired homes! Landmark colonial with a sweeping front lawn, set elegantly atop a knoll on a 2.2 ACRE lot on a quiet cul de sac, just a stone's throw to downtown Hingham. The current owner has beautifully updated this architecturally significant home to meet the needs of today, while maintaining its original elegance. Gracious 11' ceilings, floor to ceiling windows, front and back staircases and period details throughout. Fabulous recently renovated "wing" off the back of the house with a gorgeous custom kitchen flooded w/natural light OPEN to a large dining area and spacious family room. There are 5 Bedrooms and 3 baths on the second floor including a luxurious primary suite. Opportunity to craft the 3rd floor as you wish. The grounds are EXCEPTIONAL. Expansive lawn, gunite pool with pool/guest house and over an acre of manicured lawn. RARE opportunity for the discerning buyer to acquire this ICONIC home/estate.

187 Main St, Hingham

Listing courtesy of Listing Agent: Tara Coveney from Listing Office: Coldwell Banker Realty - Hingham.

$5,500,000

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.

$5,499,900

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.

$5,498,000

5 Beds ⋅ 6 Baths ⋅ 73432257 MLS

SPECTACULARLY ONE-OF-A-KIND HOME! This JAW DROPPING home is a MASTERPIECE OF CUSTOM DESIGN ON 8.5 ACRES! A backyard oasis offers a VACATION AT HOME LIFESTYLE! The STYLE & DESIGN throughout is reminiscent of the best homes available in NANTUCKET, THE HAMPTONS OR PALM BEACH! The oversized wood pivot front door opens to a MARBLE FOYER with SKY HIGH CEILINGS & A DRAMATIC DOUBLE STAIRCASE. The EXPANSIVE DINING ROOM SEATS 18! A DESIGNER KITCHEN offers stone countertops & A SEPARATE STONE DINING ISLAND, views of the backyard, SS appliances & FLOOR TO CEILING CABINETRY! A 1ST FLOOR PRIMARY SUITE stuns with a RETAIL QUALITY WALK-IN CLOSET & a spacious ensuite bath. The 2nd floor showcases 4 additional bedrooms including a 2ND FLOOR BEDROOM SUITE & a 2nd laundry room! WALK OUT FINISHED LOWER LEVEL FEELS LIKE A 1ST FLOOR & features a full MEDIA ROOM, home gym, full bath SAUNA & add'l guest space. ENJOY THE IN-GROUND POOL, 2 hot tubs, KITCHEN CABANA with a FULL WET BAR & GAZEBO! 4 CAR GARAGE!

497 Old Road To 9 Acre Corner, Concord

Listing courtesy of Listing Agent: The Zur Attias Team from Listing Office: The Attias Group, LLC.

$5,497,000

5 Beds ⋅ 7 Baths ⋅ 73509134 MLS

A rare standard of craftsmanship in Wellesley's coveted Generals neighborhood. This custom Neoclassical Colonial — completed in 2017, 6,300+ SF across four elevator-served levels — was built without compromise: whole-house radiant heat, grain-matched white oak floors, bespoke millwork, and soaring 9-foot ceilings throughout including the lower level. The chef's kitchen anchors the home with soapstone countertops, dual dishwashers, and a walk-in pantry. Five en-suite bedrooms, including a primary suite with spa bath designed for genuine restoration. The lower level delivers a private executive office, home gym, wine storage, and a Bowers & Wilkins Diamond cinema — a complete retreat beneath the main living spaces. Outdoors: custom patio, outdoor fireplace, hot tub, arborvitae-screened privacy, and two EV chargers. Two-car garage. Steps to Morses Pond, Hardy Elementary, Linden Square, and Wellesley Square. Minutes to commuter rail.

48 Marshall Rd, Wellesley

Listing courtesy of Listing Agent: Team Coyle from Listing Office: Compass.

$5,495,000

4 Beds ⋅ 7 Baths ⋅ 73544553 MLS

Introducing an extraordinary new waterfront estate on picturesque Ashumet Pond with a private dock and sandy beach, offering nearly 8,000 square feet of luxury on 1.40 exceptionally private acres. Thoughtfully designed with timeless architecture and impeccable craftsmanship, this custom residence features soaring 30-foot ceilings, dramatic walls of glass, a striking stone fireplace, and breathtaking water views from nearly every room. Outside, enjoy a spectacular pool, fire pit area, expansive patios, lush landscaping, and seamless access to your private beach and dock for swimming, boating, kayaking, or simply taking in the tranquil setting. The chef's kitchen features custom cabinetry, Viking refrigeration, Wolf appliances, a butler's pantry, and a wet bar overlooking the water. Four en-suite bedrooms, dual primary suites, a media room, office, wine cellar, home gym, lower-level kitchen, dual laundry rooms, and smart-home technology complete this remarkable legacy estate.

26 Wheeler Rd, Mashpee

Listing courtesy of Listing Agent: Vanessa Walker from Listing Office: Compass.

$5,495,000

5 Beds ⋅ 5 Baths ⋅ 73529062 MLS

Certain residences redefine the contemporary real estate aesthetic entirely. 21 White Oak Road is one of them. Set within one of Waban’s most coveted enclaves, this masterfully reimagined estate unfolds across 7,500 square feet of modern luxury. Five bedrooms, four-and-a-half baths, and soaring eighteen-foot ceilings anchor the space. Purchased prior to completion and curated to an elevated standard of living, every finish — from the chef’s kitchen to the bespoke custom millwork, private gym, and bourbon room — represents a rare fusion of vision, design, and functional elegance. Soundproof media room with surround sound, perfect for movie marathons and gaming. Step outside to a private oasis featuring a sparkling newly completed pool and outdoor kitchen ready for entertaining. More than a home, it’s a lifestyle.

21 White Oak Rd, Newton

Listing courtesy of Listing Agent: The Shulkin Wilk Group 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

7 Beds ⋅ 6 Baths ⋅ 1661671 MLS

Turnip Island is an exceptional waterfront estate on North Haven with 4.2± acres and sweeping panoramic views over Southern Harbor, Penobscot Bay, the Camden Hills, and the Fox Island Thorofare. Located at the end of a winding private road in the desirable Ames Point community, the property is unique in offering the character of a private island retreat with vehicle access. The estate includes a thoughtfully rebuilt and expanded seasonal historic house with a fully renovated annex, and a newly constructed Rockport Post & Beam barn with year-round living space. The main house retains its classic summer-cottage charm while offering updated interiors, including inviting living and dining rooms, a gourmet kitchen, and three bedrooms. The annex, connected by a covered breezeway, adds a living room with kitchenette and two additional en-suite bedrooms, including a waterside primary suite with private deck. The barn provides heated and insulated guest or overflow accommodations with two bedrooms, open living and dining space, kitchen, bath, laundry, loft, and extensive storage below. The quintessential island setting includes rolling lawn, ledge, native plantings, attractive coves, and 3,000± feet of varied shorefront with a deep-water dock, ramp, float, mooring, and access to outstanding boating throughout North Haven and Penobscot Bay.

194 Ames Point Rd, North Haven

Listing courtesy of LandVest, Inc..

$5,495,000

5 Beds ⋅ 7 Baths ⋅ 73521880 MLS

Beyond stunning custom home! Over 11,000 sq ft of incredible living along with a private pond on 2.36 acres. High ceilings, open floor plan & filled with sunlight. Designer kitchen w/ huge walk-in pantry, oversized island, gorgeous thick marble counters. Breakfast room leads to family room w/ an entire bank of windows overlooking the yard. Unique walk-in wine storage. Formal living w/ fireplace & dining room plus private study. Main bedroom w/ spa like bath & 2 walk-in closets. 4 additional bedrooms all similar in size plus laundry complete the 2nd floor. Lower level w/ bonus entertaining room w/ beverage center, 8 seat home theater & gym. Resort style 20' x 42' pool with integrated spa & covered outdoor living room w/ fireplace, TV and outdoor kitchen. Spectacular landscaping! Private street w/ only 6 homes. Only 30 minutes to Boston & 3 town centers w/ train access. Close to Nobles, DCD, St. Seb's and Dedham Country and Polo Club. Be part of Dover Sherborn schools on a cul-de-sac.

4 Wilson's Way, Dover

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

$5,495,000

5 Beds ⋅ 4 Baths ⋅ 73520860 MLS

Set on 2.5 acres within the coveted Wings Neck community, this extraordinary waterfront estate offers sweeping views of Buzzards Bay amidst total privacy. The five-bedroom home features a sunlit open layout ideally suited for casual living or grand entertaining, with a soaring great room, gourmet kitchen, and dining area with panoramic water views. Indoor and outdoor spaces blend seamlessly, with glass doors leading to an expansive deck overlooking the resort-like swimming pool and Buzzards Bay beyond. Designed for comfort and convenience, the first-floor primary suite boasts unobstructed water views and a sumptuous bathroom. Four additional bedrooms provide ample space for family and friends. A detached boat barn and two-car garage with a home gym above complete this exceptional offering. Residents of Wings Neck Trust enjoy access to two beaches, each with mooring & dinghy slip areas, pickleball & tennis courts, a deep-water dock in the harbor and miles of conservation land.

461 Wings Neck Road, Bourne

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

$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

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 ⋅ 4 Baths ⋅ 1668689 MLS

Welcome to a truly one-of-a-kind property where history, character, and opportunity come together across more than 37 acres of breathtaking coastal countryside. Ideally located between the charming fishing village of Cape Porpoise and the sandy shores of Goose Rocks Beach in Kennebunkport, this exceptional estate offers a rare chance to own a generational property with multiple residences, expansive acreage, and future potential in one of Southern Maine's most desirable coastal settings. At the heart of the property sits a charming antique farmhouse featuring 4 bedrooms, oversized living spaces, beautiful, beamed ceilings, and three fireplaces that create warmth and timeless character throughout. Rich in history and architectural detail, the home offers the perfect blend of rustic charm and comfortable living. Complementing the main residence are two separate guest cottages, ideal for extended family, guests, rental income, or caretaker accommodations. One cottage offers a cozy one-bedroom layout, while the second provides two bedrooms and additional flexibility for a variety of uses. A substantial barn adds even more possibilities, whether for agricultural pursuits, storage, workshops, events, hobbies, or future creative ventures. The 37+ acre setting is truly remarkable, featuring open fields, natural landscapes, and small development potential for those seeking to explore additional opportunities. Enjoy peaceful marsh views and distant ocean vistas that provide a stunning backdrop, and a sense of privacy rarely found in such a convenient coastal location. Whether you envision a family compound, working farm, investment property, hospitality venture, or a private retreat to be enjoyed for generations, this extraordinary offering presents a unique opportunity to create your legacy in Kennebunkport's coveted coastal corridor.

190 Mills Rd, Kennebunkport

Listing courtesy of Pack Maynard and Associates.

$5,485,000

4 Beds ⋅ 5 Baths ⋅ 73373524 MLS

Tucked on a private road in Brookline’s coveted Cottage Farm neighborhood, this exceptional Colonial-style former carriage house underwent a 2 year renovation to the highest standards, completed in 2025. Soaring ceilings and oversized windows bathe the home in natural light and frame serene views of the surrounding gardens, yard and conservation land. The 1st floor presents a stunning open plan complete with large living and dining rooms, chef’s kitchen, breakfast room and oversized deck - for seamless indoor/outdoor entertaining. The upper level features a tranquil primary suite with 2 dressing rooms and a spa-like bath, an additional bedroom suite and laundry room. The lower level includes 2 bedroom suites (or office, gym), one of which has a private entry. Set on 0.44 acres of exquisitely landscaped grounds with direct access to Amory Park, this home offers a rare combination of luxury, privacy, and convenience—just minutes to Boston, Cambridge, shops, dining and public transit.

178 Ivy Street, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$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.

$5,450,000

4 Beds ⋅ 6 Baths ⋅ 73499730 MLS

Refined Vineyard living in The Preserve. Set on a knoll overlooking the pond and sweeping grasslands, this exceptional home blends classic coastal architecture with modern luxury. The expansive great room showcases cathedral ceilings, rich millwork, and abundant natural light, with three sets of French doors opening to a bluestone patio with multiple sitting areas and a heated saltwater pool. The chef’s kitchen flows seamlessly into the dining and living spaces. One wing offers an inviting lounge and a luxurious primary suite with spa-like bath and dressing room, while the opposite wing features three guest bedrooms, each with ensuite baths and walk-in closets. Additional highlights include a proper mudroom and a finished lower level with media room, full bath, and storage. Surrounded by mature landscaping, with easy access to trails, the bike path and Farm Neck Golf Club. The Preserve is a private enclave of luxury homes and is arguably one of Oak Bluffs most exclusive neighborhoods.

8 Paddock Rd, Oak Bluffs

Listing courtesy of Listing Agent: Lesley Heidt from Listing Office: Sandpiper Realty, Inc..

$5,449,000

4 Beds ⋅ 5 Baths ⋅ 73476823 MLS

NEWLY REPOSITIONED PRICING! Located just moments from Town and the harbor, 2 Mariner Way presents a rare opportunity to own new construction in one of Nantucket’s most coveted settings. Tucked within an enclave of only 3 luxury residences, this home offers the perfect balance of in-town convenience and the serenity of nearby Monomoy’s shoreline. Enjoy easy access to Main Street, the Great Harbor Yacht Club, and scenic bike paths. The thoughtfully designed floor plan balances gathering and retreat. An open-concept kitchen, dining, and living space with fireplace anchors the first floor, complemented by a private guest suite. Upstairs, the spacious primary suite is joined by two en-suite bedrooms and a secondary living area. Fully move-in ready for the 2026 season and including a one-year developer warranty for a seamless transition, 2 Mariner Way combines location, lifestyle, and turnkey design to capture the very best of Nantucket living.

2 Mariner Way, Nantucket

Listing courtesy of Listing Agent: Janice Dumont from Listing Office: JD Advisors, Inc.

$5,400,000

3 Beds ⋅ 2 Baths ⋅ 73531359 MLS

Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking fireplace with a glacial stone hearth, while the open kitchen offers custom cabinetry and premium appliances. The primary suite includes two office spaces, a media area, walk-in closet, and spa-inspired bath. A private guest suite features a full bath with soaking tub, and the third bedroom is currently configured as a wellness space with sauna. Additional amenities include an attached two-car garage, owned solar panels, EV charging station, and a six-bedroom septic system.Seven Gates Farm residents enjoy access to private beaches, docks, tennis courts, and more.1000 acres of protected land.

35 South Bowl Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..

$5,395,000

6 Beds ⋅ 9 Baths ⋅ 73523690 MLS

Impressively sited on a quiet cul-de-sac in Dover’s sought-after Snow’s Hill neighborhood, this French country estate is surrounded by lush, newly designed landscaping with mature plantings, flowering perennials, winding paths, an orchard, and a putting green just steps from the billiard room. Inside, elegant entertaining meets everyday comfort with soaring ceilings, arched doorways, radiant floors, custom cabinetry, and an open, light-filled layout. A two-story foyer opens to a grand bridal staircase leading to five ensuite bedrooms and a bonus media room, while the first floor offers a guest suite/ primary suite. Enjoy a handsome office with gas fireplace and mahogany built-ins. The heated pool with spa, waterfalls, and water slide is complemented by a fully outfitted cabana with kitchen, full bath, laundry, and living/dining area. Extensive upgrades and renovations since 2018 reflect high quality craftsmanship and thoughtful design throughout

5 Hamlins Crossing, Dover

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

$5,350,000

5 Beds ⋅ 7 Baths ⋅ 73540738 MLS

Nestled in the heart of Wellesley’s coveted Cliff Estates, this exquisite custom-built residence by a highly regarded builder blends timeless elegance w exceptional craftsmanship. Built in 2013, the home welcomes you w a sun-drenched two-story foyer, formal fireplaced livingroom, sophisticated dining room and a private first-floor office. The expansive family room flows seamlessly into the chef’s kitchen featuring premium finishes and a spacious dining area ideal for everyday living and entertaining. The second level offers a luxurious primary suite w a spa-inspired bath and exceptional walk-in closet, along w four additional bedrooms and conveniently located laundry room. The finished lower level features an entertainment lounge, media room, wet bar, wine cellar, and home gym. Outside, impeccably manicured grounds and a stunning stone waterfall create a private outdoor retreat. Just moments from Wellesley’s top schools, shops, restaurants, and commuter routes. An elegant masterpiece!

14 Bristol Road, Wellesley

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

$5,350,000

4 Beds ⋅ 5 Baths ⋅ 73495595 MLS

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace—ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.

205 South Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..

$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 ⋅ 6 Baths ⋅ 73529545 MLS

Set on a hill with commanding ocean views framed by Minot's Light and Little Harbor, this exquisitely remodeled coastal residence offers water views from nearly every room. The open floor plan features soaring 10- to 12-foot ceilings, abundant natural light, and refined spaces designed for gracious entertaining. Highlights include 4 water-view bedrooms, a custom library/study, 4 full baths, and 2 half baths. The kitchen is appointed with custom cabinetry, a pantry/coffee bar, oversized center island, Wolf dual-fuel range, Sub-Zero refrigerator, and Miele dishwasher. A family room with custom built-ins and cocktail bar complements the formal living and dining rooms that open to an exceptional outdoor living space. A spectacular roof deck captures the panoramic vistas. Landscaping, masonry, and whole-house systems complete this exceptional offering. Moments from Cohasset Village, Sandy and Black Rock beaches, the commuter rail, and the Hingham Ferry to Boston.

3 Jerusalem Lane, Cohasset

Listing courtesy of Listing Agent: Greta Gustafson from Listing Office: LandVest, Inc..

$5,295,000

3 Beds ⋅ 7 Baths ⋅ 73496934 MLS

Set along 125 feet of private Lagoon frontage, this beautifully designed home offers over 5,400 sq. ft. of light-filled living space across three levels. High ceilings, skylights, and walls of glass capture sweeping water views, while a decorative stone fireplace anchors the main living area. The chef’s kitchen features stainless appliances, stone counters, custom cabinetry, and a large island, complemented by a wet bar and casual dining area. Three ensuite bedrooms include a primary suite with water views, a sitting area, walk-in closet, pool access, and a spa-like bath. The walk-out lower level offers a game room, media area, kitchenette, wine storage, and bonus room. Outdoors, enjoy a heated pool, spa, bluestone terrace, and direct access to calm waters for swimming, boating, and some of the best steamers, littleneck, and cherry stones on the Island. Offered furnished with strong rental history.

385 Barnes Road, Oak Bluffs

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

$5,250,000

4 Beds ⋅ 5 Baths ⋅ 73546213 MLS

Set on one of Crow Point’s most coveted streets, this exceptional NEW CONSTRUCTION home offers elevated coastal living w/ water views, sun-drenched interiors & bespoke finishes throughout. Perfectly positioned above North Beach, this 4 bed / 4.5 bath residence seamlessly blends timeless design & modern luxury. Thoughtfully designed for both everyday living & entertaining, the home features high ceilings on each level, expansive open-concept living spaces filled w/ natural light, sophisticated custom details & seamless indoor-outdoor flow. Multiple decks, including private outdoor spaces off the LR & primary suite, capture beautiful water views & ocean breezes.The luxurious primary suite features a cathedral ceiling, fireplace, spa bathroom & private deck overlooking the water. Every inch of the home reflects elevated craftsmanship, beautiful spaces & refined coastal elegance. An extraordinary opportunity to own a premier home in one of Hingham’s most desirable seaside neighborhoods.

12 Howard Road, Hingham

Listing courtesy of Listing Agent: Jeff Alexander from Listing Office: Compass.

$5,250,000

4 Beds ⋅ 4 Baths ⋅ 73529657 MLS

Perched on the waterfront in Chatham's coveted Stage Island neighborhood, this exceptional 4-bedroom, 4-bath coastal retreat offers 270-degree panoramic views of Stage Harbor, Nantucket Sound, and surrounding tidal marshes. Built to stringent post-Katrina standards and completed in 2011, the home showcases superior construction, reinforced structural tie-downs, and impact-rated windows. Designed to maximize its breathtaking setting, the light-filled open floor plan features walls of glass and stunning water views from nearly every room. The main level includes a spacious living room with fireplace, dining area, updated kitchen, two bedrooms, and a shared bath. Upstairs, two private en-suite bedrooms enjoy elevated harbor vistas. The walkout lower level offers a family room and fitness space overlooking the water. A 2025 kitchen renovation, 2019 revetment, direct water access for kayaking, paddleboarding, fishing, clamming, and swimming, make this an exceptional opportunity.

56 Stage Island Road, Chatham

Listing courtesy of Listing Agent: James Lowenstern from Listing Office: eXp Realty LLC.

$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

4 Beds ⋅ 6 Baths ⋅ 1659121 MLS

Offering an elegant lifestyle without compromise, this property spans 1.24 acres and boasts stunning ocean views, perfect for both grand celebrations and serene retreats. An array of five-star amenities enhances the private compound: an outdoor heated pool, a cabana bar with a television and grill, a putting green, an elevator, and an ocean-viewing platform with a private staircase to rugged Pint Cove. The first floor boasts open living areas that offer breathtaking views framed by expansive walls of windows. French doors lead to the covered seating and to the open sun deck, perfect for alfresco dining. The coastal ambiance is highlighted throughout the living area, with maple flooring, elegant, coffered ceilings, and a gas fireplace surrounded by handsome built-ins, raised paneling, and polished stone slabs. Ideal for gourmet cooking, the kitchen showcases an island with bar seating, a brushed stainless-steel refrigerator, an oversized gas range with double ovens, and custom cabinetry. Additional features on the first floor include a billiard room with bar, a screened-in seaside porch, a private entry guest suite, and an office with a nearby bathroom. The grand turret staircase, featuring elegant, twisted balustrades and a custom wood tray ceiling, leads to the generous primary suite. It includes a spacious living area with a wet bar and beverage refrigerator, a gas fireplace, and a door leading to a romantic balcony overlooking the sea. Double vanities, a large, jetted tub, and a separate custom-tiled shower define the primary bath. This level offers two additional guest suites and a gym nook. Downstairs, the media room features tiered theater seating, a wet bar with two beverage refrigerators, and a bar island. The temperature-controlled wine cellar features backlit wine storage and a tasting table, as well as a bathroom and ample storage. The garage offers custom closets for additional organization. Sandy Cape Neddick beach is a stroll away.

1 Cove Rd, York

Listing courtesy of Anne Erwin Sotheby's International Realty. 207-363-6640

$5,195,000

6 Beds ⋅ 6 Baths ⋅ 1659543 MLS

Experience the pinnacle of luxury living with this breathtaking waterfront estate on Long Lake. Nestled on an expansive private lot with 800 feet of pristine shoreline, this extraordinary property offers a sandy beach, private dock, and a stunning boardwalk, creating the ultimate lakeside retreat. The 5,122 sq. ft. custom-designed main home features 4 bedrooms and 4.5 bathrooms, showcasing impeccable craftsmanship and high-end finishes throughout. Step into the grand living room, where cathedral ceilings and a dramatic floor-to-ceiling stone fireplace set the tone for elegant relaxation. Walls of floor-to-ceiling windows frame breathtaking panoramic lake views, bathing the home in natural light. A gourmet chef's kitchen, adorned with rich stonework and premium appliances, makes entertaining effortless. The luxurious primary en-suite offers a serene escape with a double-sided fireplace, spa-inspired bath, and a private balcony overlooking the water. Beautiful multi-functional den/office/bedroom with full bath, floor to ceiling windows and built-ins. This property includes an attached 3-car garage and a detached 3-car carriage house topped with a 1,384 sqft, 2 bedroom open concept in-law suite with a beautiful full kitchen and center island, perfect for guests or multi-generational living. Blending timeless elegance with modern luxury, this Long Lake masterpiece offers an unparalleled waterfront lifestyle. Ideal for both private enjoyment and lavish entertaining.

3 & 4 Trestle Ln, Harrison

Listing courtesy of Landing Real Estate.

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