Refine Search
Map
Sort by
$4,300,000
4 Beds ⋅ 5 Baths ⋅ 73505446 MLS
Perched above the Ospreys with views from the living room, kitchen, bedrooms, and outside patio of Nauset Beach and the Atlantic beyond, 12 Windswept Lane sits at the edge of the National Seashore. Located in the sought-after Countryside neighborhood and built in 1995, the 4,300-square-foot, 4-bedroom, 4.5-bath house is large enough to accommodate both family and friends. The open living space is bathed in light from ever-changing ocean and marsh views. A neighborhood path runs through the Orleans Conservation Trust and leads right to Nauset Beach. Around the corner, there is ORV North Beach private access exclusively for Orleans residents. Priscilla Beach is close by, lending itself to relaxing by the calm waters of Nauset Estuary, and is very popular for Kayaking and birdwatching in the sheltered marshes. This is beach living without the worry of storms and waves.

12 Windswept Lane, Orleans

Listing courtesy of Listing Agent: Jeffrey Marcus from Listing Office: Corcoran Property Advisors.
$4,295,000
7 Beds ⋅ 7 Baths ⋅ 73532720 MLS
Set on a landscaped, level lot in coveted West Newton Hill, this 1880 Victorian blends timeless architectural character with exceptional scale and comfort. Rich period details, soaring ceilings, generous proportions, and abundant natural light define the home. The sun-filled kitchen and family room, surrounded by windows on three sides, features a gas fireplace, oversized island, dining area, built-in office nook, and direct access to a bluestone patio and flat backyard. The main level also offers elegant formal living and dining rooms, a music room, mudroom, and 2 half baths. The 2nd floor includes a spacious primary suite with private office, deck, dressing room, and bath, plus three additional bedrooms, two full baths, and laundry. The third floor offers two bedrooms, a full bath, and family room. The finished lower level includes a guest bedroom, full bath, second laundry, storage, and flexible bonus space.

14 Winthrop St, Newton

Listing courtesy of Listing Agent: The Drucker Group from Listing Office: Compass.
$4,295,000
5 Beds ⋅ 6 Baths ⋅ 73510191 MLS
Coveted in town/Dana Hall location! Incredible opportunity to live in a beautiful colonial with a complete renovation/addition. Over 5000 sq ft on 4 full floors. Large open floor plan for kitchen family room. Coffered ceilings, built-in banquette and walk-in pantry are just a few design features in this space. Formal living and dining room with private study and large mudroom with built-ins complete the first floor. Main suite with large walk-in closet and vaulted ceiling. 4 additional bedrooms and 3 full baths with laundry room. Oversized 3rd floor perfect for 2nd home office or bonus space. Lower level with room for guests with full bath plus exercise room and large playroom along with great storage. Your opportunity to customize now. Large flat yard! Block party neighborhood just short distance to Brook Path, Wellesley Center, Wellesley College, Nehoiden Golf Course and Hunnewell School.

17 Midland Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.
$4,295,000
4 Beds ⋅ 3 Baths ⋅ 73488928 MLS
Rare private beachfront offering in Manchester-by-the-Sea. This authentic shingled Arts & Crafts coastal home sits directly on the sand, offering panoramic ocean views and a private beach. Ideally located near conservation land, the village, and commuter rail to Boston. Originally built c.1928 and thoughtfully renovated, the home features classic Shingle-Style details, a floor-to-ceiling fieldstone fireplace, and walls of windows framing the sea. The chef’s kitchen with center island, stainless appliances, and vaulted ceiling captures stunning water views. Lower level includes a private guest suite with kitchen, living area, and game space. .A covered porch with gas fireplace opens to the sand and private fire pit—perfect for effortless coastal living.

53 Raymond Street, Manchester

Listing courtesy of Listing Agent: Lanse Robb from Listing Office: LandVest, Inc., Manchester -by-the-Sea.
$4,250,000
6 Beds ⋅ 7 Baths ⋅ 1673531 MLS
Welcome to an extraordinary waterfront estate nestled on one of Newport's most coveted peninsulas. Surrounded by breathtaking water views on nearly every side, this remarkable property offers the perfect blend of privacy, elegance, and Maine's natural beauty. Set among mature trees and beautifully landscaped grounds, the custom home is designed to maximize its stunning waterfront setting. Expansive windows fill the home with natural light while showcasing panoramic lake views throughout. The impressive architecture is complemented by spacious outdoor living areas, including a lakeside deck and beautifully manicured lawn--ideal for entertaining, relaxing, or simply enjoying spectacular sunsets. Boating enthusiasts will appreciate the private dock system with ample space for multiple watercraft, providing direct access to the lake for endless days of fishing, kayaking, paddleboarding, and cruising. This exceptional property offers the rare opportunity to own a private waterfront retreat while remaining just minutes from downtown Newport, local amenities, and convenient access to I-95. Whether you're searching for a year-round residence, luxury vacation home, or one-of-a-kind family retreat, 107 Barrows Point Road is a property that truly captures the essence of Maine waterfront living.

107 Barrows Point Rd, Newport

Listing courtesy of Trundy & Company Real Estate.

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

600 Fox Hill Rd, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$4,250,000
4 Beds ⋅ 3 Baths ⋅ 1667251 MLS
Located on the coveted Ocean Point peninsula in Boothbay, Edgewater is a remarkable waterfront estate with sweeping southern & western views across Linekin Bay & out to the Gulf of Maine. Encompassing 3.52 acres with deepwater frontage, the property is approached by an 800'±- private, winding drive through a beautiful grove of mature trees. The striking contemporary residence was designed to capture water views from nearly every room in the house. At the heart of the residence is a vibrant, impeccably maintained kitchen & a living room anchored by a fireplace & framed by captivating views of the bay. Expansive windows throughout create a seamless connection to the surrounding landscape & waterfront scenery. A beautiful primary suite with sweeping views across the bay & an adjacent office creates a private retreat. The second level features two bedrooms, while a guest bedroom on the main level provides comfort & privacy for visitors. Two additional rooms provide generous space for offices, studios, or creative pursuits. Outside, the property features a two-car garage & beautifully landscaped grounds. Exceptional amenities include an oversized two car garage, a deepwater dock, pier & float system, and two private moorings, providing direct access to some of Maine's most celebrated waters. Whether exploring nearby islands, fishing areas, or enjoying an afternoon on the bay, Edgewater provides an unparalleled waterfront lifestyle. Boothbay retains all the charm & maritime heritage of a classic New England coastal village, with art galleries, specialty shops, boatyards, and marinas. Nearby Boothbay Harbor is home to the largest fleet of excursion vessels in Maine providing trips to view islands, lighthouses, seals, whales, puffins, and spectacular foliage. The region is home to the acclaimed Coastal Maine Botanical Gardens & the Boothbay Harbor Country Club, further enhancing the area's appeal as one of Maine's premier coastal destinations

637 Ocean Point Rd, Boothbay

Listing courtesy of LandVest, Inc..

$4,250,000
3 Beds ⋅ 4 Baths ⋅ 1666332 MLS
Beach Life Starts Here at 832 Popham Road. 'Welcome to 832 Popham Road, where the salt air and the sound of the Atlantic are your daily companions. Nestled in the heart of the historic Phippsburg peninsula, this property offers an unparalleled gateway to Maine's most stunning coastline. Just minutes from the rolling dunes of Popham Beach State Park and the storied granite walls of Fort Popham, this home is a sanctuary for those who love the sea. Whether you're spending your days exploring the sand bars at low tide or enjoying the locally caught seafood at nearby West Point, 832 Popham Road isn't just an address--it's a front-row seat to the best of Mid Coast Maine.'

823 Popham Rd, Phippsburg

Listing courtesy of Kre Brokerage Group.

$4,250,000
5 Beds ⋅ 5 Baths ⋅ 73528794 MLS
Envision a carefree lifestyle in this exquisitely crafted, top-quality home with elevator to every floor. Extensively redesigned and practically rebuilt in 2007, no expense was spared in a complete reimagining of the home. Expansive rooms with custom installations, imported finishes and details, formal and informal tastefully created spaces - this home presents an oasis for modern living. Floor to ceiling window installations allow tremendous light to stream into every corner. Features include hand-tooled kitchen and bathroom cabinetry, top-of-the-line windows and doors, a primary suite with private deck and two large walk-in closets, a media room with radiant heated floor, and a barbecue great room leading out to a fantastic entertaining space, beneath a handsome custom-built pergola. A stunning landscape design impresses with gorgeous flowering perennials and mature trees, as well as a sweeping view of lush green lawn, surrounded by professionally manicured planting beds and bushes.

73 Countryside Road, Newton

Listing courtesy of Listing Agent: Brenda van der Merwe from Listing Office: Hammond Residential Real Estate.
$4,250,000
5 Beds ⋅ 4 Baths ⋅ 1662334 MLS
Dartholm sits along quiet Shore Road in Southwest Harbor, overlooking a picturesque harbor and offering a rich coastal heritage. Once the summer residence of a Dartmouth College president--lending the home its distinctive name--it has been thoughtfully updated into a gracious shingle-style cottage suited for comfortable year-round living. Expansive views stretch across Somes Sound, the Cranberry Islands, and Acadia's mountains, with yachts and lobster boats passing by. Beautifully restored, the home blends classic charm with modern amenities, featuring five bedrooms, including two on the first floor, along with inviting living and dining spaces, a chef's kitchen, and den. A newer, fully winterized addition includes the kitchen, dining area, and primary suite with geothermal heat, while other sections remain seasonal. A one-bedroom guest house, private dock, moorings, landscaped grounds, and proximity to Southwest Harbor's shops and dining complete this exceptional waterfront offering.

24 Shore Rd, Southwest Harbor

Listing courtesy of LandVest, Inc..

$4,250,000
5 Beds ⋅ 5 Baths ⋅ 73504708 MLS
Beautifully restored 1900s French-style residence on an acre of land in Brookline’s coveted Fisher Hill. Over 6,000 sq ft of living space featuring 5 bedrooms and 4.5 bathrooms. Inviting foyer with fireplace & custom bookshelves, an impressive great room with 15’ ceilings & fireplace, an elegant living room with period details including a fireplace, and a dining room with French doors to a stone terrace. House features a chef’s kitchen with high-end appliances and two spacious first-floor primary suites offering serene terrace views. The second floor has two bedrooms and a full bathroom. There is also a fifth bedroom with a private entrance, perfect for au pair or in-law. Four fireplaces, stone terraces, sweeping lawns, and lush landscaping complete this exceptional property, close to Brookline Reservoir, Chestnut Hill shops, Green Line public transportation, major highways & Boston.

540 Chestnut Hill Ave, Brookline

Listing courtesy of Listing Agent: The Duffy Group from Listing Office: Compass.
$4,250,000
4 Beds ⋅ 6 Baths ⋅ 73493426 MLS
The location that has it all...walk to both town, fish pier, beach and baseball games... New Farmhouse being built by Morgan and Son is well underway and expecting completion by July. Enjoy Chatham from this 4BR 5.5 baths, 3980Sq foot home. All bedrooms offer specious accommodations with private baths. First floor boasts a primary suite, an inviting study, living room with vaulted ceilings large slider with views overloooking the new pool and patio area, airy chef's kitchen and dining area. A detached outer building houses a one car garage and a seperate

222 Barcliff, Chatham

Listing courtesy of Listing Agent: Lori Fanning Smith from Listing Office: Compass.
$4,249,000
6 Beds ⋅ 5 Baths ⋅ 73426596 MLS
WATERFRONT ESTATE – This rare Cape Cod retreat blends classic coastal architecture with modern refinement. Refreshed with new siding and a Red Cedar roof (August 2025), the home offers 6 bedrooms and 5 baths, a chef’s kitchen with Viking professional gas range, Sub-Zero refrigerator, and center island with prep sink flows seamlessly into the sun-filled living room, dining area, and waterfront sunroom. The main residence includes a 2-car garage and full basement, while a versatile guest house with its own 2-car garage and striking fieldstone fireplace invites endless possibilities as a one or two-bedroom retreat, artist’s studio, game room, or workshop. Set on 3.8 private acres, the estate features a heated in-ground pool, landscaped grounds, and direct access to tidal waters. More than a residence, it is a private Cape Cod sanctuary offering beauty, privacy, and an unparalleled coastal lifestyle. 2-Year Choice ULTIMATE Home Warranty included. Some photos virtually staged.

4390 Main, Barnstable

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

226 Cochituate Rd, Wayland

Listing courtesy of Listing Agent: The Joni Shore Group from Listing Office: Douglas Elliman Real Estate - Wellesley.
$4,200,000
6 Beds ⋅ 5 Baths ⋅ 1666723 MLS
A rare beachfront gem at South Point in Biddeford Pool. Embracing clean lines with expansive walls of glass. This stunning contemporary home's design frames breathtaking, unobstructed views from every vantage point. This ultra-efficient home features high performance heat pumps powered by a private solar array and backed up by Tesla power banks for seamless energy independence. Spanning 3,851 Square feet of living space, with a additional 1456 Square feet below grade. The thoughtfully executed floor plan accommodates 6 Bedrooms and 5 bathrooms, offering unparalleled space for family and guests. The finished basement offers potential for a gym, movie theatre, or game room with fireplace. Situated on a .24-acre lot, the property features exquisitely landscaped grounds that transition into the pristine sandy Beach. Views span the Biddeford coastline south to Kennebunkport. Experience coastal luxury living redefined in one of Southern Maine's most coveted seaside communities. The existing home was re-Designed by Kaplan Thompson and masterfully constructed by Bowley Builders in 2018. Featured in Maine Home+Design December 2021.

1 Bay St, Biddeford

Listing courtesy of Legacy Properties Sotheby's International Realty.

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

30 Indian Trail, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$4,200,000
6 Beds ⋅ 5 Baths ⋅ 73488577 MLS
Meticulously renovated to the highest standards of design, this striking home artfully preserves its Victorian details while introducing luxurious modern amenities. Restored period features include soaring ceilings, grand proportions, intricate millwork, bay & bow windows, stained glass, pocket doors, built-ins, & wainscoting. Lavish updates include an entire wall of Hope's steel windows, app-controlled lighting & blinds, exquisite stonework, electric car charging, & irrigation. The sleek eat-in kitchen showcases custom cabinetry, a waterfall island, mirrored backsplash, and top-of-the-line appliances including a 6-burner gas range. An adjacent butler's pantry offers glass-fronted cabinets lined with antique mirror, a beverage cooler, & unlacquered brass counters & backsplash. An elegant primary suite is comprised of a bedroom with a fireplace, custom walk-in closet, and opulent bath with floor-to-ceiling marble, a glass-enclosed walk-in shower, and floating double vanity.

12 Martin Street, Cambridge

Listing courtesy of Listing Agent: Gail Roberts, Ed Feijo & Team from Listing Office: Coldwell Banker Realty - Cambridge.
$4,200,000
4 Beds ⋅ 3 Baths ⋅ 73453125 MLS
Northern California coast meets Boston's Gold Coast in this iconic, 4-bedroom, 3-bath direct waterfront Mid-century Modern house in Prides Crossing. Designed by famous architect John Lawrence Jr. as a weekend retreat, this home enjoys an unparalleled level of privacy and panoramic, 180-degree vistas of Manchester-by-the-Sea, Marblehead, Salem Sound to Misery and beyond. Sited on 2+ acres abutting RockMarge Estate to the west and 18 acres of conservation land to the east, the elevated living space is framed by seagrass covered dunes at the very end of a secluded, winding road lined with lush vegetation. Ideal for entertaining or intimate gatherings, this property is a slice of heaven. Looking to create something completely new? This offering includes city approvals and plans in hand to build a new 4,600+ sq. ft. primary residence and preserve 1,300 sq. ft. of existing home as a beach cabana. This is an exceptional opportunity.

68 Paine Ave, Beverly

Listing courtesy of Listing Agent: Alexandra Cutler from Listing Office: J. Barrett & Company.
$4,150,000
3 Beds ⋅ 3 Baths ⋅ 73536468 MLS
Step into timeless Sconset charm at 9 Carew Lane. Tucked away this classic 1920 cottage embodies the quiet magic that has drawn visitors and homeowners to this storied village for generations. This three-bedroom, two-and-a-half bath home has been lovingly preserved, retaining the architectural character and warmth that define the 'Sconset aesthetic. With 2,655 square feet of living space spread across two floors, the home offers generous room to gather while never losing its intimate cottage feel. A wood-burning fireplace anchors the living space, lending the kind of cozy ambiance that makes a Nantucket evening something to savor. The patio and garden offer a peaceful retreat. Original details and craftsmanship speak to the home's rich history, while thoughtful updates including central A/C, poured concrete foundation, oil/FHA heat, town water and sewer, and on-site parking are the practical details equally well-considered.

9 Carew Lane, Nantucket

Listing courtesy of Listing Agent: Nicole Tirapelli from Listing Office: Douglas Elliman Real Estate - Park Plaza.
$4,150,000
6 Beds ⋅ 8 Baths ⋅ 73520778 MLS
Perched atop 8.58 private acres at one of Manchester’s highest elevations, Ocean Ledge commands breathtaking distant ocean vistas and mesmerizing celestial views. This grand residence offers an exceptional sense of privacy and scale, perfectly positioned to capture both sunrise over the water and starlit evening skies.The estate is complemented by a charming carriage house featuring an apartment above a spacious three-car garage—ideal for guests, extended family, or additional income. Equestrian enthusiasts will appreciate the four-stall barn complete with tack room and paddock, while leisure amenities abound with a Har-Tru tennis court and a stunning 40-foot pool, creating a true resort-like setting. A rare opportunity to own an elevated coastal retreat that seamlessly blends elegance, recreation, and panoramic beauty.

73 Forest, Manchester

Listing courtesy of Listing Agent: Lynda Surdam from Listing Office: Coldwell Banker Realty - Manchester.
$4,149,000
6 Beds ⋅ 8 Baths ⋅ 73481956 MLS
Set on a beautifully landscaped one-acre lot, this exceptional new construction home offers the prestige of the estate side of town with a rare sense of privacy and space. Spanning over 7,100 sq ft, the residence features 6 beds, 7.5 baths, and refined craftsmanship throughout. The chef’s kitchen includes top-of-the-line appliances, an oversized island, and a working pantry, opening to a sun-filled family room overlooking the expansive, private yard. The acre setting offers outstanding potential for a pool, sports court, & outdoor living. The main level features a first-floor en suite bedroom & formal dining room. Upstairs, the primary suite offers a spa-like bath & generous walk-in closet. Each bedroom is thoughtfully designed w/ an en suite bath. A finished lower level provides flexible space for a gym or media room. Complete with a 3-car garage, custom millwork, & designer finishes, this home offers a rare blend of elegance & convenience minutes from top rated schools & town center.

8 Crestview Road, Needham

Listing courtesy of Listing Agent: Connor Gillen from Listing Office: Keller Williams Realty.
$4,000,000
5 Beds ⋅ 4 Baths ⋅ 73542491 MLS
A private estate spanning 11 spectacular acres, this distinguished 1912 residence offers timeless character and exceptional privacy in one of the Boston area's most coveted settings. The five-BR home features 4,500+ square feet of beautifully maintained living space blending classic architectural details with modern comfort. Grand living and dining rooms, a sun-drenched conservatory, and an intimate library create a sophisticated backdrop for entertaining. Center island chef's kitchen and FP'd family room. Period details include custom millwork, French doors, a spacious butler’s pantry and multiple fireplaces. Expansive porches and patios overlook lush gardens and sweeping grounds, leading to a tucked-away pool. An oversized 3-car carriage house with loft adds further versatility. This rare offering includes a separate buildable lot, providing an opportunity for expansion or legacy compound. Minutes to the commuter rail, major routes, and premier shopping. An irreplaceable opportunity.

157 Grove Street, Westwood

Listing courtesy of Listing Agent: Bell Property Partners from Listing Office: Compass.
$4,000,000
5 Beds ⋅ 2 Baths ⋅ 73513139 MLS
Surrounded by endless gardens and green space this expansive cape house sits on a vast 10,000+ square foot lot, perched above the first hole of Fresh Pond Golf Course overlooking Fresh Pond across from the acres worth of Grove Street Playground and Park, right on the Belmont line. The home has been meticulously maintained, updated and has lots of windows and sunlight, hardwood floors, a vaulted ceiling sunroom with radiant heated floors, two working fireplaces, a great floor plan, solar panels, two car parking with EV charger, a deck to soak up the view and endless options for bedrooms, office, workout and lounge or living space. This is a can't miss opportunity to live in one of the very best locations in Cambridge.

175 Grove Street, Cambridge

Listing courtesy of Listing Agent: Jaclyn Kryzak from Listing Office: Labrava Realty, LLC.
$3,999,999
5 Beds ⋅ 6 Baths ⋅ 73496678 MLS
This beautiful Coastal New England / Nantucket-style shingle home overlooks scenic W. Dennis Beach and is abutted by Uncle Stephen’s Pond. Custom built in 2016 by Pecoy Signature Homes, the residence spreads 5-bedrooms and 5.5 baths over 4,834 square feet of thoughtfully designed living space, with natural light and water views showcased throughout. A gracious entry introduces an expansive open-concept layout. The main level features a stunning great room, private office, mudroom, laundry, and multiple dining areas, all centered around a showpiece chef’s kitchen. Appointed with an oversized quartz island, custom cabinetry, a vented NXR range, wet bar, and a generous walk-in pantry. The main-level primary suite offers an ensuite. Three ensuite bedrooms are located on the 2nd level the third-floor loft serves as a sophisticated lounge with wet bar, opening to a private deck with panoramic ocean views. The houses on Uncle Stephens share a private ocean beach (pictured).

10 Uncle Stephens Rd, Dennis

Listing courtesy of Listing Agent: Chris Bowser from Listing Office: Conway - Mattapoisett.
$3,999,999
4 Beds ⋅ 3 Baths ⋅ 73494430 MLS
Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its finest. Set on 2.25 secluded acres, panoramic views stretch across the shimmering waters, a private haven for kayaking, sailing, and peaceful exploration. Inside, four bedrooms and three full bathrooms are complemented by generous windows framing breathtaking water views from nearly every room. A family room and library, formal living room, and a private guest suite on the far side of the residence provide ample space for all. Outside, the lawn sweeps to the water's edge, where a sandy shoreline invites you to launch a kayak, cast a line, or linger over a sunset picnic. A detached three-car garage with a finished room above offers generous storage for watercraft, paddleboards, and all the trappings of Island adventure. Minutes from shops, restaurants, and the harbor, yet worlds away in feeling.

94 Weaver Lane, Tisbury

Listing courtesy of Listing Agent: Emma Kennedy from Listing Office: Sandpiper Realty, Inc..
$3,999,000
5 Beds ⋅ 6 Baths ⋅ 73540147 MLS
Hi my name is 20 Boulder... but you can call me Home. Experience exceptional scale, sophistication & architectural detail in this striking custom residence. A soaring 2-story foyer welcomes you to elegant living spaces, including formal living & dining rms, highlighted by dramatic arched windows & access to a covered patio w/ a masonry fireplace.The main level also offers a private home office w/ custom built-ins, a flexible ensuite BR ideal for guests, a chef’s kitchen w/ custom cabinetry, oversized center island & sun-filled breakfast area, plus a powder rm, mudrm & direct access to the heated 3-car garage. 2nd floor the luxurious primary suite features a spa bath, expansive dressing room & private Juliet balcony & additional ensuite BRs. Top floor offers versatile space for changing chapters of life with comfort & privacy. Space for a guest suite, media rm, playrm or creative studio. Ideally located near top-rated Newton schools, Chestnut Hill shopping,easy access to highways&Boston

20 Boulder Rd, Newton

Listing courtesy of Listing Agent: Esin Susol from Listing Office: William Raveis R. E. & Home Services.
$3,999,000
5 Beds ⋅ 9 Baths ⋅ 73322653 MLS
Discover the epitome of luxury at this exquisite waterfront estate, a haven of tranquility and elegance. Built in 2002 and meticulously renovated, this stunning home offers unmatched comfort and privacy on 4.32 acres. With prime waterfront access and breathtaking views, this expansive 16-room residence features 5 spacious bedrooms and 9 baths including steam shower. The interior boasts two elegant primary suites with gas fireplaces, expansive walk-in closets, and deep hydro-massaging tubs. The masterfully crafted kitchen is equipped with top-line appliances, custom cabinets and granite countertops. The lower level includes hobby and pool table rooms, a kitchenette, an entertainment center and substantial storage. Outdoors, enjoy a stunning heated saltwater pool, oversized hot tub, waterfalls, multilevel stone terrace, outdoor shower, cabana with full bath and a built-in cooking area.This waterfront estate is more than just a home; it's a lifestyle.

26 Walkerwoods Dr, Harwich

Listing courtesy of Listing Agent: Karen Lopez from Listing Office: Great Estates Realty, Inc..
$3,998,000
5 Beds ⋅ 6 Baths ⋅ 73451336 MLS
East Hill Farm offers 227 acres of protected quiet, anchored by the elegant 1798 Thomas Shepard House. A private hilltop world.Main house: Georgian-Federal; 5 BR, 5.5 BA, ~5,000 SF; 5 fireplaces; unusually high ceilings, wide-board floors, antique glass, rooms that hold the light, views that connect. Graceful, welcoming.A complete estate that also can be a working-farm or equine property: barns + outbuildings, pastures, private trails + roads, 4+ acre pond, gardens + orchard, pool, pool house, greenhouse, tennis.A vast former Arabian horse barn, now guest compound, or for you to reimagine. Preserved with rigor, lived in with joy, and rooted in the land and history that defines the Berkshires. One of the most complete and intact agricultural landscapes remaining in Southern Berkshire County, has no true comparable. Read the history. Experience East Hill Farm. Reach out.

764 East Hill Road, New Marlboro

Listing courtesy of Listing Agent: Chapin Fish from Listing Office: William Pitt Sotheby's International Realty.
$3,995,000
3 Beds ⋅ 4 Baths ⋅ 1671349 MLS
Distinctive opportunity to live at the renowned Boothbay Harbor Country Club, recognized as the best golf and country club experience in Maine. This exceptionally designed and appointed home will be built with supreme quality and luxury, including a ground floor ensuite bedroom, and a spectacular primary bedroom suite upstairs with his & hers bathrooms, closets, and a study that could serve as an extra bedroom. The open concept kitchen and great room makes for satisfying everyday use, as does the abundanta outdoor living space, be it the screened porch, veranda, open deck, and granite patios. Sumptuously comfortable, the home offers owners an effortless club lifestyle, with golf cart access to Club amenities that feature the 18-hole course, lavish spa, family pool, fitness center, tennis & pickleball courts, dining facilities, and more. Club-maintained gardens & landscaping, municipal water & sewer, and other attributes make for ''lock and leave'' convenience, just up the hill from downtown Boothbay Harbor.

Lot 7 Whispering Pines, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$3,995,000
5 Beds ⋅ 3 Baths ⋅ 73542542 MLS
A rare opportunity to create a premier in-town compound in one of Edgartown’s most desirable locations. Set on High Street, just moments from downtown Edgartown, this exceptional 16,000+ square foot lot offers tremendous potential to create a substantial five-bedroom residence while enjoying the convenience and charm of village living. The property currently features a 4 bedroom main house, attached 1 bedroom apartment, and an oversized garage with an attached 556-square-foot barn. The property provides a unique foundation for expansion, renovation, or a thoughtfully designed new build. With its generous lot size and coveted location, 49 High Street presents a rare opportunity to create a legacy property within walking distance of Edgartown’s shops, restaurants, harbor, and village amenities.

49 High Street, Edgartown

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal,noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

This information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be intrested in purchasing.

Privacy Policy

Your privacy on the Internet is important to us. This Privacy Statement is to inform you that we will not provide your personal information to any third parties except as required by law or expressly authorized by you. We do not sell, trade, barter, or share information obtained from use of this site with any other businesses or people. All information gathered from a visitor to this web site is used solely by this office and/or its affiliated licensee(s). For additional information, please contact this office.