Homes with Basements for Sale in 02535, MA

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ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets. The home centers on a soaring great room with 17-foot vaulted ceiling, fieldstone fireplace, oak post-and-beam detailing, chef's kitchen, and walls of glass opening to the landscape. Five bedrooms are complemented by two offices, a gym, bunk room, and walkout recreation room. Across the lawn, a finis

$16,250,000

6 beds7 baths8,648 sq ft

Dramatic views • Fieldstone fireplace • Chef's kitchen

25 Brickyard Rd, Chilmark, MA 02535

ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming living room, anchored by a pristine Vermont Castings wood stove, opens seamlessly to a covered porch and spacious deck--perfect for morning coffee or evening gatherings. The spacious first-floor primary suite provides a private retreat with two en-suite baths and two walk-in closets. Upstairs, you'll fi

$1,795,000

3 beds3 baths3,702 sq ft

Covered porch • Spacious deck • Eat-in kitchen

174 Middle Rd, Chilmark, MA 02535

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ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired baths. Dramatic living spaces with soaring cathedral ceilings open to expansive decks and a screened porch overlooking the pond. Exceptional amenities include two chef’s kitchens, a private theater, wine cellar, outdoor shower, and a hilltop writer’

$45,000,000

7 beds12 baths11,200 sq ft

Waterfront estate • Private theater • Wine cellar

18 Point Inner Way, Chilmark, MA 02535

ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
Bright & Airy Black Point Retreat with Private Access to Black Point Beach. Nestled on 5.4 private acres just off Black Point Road in Chilmark, this beautifully maintained retreat offers tranquility and comfort where the sound of the ocean provides a constant backdrop and the shoreline is just moments away. Included with the property is a coveted beach lot (key) to this private south shore beach. Thoughtfully designed, the home's welcoming entry opens into a light-filled living, dining, and kitchen area that flows seamlessly onto a screened porch and expansive sun deck, creating an ideal setting for indoor-outdoor living and entertaining. The upper level features a serene primary suit

$2,950,000

3 beds3 baths1,469 sq ft

Finished guest suite • Screened porch • Expansive sun deck

28 Black Point Rd, Chilmark, MA 02535

ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living are

$15,400,000

6 beds8 baths6,967 sq ft

Sport court • Outdoor living areas • Protected views

8 Snail Rd, Chilmark, MA 02535

Property at 35 South Bowl Rd, Chilmark, MA 02535, 3 beds, 2 baths

$4,995,000

3 beds2 baths2,710 sq ft

35 South Bowl Rd, Chilmark, MA 02535

Property at 96 Hammett Ln, Chilmark, MA 02535, 3 beds, 3 baths

$3,795,000

3 beds3 baths3,426 sq ft

96 Hammett Ln, Chilmark, MA 02535

Property at 49 Gosnolds Way, Chilmark, MA 02535, 5 beds, 3.5 baths

$5,200,000

5 beds3.5 baths4,044 sq ft

49 Gosnolds Way, Chilmark, MA 02535

Property at 205 South Rd, Chilmark, MA 02575, 4 beds, 4.5 baths

$4,995,000

4 beds4.5 baths5,402 sq ft

205 South Rd, Chilmark, MA 02575

Property at 26 Bijahs Way, Chilmark, MA 02535, 3 beds, 2 baths

$2,395,000

3 beds2 baths2,510 sq ft

26 Bijahs Way, Chilmark, MA 02535

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ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious two-bedroom, one-bathroom Guest Studio with a fireplace, offering a combined 3,771 square feet of living space. A gunite swimming pool, gardens, expansive lawn areas, outdoor shower, and one-car garage complete the setting. Renovated in 2013 and equipped with central air conditioning, the property feels wonderfully secluded while remaining centrally located for convenient access to both up an

$2,200,000

4 beds3 baths3,771 sq ft

Private acres • Gunite swimming pool • Future expansion

99 Oak Ln, West Tisbury, MA 02575

ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
Discover the charm of West Tisbury with the perfect blend of country living and village convenience. Ideally located just a short stroll from the heart of town, you'll enjoy easy access to all the West Tisbury Village has to offer. Set on a lovely lot, the home features a spacious southeast-facing deck overlooking a sunny yard. Four detached outbuildings. A generous south-facing living room is filled with natural light and offers peaceful views of the surrounding landscape. The kitchen provides an opportunity to create a space tailored to your vision. Off the kitchen is a large dinning area with a beautiful custom cabinet. The primary suite includes a sitting area and sunroom, while a secon

$1,350,000

2 beds2 baths1,996 sq ft

Natural light • Outdoor shower • Custom cabinet

29 Scotchmans Ln, West Tisbury, MA 02575

ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you will find two large bedrooms, a full bathroom with walk-in shower and plenty of attic storage. Set on a picturesque two-acre parcel, the property also features a detached 384-square-foot studio, offering exceptional flexibility. Set back and private from the main house, it is independent and private

$1,600,000

4 beds2.5 baths2,334 sq ft

Private parking area • First-floor bedroom • Open-concept kitchen

150 Field View Ln, West Tisbury, MA 02575

ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
Year-round living in the desirable Island Farms Road neighborhood of West Tisbury. This well-built three-bedroom, two-bath home offers a comfortable layout with a first-floor primary bedroom. While ready for your personal updates, it provides a solid foundation to create your forever home. The open kitchen and living area offer a welcoming space for everyday living while the screened porch extends the living area outdoors—perfect for summer dining or simply relaxing in the peaceful surroundings. Mature landscaping, cultivated over many years, creates a private and tranquil setting. Additional amenities include an outdoor shower and garden shed. Ideally located just minutes from Lamber

$1,225,000

3 beds2 baths1,800 sq ft

Screened porch • Outdoor shower • Garden shed

52 Oak Knl, West Tisbury, MA 02575

ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home offices, this residence offers perfect versatility for modern living—whether you require a quiet library or a remote workspace. Step outside onto the welcoming farmer’s porch to take in the beautifully manicured grounds, complete with lush perennial gardens supported by an irrigation sy

$3,495,000

4 beds4 baths3,200 sq ft

In-ground pool • Hot tub spa • Farmers porch

64 Christiantown, West Tisbury, MA 02575

ABOUT THIS HOME
Home with Basement for sale in 02535, MA:
4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting. Built by South Mountain Company, the home was designed with quality craftsmanship, natural light, and efficient living in mind. The expansive open living, kitchen, and dining area creates an inviting gathering space, anchored by warm cherry cabinetry, a wood stove, and oversized windows that bring the outdoors in. An atrium add

$1,140,000

4 beds2 baths2,059 sq ft

Natural light • Atrium addition • Greenhouse addition

4 Rock Pond Rd, West Tisbury, MA 02575

Property at 20 James Pond Way, West Tisbury, MA 02575, 5 beds, 3 baths

$3,600,000

5 beds3 baths2,701 sq ft

20 James Pond Way, West Tisbury, MA 02575

Property at 188 Vineyard Meadow Farms Rd, West Tisbury, MA 02575, 4 beds, 3 baths

$1,800,000

4 beds3 baths3,158 sq ft

188 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

Property at 111 Charles Neck Way, West Tisbury, MA 02575, 3 beds, 2 baths

$1,499,000

3 beds2 baths1,562 sq ft

111 Charles Neck Way, West Tisbury, MA 02575

Property at 85 North Reservoir Rd, West Tisbury, MA 02575, 5 beds, 6 baths

$7,500,000

5 beds6 baths4,531 sq ft

85 North Reservoir Rd, West Tisbury, MA 02575

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than Redfin are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated Thu Aug 20 2026. Neither the listing broker nor Redfin shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision. All properties are subject to prior sale, changes, or withdrawal. © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Homes with Basements for Sale in 02535

There are currently 10 homes with basements for sale in 02535 at a median listing price of $4.39M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 02535 stay on the market for 70 days. This map is refreshed with the newest listings in 02535 every 15 minutes.

In the past month, 1 home has been sold in 02535. In addition to houses in 02535, there were also 0 condos, 0 townhouses, and 1 multi-family unit for sale in 02535 last month. Find your dream home in 02535 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 02535 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 02535. If you're looking to sell your home in the 02535 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 02535 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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