East Chop, MA homes for sale & real estate

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3D WALKTHROUGH

12 & 14 Maple Ave, Oak Bluffs, MA 02557
12 & 14 Maple Ave, Oak Bluffs, MA 02557
12 & 14 Maple Ave, Oak Bluffs, MA 02557
ABOUT THIS HOME
East Chop, MA Homes for Sale
Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island's most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history--just a short distance to the harbor, downtown, and the beloved Winston's takeout. Built at a time when automobiles were rare, these homes were sited with ease of access in mind. Though they have no driveways, convenient on-street parking is always available--local residents often find it easier to stroll, or bike, into town than drive. Both homes are separately deeded, giving you the flexibility to own them joi

$1,830,000

4 beds4 baths1,600 sq ft

12 & 14 Maple Ave, Oak Bluffs, MA 02557

4,356 sq ft lot • Somewhat walkable

47 Winemack St, Oak Bluffs, MA 02557
47 Winemack St, Oak Bluffs, MA 02557
47 Winemack St, Oak Bluffs, MA 02557
ABOUT THIS HOME
East Chop, MA Homes for Sale
Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a separate utility room. Recent upgrades includes new roofs, new electrical service in front house, and a new 3-bedroom title 5 septic system.

$1,250,000

2 beds1 bath742 sq ft

47 Winemack St, Oak Bluffs, MA 02557

4,792 sq ft lot • Car-dependent

150 East Chop Dr, Oak Bluffs, MA 02557
150 East Chop Dr, Oak Bluffs, MA 02557
150 East Chop Dr, Oak Bluffs, MA 02557
ABOUT THIS HOME
East Chop, MA Homes for Sale
Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J. G. Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast room flow seamlessly into the great room and screened porch. Spectacular dining room, reading room, laundry and 1st floor bedroom suite. The primary suite features panoramic water views, a private balcony, fireplace, outdoor shower, spa-like bath, and two dressing rooms. Seven additio

$9,900,000

8 beds8 baths8,560 sq ft

150 East Chop Dr, Oak Bluffs, MA 02557

0.64 acre lot • 2 garage spots • Car-dependent

16 Atlantic Ave, Oak Bluffs, MA 02557
16 Atlantic Ave, Oak Bluffs, MA 02557
16 Atlantic Ave, Oak Bluffs, MA 02557
ABOUT THIS HOME
East Chop, MA Homes for Sale
East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most importantly, the modern comforts today's lifestyle demands. Set on a generous, level parcel, with an existing seven-bedroom septic system--providing ample opportunity for future expansion and customization. Located in the heart of East Chop, a cherished community known for its neighborly spirit, you're ju

$2,495,000

5 beds2.5 baths2,577 sq ft

16 Atlantic Ave, Oak Bluffs, MA 02557

0.5 acre lot • Garage • Car-dependent

47 E East Chop Dr #5, Oak Bluffs, MA 02557
47 E East Chop Dr #5, Oak Bluffs, MA 02557
47 E East Chop Dr #5, Oak Bluffs, MA 02557
ABOUT THIS HOME
East Chop, MA Homes for Sale
East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Captain's Quarters'', features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch over-looking the water (see floor plans). The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at

$1,495,000

1 bed1 bath650 sq ft

47 E East Chop Dr #5, Oak Bluffs, MA 02557

0.29 acre lot • $1,250 HOA

Property at 47 E Chop Dr #4, Oak Bluffs, MA 02557, 2 beds, 1 bath

$1,995,000

2 beds1 bath879 sq ft

47 E Chop Dr #4, Oak Bluffs, MA 02557

Property at 47 E Chop Dr #3, Oak Bluffs, MA 02557, 2 beds, 1 bath

$1,995,000

2 beds1 bath802 sq ft

47 E Chop Dr #3, Oak Bluffs, MA 02557

Property at 47 E Chop Dr #2, Oak Bluffs, MA 02557, 1 bed, 1 bath

$1,495,000

1 bed1 bath736 sq ft

47 E Chop Dr #2, Oak Bluffs, MA 02557

Property at 47 E Chop Dr #1, Oak Bluffs, MA 02557, 1 bed, 1 bath

$1,495,000

1 bed1 bath731 sq ft

47 E Chop Dr #1, Oak Bluffs, MA 02557

Property at 4 Dempster Park, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$2,195,000

4 beds2.5 baths1,825 sq ft

4 Dempster Park, Oak Bluffs, MA 02557

Property at 47 E Chop Dr, Oak Bluffs, MA 02557, 8 beds, 6 baths

$10,500,000

8 beds6 baths3,888 sq ft

47 E Chop Dr, Oak Bluffs, MA 02557

Property at 47 East Chop Dr, Oak Bluffs, MA 02557, 7 beds, 6 baths

$10,500,000

7 beds6 baths3,888 sq ft

47 East Chop Dr, Oak Bluffs, MA 02557

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Nearby homes that match your criteria

13 County Rd, Oak Bluffs, MA 02557
13 County Rd, Oak Bluffs, MA 02557
13 County Rd, Oak Bluffs, MA 02557
ABOUT THIS HOME
East Chop, MA Homes for Sale
Welcome to an inviting single-story ranch nestled in the heart of Oak Bluffs. This cozy and charming home offers a comfortable living space and is set on a generous, water view landscaped lot with mature trees and natural privacy. Inside, the home features a functional layout with a mix of wood and carpet flooring, a cozy wood-burning fireplace, and abundant natural light throughout. The classic ranch design includes a seamless flow between living, dining, and kitchen spaces—ideal for both everyday living and seasonal retreats. Enjoy the outdoors from the wood deck or rinse off in the outdoor shower after a day at the beach. A detached garage provides added storage and parking conveni

$1,199,000

3 beds1 bath1,176 sq ft

13 County Rd, Oak Bluffs, MA 02557

1 acre lot • Garage • Car-dependent

9 Brunswick Ave, Oak Bluffs, MA 02557
9 Brunswick Ave, Oak Bluffs, MA 02557
9 Brunswick Ave, Oak Bluffs, MA 02557
ABOUT THIS HOME
East Chop, MA Homes for Sale
PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively updated inside and out. Enjoy peace of mind with a new septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new heat/AC systems for year-round comfort. Recently installed professional landscaped grounds offer curb appeal and outdoor enjoyment, complete with shower and patio furniture for al fresco dining and relaxing. Also included are all furnishings and a handy ow

$1,795,000

3 beds1 bath1,033 sq ft

9 Brunswick Ave, Oak Bluffs, MA 02557

3,485 sq ft lot • Somewhat walkable

23 Circuit Ave Ext, Oak Bluffs, MA 02557
23 Circuit Ave Ext, Oak Bluffs, MA 02557
23 Circuit Ave Ext, Oak Bluffs, MA 02557
ABOUT THIS HOME
East Chop, MA Homes for Sale
Rare Opportunity with Endless Possibilities - Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound--a setting that captures the very best of island living. From your front yard, watch ferries come and go, boats drift through the harbor, and enjoy the stunning backdrop of open water stretching toward Vineyard Sound. This is a property that puts you right in the middle of everything, while still offering the charm and charac

$3,100,000

3 beds1 bath1 sq ft

23 Circuit Ave Ext, Oak Bluffs, MA 02557

6,483 sq ft lot • Garage • Somewhat walkable

71 Netock Ave, Oak Bluffs, MA 02557
71 Netock Ave, Oak Bluffs, MA 02557
71 Netock Ave, Oak Bluffs, MA 02557
ABOUT THIS HOME
East Chop, MA Homes for Sale
On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated 4-bed home w/ separate, office or studio space, ensconced in professionally landscaped grounds. Blending modern comfort w/ timeless island charm, house features wide plank white oak floors, beautiful ceiling height & natural light, open-concept living-dining space w/ new kitchen, 1st-floor primary bedroom w/ ensuite bath, powder room & laundry room. Upstairs are 3 additional spacious bedrooms & 2 full baths. New roof, siding, and central air enhance comfort. Outside, enjoy a wide back deck, welcoming front porch, & expansive yard w/ irrigation, new sod lawn, lush evergreen & privet hedge

$2,295,000

4 beds4 baths2,820 sq ft

71 Netock Ave, Oak Bluffs, MA 02557

0.23 acre lot • Car-dependent

22 Greenleaf Ave, Oak Bluffs, MA 02557
22 Greenleaf Ave, Oak Bluffs, MA 02557
22 Greenleaf Ave, Oak Bluffs, MA 02557
ABOUT THIS HOME
East Chop, MA Homes for Sale
Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks. This home blends classic Vineyard character with thoughtful design by Island architect Jaime Weisman. Lovingly maintained by one family for over 27 years, it now awaits its next chapter. Fairview includes three bedrooms, a finished basement for flexible living or work space, and a multipurpose outbuilding that functions as both shed and garage. With off-street parking and a generous y

$2,290,000

3 beds2 baths1,608 sq ft

22 Greenleaf Ave, Oak Bluffs, MA 02557

7,841 sq ft lot • Garage • Somewhat walkable

Average home prices near East Chop, MA

Cities

Neighborhoods

Martha's Vineyard homes for sale
$2,445,000

East Chop, MA real estate trends

$1.67M

Sale price

$691

Sale $/sq ft

Under list price

4.9%

Days on market

Down payment

—

Total homes sold

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