Martha's Vineyard, MA Homes

/45
$2,575,000
- 4 Beds
- 2.5 Baths
- 1,910 Sq Ft
76 Washque Ave, Edgartown, MA 02539

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends

Katherine Donahue Sandpiper Realty Inc

76 Washque Ave, Edgartown, MA 02539
/15
$5,000 per month plus fees
- 4 Beds
- 2.5 Baths
- 2,300 Sq Ft
- House for Rent
6 Briar Path, Aquinnah, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Down a private country road, this bright and breezy post and beam home sits on a 3-acre rolling wooded parcel. With southern views of the Atlantic Ocean, it's just a short drive or bike to Philbin and Lobsterville beaches and Gay Head cliffs. This very Vineyard house offers three levels of living space, chef's kitchen, spacious

Karen Overtoom Karen M. Overtoom R.E.

6 Briar Path, Aquinnah, MA 02535
/40
$2,300,000 Sold Aug 21, 2025
- 3,213 Sq Ft
- $716/SF
- 75 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2011
174 Tashmoo Ave, Vineyard Haven, MA 02568

Welcome to your dream home! The perfect blend of comfort and luxury awaits you in this custom-designed 5-bedroom, 4.5-bathroom residence. Over 3200 square feet of spacious living, upscale furnishings, finished basement with entertainment bar, and all the right touches to make every day feel like a retreat. Conveniently located under a half mile from downtown Vineyard Haven, where you will find

Lisa Lucier Anchor Realty of Martha's Vineyard

174 Tashmoo Ave, Vineyard Haven, MA 02568

/36
Est $3,940,305 Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 3,902 Sq Ft
94 Marthas Rd, Edgartown, MA 02539

94 Marthas Rd, Edgartown, MA 02539

/34
$3,450,000
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
6 Brewster Ave, Oak Bluffs, MA 02557

Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

Katherine Donahue Sandpiper Realty Inc

6 Brewster Ave, Oak Bluffs, MA 02557
/42
$19,000 per month plus fees
- 6 Beds
- 6.5 Baths
- 6,950 Sq Ft
- House for Rent
40 Sweet William Way, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

Karen Overtoom Karen M. Overtoom R.E.

40 Sweet William Way, West Tisbury, MA 02575
/19
$1,449,000 Sold Aug 19, 2025
- 2,284 Sq Ft
- $634/SF
- 263 Days On Market
- 3 Beds
- 3 Baths
- Built 1987
14 High Meadow Ln, Oak Bluffs, MA 02557

MEADOW VIEW FARM/OAK BLUFFS - Owned by the same family for over 30 years, this sun-drenched, contemporary reverse-style home is located in Meadow View Farms. Well-maintained over those years, this 3 bedroom, 2 full and 2 half baths multi-level home has so much to offer and boundless potential. The second-level features a bright, open floor plan with cathedral ceilings and 3 sliding doors that

Michele Moore Island Real Estate

14 High Meadow Ln, Oak Bluffs, MA 02557

/20
Est $1,556,866 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,532 Sq Ft
39 Prices Way, Edgartown, MA 02539

39 Prices Way, Edgartown, MA 02539

/63
$4,295,000
- 7 Beds
- 6 Baths
- 9,686 Sq Ft
56 N Neck Rd, Edgartown, MA 02539

A RARE CHAPPAQUIDDICK LEGACY ESTATE — Privacy & Island Living at its finest.Step into a world where time slows, ocean breezes carry the scent of salt and cedar, and each day begins and ends with the relaxing sounds of the local fauna and the Vineyard Sound. This 18.4-acre multi-residence estate, with 4 conforming parcels, on Martha’s Vineyard’s treasured Chappaquiddick Island is more than a

Leslie C. Floyd Portfolio Real Estate, Inc.

56 N Neck Rd, Edgartown, MA 02539
/27
$18,840 per month plus fees
- 3 Beds
- 2.5 Baths
- House for Rent
21 William St Vh430, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

Karen Overtoom Karen M. Overtoom R.E.

21 William St Vh430, Tisbury, MA 02568
/41
$1,310,000 Sold Aug 18, 2025
- 1,964 Sq Ft
- $667/SF
- 0 Days On Market
- 3 Beds
- 2 Baths
- Built 1965
35 E Side Rd, Oak Bluffs, MA 02557

Close to the Lagoon - This three-bedroom, two-bath home sits on an oversized corner lot and has been lovingly maintained over the years. Recent upgrades include the addition of mini splits, interior painting, and lighting. The sunroom provides additional year-round living space and the wraparound deck is ideal for summer use. Bring your vision to the partially finished lower level where

Kristin Buck Donnelly + Co

35 E Side Rd, Oak Bluffs, MA 02557

/14
Est $2,709,570 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,926 Sq Ft
30 Pond Ln, Vineyard Haven, MA 02568

30 Pond Ln, Vineyard Haven, MA 02568

/76
$2,345,000
- 4 Beds
- 2 Baths
- 1,545 Sq Ft
15 Night Heron Rd, Edgartown, MA 02539

KATAMA - NEWLY RENOVATED! This Quintessential Martha’s Vineyard saltbox blends timeless island character with wonderful thoughtful updates, having been recently renovated. Set in a quiet location, Island Grove, one of the most popular locations in Edgartown, you're just a short drive to Wilson's Landing, South Beach and downtown Edgartown, an ideal location for summer escapes, year-round living,

Alisan Lohan-Conway Alisan Lohan-Conway Properties

15 Night Heron Rd, Edgartown, MA 02539
/25
$10,800 per month plus fees
- 2 Beds
- 4 Baths
- 1,800 Sq Ft
- House for Rent
256 Sandpiper Lane Vh417, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

Karen Overtoom Karen M. Overtoom R.E.

256 Sandpiper Lane Vh417, Tisbury, MA 02568
/17
$929,000 Sold Aug 18, 2025
- 1,286 Sq Ft
- $722/SF
- 6 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1950
299 Franklin St, Vineyard Haven, MA 02568

Walkable to downtown Vineyard Haven, offering shops, dining, and waterfront access. Close to everything, yet tucked away on a peaceful corner lot is this classic 3-bedroom, 1.5-bathroom ranch home. The possibilities abound on a spacious .27-acre level yard where you can add more bedrooms and an ADU. The extra long detached 2-car garage with high ceilings is a great spot to store your vehicles or

Lisa Lucier Anchor Realty of MV

299 Franklin St, Vineyard Haven, MA 02568

/36
Est $1,273,428 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,780 Sq Ft
16 Rock Pond Rd, Vineyard Haven, MA 02568

16 Rock Pond Rd, Vineyard Haven, MA 02568

/28
$2,495,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
268 Tashmoo Ave, Vineyard Haven, MA 02568

Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

Michele Casavant Vineyard Village Realty

268 Tashmoo Ave, Vineyard Haven, MA 02568
/18
$10,000 per month plus fees
- 3 Beds
- 1.5 Baths
- 1,144 Sq Ft
- House for Rent
100 Franklin Terrace Vh411, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and

Karen Overtoom Karen M. Overtoom R.E.

100 Franklin Terrace Vh411, Tisbury, MA 02568
/36
$1,765,000 Sold Aug 18, 2025
- 2,450 Sq Ft
- $720/SF
- 25 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1988
34 Tower Ridge Rd, Oak Bluffs, MA 02568

Nestled on a beautifully landscaped lot with lush gardens and mature trees, 34 Tower Ridge offers the perfect blend of privacy and convenience. Ideally located just minutes from downtown Oak Bluffs and the Farm Neck Golf Course, this well-maintained property is suited for comfortable year-round living or as a serene Island retreat. Inside, the bright and open layout features an updated kitchen

Katie Donahue Sandpiper Realty

34 Tower Ridge Rd, Oak Bluffs, MA 02568

/40
Est $1,845,394 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1 Sq Ft
179 Main St, Vineyard Haven, MA 02568

179 Main St, Vineyard Haven, MA 02568

/51
$2,750,000
- 5 Beds
- 4.5 Baths
- 4,982 Sq Ft
79 David Ave, Vineyard Haven, MA 02568

BEAUTIFUL CUSTOM-BUILT RETREAT- LAMBERT'S COVE This impressive property offers the perfect blend of privacy and convenient access to downtown and the picturesque James Pond Reserve at Lambert's Cove Beach. Step inside to discover over 4,900 sq ft of recently renovated living space. The home boasts 5 bedrooms and 4.5 bathrooms, including a stunning chef's kitchen that will ignite your culinary

Tina Miller Donnelly + Co

79 David Ave, Vineyard Haven, MA 02568
/28
$32,000 per month plus fees
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
- House for Rent
37 Mempremagog Ave Vh410, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

Karen Overtoom Karen M. Overtoom R.E.

37 Mempremagog Ave Vh410, Tisbury, MA 02568
/39
$3,515,000 Sold Aug 18, 2025
- 4,218 Sq Ft
- $833/SF
- 60 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2010
7 Whistling Swan Cir, Edgartown, MA 02539

Located in the exclusive Island Grove neighborhood, this Edgartown retreat is conveniently located near Morning Glory Farm, Downtown Edgartown, and South Beach. The home was designed with entertaining in mind. The first floor offers a den, custom kitchen, a large dining room, living room, half bathroom, and screened porch, all while flowing seamlessly to the outdoor living areas and pool. In

Jarrett Hurwitz Keller Williams Realty

7 Whistling Swan Cir, Edgartown, MA 02539

/23
Est $2,120,773 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,704 Sq Ft
31 Pulpit Ln, Edgartown, MA 02539

31 Pulpit Ln, Edgartown, MA 02539

/42
$2,750,000
- 5 Beds
- 4.5 Baths
- 4,982 Sq Ft
79 David Ave, Vineyard Haven, MA 02568

BEAUTIFUL CUSTOM-BUILT RETREAT – LAMBERT’S COVE This impressive 4,900+ sq ft home offers privacy with easy access to downtown and James Pond Reserve at Lambert’s Cove Beach. Featuring 5 bedrooms, 4.5 baths, and a stunning chef’s kitchen, perfect after trips to local farm stands. Enjoy multiple living areas—oversized family/media room, dining room, sunny living room, and game room. Outdoor

Tina Miller Donnelly + Co.

79 David Ave, Vineyard Haven, MA 02568
/15
$7,500 per month plus fees
- 2 Beds
- 1 Bath
- 800 Sq Ft
- House for Rent
83 Ashtons Way, Vineyard Haven, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be

Karen Overtoom Karen M. Overtoom R.E.

83 Ashtons Way, Vineyard Haven, MA 02568
/4
$1,350,000 Sold Aug 15, 2025
- 1,864 Sq Ft
- $724/SF
- 12 Days On Market
- 3 Beds
- 2 Baths
- Built 1970
35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

Charming Home Steps from Lagoon Pond - This three bedroom, two bath home is just 550 feet from the sandy shores and calm waters of Lagoon Pond, perfect for swimming, boating and shell fishing. Ideal for both year-round living or vacationing, the home offers an open floor plan, a private primary suite with a walk-in closet and en-suite bath, two guest bedrooms plus a den/office. The finished

Lesley Heidt Sandpiper Realty Inc

35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

/48
Est $2,915,234 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 3,440 Sq Ft
8 Coffins Field Rd, Edgartown, MA 02539

8 Coffins Field Rd, Edgartown, MA 02539

/45
$2,895,000
- 3 Beds
- 3.5 Baths
- 2,898 Sq Ft
4 Pip'N Rd, Edgartown, MA 02539

Chappaquiddick charm meets Edgartown elegance at this meticulously maintained property. No detail has been overlooked in this spacious custom home. The foyer entry greets you with a sizable dining room to your right which flows into an open eat in kitchen with a built in banquet, a granite kitchen island overlooking the masonry fireplace and wall of glass sliders in the living room. A wet bar

Michele Casavant Vineyard Village Realty

4 Pip'N Rd, Edgartown, MA 02539
/3
$13,200 per month plus fees
- 2 Beds
- 2 Baths
- 1,344 Sq Ft
- House for Rent
224 N Rd Ch248, Chilmark, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

Karen Overtoom Karen M. Overtoom R.E.

224 N Rd Ch248, Chilmark, MA 02535
/7
$650,000 Sold Aug 14, 2025
- Land
- 0.2 Acre
- $3,250,000 per Acre
- 7 Days On Market
00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

Spectacular Hancock beach lot on the Atlantic Ocean. Ownership of this lot allows you access to one of the world's most beautiful beaches, plenty of parking and away from the crowds. It is a most enjoyable spot to spend a relaxing day on the Vineyard, sunbathing, fishing, kayaking, canoeing, etc. as you also gain access to Chilmark Pond. Any property on the Vineyard would be greatly enhanced by

Deb Hancock Hancock Real Estate

00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

/49
Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,092 Sq Ft
670 State Rd, Vineyard Haven, MA 02568

670 State Rd, Vineyard Haven, MA 02568

/81
$2,998,000
- 3 Beds
- 2 Baths
- 2,558 Sq Ft
12 Duarte Cir, Edgartown, MA 02539

Nestled in the coveted Katama neighborhood of Edgartown, this stylish 3-bedroom, 2-bathroom contemporary home offers a perfect blend of comfort, location, and opportunity. Designed with an open and airy layout, the home features vaulted ceilings, abundant natural light, and a seamless connection to the outdoor living spaces. Set on a generous lot, the property presents a variety of expansion

Jessie Holtham Wallace & Co. Sotheby's

12 Duarte Cir, Edgartown, MA 02539
/40
$32,500 per month plus fees
- 6 Beds
- 4.5 Baths
- 3,222 Sq Ft
- House for Rent
100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

Karen Overtoom Karen M. Overtoom R.E.

100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
/14
$449,000 Sold Aug 14, 2025
- Land
- 0.6 Acre
- $748,333 per Acre
- 89 Days On Market
517 Edgartown Rd Unit 8.11, Tisbury, MA 02568

A wonderful opportunity to build your island home on this high, level, and beautifully wooded parcel just minutes from town. With electricity and water already in place, the lot is ready for development. Mature trees provide natural privacy and a serene setting. Located next to the trailhead for the Land Bank’s Beech Tree Preserve, you’ll enjoy scenic walks that lead to the Lagoon—perfect for

Meg Bodnar Tea Lane Associates

517 Edgartown Rd Unit 8.11, Tisbury, MA 02568

/35
Est $1,210,701 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,368 Sq Ft
29 Dunham Ave, Vineyard Haven, MA 02568

29 Dunham Ave, Vineyard Haven, MA 02568

/30
$2,750,000
- 3 Beds
- 4 Baths
- 2,830 Sq Ft
42 Deacon Vincent Way, Edgartown, MA 02539

Katama ~ Turnkey Retreat in Edgartown Estates. Located on a quiet, paved road in sought-after Edgartown Estates, this meticulously maintained home offers the perfect blend of privacy, space, and convenience. Ideally positioned equidistant to South Beach and downtown Edgartown, and just moments from the bike path, it’s an ideal Vineyard getaway or year-round residence. Thoughtfully designed for

Stephanie Roache Donnelly + Co

42 Deacon Vincent Way, Edgartown, MA 02539
/17
$12,000 per month plus fees
- 3 Beds
- 2 Baths
- 1,750 Sq Ft
- House for Rent
223 Sandpiper Lane Vh405, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

Karen Overtoom Karen M. Overtoom R.E.

223 Sandpiper Lane Vh405, Tisbury, MA 02568
/34
$1,633,000 Sold Aug 14, 2025
- 1,918 Sq Ft
- $851/SF
- 66 Days On Market
- 5 Beds
- 2 Baths
- Built 1870
35 Tuckernuck Ave, Oak Bluffs, MA 02557

Location, Location, Location! Welcome to your dream retreat in the charming historic area of Oak Bluffs. Walk to Inkwell beach, ferries, restaurants and dining. Sited across the street from Waban Park, this delightful home offers an inviting blend of comfort and convenience.As you step inside, you'll immediately appreciate the spacious layout featuring well-appointed living areas, a

Jennifer DaSilva Compass | Point B

35 Tuckernuck Ave, Oak Bluffs, MA 02557

/75
Est $3,845,080 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,362 Sq Ft
4 Tilton Rd, Chilmark, MA 02535

4 Tilton Rd, Chilmark, MA 02535

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