Martha's Vineyard, MA Homes

/42
$3,695,000 Pending
- 4 Beds
- 2.5 Baths
- 2,500 Sq Ft
37 Road To the Plains, Edgartown, MA 02539

Exceptional Opportunity to Create Your Signature Vineyard Compound. Behind a charming white picket fence with blooming hydrangeas, this beautifully renovated Edgartown property blends island charm with new construction. Renovated in 2024 by top-tier builders, the nearly new home offers immediate comfort and timeless style, with potential for expansion into a luxury compound. On a private

Wendy Harman

Compass

(508) 274-5363

37 Road To the Plains, Edgartown, MA 02539
/26
$7,000 per month plus fees
- 7 Beds
- 1.5 Baths
- 2,900 Sq Ft
- House for Rent
39 N Neck Rd, Edgartown, MA 02539

Historic Quaint Waterfront Cottage with spectacular 180 degree views of Edgartown Harbor, Oak Bluffs, Cape Cod and Cape Poge, Over 200 feet of secluded, completely private beach, The back yard abuts the fairways and club house of the ''Royal Ancient Chappaquiddick Links'' Private Golf Course. (You must pay dues to play golf), Great outdoor shower. You can see the fireworks (in 5 locations at

Charles Petitti Coldwell Banker Realty - Newton

39 N Neck Rd, Edgartown, MA 02539
/37
$1,925,000 Sold Aug 28, 2025
- 1,736 Sq Ft
- $1,109/SF
- 0 Days On Market
- 3 Beds
- 2 Baths
- Built 1965
50 Bradley Martin Rd, Vineyard Haven, MA 02568

Two level contemporary residence located in West Tisbury off Tiah's Cove Road, close to the 174 Acre Land Bank Sepiessa Point Reserve on Tisbury Great Pond. Light filled rooms with high ceilings, solarium, large screened in porch & fireplace in this completely renovated home. Private 3 acre site is laden with specimen trees, walking trails and meditation gardens. Close proximity to West Tisbury

Rebecca V Conroy Conroy & Company R.E., Inc.

50 Bradley Martin Rd, Vineyard Haven, MA 02568

/45
Est $1,802,171 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,576 Sq Ft
38 Edgewood Dr, Edgartown, MA 02539

38 Edgewood Dr, Edgartown, MA 02539

/29
$2,395,000 Pending
- 3 Beds
- 2 Baths
- 1,764 Sq Ft
29 Pradas Way, Edgartown, MA 02539

The Perfect Katama Retreat - Just one mile from South Beach and steps from the bike path connecting Edgartown and the beach, this charming property offers the ultimate Vineyard lifestyle. Built in 1998 by a respected Island contractor, it sits privately among pines and welcomes you with a classic farmer’s porch. The traditional, relaxed floor plan features a sunlit open kitchen, dining, and

Wendy Harman

Compass

(508) 290-4574

29 Pradas Way, Edgartown, MA 02539
/12
$6,180 per month plus fees
- 3 Beds
- 3.5 Baths
- 1,872 Sq Ft
- House for Rent
44 Music St Wt153, West Tisbury, MA 02575

PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

Karen Overtoom Karen M. Overtoom R.E.

44 Music St Wt153, West Tisbury, MA 02575
/50
$4,295,000 Sold Aug 27, 2025
- 2,792 Sq Ft
- $1,538/SF
- 64 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1880
118 William St, Vineyard Haven, MA 02568

The Captain George Harding Home sits gracefully on the westerly side of iconic William Street overlooking Vineyard Haven village with distant views of the harbor. This immaculate and re-imagined Gothic Revival offers both timeless elegance and modern luxury. Completed in 2024, the comprehensive down-to-the-studs renovation includes all new systems like central air and dehumidification. Every

Alexis Holden Tea Lane Associates

118 William St, Vineyard Haven, MA 02568

/41
Est $2,572,834 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,704 Sq Ft
53 Peases Point Way N, Edgartown, MA 02539

53 Peases Point Way N, Edgartown, MA 02539

/39
$2,645,000 Pending
- 3 Beds
- 2 Baths
- 1,350 Sq Ft
31 The Blvd, Edgartown, MA 02539

Waterfront Charmer on Sengekontacket Pond - Perched on the shoreline, this contemporary cottage is enveloped by stone walls, lush gardens, and stunning water views. Inside, a bright, airy living space features an open dining area and a well-appointed kitchen. The all-white interior is complemented by hardwood floors, vaulted ceilings, skylights, air conditioning, and ceiling fans. Three sliding

Wendy Harman

Compass

(508) 301-9323

31 The Blvd, Edgartown, MA 02539
/12
$15,000 per month plus fees
- 5 Beds
- 6.5 Baths
- 4,137 Sq Ft
- House for Rent
41 Naushon Rd Wt116, Aquinnah, MA 02575

Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

Karen Overtoom Karen M. Overtoom R.E.

41 Naushon Rd Wt116, Aquinnah, MA 02575
/27
$1,875,000 Sold Aug 27, 2025
- 1,728 Sq Ft
- $1,085/SF
- 71 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1984
212 Charles Neck Way, Vineyard Haven, MA 02568

This beautifully renovated South Shore retreat, located in a tranquil setting, features 3 bedrooms, 2 1/2 bathrooms, central air, all new Bosch appliances, in ground pool and mature perennial gardens galore! Sitting on 1.5 acres, this location provides easy access to Long Point Beach and the Red Pony Farm equestrian center and, includes access to the coveted Lamberts Cove Beach. The first floor

Perry Patterson MV Luxury Homes LLC

212 Charles Neck Way, Vineyard Haven, MA 02568

/79
Not Listed For Sale
- 6 Beds
- 2.5 Baths
- 2,604 Sq Ft
260 South Rd, Chilmark, MA 02535

260 South Rd, Chilmark, MA 02535

/32
$1,550,000 Pending
- 4 Beds
- 1.5 Baths
- 1,304 Sq Ft
11 John Wesley Ave, Oak Bluffs, MA 02568

East Chop Living in this 4 Bedroom Victorian home perched near the shoreline in Oak Bluffs-just a short stroll to the harbor, the shores of East Chop beaches, and the shops and restaurants of downtown Oak Bluffs. Built in 1905, and updated throughout the years, with its Victorian architecture softened by time and salt air, giving it an inviting, warm charm.The exterior features a wide

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 682-5574

11 John Wesley Ave, Oak Bluffs, MA 02568
/11
$20,000 per month plus fees
- 4 Beds
- 4.5 Baths
- 2,306 Sq Ft
- House for Rent
3 E Pasture Ln, Aquinnah, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of your favorite hot beverage. PLEASE TAKE NOTE!!!!!THIS IS

Karen Overtoom Karen M. Overtoom R.E.

3 E Pasture Ln, Aquinnah, MA 02535
/37
$2,100,000 Sold Aug 27, 2025
- 3,310 Sq Ft
- $634/SF
- 60 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2009
42 Daggett Ave, Vineyard Haven, MA 02568

This elegant farmhouse awaits your arrival! Nestled in the heart of Vineyard Haven, the desirable location is within close proximity to the Vineyard Haven Yacht Club and harbor, public beach access, ferry, downtown shops & restaurants, MV Playhouse, Owen Park Beach, new public tennis courts. Open the door to be greeted by a lovely entry way that leads into a light filled living area with

Rene Jackson Island Real Estate

42 Daggett Ave, Vineyard Haven, MA 02568

/35
Est $7,413,109 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,207 Sq Ft
93 S Water St, Edgartown, MA 02539

93 S Water St, Edgartown, MA 02539

/29
$2,695,000
- 4 Beds
- 3 Baths
- 2,001 Sq Ft
2 Orchard Ln, Edgartown, MA 02539

EDGARTOWN GEM: WALK TO TOWN + RELAX BY THE POOL. Nestled just a short stroll from all the best of Edgartown Village, this beautifully renovated retreat offers the ideal balance of Vineyard charm and modern convenience. Designed across three levels of living spaces, the home provides a flexible layout that works beautifully for entertaining, relaxing, or hosting guests.The main floor

Wendy Harman Compass | Point B

2 Orchard Ln, Edgartown, MA 02539
/8
$8,250 per month plus fees
- 7 Beds
- 5 Baths
- 3,528 Sq Ft
- House for Rent
227 S Gate Rd Wt120, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through

Karen Overtoom Karen M. Overtoom R.E.

227 S Gate Rd Wt120, West Tisbury, MA 02575
/21
$435,000 Sold Aug 26, 2025
- Land
- 0.1 Acre
- $4,350,000 per Acre
- 20 Days On Market
0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

Stunning Quansoo Beach Lot available NOW. With this ownership you will gain access to gated parking and endless beach days along the Islands expansive South Shore and Tisbury Great Pond! Skip the lines and parking worries and enjoy the freedom to come and go as you please. If you have been dreaming of endless beach days, long walks on private shores... here is your chance. ***Note: This is not a

Emma Bryant Landmarks at TODAY Real Estate

0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

/32
Est $1,868,579 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,448 Sq Ft
81 Washque Ave, Edgartown, MA 02539

81 Washque Ave, Edgartown, MA 02539

/17
$2,500,000
- 3 Beds
- 3 Baths
- 1,984 Sq Ft
19 Katama Dr, Edgartown, MA 02539

Just over a mile from South Beach, this inviting Katama retreat is a perfect getaway. This sunlit home and detached living space offer three bedrooms and three baths, providing plenty of room for everyone. Set on a landscaped 3⁄4-acre lot with pastoral views and peeks of the Ocean from the upper-level deck, the property features a wraparound deck for barbecues and a spacious backyard for games or

Emma Kennedy Sandpiper Realty

19 Katama Dr, Edgartown, MA 02539
/8
$18,500 per month plus fees
- 4 Beds
- 3.5 Baths
- 1,714 Sq Ft
- House for Rent
4 Windy Way Wt143, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

Karen Overtoom Karen M. Overtoom R.E.

4 Windy Way Wt143, West Tisbury, MA 02575
/22
$435,000 Sold Aug 26, 2025
- Land
- 0.1 Acre
- $4,350,000 per Acre
- 18 Days On Market
0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535

Stunning Quansoo Beach Lot available NOW. With this ownership you will gain access to gated parking and endless beach days along the Islands expansive South Shore and Tisbury Great Pond! Skip the lines and parking worries and enjoy the freedom to come and go as you please. If you have been dreaming of endless beach days, long walks on private shores... here is your chance. ***Note: This is not a

Emma Kiley Bryant Landmarks at TODAY Real Estate

0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535

/31
Est $3,105,492 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,300 Sq Ft
68 Meeting House Rd, Chilmark, MA 02535

68 Meeting House Rd, Chilmark, MA 02535

/24
$4,695,000
- 5 Beds
- 2.5 Baths
- 3,885 Sq Ft
18 Homeward Way, Chilmark, MA 02535

Welcome to 18 Homeward Way — a peaceful Chilmark retreat tucked off scenic North Road, just minutes from the storied fishing village of Menemsha. This rare 15-acre offering includes two buildable parcels, creating an extraordinary opportunity for a Vineyard compound.The impeccably maintained residence, built in 1986, radiates classic Vineyard charm. Its thoughtful single-level layout

Bill Rossi Studio Realty

18 Homeward Way, Chilmark, MA 02535
/8
$4,800 per month plus fees
- 3 Beds
- 3 Baths
- 3,279 Sq Ft
- House for Rent
165 Christiantown Rd, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

Karen Overtoom Karen M. Overtoom R.E.

165 Christiantown Rd, West Tisbury, MA 02575
/23
$1,800,000 Sold Aug 26, 2025
- 1,351 Sq Ft
- $1,332/SF
- 0 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1910
12 Martha's Park Rd, Oak Bluffs, MA 02557

Harthaven Cottage - This magical cottage, tucked away just 2/10's of a mile from the private association beach, is waiting for you to call it your own. A covered porch welcomes you. Once inside, you begin to take in the charming details of this classic 3-season home. There are cathedral ceilings with exposes painted beams. Home features 4 bedrooms, 1 1/2 baths and outdoor shower. Both bathrooms

Michele Moore Island Real Estate

12 Martha's Park Rd, Oak Bluffs, MA 02557

/7
Not Listed For Sale
- 4 Beds
53 N Neck Rd, Edgartown, MA 02539

53 N Neck Rd, Edgartown, MA 02539

/39
$2,700,000
- 3 Beds
- 4 Baths
- 2,300 Sq Ft
229 Oak Ln, West Tisbury, MA 02575

A hidden gem in West Tisbury! Beautifully manicured, fenced in 2.2 - acre parcel with 100% privacy, and 84 evergreen trees. This modern, contemporary well maintained home is 3-bedroom, 3 bath with two levels of living and a partially finished basement. The first floor is a sunlight filled, open kitchen and dinning room, with hardwood floors throughout. There are multiple decks leading out

Doug Burke Cronigs Real Estate

229 Oak Ln, West Tisbury, MA 02575
/8
$19,000 per month plus fees
- 5 Beds
- 5 Baths
- 3,137 Sq Ft
- House for Rent
19 Morse St, Edgartown, MA 02539

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, office/den and a full bath all

Karen Overtoom Karen M. Overtoom R.E.

19 Morse St, Edgartown, MA 02539
/18
$1,450,000 Sold Aug 26, 2025
- 2,311 Sq Ft
- $627/SF
- 85 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
61 Dodgers Hill Rd, Edgartown, MA 02539

Located in the sought-after Dodgers Hole neighborhood, this beautifully renovated home blends modern style with coastal ease. Sunlight fills the main living area, where cathedral ceilings and hardwood floors create a bright and welcoming space. The kitchen has been completely redone with fresh finishes and thoughtful design, and the brand-new baths add to the turnkey appeal. The finished lower

Ellen Valentgas Sotheby's International Realty

61 Dodgers Hill Rd, Edgartown, MA 02539

/14
Est $6,814,797 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,193 Sq Ft
100 Meetinghouse Way, Edgartown, MA 02539

100 Meetinghouse Way, Edgartown, MA 02539

/36
$4,695,000
- 5 Beds
- 5.5 Baths
- 4,003 Sq Ft
97 Longview Rd, Vineyard Haven, MA 02568

This beautifully designed post-and-beam home features stunning views of the Vineyard Sound, Elizabeth Islands, and unforgettable sunsets. Surrounded by beautiful stone walls, sited on 2.2 acres, this serene property offers luxury and comfort, exuding tranquility and timeless charm. The main home spans three spacious levels with generous decks ideal for outdoor living and entertaining. The upper

Stephanie Roache Donnelly + Co.

97 Longview Rd, Vineyard Haven, MA 02568
/8
$4,500 per month plus fees
- 2 Beds
- 2 Baths
- 1,393 Sq Ft
- House for Rent
33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

Karen Overtoom Karen M. Overtoom R.E.

33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
/17
$1,450,000 Sold Aug 26, 2025
- 2,311 Sq Ft
- $627/SF
- 78 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
61 Dodgers Hole Rd, Edgartown, MA 02539

Located in the sought-after Dodgers Hole neighborhood, this beautifully renovated home blends modern style with coastal ease. Sunlight fills the main living area, where cathedral ceilings and hardwood floors create a bright and welcoming space.The kitchen has been completely redone with fresh finishes and thoughtful design, and the brand-new baths add to the turnkey appeal. The finished lower

Ellen Valentgas Sotheby's International Realty

61 Dodgers Hole Rd, Edgartown, MA 02539

/2
Est $1,366,732 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,400 Sq Ft
45 Pine Tree Ln, Vineyard Haven, MA 02568

45 Pine Tree Ln, Vineyard Haven, MA 02568

/39
$2,700,000
- 6 Beds
- 3.5 Baths
- 3,000 Sq Ft
63 Crowell Ln, Vineyard Haven, MA 02568

Extraordinary West Chop Opportunity - Two Homes on 1.80 Acres in Vineyard HavenNestled next to the desirable West Chop/Mink Meadows neighborhoods, this unique property is less than two miles from the center of town and the beach. The property features two dwellings, making it a perfect opportunity for multi-generational living, guest accommodations, or rental potential.The welcoming,

Heather Dyas-Fried Tea Lane Associates

63 Crowell Ln, Vineyard Haven, MA 02568
/8
$8,000 per month plus fees
- 4 Beds
- 4.5 Baths
- 3,600 Sq Ft
- House for Rent
56 Chilmark Rd, Chilmark, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and

Karen Overtoom Karen M. Overtoom R.E.

56 Chilmark Rd, Chilmark, 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 $1,713,994 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,122 Sq Ft
62 Whalers Walk, Edgartown, MA 02539

62 Whalers Walk, Edgartown, MA 02539

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