Homes with Pools for Sale in Martha's Vineyard, MA

138 homes

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ABOUT THIS HOME
Home with a Pool for sale in Martha's Vineyard, MA:
This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown's finest restaurants and shops, this stunning property has been completely renovated by SternMcCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon entering, you'll be greeted by a sophisticated interior with open-plan living spaces designed for easy entertaining. The mainlevel features sleek modern furnishings, flowing from the kitchen and dining area through French doors to a beautifully landscapedoutdoor patio, ideal for al fresco dining and relaxati

$15,500,000

6 beds7.5 baths1,320 sq ft

68 N Water St, Edgartown, MA 02539

0.31 acre lot • 3 garage spots • Pool

ABOUT THIS HOME
Home with a Pool for sale in Martha's Vineyard, MA:
Downtown Oak Bluffs an investment opportunity awaits at the top of Circuit Ave. Dual zoned this is two properties in one. An existing 6 bedroom 3.5 bath Victorian home in the popular Copeland District a couple blocks to the beach even closer to restaurants shops and entertainment. On town sewer it's ideal for weekly rentals. The other side of the property facing Circuit Ave. is zoned Commercial giving you a wide arrange of business opportunities several ideas have been previously approved. An ADU dwelling is also another possibility While waiting for permitting you can easily lease up to 9 parking spaces (see attached plan). Calling all investors this property is priced to sell.

$2,250,000

6 beds2.5 baths1,666 sq ft

34 Massasoit Ave, Oak Bluffs, MA 02557

6,534 sq ft lot • Built 1900 • Listed 335 days

ABOUT THIS HOME
Home with a Pool for sale in Martha's Vineyard, MA:
New Construction with POOL, GUEST HOUSE and PRIMARY HOME, all within close proximity to Main Street, Edgartown. This four bedroom gambrel homes welcomes you with a two story foyer which opens to a great room with a gourmet kitchen, a bar area and a central island offering seating for at least four. The kitchen flows into the open dining and living room with a gas fireplace. The great room overlooks the outdoor pool and entertaining area. Off the kitchen is a large walk in laundry/pantry room. The 1st floor primary suite has access to the abutting private study. The 2nd floor offers an open lounge area, central to the three bedrooms which all have their own private bathroom. Completing the 2

$4,900,000

6 beds5.5 baths5,394 sq ft

23 Pinehurst Rd, Edgartown, MA 02539

Central island • Open dining • Gourmet kitchen

ABOUT THIS HOME
Home with a Pool for sale in Martha's Vineyard, MA:
Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone countertops, stainless appliances, an island, and a wet bar. Enjoy three spacious bedrooms and 4.5 baths, including a primary suite with pool access and spa-like bath. The second floor offers an open lounge and two en suite bedrooms. The lower level is perfect for entertaining with a family room, w

$5,995,000

3 beds4.5 baths3,608 sq ft

385 Barnes Rd, Oak Bluffs, MA 02557

Whirlpool spa • Wine cellar • Gourmet kitchen

ABOUT THIS HOME
Home with a Pool for sale in Martha's Vineyard, MA:
Beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine refrigerator. There are sliders that take you to an oversized deck and stairs to a blue stone patio and beautiful gardens. The screened-in porch off the living room steps out to the side yard, patio and outdoor shower. First floor Primary with walk-in closet, access to the deck and a private en-s

$3,995,000

3 beds3 baths3,426 sq ft

96 Hammett Ln, Chilmark, MA 02535

Wolfe 8 burner stove • Gourmet kitchen • Custom built-ins

Property at 135 The Boulevard &110 Pilgrim Rd, Edgartown, MA 02539, 4 beds, 3.5 baths

$5,999,000

4 beds3.5 baths2,995 sq ft

135 The Boulevard &110 Pilgrim Rd, Edgartown, MA 02539

Property at 12 Park Ave, Vineyard Haven, MA 02568, 3 beds, 2 baths

$1,045,000

3 beds2 baths1,469 sq ft

12 Park Ave, Vineyard Haven, MA 02568

Property at 72 Chappaquiddick Ave, Edgartown, MA 02539, 8 beds, 7.5 baths

$2,999,000

8 beds7.5 baths3,770 sq ft

72 Chappaquiddick Ave, Edgartown, MA 02539

Property at 4 Somerset Ln, Edgartown, MA 02539, 4 beds, 4.5 baths

$5,750,000

4 beds4.5 baths3,643 sq ft

4 Somerset Ln, Edgartown, MA 02539

Property at 357 W Tisbury Rd, Edgartown, MA 02539, 5 beds, 4.5 baths

$2,650,000

5 beds4.5 baths4,115 sq ft

357 W Tisbury Rd, Edgartown, MA 02539

Property at 7 Clark Dr, Edgartown, MA 02539, 4 beds, 5 baths

$4,800,000

4 beds5 baths4,280 sq ft

7 Clark Dr, Edgartown, MA 02539

Property at 261 Sandpiper Ln #12, Vineyard Haven, MA 02568, 3 beds, 3 baths

$1,250,000

3 beds3 baths1,628 sq ft

261 Sandpiper Ln #12, Vineyard Haven, MA 02568

Property at 267 Barnes Rd, Oak Bluffs, MA 02557, 3 beds, 5.5 baths

$4,395,000

3 beds5.5 baths4,046 sq ft

267 Barnes Rd, Oak Bluffs, MA 02557

Property at 8 Court St, Edgartown, MA 02539, 3 beds, 2 baths

$1,500,000

3 beds2 baths1,188 sq ft

8 Court St, Edgartown, MA 02539

Property at 36 Smith Hollow Dr, Edgartown, MA 02539, 6 beds, 2.5 baths

$1,985,000

6 beds2.5 baths2,836 sq ft

36 Smith Hollow Dr, Edgartown, MA 02539

Property at 25 Dock St, Edgartown, MA 02539, 4 beds, 4.5 baths

$25,000,000

4 beds4.5 baths2,347 sq ft

25 Dock St, Edgartown, MA 02539

Property at 25 Fulling Mill Rd, Chilmark, MA 02535, 4 beds, 3 baths

$2,395,000

4 beds3 baths1,918 sq ft

25 Fulling Mill Rd, Chilmark, MA 02535

Property at 30 Franklin Ave, Oak Bluffs, MA 02557, 2 beds, 2.5 baths

$2,150,000

2 beds2.5 baths2,137 sq ft

30 Franklin Ave, Oak Bluffs, MA 02557

Property at 28 Martha's Rd, Edgartown, MA 02539, 4 beds, 3.5 baths

$2,750,000

4 beds3.5 baths2,566 sq ft

28 Martha's Rd, Edgartown, MA 02539

Property at 53 Stoney Hill Rd, West Tisbury, MA 02575, 3 beds, 3.5 baths

$3,299,000

3 beds3.5 baths3,082 sq ft

53 Stoney Hill Rd, West Tisbury, MA 02575

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 26 Union Ct #7, Vineyard Haven, MA 02568, 2 beds, 2.5 baths

$1,625,000

2 beds2.5 baths1,532 sq ft

26 Union Ct #7, Vineyard Haven, MA 02568

Property at 4 High Meadow Ln, Oak Bluffs, MA 02557, 4 beds, 3.5 baths

$2,260,000

4 beds3.5 baths2,810 sq ft

4 High Meadow Ln, Oak Bluffs, MA 02557

Property at 7 Martha's Way, Edgartown, MA 02539, 4 beds, 4.5 baths

$4,800,000

4 beds4.5 baths3,816 sq ft

7 Martha's Way, Edgartown, MA 02539

Property at 150 Cove Rd #10, Vineyard Haven, MA 02568, 2 beds, 3 baths

$1,699,000

2 beds3 baths1,737 sq ft

150 Cove Rd #10, Vineyard Haven, MA 02568

Property at 47 E East Chop Dr #5, Oak Bluffs, MA 02557, 1 bed, 1 bath

$1,495,000

1 bed1 bath650 sq ft

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

Property at 99 Old Purchase Rd, Edgartown, MA 02539, 4 beds, 2.5 baths

$1,895,000

4 beds2.5 baths2,064 sq ft

99 Old Purchase Rd, Edgartown, MA 02539

Property at 1 Field Club Dr, Edgartown, MA 02539, 5 beds, 4 baths

$9,250,000

5 beds4 baths3,550 sq ft

1 Field Club Dr, Edgartown, MA 02539

Property at 4 Boldwater Rd, Edgartown, MA 02539, 4 beds, 3.5 baths

$4,150,000

4 beds3.5 baths3,552 sq ft

4 Boldwater Rd, Edgartown, MA 02539

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 63 Bayes Hill Rd Rd, Oak Bluffs, MA 02557, 4 beds, 4 baths

$3,150,000

4 beds4 baths5,165 sq ft

63 Bayes Hill Rd Rd, 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

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 #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 #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 36 Boylston Dr, Edgartown, MA 02539

$475,000

— beds— baths— sq ft

36 Boylston Dr, Edgartown, MA 02539

Property at 39 Slough Cove Road part of, Edgartown, MA 02539

$2,850,000

— beds— baths— sq ft

39 Slough Cove Road part of, Edgartown, MA 02539

Property at 25 Coffins Field Rd, Edgartown, MA 02539

$1,100,000

— beds— baths— sq ft

25 Coffins Field Rd, Edgartown, MA 02539

Property at 5 Louis Fld, Edgartown, MA 02539

$2,000,000

— beds— baths— sq ft

5 Louis Fld, Edgartown, MA 02539

Property at 9 Maqua Way, Edgartown, MA 02539

$2,450,000

— beds— baths— sq ft

9 Maqua Way, Edgartown, MA 02539

Property at 9 Beach Pebble Rd, Vineyard Haven, MA 02568

$1,595,000

— beds— baths— sq ft

9 Beach Pebble Rd, Vineyard Haven, MA 02568

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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 Dec 04 2025. 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. © 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Homes with Pools for Sale in Martha's Vineyard

There are currently 138 homes with pools for sale in Martha's Vineyard at a median listing price of $2M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Martha's Vineyard stay on the market for 144 days. Popular neighborhoods include Edgartown Village Historic District, Chappaquiddick, Upper Cape, and East Chop. This map is refreshed with the newest listings in Martha's Vineyard every 15 minutes.

In the past month, 13 homes have been sold in Martha's Vineyard. In addition to houses in Martha's Vineyard, there were also 10 condos, 2 townhouses, and 6 multi-family units for sale in Martha's Vineyard last month. Find your dream home in Martha's Vineyard 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 Martha's Vineyard are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Martha's Vineyard. If you're looking to sell your home in the Martha's Vineyard area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Martha's Vineyard with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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