Luxury homes for sale & real estate in 02568, MA

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ABOUT THIS HOME
Luxury Home for sale in 02568, MA:
WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in chara

$2,995,000

4 beds1.5 baths3,462 sq ft

Dock • Harbor views • Waterfront

27 Beach Rd, Oak Bluffs, MA 02557

ABOUT THIS HOME
Luxury Home for sale in 02568, MA:
Rarely does such a unique, waterfront location become available. With amazing, 180+ degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Wake up to glorious sunrises. Be entertained by a variety of waterfowl throughout the seasons. Have your vessel at the ready right off the shore. The moment you walk onto the property, the tranquil feel and the cooling shade trees will make you forget that you are still so close to town and ferry. The property is hugged by the Lagoon on one side and Vineyard Haven Harbor across the street on the other. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The

$1,895,000

3 beds2 baths1,864 sq ft

Waterside patio • Private water access • Perennial gardens

Undisclosed address, Vineyard Haven, MA 02568

NEW CONSTRUCTIONFLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in 02568, MA:
Due to ongoing construction, the property may pose safety risks. Entry is at your own risk, and access is permitted only when accompanied by a licensed real estate agent. The agent of the buyer must be present at all buyer-client showings, inspections, and walkthroughs unless otherwise agreed to in advance by the listing agent.

$2,678,000

4 beds3.5 baths2,363 sq ft

0.27 acre lot • Built 2026 • Listed 2 days

31 Temahigan Ave, Oak Bluffs, MA 02557

ABOUT THIS HOME
Luxury Home for sale in 02568, MA:
Tucked away on a quiet street in coveted West Chop, this pristine property offers exceptional privacy, stunning scenery, and easy access to downtown Vineyard Haven. Designed for effortless indoor-outdoor living, this sophisticated compound combines timeless charm with every modern amenity. The first floor features an inviting open-concept layout ideal for both relaxed family living and entertaining. The kitchen overlooks the dining area, an intimate sitting area, and a versatile game and reading area beyond. The spacious TV and family room features custom built-in bookcases and French doors that open onto a bluestone patio and the pool area beyond. A generous screened porch provides additio

$6,150,000

6 beds6 baths5,034 sq ft

Bluestone patio • Screened porch • Exceptional privacy

59 Hagerty Dr, Vineyard Haven, MA 02568

ABOUT THIS HOME
Luxury Home for sale in 02568, MA:
Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you'll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping, restaurants, and all the attractions that make this area of Martha's Vineyard so special. Martha's Vineyard Hospital is also just a short two-minute drive away. Built in 1988, the home offers approximately 1,456 square feet of living area, with prefinished wood flooring in the living room and bedrooms. The ro

$1,195,000

3 beds2 baths2,173 sq ft

Off street parking • 5,000 sq ft lot • 3 parking spots

2 Winemack St, Oak Bluffs, MA 02557

Property at 36 Hines Point Rd, Vineyard Haven, MA 02568, 3 beds, 1 bath

$3,100,000

3 beds1 bath973 sq ft

36 Hines Point Rd, Vineyard Haven, MA 02568

Property at 41 Cook Rd, Vineyard Haven, MA 02568, 3 beds, 2.5 baths

$1,285,000

3 beds2.5 baths2,347 sq ft

41 Cook Rd, Vineyard Haven, MA 02568

Property at 11 Stanley St, Oak Bluffs, MA 02557, 3 beds, 1.5 baths

$1,255,000

3 beds1.5 baths912 sq ft

11 Stanley St, Oak Bluffs, MA 02557

Property at 528 Main St, Vineyard Haven, MA 02568, 4 beds, 4 baths

$1,800,000

4 beds4 baths2,670 sq ft

528 Main St, Vineyard Haven, MA 02568

Property at 323 County Rd, Oak Bluffs, MA 02557, 1 bed, 2 baths

$1,225,000

1 bed2 baths1,428 sq ft

323 County Rd, Oak Bluffs, MA 02557

Property at 30 Water Gate Rd, Vineyard Haven, MA 02568, 5 beds, 4.5 baths

$3,995,000

5 beds4.5 baths4,816 sq ft

30 Water Gate Rd, Vineyard Haven, MA 02568

Property at 124 Main St, Vineyard Haven, MA 02568, 5 beds, 4 baths

$2,695,000

5 beds4 baths2,374 sq ft

124 Main St, Vineyard Haven, MA 02568

Property at 150 Field View Ln, West Tisbury, MA 02575, 4 beds, 2.5 baths

$1,600,000

4 beds2.5 baths2,334 sq ft

150 Field View Ln, West Tisbury, MA 02575

Property at 31 Josiah Sachem Way, West Tisbury, MA 02575, 7 beds, 4.5 baths

$4,125,000

7 beds4.5 baths3,313 sq ft

31 Josiah Sachem Way, West Tisbury, MA 02575

Property at 41 Edgartown Rd, Vineyard Haven, MA 02568, 5 beds, 2 baths

$1,399,000

5 beds2 baths1,968 sq ft

41 Edgartown Rd, Vineyard Haven, MA 02568

Property at 135 Mayflower Ln, Vineyard Haven, MA 02568, 5 beds, 3 baths

$1,995,000

5 beds3 baths3,480 sq ft

135 Mayflower Ln, Vineyard Haven, MA 02568

Property at 28 Beach Rd, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$3,675,000

4 beds2.5 baths1,800 sq ft

28 Beach Rd, Oak Bluffs, MA 02557

Property at 52 Oak Knl, West Tisbury, MA 02575, 3 beds, 2 baths

$1,225,000

3 beds2 baths1,800 sq ft

52 Oak Knl, West Tisbury, MA 02575

Property at 33 Vineyard Ave, Oak Bluffs, MA 02557, 3 beds, 2.5 baths

$1,875,000

3 beds2.5 baths1,431 sq ft

33 Vineyard Ave, Oak Bluffs, MA 02557

Property at 28 Grovedale Rd, Oak Bluffs, MA 02568, 3 beds, 3.5 baths

$1,750,000

3 beds3.5 baths2,376 sq ft

28 Grovedale Rd, Oak Bluffs, MA 02568

Property at 21 W Spring St, Vineyard Haven, MA 02568, 4 beds, 3 baths

$1,450,000

4 beds3 baths1,270 sq ft

21 W Spring St, Vineyard Haven, MA 02568

Property at 29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568, 5 beds, 4 baths

$3,295,000

5 beds4 baths2,330 sq ft

29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568

Property at 11 Beach Rd, Oak Bluffs, MA 02557, 2 beds, 1 bath

$1,745,000

2 beds1 bath561 sq ft

11 Beach Rd, Oak Bluffs, MA 02557

Property at 68 Front St, Oak Bluffs, MA 02557, 3 beds, 3 baths

$1,755,000

3 beds3 baths2,695 sq ft

68 Front St, Oak Bluffs, MA 02557

Property at 27 Double Ox Rd, Oak Bluffs, MA 02557, 3 beds, 4.5 baths

$3,400,000

3 beds4.5 baths3,260 sq ft

27 Double Ox Rd, Oak Bluffs, MA 02557

Property at 3 Troy St, Oak Bluffs, MA 02557, 3 beds, 2 baths

$1,295,000

3 beds2 baths1,863 sq ft

3 Troy St, Oak Bluffs, MA 02557

Property at 33 Alyssa Ln, Vineyard Haven, MA 02568, 4 beds, 3 baths

$1,395,000

4 beds3 baths2,304 sq ft

33 Alyssa Ln, Vineyard Haven, MA 02568

Property at 8 Paddock Rd, Oak Bluffs, MA 02557, 4 beds, 5.5 baths

$5,450,000

4 beds5.5 baths3,300 sq ft

8 Paddock Rd, Oak Bluffs, MA 02557

Property at 312 E Chop Dr, Vineyard Haven, MA 02568, 3 beds, 2 baths

$2,295,000

3 beds2 baths1,425 sq ft

312 E Chop Dr, Vineyard Haven, MA 02568

Property at 47 Winemack St, Oak Bluffs, MA 02557, 3 beds, 2 baths

$1,199,000

3 beds2 baths1,302 sq ft

47 Winemack St, Oak Bluffs, MA 02557

Property at 29 and 33 Lagoon Pond Rd, Vineyard Haven, MA 02568, 5 beds, 4 baths

$3,295,000

5 beds4 baths2,330 sq ft

29 and 33 Lagoon Pond Rd, Vineyard Haven, MA 02568

Property at 312 East Chop Dr, Oak Bluffs, MA 02557, 3 beds, 3 baths

$2,295,000

3 beds3 baths1,425 sq ft

312 East Chop Dr, Oak Bluffs, MA 02557

Property at 44 Tiffany Dr, Oak Bluffs, MA 02557, 4 beds, 4.5 baths

$2,800,000

4 beds4.5 baths3,927 sq ft

44 Tiffany Dr, Oak Bluffs, MA 02557

Property at 6 Brewster Ave, Oak Bluffs, MA 02557, 4 beds, 3 baths

$3,250,000

4 beds3 baths1,728 sq ft

6 Brewster Ave, Oak Bluffs, MA 02557

Property at 5 Pinetree Ln, Vineyard Haven, MA 02568, 4 beds, 3 baths

$1,999,000

4 beds3 baths2,730 sq ft

5 Pinetree Ln, Vineyard Haven, MA 02568

Property at 31 Lambert's Cove Rd, Vineyard Haven, MA 02568, 6 beds, 7.5 baths

$5,800,000

6 beds7.5 baths5,732 sq ft

31 Lambert's Cove Rd, Vineyard Haven, MA 02568

Property at 64 Christiantown, West Tisbury, MA 02575, 4 beds, 4 baths

$3,495,000

4 beds4 baths3,200 sq ft

64 Christiantown, West Tisbury, MA 02575

Property at 299 Daggett Ave Unit A, Vineyard Haven, MA 02568, 3 beds, 1 bath

$1,175,000

3 beds1 bath998 sq ft

299 Daggett Ave Unit A, Vineyard Haven, MA 02568

Property at 261 Sandpiper Ln #12, Tisbury, MA 02539, 3 beds, 3 baths

$1,250,000

3 beds3 baths1,682 sq ft

261 Sandpiper Ln #12, Tisbury, MA 02539

Property at 159 Lake St, Vineyard Haven, MA 02568, 5 beds, 4 baths

$2,195,000

5 beds4 baths3,328 sq ft

159 Lake St, Vineyard Haven, MA 02568

Property at 94 Weaver Ln, Vineyard Haven, MA 02568, 4 beds, 3 baths

$3,999,999

4 beds3 baths2,715 sq ft

94 Weaver Ln, 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 Fri Aug 21 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.

Luxury Homes for Sale in 02568

There are currently 56 luxury homes for sale in 02568 at a median listing price of $1.75M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 02568 stay on the market for 84 days. This map is refreshed with the newest listings in 02568 every 15 minutes.

In the past month, 4 homes have been sold in 02568. In addition to houses in 02568, there were also 3 condos, 1 townhouse, and 2 multi-family units for sale in 02568 last month. Find your dream home in 02568 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 02568 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 02568. If you're looking to sell your home in the 02568 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 02568 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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