MLS Listings for Sale in Oak Bluffs, MA

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ABOUT THIS HOME
MLS Listings for Sale in Oak Bluffs, MA
Custom-built 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, charming town centers and year-round ferries. Features include a large primary bedroom, a convenient first floor bedroom, and an open kitchen dining area flowing to a spacious wooden deck and outdoor shower--perfect for indoor-outdoor living. Beautifully maintained with wood floors, skylights, and abundant natural light throughout, this move-in-ready home blends comfort and style. Ideal for year-round living or seasonal retreat.

$1,095,000

3 beds1.5 baths1,487 sq ft

12 Wheelhouse Way, Oak Bluffs, MA 02557

8,861 sq ft lot • Built 1999 • Listed 4 days

ABOUT THIS HOME
MLS Listings for Sale in Oak Bluffs, MA
Nestled in the heart of the historic Martha’s Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs’ campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort — featuring upgraded systems and finishes that make it as cozy in winter as it is bright and breezy in summer. Enjoy easy access to Oak Bluffs Harbor, beaches, restaurants, shops, and all the vibrancy the town has to offer, just moments from your front porch. Ownership includes membership in the MVCMA, providing access to this

$640,000

1 bed1 bath354 sq ft

2 Lincoln Ave, Oak Bluffs, MA 02557

Fully renovated • Year round living • Charming cottages

ABOUT THIS HOME
MLS Listings for Sale in Oak Bluffs, MA
Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort, and convenience in one of Oak Bluffs' most desirable locations. The main living area, filled with natural light and soaring ceiling, offers an open layout that is warm and inviting. A third floor den and exterior decks on all levels provide ample living space both indoors and out. Set within the sought-after Meadow View Farms community, residents enjoy access to beautifully maintained common meadows, as well as association tennis and pickleball courts. The neighborhood's peaceful setting fosters a true sense of community, while its prime location, just off the bike path, places Farm Neck Golf Club and

$1,825,000

4 beds3 baths3,142 sq ft

7 South Meadow Ln, Oak Bluffs, MA 02557

Third floor den • Exterior decks • 0.66 acre lot

ABOUT THIS HOME
MLS Listings for Sale in Oak Bluffs, MA
Your private oasis with a POOL awaits in this beautifully updated Lagoon Hills retreat on over 1.5 acres. Enjoy a carefree, single-level lifestyle featuring an open-concept kitchen and dining area, spacious living room, office and exercise room — all thoughtfully designed for comfort and flow. Step outside to a stunning backyard anchored by a sparkling pool, surrounded by decks, patios, and lush landscaping with stone walls, specimen trees, and a goldfish pond with a waterfall. Additional amenities include a pool house, a detached one-car garage/workshop, an oversized two-car garage, and a full basement—perfect for extra storage or hobbies. With private access to Lagoon Pond, th

$2,499,000

4 beds2.5 baths2,544 sq ft

47 Tiffany Dr, Oak Bluffs, MA 02557

Pool house • Private oasis • Full basement

ABOUT THIS HOME
MLS Listings for Sale in Oak Bluffs, MA
Nestled in the heart of the historic Martha's Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs' campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort -- featuring upgraded systems and finishes that make it as cozy in winter as it is bright and breezy in summer. Enjoy easy access to Oak Bluffs Harbor, beaches, restaurants, shops, and all the vibrancy the town has to offer, just moments from your front porch. Ownership includes membership in the MVCMA, providing access to this unique and stori

$640,000

0 beds1 bath354 sq ft

2 Lincoln Ave Ave, Oak Bluffs, MA 02557

Fully renovated • Year round living • Charming cottages

Property at 26 Hampson Ave, Oak Bluffs, MA 02557, 2 beds, 2 baths

$999,999

2 beds2 baths1,078 sq ft

26 Hampson Ave, Oak Bluffs, MA 02557

Property at 50 Canonicus Ave, Oak Bluffs, MA 02557, 2 beds, 0.5 baths

$970,000

2 beds0.5 baths953 sq ft

50 Canonicus Ave, Oak Bluffs, MA 02557

Property at 400 Barnes Rd, Oak Bluffs, MA 02557, 6 beds, 5.5 baths

$6,395,000

6 beds5.5 baths7,000 sq ft

400 Barnes Rd, Oak Bluffs, MA 02557

Property at 60 -R Carol Ln, Oak Bluffs, MA 02557, 2 beds, 1 bath

$799,000

2 beds1 bath624 sq ft

60 -R Carol Ln, Oak Bluffs, MA 02557

Property at 9 Brunswick Ave, Oak Bluffs, MA 02557, 3 beds, 1 bath

$1,449,000

3 beds1 bath1,033 sq ft

9 Brunswick Ave, 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 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 150 East Chop Dr, Oak Bluffs, MA 02557, 8 beds, 8 baths

$8,900,000

8 beds8 baths8,560 sq ft

150 East Chop Dr, Oak Bluffs, MA 02557

Property at 5 Bayes Hill Cir, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$1,675,000

4 beds2.5 baths2,855 sq ft

5 Bayes Hill Cir, Oak Bluffs, MA 02557

Property at 7 Upper Meadow Ln, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$1,850,000

4 beds2.5 baths3,268 sq ft

7 Upper Meadow Ln, Oak Bluffs, MA 02557

Property at 44 Iron Hill Rd, Oak Bluffs, MA 02557, 3 beds, 1.5 baths

$1,250,000

3 beds1.5 baths1,496 sq ft

44 Iron Hill Rd, Oak Bluffs, MA 02557

Property at 70 Carol Ln, Oak Bluffs, MA 02557, 2 beds, 2.5 baths

$1,200,000

2 beds2.5 baths1,500 sq ft

70 Carol Ln, Oak Bluffs, MA 02557

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

$5,325,000

6 beds4 baths2,890 sq ft

4 Canonicus Ave, Oak Bluffs, MA 02557

Property at 15 Tamarack Ln, Oak Bluffs, MA 02557, 6 beds, 5.5 baths

$4,999,000

6 beds5.5 baths3,214 sq ft

15 Tamarack Ln, Oak Bluffs, MA 02557

Property at 16 Atlantic Ave, Oak Bluffs, MA 02557, 5 beds, 2.5 baths

$2,495,000

5 beds2.5 baths2,577 sq ft

16 Atlantic Ave, Oak Bluffs, MA 02557

Property at 34 Massasoit Ave, Oak Bluffs, MA 02557, 6 beds, 2.5 baths

$2,250,000

6 beds2.5 baths1,666 sq ft

34 Massasoit Ave, Oak Bluffs, MA 02557

Property at 12 & 14 Maple Ave, Oak Bluffs, MA 02557, 4 beds, 4 baths

$1,830,000

4 beds4 baths1,600 sq ft

12 & 14 Maple Ave, Oak Bluffs, MA 02557

Property at 96 Machester Ave, Oak Bluffs, MA 02557, 3 beds, 2 baths

$1,149,000

3 beds2 baths1,596 sq ft

96 Machester Ave, Oak Bluffs, MA 02557

Property at 47 Winemack St, Oak Bluffs, MA 02557, 2 beds, 1 bath

$1,250,000

2 beds1 bath742 sq ft

47 Winemack St, Oak Bluffs, MA 02557

Property at 23 Circuit Ave Ext, Oak Bluffs, MA 02557, 3 beds, 1 bath

$2,700,000

3 beds1 bath1 sq ft

23 Circuit Ave Ext, Oak Bluffs, MA 02557

Property at 385 Barnes Rd, Oak Bluffs, MA 02557, 3 beds, 4.5 baths

$5,995,000

3 beds4.5 baths3,608 sq ft

385 Barnes Rd, 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 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 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 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 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 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 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 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 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 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 56 Holmes Hole Rd, Oak Bluffs, MA 02557

$674,000

— beds— baths— sq ft

56 Holmes Hole Rd, Oak Bluffs, MA 02557

Property at 37 Double Ox Rd, Oak Bluffs, MA 02557

$599,000

— beds— baths— sq ft

37 Double Ox Rd, Oak Bluffs, MA 02557

Property at 0 Barnes Rd, Oak Bluffs, MA 02557

$495,000

— beds— baths— sq ft

0 Barnes Rd, Oak Bluffs, MA 02557

Property at 7 Overview Ln, Oak Bluffs, MA 02557

$5,100,000

— beds— baths— sq ft

7 Overview Ln, Oak Bluffs, MA 02557

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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 Wed Nov 12 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.

MLS Listings for Sale in Oak Bluffs

There are currently 41 mls listings for sale in Oak Bluffs at a median listing price of $1.85M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Oak Bluffs stay on the market for 120 days. Popular neighborhoods include Martha's Vineyard, and East Chop. This map is refreshed with the newest listings in Oak Bluffs every 15 minutes.

In the past month, 4 homes have been sold in Oak Bluffs. In addition to houses in Oak Bluffs, there were also 7 condos, 1 townhouse, and 2 multi-family units for sale in Oak Bluffs last month. Find your dream home in Oak Bluffs 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 Oak Bluffs are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Oak Bluffs. Our Oak Bluffs real estate stats and trends will give you more information about home buying and selling trends in Oak Bluffs. If you're looking to sell your home in the Oak Bluffs area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Oak Bluffs with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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