Oak Bluffs, MA homes for sale & real estate

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FLOOR PLAN

ABOUT THIS HOME
Oak Bluffs, MA Homes for Sale
Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living spaces, along with an additional 700+ square feet of newly finished recreation space above the two-car garage, complete with a private entrance and second-floor deck. The inviting first floor is designed for comfortable living and entertaining, featuring a spacious kitchen with a center island and abundant counter space. The adjacent dining room provides a warm gathering space with a wood stove, while glass doors open to a wood deck and bluestone patio for easy indoor-outdoor living. Multiple sitting areas, a living room with a gas fireplace, and a private office offer plenty of room to relax, gat

$1,755,000

3 beds3 baths2,815 sq ft

68 Front St, Oak Bluffs, MA 02557

Quiet street • Bluestone patio • Wood deck

OPEN SAT, 12PM TO 2PM

ABOUT THIS HOME
Oak Bluffs, MA Homes for Sale
Nestled in Oak Bluffs’ desirable Hidden Cove community, this Contemporary residence offers a quintessential Martha’s Vineyard retreat centered on outdoor recreation and coastal living. Residents enjoy premier neighborhood amenities, including direct water access to Sengekontacket Pond for seamless kayaking and paddleboarding, as well as community tennis courts just steps from your front door. Set on a private, wooded lot, the home showcases classic Vineyard cedar siding, a striking two-story fireplace, an expansive wood deck, a screened porch, and an outdoor shower for effortless post-beach relaxation. Featuring 1,898 square feet of above-grade living space plus a 512 square foo

$1,595,000

4 beds3 baths1,898 sq ft

20 Hidden Cv, Oak Bluffs, MA 02557

Private wooded lot • Cedar siding • Sengekontacket pond

FLOOR PLAN

ABOUT THIS HOME
Oak Bluffs, MA Homes for Sale
Location, location, location: This 1999 home with all the comforts of the 21st Century is nestled on a landscaped lot within mellow surroundings. And yet … it’s located within mere moments of town, beach, bike path, bus line, parks, recreation, Farm Pond and a Land Bank trail. The situation hardly gets better. The 3BR/2.5BA house features a deep wraparound farmer’s porch, Brazilian cherry floors, an open and flexible layout, recent kitchen and bath updates, a generous 2nd floor bonus room and an attached single-car garage. The poured basement stands ready for your finishing whims. Kick back in your sunny backyard or on your shady porch with the distant peek of Nantucket S

$2,200,000

3 beds2.5 baths2,420 sq ft

61 Canonicus Ave, Oak Bluffs, MA 02557

Poured basement • Landscaped lot • Sunny backyard

ABOUT THIS HOME
Oak Bluffs, MA Homes for Sale
Welcome to this sun-drenched, reverse contemporary-style home located in the lovely Meadow View Farms community! This multi-level home has boundless potential. The second level features a bright, open floor plan with cathedral ceilings, living, dining, and kitchen areas, and 3 sliding doors that take you outside to the upper deck. Open the sliders to the expansive deck and you will almost double the living space on the upper level. There is also a powder room on the upper level. The main floor features the primary suite with bath, walk-in closet, air conditioning, and sliders that open to the first-floor deck; that level offers 2 more spacious bedrooms and a shared bath. Venture downstairs

$1,750,000

3 beds2 baths1,932 sq ft

14 High Meadow Ln, Oak Bluffs, MA 02557

Open floor plan • Walk-in closet • Cathedral ceilings

FLOOR PLAN

ABOUT THIS HOME
Oak Bluffs, MA Homes for Sale
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

31 Temahigan Ave, Oak Bluffs, MA 02557

0.27 acre lot • Built 2026 • Listed 33 days

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 2 Winemack St, Oak Bluffs, MA 02557, 3 beds, 2 baths

$1,095,000

3 beds2 baths2,173 sq ft

2 Winemack St, Oak Bluffs, MA 02557

Property at 27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02557, 1 bed, 1 bath

$287,500

1 bed1 bath388 sq ft

27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02557

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

$785,000

2 beds1 bath624 sq ft

60R Carol Ln, Oak Bluffs, MA 02557

Property at 21 Island Inn Rd Unit 38 G, Oak Bluffs, MA 02557, 1 bed, 1.5 baths

$389,000

1 bed1.5 baths590 sq ft

21 Island Inn Rd Unit 38 G, Oak Bluffs, MA 02557

Property at 27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02557, 1 bed, 1 bath

$310,000

1 bed1 bath783 sq ft

27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02557

Property at 33 Island Inn Rd Unit 25 F, Oak Bluffs, MA 02557, 1 bed, 1 bath

$260,000

1 bed1 bath319 sq ft

33 Island Inn Rd Unit 25 F, Oak Bluffs, MA 02557

Property at 27 Beach Rd, Oak Bluffs, MA 02557, 5 beds, 1.5 baths

$2,995,000

5 beds1.5 baths1,731 sq ft

27 Beach Rd, Oak Bluffs, MA 02557

Property at 59 Tuckernuck Ave, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$2,595,000

4 beds2.5 baths1,858 sq ft

59 Tuckernuck Ave, Oak Bluffs, MA 02557

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

$2,195,000

3 beds2 baths1,425 sq ft

312 E Chop Dr, Vineyard Haven, MA 02568

Property at 7 Ploughshare Ln, Oak Bluffs, MA 02557, 3 beds, 2.5 baths

$1,499,000

3 beds2.5 baths1,645 sq ft

7 Ploughshare Ln, Oak Bluffs, MA 02557

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 43 Sengekontacket Rd, Oak Bluffs, MA 02557, 3 beds, 3 baths

$5,495,000

3 beds3 baths2,234 sq ft

43 Sengekontacket Rd, Oak Bluffs, MA 02557

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 40 Hidden Cove Road Unit 2 #2, Oak Bluffs, MA 02557, 3 beds, 3.5 baths

$1,495,000

3 beds3.5 baths2,739 sq ft

40 Hidden Cove Road Unit 2 #2, Oak Bluffs, MA 02557

Property at 19 Perkins Ave, Oak Bluffs, MA 02557, 2 beds, 1 bath

$825,000

2 beds1 bath985 sq ft

19 Perkins Ave, Oak Bluffs, MA 02557

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

$1,100,000

3 beds2 baths1,302 sq ft

47 Winemack St, Oak Bluffs, MA 02557

Property at 37 Circuit Ave Unit 4, Oak Bluffs, MA 02557, 2 beds, 1 bath

$879,000

2 beds1 bath990 sq ft

37 Circuit Ave Unit 4, 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 44 Tiffany Dr, Oak Bluffs, MA 02557, 4 beds, 4.5 baths

$2,595,000

4 beds4.5 baths3,927 sq ft

44 Tiffany Dr, Oak Bluffs, MA 02557

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

$3,100,000

4 beds3 baths1,728 sq ft

6 Brewster Ave, Oak Bluffs, MA 02557

Property at 37 Circuit Ave Unit 5, Oak Bluffs, MA 02557, 1 bed, 1 bath

$849,000

1 bed1 bath797 sq ft

37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

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

$4,600,000

6 beds5.5 baths3,998 sq ft

15 Tamarack Ln, Oak Bluffs, MA 02557

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

$5,225,000

6 beds4 baths2,890 sq ft

4 Canonicus Ave, Oak Bluffs, MA 02557

Property at 18 Wood Duck Way, Edgartown, MA 02539, 4 beds, 3 baths

$1,800,000

4 beds3 baths2,864 sq ft

18 Wood Duck Way, Edgartown, MA 02539

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

$849,000

2 beds0.5 baths953 sq ft

50 Canonicus Ave, Oak Bluffs, MA 02557

Property at 15 Roger's Way, Oak Bluffs, MA 02557

$850,000

Land0.25 acre (lot)

15 Roger's Way, Oak Bluffs, MA 02557

Property at 0 Heather Ln, Oak Bluffs, MA 02557

$399,000

Land7,841 sq ft (lot)

0 Heather Ln, Oak Bluffs, MA 02557

Property at 24 Towanticut St, Vineyard Haven, MA 02568

$789,000

Land0.39 acre (lot)

24 Towanticut St, Vineyard Haven, MA 02568

Property at 68 Pond View Dr, Oak Bluffs, MA 02557

$975,000

Land1.07 acres (lot)

68 Pond View Dr, Oak Bluffs, MA 02557

Property at 112 Dukes County, Oak Bluffs, MA 02557

$549,000

Land3,200 sq ft (lot)

112 Dukes County, Oak Bluffs, MA 02557

Property at 0 Temahigan Ave & Dover St, Oak Bluffs, MA 02557

$1,049,000

Land0.25 acre (lot)

0 Temahigan Ave & Dover St, Oak Bluffs, MA 02557

Property at 7 Overview Ln, Oak Bluffs, MA 02557

$5,100,000

Land2.34 acres (lot)

7 Overview Ln, Oak Bluffs, MA 02557

Property at 7 Highland Ave, Oak Bluffs, MA 02557

$809,000

Land0.39 acre (lot)

7 Highland Ave, 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 Mon Sep 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.

Average home prices near Oak Bluffs, MA

Cities

Neighborhoods
Zip Codes

Martha's Vineyard homes for sale
$2,440,000
Eastville homes for sale
$2,211,500
East Chop homes for sale
$2,195,000

Oak Bluffs, MA real estate trends

All Home Types trends in Oak Bluffs, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,274,157

-17.3% YoY | Aug 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Aug 2026

Growth

% YoY

Oak Bluffs, MA

$1,274,157

-17.3%

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