- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
32 Properties Available In Oak Bluffs
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$2,390,000
Single Family Home
22 Greenleaf Avenue, Oak Bluffs, MA 02539
Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary locati...
Listed by Jen O'Hanlon of Compass

$4,500,000
Single Family Home
267 Barnes Road, Oak Bluffs, MA 02557
Enjoy waterfront living at its best with 163' of Lagoon frontage including a private sandy beach. Sited on 1.25 acres of...
Listed by Stephanie Roache of Donnelly + Co.

$2,495,000
Single Family Home
6 Martha's Park Road, Oak Bluffs, MA 02557
Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breath...
Listed by Jennifer DaSilva of Compass

$1,169,999
Single Family Home
96 Manchester Ave, Oak Bluffs, MA 02557
Nestled in the sought-after Lagoon Heights in Oak Bluffs, 96 Manchester Ave is a charming Cape-style home offering a per...
Listed by The J. Pavao Team of Keller Williams South Watuppa

$749,000
Single Family Home
2 Fisk Ave, Oak Bluffs, MA 02557
Gingerbread Cottage full of character and personality! Part of Martha's Vineyard Camp Meeting Association, this Oak Bluf...
Listed by Julie Walker of Century 21 North East

$1,690,000
Single Family Home
8 School House Village, Oak Bluffs, MA 02557
Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attractive colorful landscaping, this...
Listed by Stephanie Roache of Donnelly + Co.

$1,850,000
Single Family Home
34 Tower Ridge Road, Oak Bluffs, MA 02557
Welcome to a modern oasis nestled in the lovely community of Tower Ridge. This exquisite residence offers generous livin...
Listed by Jennifer DaSilva of Compass

$975,000
Single Family Home
51 Manchster, Oak Bluffs, MA 02557
Addorablily Cozy 2 bedroom 1 bath home in a wonderful quiet neighborhood. Well maintained, with stone patio and beautif...
Listed by Roy Cutrer of LAER Realty Partners

$13,200,000
Single Family Home
150 East Chop Drive, Oak Bluffs, MA 02557
Welcome to your dream retreat in Oak Bluffs. A magnificent 8 br oceanview estate. This property is designed to accommoda...
Listed by Reciprocal Reciprocal of Cape Cod Reciprocal

$14,000
Single Family Home
55 Samoset Ave, Oak Bluffs, MA 02557
Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, fer...
Listed by Allison Cameron Parry of Douglas Elliman Real Estate - Nantucket

$28,500
Single Family Home
9 Tuckernuck Ave, Oak Bluffs, MA 02557
**PEAK SUMMER WEEKLY RATE** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ ...
Listed by Allison Cameron Parry of Douglas Elliman Real Estate - Nantucket

$20,000
Single Family Home
55 Samoset Ave Ob503 #1, Oak Bluffs, MA 02557
THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central A...
Listed by Karen M. Overtoom of Karen M. Overtoom R.E.

$1,999,000
Single Family Home
28 Rogers Way, Oak Bluffs, MA 02557
NEW CONSTRUCTION, contemporary farmhouse style home with wrap around deck and outdoor shower. This home features a first...
Listed by Michele Casavant of Vineyard Village Realty

$10,500,000
Single Family Home
47 East Chop Drive, Oak Bluffs, MA 02557
East Chop direct waterfront – Enjoy the ultimate. in waterfront living experiences. Features 6 bedrooms, spectacular wat...
Listed by Perry Patterson of MV Luxury Homes LLC

$64,000
Single Family Home
385 Barnes Rd Ob534, Oak Bluffs, MA 02557
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY P...
Listed by Karen M. Overtoom of Karen M. Overtoom R.E.

$24,000
Single Family Home
5 Laurel Ave Ob532, Oak Bluffs, MA 02557
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PR...
Listed by Karen M. Overtoom of Karen M. Overtoom R.E.

$20,000
Single Family Home
291 Barnes Rd Ob516, Oak Bluffs, MA 02557
THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront...
Listed by Karen M. Overtoom of Karen M. Overtoom R.E.

$20,000
Single Family Home
40 Hidden Cove 5 Ob537, Oak Bluffs, MA 02557
THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condo...
Listed by Karen M. Overtoom of Karen M. Overtoom R.E.

$14,200
Single Family Home
59 Prospect Ave Ob502, Oak Bluffs, MA 02557
THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neigh...
Listed by Karen M. Overtoom of Karen M. Overtoom R.E.

$725,000
Single Family Home
181 Circuit Avenue, Oak Bluffs, MA 02557
Location, location, location!! This chic, turnkey cottage has been completely renovated! Park your car, drop your bags a...
Listed by Jennifer DaSilva of Point B Realty, LLC

$21,000
Single Family Home
12 John Wesley Ave Ob519, Oak Bluffs, MA 02557
THIS IS A SUMMER RENTAL ONLY. EAST CHOP LOCATION!! Located across from the historic Baptist Temple Town Park. This cha...
Listed by Karen M. Overtoom of Karen M. Overtoom R.E.

$12,500
Single Family Home
11 Wamsutta Ave, Ob540, Oak Bluffs, MA 02557
THIS IS A SUMMER RENTAL ONLY. This antique Vineyard home is thoughtfully styled with classic country-chic interior dec...
Listed by Karen M. Overtoom of Karen M. Overtoom R.E.

$21,000
Single Family Home
24 Deer Run Rd. #OB521, Oak Bluffs, MA 02557
THIS IS A SUMMER RENTAL ONLY. Centrally located to Edgartown, Vineyard Haven and Oak Bluffs. Just a short drive will ta...
Listed by Karen M. Overtoom of Karen M. Overtoom R.E.

$20,000
Single Family Home
67 New York Ave #OB536, Oak Bluffs, MA 02557
THIS IS A SUMMER RENTAL ONLY. 1900 Oak Bluffs Victorian. Ten minute walk to Nancy's restaurant/downtown OB and 1/2 mil...
Listed by Karen M. Overtoom of Karen M. Overtoom R.E.