Oak Bluffs Properties

Originally called “Cottage City”, Oak Bluffs is a classic beach town, filled Downtown Oak Bluffs Martha's Vineyardwith fun restaurants, bars, shops and beaches. It’s one of the island’s principal points of arrival for summer tourists, and is home to the Camp Meeting Association, or “Campgrounds”; a renowned area consisting of hundreds of colorful, unique “gingerbread” cottages in the center of town. Also in Oak Bluffs is Circuit Avenue, the commercial heart of the town with restaurants, souvenirs, and ice cream shops, as well as the spacious waterfront grounds of Ocean Park, and the long stretch of Joseph A. Sylvia State Beach that extends into Edgartown.

Within Oak Bluffs you’ll find properties along the winding roads on East Chop, historic cottages in Ocean Park and the Campground, and waterfront properties along the long stretch of Lagoon Pond.

Contact Sandpiper Realty to learn more about one of the Oak Bluffs real estate listings below. Register with our site if you would like to stay up to date on your favorite Oak Bluffs homes.

You might also like to view Vineyard Haven properties or Chilmark properties.

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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44 Windemere Road Marthas Vineyard MA

MLS Number 30201

  • Residential
  • Village Oak Bluffs
  • Square Feet 2304
  • Bedrooms 3
  • Bathroom 3

A Stunning & Impressive Location! Fabulous Water Views from almost every room in the house over the Lagoon, Brush Pond & Vineyard Haven Harbor, mixed w/quality construction, a terrific floor plan & lots of windows. A combination you always hope for but rarely find. Main living level has open floor plan w/views in every direction! Custom Kitchen, painted solid wood cabinetry, granite counters, stainless appliances, requisite gas stove & wide plank oak floors. Living room has riverstone, woodburning fireplace w/granite hearth. French doors, opening towards Lagoon onto 40ft wide covered, mahogany, wraparound deck w/outdoor fireplace. Upstairs, a 'real' master bedroom w/ensuite (two sinks!), private balcony & SUPER views of the Lagoon. Two guest rooms, one w/balcony, shared bath & separate laundry. Oak flooring throughout, Central Air Conditioning, Storm Watch windows, On Demand hot water, Seamless Glass showers (a bath tub also), ceiling fans, recessed downlighter, colorful plantings..all this & only STEPS to the BEACH!! TRULY A MUST SEE....a Very Special property.

Listed by Alisan Lohan-Conway Properties

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$/month over payments
Federal 30-year interest rate: 3.66% last updated on Apr 28, 2016
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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285 Barnes Road Marthas Vineyard MA

MLS Number 30192

  • Residential
  • Village Oak Bluffs
  • Square Feet 3403
  • Bedrooms 4
  • Bathroom 3

WATERFRONT HOME with 122ft DOCK and 100ft of BEACH. This is the house for Entertaining! Fabulous, Waterfront location with wonderful sunsets, on just under an acre of land that rolls down to the water. Floor plan designed to take advantage of its location, abounding with water views. Main level, with its soaring ceilings, is comprised of a large living, dining and sitting area with custom kitchen and sliders leading onto a huge mahogany deck, with full views of the Lagoon. First floor Master Bedroom has views over the Lagoon, Ensuite bathroom and Private Enclosed Porch with Separate Entrance and direct access to Mahogany Deck. Super 500 sq.ft. Detached Media Room, with Projector TV and Retractable Screen. Great for movies or game night! This separate space would also make a terrific office. New Four (4) Bedroom Septic Installed in 2014. Second Deck overlooking the Dock commands beautiful views of the Lagoon. Deep Water Dock with electricity and water supply. Minutes from Downtown Oak Bluffs and easy access to all island towns.

Listed by Alisan Lohan-Conway Properties

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$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Apr 28, 2016
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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21 Siloam Avenue Marthas Vineyard MA

MLS Number 30037

  • Residential
  • Village Oak Bluffs
  • Square Feet 768
  • Bedrooms 3
  • Bathroom 1

Year round Campground Cottage with views over Sunset Lake. A cute little bungalow that has been totally winterized with many new upgrades. A Rennai propane tankless hot water heater, new stove, propane furnace (FHA heat), electrical and plumbing upgrades. There is one parking space directly behind the cottage and the Seller rents another space in the lot across street for $100.00 per year. Ideal In-town location, close to ferry, Oak Bluffs Harbor (end of the street) and a beautiful swimming beach around the corner. There are five weeks of rentals already booked this Summer. To learn more about the Campground Association visit: www.mvcma.org.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Apr 28, 2016
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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34 Puritan Drive Marthas Vineyard MA

Oak Bluffs MA34 Puritan Drive

Price$875,000

Est. Mortgage: $/month

MLS Number 30127

  • Residential
  • Village Oak Bluffs
  • Square Feet 2641
  • Bedrooms 3
  • Bathroom 2

Bright, Classic, Pristine - Located in Tower Ridge, a delightful home in an established, well planned neighborhood of meticulously maintained homes where all properties complement each other. This classic New England Colonial sits well on the large parcel of land providing a buffer off the road and an expansive yard. You can enter through the sun filled three season room off the kitchen or use the formal foyer at the front of the house. The newly updated bright kitchen is an invitation to the comfortable living at the back of the house. A breakfast area is located in a bay overlooking the back yard. The spacious living room with fireplace and new set of French Doors to the new deck provides ample space for many gatherings. Did we mention the formal dining room to the right of the foyer for special occasions? There is a well thought out computer room and a powder room off the mudroom. The space on the second floor is as generous as it is on the first level. The master suite with huge walk in closet and larger than life bathroom are an absolute luxury. It is not just a bedroom but has space for an office or quiet reading area. There are two additional bedrooms with great closet space and full bath on the second floor. There are hardwood floors throughout the house. As generous as the space is on the first and second floor there is a finished third floor with two rooms. One currently used for storage and the other for guest overflow. This area is not heated however it is plumbed and has a thermostat that allows for an easy conversion. A truly special property that deserves your attention.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Apr 28, 2016
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23 East Chop Drive Marthas Vineyard MA

MLS Number 30153

  • Residential
  • Village Oak Bluffs
  • Square Feet 2702
  • Bedrooms 5
  • Bathroom 3

Harborfront with Deep Water Dock- The perfect property for the boating enthusiast with a private deep water dock and 175' of harbor frontage. Enjoy spectacular views of the harbor and Nantucket Sound beyond from the veranda, enclosed sun porch and nearly all rooms in the house. The "Red House" as it is fondly known exudes the charm of a by-gone era but has been well maintained and undergone some renovations over more recent years. You will find plenty of space all to gather as well as accommodate many over-night guests with 5 bedrooms in the main house and extra space for over flow above the boathouse/garage. The home has been adored by generations and is the place where summer memories are made. Experience the luxury of living on the water with all the conveniences of town and beach just a short stroll away.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Apr 28, 2016
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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47 Monroe Avenue Marthas Vineyard MA

MLS Number 30124

  • Residential
  • Village Oak Bluffs
  • Square Feet 1843
  • Bedrooms 3
  • Bathroom 2

East Chop Highland... Nicely wooded site, house sits on a knoll in a very quite neighborhood. Convenient access to town, beaches, and ferry. Three bedroom 2 full baths which includes the finished basement in-law-apartment . Needs a thorough renovation and would be an exciting project for a Buyer with imagination. Owner occupied... 24 Hour notice for showings. *Property Being Sold "As Is"

Listed by Island Home Realty Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Apr 28, 2016
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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7 Oakland Avenue Marthas Vineyard MA

MLS Number 30146

  • Commercial
  • Area Oak Bluffs

This is sold as a turnkey restaurant, all existing equipment included. Adjacent house currently on the property, will be subdivided and is NOT included in the sale

Listed by Arrowhead Homes

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$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Apr 28, 2016
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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10 Meshacket Way Marthas Vineyard MA

MLS Number 30136

  • Residential
  • Village Oak Bluffs
  • Square Feet 2983
  • Bedrooms 5
  • Bathroom 3

Spacious and gracious large rambling cape style home with a "Williamsburg" appeal. Light and Bright formal dining room opens to the living room, complete with wood burning fireplace. A separate breakfast nook is just off the efficiently designed kitchen (recently remodeled with 6 burner commercial range and granite counter tops) and the main level laundry is adjacent to the 2 car garage. 5 bedrooms/3 baths includes a massive master bedroom suite that is separate from the rest. Outside is a wonderful deck and large back yard. Central air conditioning, outdoor shower and room for a pool! Centrally located near the high school and YMCA, bike path and with easy access to all things down island.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Apr 28, 2016
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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21 Island Inn Road Marthas Vineyard MA

Oak Bluffs MA21 Island Inn Road

Price$134,900

Est. Mortgage: $/month

MLS Number 30132

  • Condominium
  • Village Oak Bluffs
  • Square Feet 584
  • Bedrooms 2
  • Bathroom 1

Vacation Vacation!! This fully equipped condo is bright and lively. New wood floors and decorated with coastal charm, this floor plan configuration is highly sought after. Fully furnished, AC, Fireplace, Pool, BBQ area, Tennis and plenty of parking. Beautiful sandy beach just a walk or bike away - bike paths and so much more. More interior photos soon -

Listed by Jane Brown Assoc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Apr 28, 2016
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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63 Webster Avenue Marthas Vineyard MA

MLS Number 30114

  • Residential
  • Village Oak Bluffs
  • Square Feet 3494
  • Bedrooms 5
  • Bathroom 4

Lovely 4-bedroom main house with attached 1-bedroom guest wing, sits on 0.63 landscaped acres, with partial water views of Vineyard Sound and Crystal Lake. Located in the heart of the upscale but laid back East Chop family oriented community, the property offers convenient access to beaches, tennis club, beach club, yacht club, downtown Oak Bluffs and ferry service. Main house is a two-story contemporary custom Cape with two bedrooms on the first floor and two on the second floor that open out to sun deck. Open floor plan kitchen, dining room, living room with fireplace, opens out to enclosed sun porch, deck, patio, outdoor shower and gardens. Guest wing includes 1-bedroom, full bathroom, vaulted ceiling above living room/kitchen/dining area and bar, that opens out to deck with partial water views. Two car garage plus ample parking in driveway for multiple vehicles. Mini-splits A/C. Some furniture available separately. Offers excellent rental income opportunities.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Apr 28, 2016
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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