Downtown Oak Bluffs Real Estate

View current real estate listings in Downtown Oak Bluffs on Martha's Vineyard below.

Downtown Oak Bluffs Homes for Sale

Call Ocean Park Realty at 508-693-4210 if you have questions about any of these properties or would like to set up a private tour.

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10 Winemack Street Oak Bluffs MA

Oak Bluffs, MA10 Winemack Street

Price$579,000

Est. Mortgage: $/month

MLS Number 37003

  • Residential
  • Square Feet 651
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.3

Charming two story home on a spacious well treed lot in an established neighborhood offering easy access to downtown Oak Bluffs, Eastville Beach, Lagoon Pond ,Vineyard Haven and the Hospital. The house is a campground cottage that was moved to this site and set on four pillars. A narrow covered front porch leads into an open kitchen, dining, living area on the first floor. A door off the kitchen leads to the deck in the backyard to the outdoor entertainment area. It has been a three season retreat for over twenty years by the current owners who use it until Thanksgiving. The property is 100 years old and offers many possibilities only limited by your imagination as well as the building codes. There is a cesspool that would need to be replaced with a septic. The design and installation of the septic is the buyers responsibility. The house is being sold AS IS and includes some of the furnishings.

Listed by Martha's Vineyard Seacoast Properties

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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31 New York Avenue Oak Bluffs MA

Oak Bluffs, MA31 New York Avenue

Price$1,195,000

Est. Mortgage: $/month

MLS Number 37020

  • Residential
  • Square Feet 2390
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.1733

This East Chop home is a true example of New England's classic shingle style architecture. This 1920's Craftsman style home offers the charm and sophistication of its time with impeccably preserved wainscoting, a traditional foyer and high ceilings throughout the entire first floor. The sun-filled living and dining area share one side of the first floor and is a perfect space for entertaining especially around the beach stone fireplace. The kitchen is at the center of the home and, renovated in 2009, offers a warm and inviting space with top of the line appliances, concrete countertops, custom cabinetry and with many of the same aesthetics of wainscoting and high ceilings. This 4-br home has one bedroom on the first floor, plus a laundry room/office space, mudroom, with three more bedrooms on the second floor. The signature front porch overlooks thoughtfully planned perennial gardens, lawn space and mature plantings. There's also a 1-br guest house and it's equally charming! Built in 2013, its wood walls, high ceilings, concrete floor and en suite bedroom with balcony make this 720 sf dwelling perfect for family overflow, guests wanting privacy or can be used as an income-generating property. The fenced in yard is surrounded by tall privet hedge and offers a private, courtyard feeling among the gardens, dogwoods, and other mature plantings. There's a bluestone patio and firepit for summer and winter evening gatherings alike. Only a short walk to East Chop beach, harbor and downtown shops, this one set up for Vineyard living!

Listed by Tea Lane Associates

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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21 Siloam Avenue Oak Bluffs MA

Oak Bluffs, MA21 Siloam Avenue

Price$679,000

Est. Mortgage: $/month

MLS Number 36998

  • Residential
  • Square Feet 768
  • Bedrooms 2
  • Bathroom 1
  • Update Type NONE

In the heart of Oak Bluffs and part of the Campground Meeting Association, yet feels open and airy with views of Sunset Lake. Easy access to the harbor, Circuit Avenue and all of the restaurants and activities offered in Oak Bluffs. There is parking in front as well as a space behind the property. Enjoy Illumination night and the Fireman's Fireworks next August!

Listed by The Vineyard Life Brokered by eXp Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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90 Dukes County Avenue Oak Bluffs MA

Oak Bluffs, MA90 Dukes County Avenue

Price$2,195,000

Est. Mortgage: $/month

MLS Number 36887

  • Multi-Family
  • Village Downtown
  • Bedrooms 5
  • Bathroom 5
  • Half Bath 1

ULTRA CHIC + LUXE: RESIDENTIAL and COMMERCIAL PROPERTY. Located within walking distance to Oak Bluffs town center and harbor, this luxurious designer's own property offers a one-of-a-kind opportunity -- with three residential living spaces, multiple commercial office spaces, plus off-street parking spaces for up to nine (9) cars. Ideal for a savvy investor or business person looking for a condominium conversion OR a live-work situation with opportunity to do use rental income to offset ownership costs. The property currently generates $120,000+/year in combined commercial and residential rental income. The compound is anchored by a private and beautifully landscaped courtyard. The different spaces are as follows: THE TREE HOUSE (1,668 sq. feet) 3-Bedroom | 3-Bath second-floor unit with private deck; THE GARDEN HOUSE (797 sq. feet): 1-Bedroom | 1-Bath ground-floor unit; THE GATE HOUSE (1,350 sq. feet) 1-Bedroom | 1-Bath ground floor unit; LOWER LEVEL (1,466 sq. feet - not included in total SF shown) and featuring 12-foot ceilings, multiple rooms and a half bathroom. There is also a 1-car garage or storage shed on the first floor of the compound. There are superlative architectural and designer touches throughout this amazing property. Select furnishings are available for separate purchase. There is no other offering like this unique property . . truly a must see!

Listed by Point B Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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7 Pennacook Avenue Oak Bluffs MA

Oak Bluffs, MA7 Pennacook Avenue

Price$1,690,000

Est. Mortgage: $/month

MLS Number 33956

  • Multi-Family
  • Village Downtown
  • Bedrooms 8
  • Bathroom 4
  • Half Bath 1

**Unoccupied and easy to show virtually or in socially-distant person.** In the coveted Copeland District, steps from beach and town: An unparalleled palace of a property awaits the fortunate investor. Dunmere-by-the-Sea, a soaring, three-story edifice was once an elegant hotel of Oak Bluffs' heyday as a swinging Victorian resort. For the past 40-plus years, this "wedding cake" with panaromic views of Nantucket Sound has served its owners well as a three-unit apartment building. Vacation tenants hail from as near as Boston and as far as Budapest, including many longtime repeaters. Updates over the years have spared many elements of period charm -- the mansard roof, substantial "gingerbread" trimmings, the serpentine interior stairway. Each unit enjoys bright and spacious floor-through living, with open common areas, full kitchens and baths, two-plus bedrooms and water views. They share use of a laundry, a deep wraparound porch, four parking spaces and generous yard space for lounging and cookouts. The raised finished basement, inclusive of full bath and laundry, has full windows and both indoor and outdoor entries. The opportunities abound: Glamorously upgrade or simply refresh the "old school" cottage ambience. Continue the lucrative landlord tradition. Create condominiums (subject to town permitting). Or go rogue and transform the building into your personal, palatial single-family domain. Property is eligible for tie-in to the town sewer.

Listed by Coldwell Banker Landmarks

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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 TourAsk A QuestionMore Details