Oak Bluffs Real Estate

Oak Bluffs on Martha's Vineyard Aerial View

Oak Bluffs is the classic seaside Victorian resort town located in the heart of the Vineyard and famous for its warm pristine water and popular sandy beaches where the public is invited. Originally visited and settled in the early 1800s by religious leaders who made camp each year in the lofty oak groves where thousands of people would partake in the sermons. The campsites evolved into tents and cottages and the settlement became known as Cottage City until 1907 when it was renamed Oak Bluffs.

Homes for sale in Oak Bluffs are very popular because the area explodes with excitement in the Summer.  Oak Bluffs is The Camp Grounds filled with gingerbread cottages, it’s the Ink Well beach, it’s the Farm Neck Golf Course, the fireworks, Illumination Night, the Harbor, East Chop, and Circuit Avenue with wonderful restaurants and shopping. There is always something to do and someplace to go and it’s the only Down Island town with no traffic jams.

Learn more about Life in Oak Bluffs

Oak Bluffs MA Real Estate

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Oak Bluffs Real Estate Statistics

Average Sale Price for Oak Bluffs in 2018: $720,097

Average Sale Price for Oak Bluffs in 2019: $809,427

Average Sale Price for Oak Bluffs in 2020: $790,632

Average Days on Market for Properties Sold in Oak Bluffs for 2020: 151

Oak Bluffs MIL (tax) Rate 2020: 7.44

Oak Bluffs MIL (tax) Rate 2021: 7.37

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Men diving into ocean at Oak Bluffs beachOak Bluffs waterfront

Oak Bluffs Golf

Farm Neck Golf Club Oak Bluffs

 

58 New York Avenue Oak Bluffs MA 02557

Oak Bluffs, MA58 New York Avenue

Price$1,295,000

Est. Mortgage: $/month

MLS Number 39990

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 2
  • Acreage 0.1291

Sprawling 6 bedroom house close to Oak Bluffs Harbor and town center. Great for year-round living with a strong seasonal rental history. Many unique features include high ceilings, a Mansard roof, air conditioning, 2 first floor bedrooms, front and back porches, and a side deck. A grassy yard with a detached building, outdoor shower, and fenced yard complete this wonderful home.

Listed by Lisa Lucier of Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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 Oak Bluffs MA 02557

Oak Bluffs, MA34 Puritan Drive

Price$1,999,000

Est. Mortgage: $/month

MLS Number 40121

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.8146

OPEN HOUSE SAT 9/24 and SUN. 9/25 from 11 am-1pm ~MOVE RIGHT INTO this BEAUTIFUL CLASSIC COLONIAL 3+ Bedrooms in the highly desirable neighborhood of Tower Ridge which is conveniently located off the bike path on County Road. Situated on a sweeping .81 acre lot, detached 2 car garage (built in 2018) with unfinished space above. The home is TURNKEY includes all the furnishings, 4 TV's, stereo with surround sound speakers, brand new Weber grill, outdoor furniture, beach chairs & umbrellas and John Deere Mower! A well thought out design and a welcoming entrance from the side BRIGHT SUN Porch that leads into into an OPEN and SPACIOUS Kitchen, Living and Dining Area. The Kitchen was updated in 2021 with gleaming Granite counters, accent lighting, appliances and modern finishes. Highlights include a separate first floor laundry room, wood burning fireplace and lots of closets throughout! There are 3 generous bedrooms and a bonus third floor finished space with access from one of the bedrooms. The Primary En Suite has a double vanity with a glass shower and 3 closets. Many of the updates include new exterior Cedar Siding, asphalt roof in 2018, windows 2020, wood flooring refinished in 2021, 2 mini splits in 2021. 4 BEDROOM TITLE 5 SEPTIC SYSTEM, ROOM for a POOL with town approval and proven RENTAL HISTORY! TERRIFIC INVESTMENT OPPORTUNITY!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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42 Pennacook Avenue Oak Bluffs MA 02557

Oak Bluffs, MA42 Pennacook Avenue

Price$1,950,000

Est. Mortgage: $/month

MLS Number 40103

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 3
  • Acreage 0.08

Classic antique Victorian home centrally located in the coveted neighborhood of the Copeland and Cottage City Historic District. One block from Inkwell Beach. A rare opportunity to purchase a home with unique architectural details, separate cottage, walking distance to everything, expansive front porch and enormous potential for vacation rental income or personal enjoyment with family and friends. Ability to tie into town sewer for a five bedroom house is in place.

Listed by Christine Todd of Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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4 Montgomery Square Oak Bluffs MA 02557

Oak Bluffs, MA4 Montgomery Square

Price$925,000

Est. Mortgage: $/month

MLS Number 40119

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3

Located in the heart of Oak Bluffs a few blocks from the beach and even closer to shops, restaurants, and entertainment. Move right in to this 4 bedroom 3 bathroom home with year-round living on the first floor. A spacious basement with 200 amp service. Part of the MVCMA, please see owners rules at www.mvcma.org. This wonderful space has 3 separate living areas and a massive 16' X 31' family room, most recently an artist's studio - Let your imagination create what it will be next. Second floor has a large private deck with trellised patio below.

Listed by Lisa Lucier of Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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59 Brush Pond Road Oak Bluffs MA 02557

Oak Bluffs, MA59 Brush Pond Road

Price$999,000

Est. Mortgage: $/month

Active With Contract

MLS Number 40107

  • Residential
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.23

One of the most special places to live in Oak Bluffs-Brush Pond. This 3 bedroom home offers water views, is in move in condition and is just steps from the water. Enjoy the views of Brush Pond & the Lagoon and savor the spectacular sunsets from the deck overlooking the lovely yard. You will not find a better location at this price!

Listed by Barbara Twiss Stringfellow of Laer Realty Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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 Mourning Dove Way Oak Bluffs MA 02557

Oak Bluffs, MA7 Mourning Dove Way

Price$1,899,000

Est. Mortgage: $/month

MLS Number 39754

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.8399

SERENE SETTING in SENGEKONTACKET OAK BLUFFS Beautiful and Spacious 4 Bedroom and 2 Bathroom POND-FRONT RESIDENCE located in DESIRABLE SENGEKONTACKET with Tranquil Views Overlooking the Fresh Water Pond and common lands. An open floor plan with an abundance of natural light throughout. The setting is serene with picturesque views through the Tall Pitch Pines. This Renovated Contemporary Year Round Home situated in the Waterfront Community of Sengekontacket with easy access to the bike path equidistant to all the down island towns! Private amenities that include access to both fresh and salt water ponds, community dock, potential for a boat mooring , with kayak storage and boat ramp, a community clubhouse on the fresh pond (available for private events), tennis courts, and community services such as curbside trash pick-up and snow removal. ROOM FOR A POOL with approvals from town. This is an EXCEPTIONAL and RARE Offering. FIRST SHOWING WED September 14th

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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71 Rogers Way Oak Bluffs MA 02575

Oak Bluffs, MA71 Rogers Way

Price$1,149,000

Est. Mortgage: $/month

Active With Contract

MLS Number 40069

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.3399

This contemporary ranch is located in an ideal area that's tucked away on the edge of town and convenient to all that Oak Bluffs has to offer. Spacious open floor plan in the living room, dining room and kitchen features high ceilings, wood floors, and a beautiful central fireplace. Large primary bedroom with private full bath. Two more bedrooms, full bath and laundry all on the first floor. This home will make an ideal year-round residence or an excellent vacation rental or investment property. Open House Saturday Sept. 10 from noon to 2pm and Sunday, Sept. 11 from 2 to 4pm. Please submit all offers by 5pm on Monday, Sept. 12.

Listed by Amy Kurth of Vineyard Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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45 Menahan Street Oak Bluffs MA 02557

Oak Bluffs, MA45 Menahan Street

Price$589,000

Est. Mortgage: $/month

MLS Number 40070

  • Land
  • Mls Status Active
  • Acreage 0.1148

OAK BLUFFS - 4 Bedroom lot in a quiet location, down a lovely treed street, yet less than a mile to all the activity of beautiful Oak Bluffs Harbor, boating, restaurants and stores! Close enough to Town for easy access by foot, bike or car, yet distant enough for quieter living. Included in the sale - Septic Approval in hand for 4 Bedrooms from Oak Bluffs Board of Health. Sale is contingent upon Seller's approval of proposed house design. Property Taxes will be determined once new house has been completed.

Listed by Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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4 Troy Street Oak Bluffs MA 02557

Oak Bluffs, MA4 Troy Street

Price$5,800,000

Est. Mortgage: $/month

Active With Contract

MLS Number 40000

  • MultiFamily
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 0.8386

Standing majestically on this beautiful double lot overlooking Vineyard Sound is this distinctive Victorian style home that incorporates the best of the new and old-world design. The home offers multiple patios, porches, decks and balconies from which to enjoy the lovely view over to Falmouth, a vintage wine tasting library, formal and informal living areas as well as a workout room and recreational room in the basement with a full-service bar area and media area in which to entertain guests and family on movie nights. The home offers two large, beautiful primary suites as well as 2 large guest bedrooms and a full third floor with lots of sleeping area for the kids. There is a four-season porch with a mini split for year-round enjoyment. Built in sound system. In addition to the main house there is a separate guest house which offers full privacy from the main house, its own deck, shower, a guest bedroom with a balcony, living room, full kitchen and a 2-car heated garage. Please note that the finished basement and third floor represent another 3538 sq feet for a total of 7103 sq ft of finished space. Hot Tub on the back deck is included with the sale and the lovely furnishings package is negotiable.

Listed by Jean Kelleher of Kelleher R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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32 Meshaket Way Oak Bluffs MA 02557

Oak Bluffs, MA32 Meshaket Way

Price$1,495,000

Est. Mortgage: $/month

MLS Number 40003

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.447

This move in ready, single level, home is centrally located, just a quick 10 minute drive to any of the down island towns, restaurants, shops and ferries. Positioned on a generous 1.447 acre lot, down a private paved road, this property replicates the serene atmosphere of an up island home yet is just minutes away from The Y, The Performing Arts Center, The State Forest, Farm Neck Golf Course, and countless beaches and walking trails. There is a sweet established vegetable garden and garden shed as well as an oversized garage for all of your storage needs. The outdoor shower and lovely front & back porch are surrounded by decorative trees and plantings, allowing you to enjoy indoor/outdoor living at it's best. This 1,400 sqft home (with new bonus room in the basement) has been lovingly maintained over the years. It has new tile, carpet, bathroom upgrades, mini splits, and a partially finished basement there is little left to do, but yet so much potential for expansion! The 4 bedroom septic just passed Title 5, so if desired there is immediate potential for expansion. With 50ft setbacks this property could also potentially allow for accessory structures and possibly a pool with proper permits. *Note Buyer will assume responsibility for $15,000.00 HOA Road Association Betterment Fee Please ask for more information

Listed by Emma Kiley Bryant of Landmarks at TODAY Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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"Based on information submitted to MA_LINKMV as of September 25, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing."

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