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

Oak Bluffs MIL (tax) Rate 2022: 6.79

Oak Bluffs MIL (tax) Rate 2023: 5.28

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Men diving into ocean at Oak Bluffs beachOak Bluffs waterfront

Oak Bluffs Golf

Farm Neck Golf Club Oak Bluffs

 

2 East Side Road & 60 Bay View Avenue Oak Bluffs MA 02557

MLS Number 41587

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.25

Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the covered porch. Watch the ferries come and go and delight in the dazzling colors of the setting sun. Recent renovations include raising the house and the pouring of a foundation offering an additional 930 square feet of lower level living area. Experience true Vineyard living at its best, just steps away is easy access to the Lagoon with clamming, swimming, and boating. Bring your vision to the open and airy studio/ bunkhouse that is included in this offering at 60 Bay View Avenue and features the same wonderful vistas. Two unbuildable lots abut this property so you will never lose sight of the breathtaking scenery. This classic home is a rare Vineyard offering and not to be missed.

Listed by Carol Shore of Donnelly + Co

$
$
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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 High Meadow Lane Oak Bluffs MA 02557

Oak Bluffs, MA4 High Meadow Lane

Price$2,650,000

Est. Mortgage: $/month

MLS Number 41548

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.8899

Set back and overlooking a sprawling front yard from the quintessential farmer’s porch you can envision family and friends enjoying the outdoors! Soaring cathedral ceilings and beautiful craftsmanship will immediately capture your attention upon entering this expansive cape style home. Many upgrades make this a gracious charmer from the get go.. The floor plan is fabulous, from the bright large kitchen outfitted with ample granite counters, rugged commercial Wolf stove, wine fridge and eat-in counter plus table eating is perfect for family gatherings and entertaining. SOLID is the best way to describe what you will experience when you visit this home. Post and Beam construction levels up with Energy Efficient SIP style of insulation plus Radiant heat through the floors. Central AC and great use of sized windows lets all the light in! First floor primary bedroom is spacious with walk in closet and full bathroom with tub. There is a 2nd bedroom that is currently being used as a TV room. 2 more sizeable bedrooms ensuite and closets complete the 2nd floor. The Lower level is partially finished with key and perfect for multigenerational flex space and or a game room or office. Bring your imagination and personalize the possibilities! There is more! A large Garage with additional space above that can be finished for other creative use. Situated on .89 acres of land, so much yard for all occasions. Lawn games, get togethers outdoor fun all surrounded by beautiful landscaping and Abutting a buffer of Common Land! This is an impressive home base perfect for year-round, a fabulous vacation spot and or generate impressive rental income. Meadow View Farms is a lovely welcoming community that offers beautiful walking paths, along with Association Tennis courts. Perfectly convenient to the bike paths, bus routes central to the down island towns. Title V inspection has been completed and passed.

Listed by Martha Smith of C McManus Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 Hudson Avenue Oak Bluffs MA 02557

Oak Bluffs, MA21 Hudson Avenue

Price$2,950,000

Est. Mortgage: $/month

MLS Number 41542

  • MultiFamily
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 4.5
  • Acreage 0.4399

Income Generating Wonder! Calling all Contractors, Business Owners, Entrepreneurs, Investors with vision., Now is the perfect time to make a smart move in real estate ownership that provides choices and many possibilities. Do you need housing for your employees? This property has it! Originally designed as the owner's apartment and housing for the entire staff of the Pequot Hotel, the property includes an oversize two-bedroom “owners’ apartment” with large kitchen and two baths. Alongside is a shared dormitory style rental space, 8 bedrooms with common XL Kitchen and three baths. There are two large garage bays with large storage ability, featuring a half bath and an office. 11-foot ceilings, and plentiful shelving, heat etc. Perfect for storing all types of equipment or even space for boats. Set back privately on the backside of the lot there is also plenty of parking and a lovely yard for outdoor enjoyment. 21 Hudson is situated in the sought-after zip code 02557, conveniently located within walking distance to the bus route and bike paths, off County Rd. Whether you're looking to live, work, or rent, this property is ready for you! A Truly RARE REAL ESTATE GEM! Square Footage is a total of both units and all data included here is from Town of OB Assessors.. This is a unique offering - A Must See to understand and appreciate all that it offers.

Listed by Martha Smith of C McManus Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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2b Lauras Way Oak Bluffs MA 02557

Oak Bluffs, MA2b Lauras Way

Price$1,295,000

Est. Mortgage: $/month

Active With Contract

MLS Number 41546

  • Residential
  • Bedrooms 2
  • Bathroom 3
  • Acreage 0.3525

Centrally located to shops, restaurants, beaches, and schools, this completely renovated home will satisfy the most discerning buyer. The first floor offers an open concept floor plan with a state of the art kitchen, dining area, and living room. There is also a large bedroom and full bathroom. The second floor offers a den, bonus room / office, full bathroom, and primary bedroom suite. The finished lower level offers endless possibilities. Highlights include a large fenced in yard, outdoor shower, oak hardwood flooring, storage shed, renovated bathrooms, and stainless steel Bosch appliances. Move right in and enjoy.

Listed by Jarrett Hurwitz of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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24 Dolly Lane Oak Bluffs MA 02557

Oak Bluffs, MA24 Dolly Lane

Price$650,000

Est. Mortgage: $/month

MLS Number 41533

  • Land
  • Mls Status Active
  • Acreage 0.6864

Look no further --- This is an attractive, reasonably priced building lot in the established and well maintained Deer Run neighborhood. It is partially cleared and level with sufficient trees and foliage on the perimeter to ensure privacy. This rectangular 29,900 square foot, .69 acre parcel allows for a three bedroom home with a nitrogen reducing septic system. The bounds are flagged. Deer Run is centrally located on the island and is convenient to all three down island towns and the bike path. This development also has a generous amount of Association Common land for recreation purposes as well as Conservation land in multiple locations in the neighborhood. The rear of this Lot abuts one of those Association parcels. This is a great opportunity to build a new home to suit your own tastes and needs, whether for seasonal or year-round use.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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54 Cannahoot Street Oak Bluffs MA 02557

Oak Bluffs, MA54 Cannahoot Street

Price$1,575,000

Est. Mortgage: $/month

MLS Number 41535

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.2295

Located on East Chop, in pristine condition and just a short walk to the beaches, tennis courts, yacht club/harbor, downtown restaurants and the ferries, is this contemporary style 2-bedroom main house, being sold partially furnished plus detached 1-bedroom/1-bathroom. The main house’ modern design features radiant floor heating, cathedral ceilings, modern kitchen, a central concrete block wall behind the floor to ceiling wood burning Rais-Wittus Shaker bench wood stove and access to exterior decks from both the main entrance and the downstairs bedroom. The steel staircase to the second floor is showcased by a wall of light from the hallway. The second floor features an ensuite master bedroom that has its own balcony deck with outdoor shower. It is located on 10,000 sq. ft. (0.23 acres), that includes a front and side yard and parking for 2-3 vehicles. New Title V septic installed 2022.

Listed by Perry Patterson of MV Luxury Homes

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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3 Canonicus Avenue Oak Bluffs MA 02557

Oak Bluffs, MA3 Canonicus Avenue

Price$2,495,000

Est. Mortgage: $/month

MLS Number 41509

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.0899

WATER VIEWS!!! Steps to the Beach - walk along the most scenic drive on Martha's Vineyard! This stunning property is a true gem, offering an exceptional combination of classic charm, modern amenities, and an ideal location for enjoying the island's relaxed lifestyle. Nestled in the heart of Oak Bluffs, this home is a short stroll to beaches, restaurants, and shops. The scenic harbor and parks are also just moments away, making it perfect for experiencing the best of the Vineyard. This renovated antique home boasts timeless architectural features and a welcoming front porch creating an inviting and picturesque curb appeal. The interior is a blend of elegance and modern convenience offering an inviting atmosphere for family and friends to gather. Enjoy the serene outdoor spaces, including a patio area for outdoor dining and rooftop deck (widow's walk) that features panoramic ocean views! With its prime location and strong rental income history, this property can serve as both your idyllic vacation retreat and a smart real estate investment. Don't miss the garage and surprise bonus area. Come experience the timeless allure of Martha's Vineyard, and make this extraordinary property your island haven. OWNER FINANCING IS AVAILABLE.

Listed by Jennifer B. DaSilva of Compass | Point B

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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35 Temahigan Avenue Lot 6 Oak Bluffs MA 02557

MLS Number 41445

  • Land
  • Mls Status Active
  • Acreage 0.2668

Wonderful opportunity--------------------- Buildable lot in an area of very substantial homes. Possibly, water views of Vineyard Haven harbor. Imagine owning a home at this prestigious location, which is very convenient to both downtown Oak Bluffs and Vineyard Haven. Your future house can possibly have up to 7 bedrooms subject to the Board of Health's approval of septic plans. There are several available house plans or if desired, Arrowhead Homes could build your custom dream house. The pictures taken by a drone, give you a nice sense of how special this location is.

Listed by Arrowhead Homes

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 Netock Avenue Oak Bluffs MA 02557

Oak Bluffs, MA71 Netock Avenue

Price$1,395,000

Est. Mortgage: $/month

Pending

MLS Number 40962

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 4.5
  • Acreage 0.23

Cape style home set on a .25 acre lot with close proximity to East Chop and OB harbor. Expansion possibilities for additional bedrooms. This 4 bedroom and 4.5 bathroom home with attached finished garage is being sold "AS IS" . Tenants are in place.

Listed by Paul Thoutsis of Dockside Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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311 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA311 East Chop Drive

Price$3,250,000

Est. Mortgage: $/month

MLS Number 41412

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.25

This classic East Chop Drive gem lies on a 10,000 sq. ft. lot nestled in the sand dunes, just steps to the waters edge and private dock. The 4-bedroom/2.5-bath cottage went through a substantial renovation years ago with the majority of mechanicals, electrical and plumbing being updated. There is an open floor plan with kitchen, dining and living space with cathedral ceiling and wood burning fireplace. There is a ground floor master with private bath and lots of glass, a second bedroom with half bath and laundry/mudroom. The second-floor features 2-bedrooms and a shared bath. The cottage style structure is super charming inside and out and has a wonderful water facing brick terrace with built-in planter, a covered porch and a one-car garage. Beautiful landscaping with lawns and gardens complete this very special property. Let's not forget to mention, it offers some of the best seats on the Island to take in the incredible sunsets.

Listed by Gerrett Conover of Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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

Based on information submitted to LINKMV as of December 7, 2023 . All data is obtained from various sources and has not been, and will not be, verified by broker or 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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