Oak Bluffs Homes for Sale

Oak Bluffs has a wonderful array of single family homes on Martha’s Vineyard. From beach cottages and waterfront homes to homes within walking distance to downtown, shops, and restaurants, you’re sure to find the perfect Martha’s Vineyard home in Oak Bluffs. Scroll down to explore Oak Bluffs houses for sale on Martha’s Vineyard. Learn about the town of Oak Bluffs >>

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2 Farm Path Oak Bluffs MA 02557

Oak Bluffs, MA2 Farm Path

Price$1,299,000

Est. Mortgage: $/month

MLS Number 38601

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.89

Classic Oak Bluffs Custom Cape is situated on almost an acre of level land abutting the State Forest. Features a sweeping farmer's porch in the front and a large exterior deck in the rear offering protected views into the meadow, a separate oversized builders garage that includes office space and the potential for a guest house is sited in front corner of the property, there is a finished basement with built in bar and utility room, and there is room for a SWIMMING POOL off the rear deck. This wonderful family home has an Open floor plan with cathedral ceilings, sky lights, and a first floor bedroom and full bathroom,. Brand new exterior cedar shingle siding and trim.. WELL KEPT CHARMING home & location is equidistant to all the down island towns. Seller is installing a new 4 Bedroom Septic System. MUST SEE!

Listed by Ocean Park Realty Inc

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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22 Paddock Road Oak Bluffs MA 02557

Oak Bluffs, MA22 Paddock Road

Price$4,995,000

Est. Mortgage: $/month

MLS Number 38557

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 6.5
  • Acreage 1.867

THIS IS THE ONLY LOT AVAILABLE in the PRESERVE at The WOODLANDS! COMING SOON...TO BE BUILT...by SHAWN CHAPPS...UNDER EARLY STAGES OF DESIGN and STILL TIME to CUSTOMIZE with YOUR OWN PERSONAL TOUCHES! Sophisticated Sprawling Contemporary Barn Style Residence with Clean Classic Lines, Natural Timber Beams, Field Stone Fireplace and Soaring Ceilings. This Spacious Airy Open Floor Plan will have no shortage of living areas with multiple intimate gathering spaces surrounded by lots of glass that ddisplays an unobstructed panorama of the lush landscaped backyard and 20x 40 Gunite Pool and Spa. The Decked Out Chefs Kitchen will be a fusion of modern design, rustic accents and State of the Art Appliances. Boasting 6 en suite luxury bedrooms and unmatched bathrooms, with deep soaking tubs, artistic tiled showers, custom vanities, walk-in closets, and sitting areas all designed for convenience and comfort. A generous walk-out finished basement, containing over 2000 square feet, will include additional living areas along with a custom home bar, gym/media room and or wine cellar. Other Rare feature is the "Show Stopping Two Story Vaulted Stairway" This Unparalleled design with exceptional visuals highlighted by exquisitely detailed finishes will be SUPER DELUXE; So Be prepared for the "WOW FACTOR " Don't Wait...Call Today to Secure this RARE OFFERING in the POSH PRESERVE Oak Bluffs' Newest Luxury En Clave abutting conservation land and trails for hiking, walking and biking!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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8 School House Village Oak Bluffs MA 02557

Oak Bluffs, MA8 School House Village

Price$1,399,000

Est. Mortgage: $/month

Open House

MLS Number 38433

  • Residential
  • Next Open House: Tue 08/3 11:00 am. to 1:00 pm.
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3.5

OAK BLUFFS CLASSIC COLONIAL and SPARKLING COMPLETELY RENOVATED 1 Bedroom/ 1 bath APARTMENT nestled above a detached 2 car detached garage! TERRIFIC LOCATION with easy access to bike path .. Minutes to YMCA, high school and town parks. Centrally located to all the down island towns! Surrounded by mature plantings and attractive colorful landscaping with 3 bedrooms , one en suite with double vanities and tiled walk in glass shower. 2.5 tiled bathrooms airy sun filled open spacious kitchen, living area and huge outdoor deck Coastal Chic décor included to make this a TURNKEY OFFERING.

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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17 School Street Oak Bluffs MA 02557

Oak Bluffs, MA17 School Street

Price$899,000

Est. Mortgage: $/month

Pending

MLS Number 38577

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 1
  • Acreage 0.6

Oak Bluffs New Listing ~Charming Victorian Style Home with 4 bedrooms 1 bathroom situated on an OVERSIZED INTOWN lot with pictureque sweeping grassy yard and peaceful meadow views There are wild grapes, fruit trees and natural native grasses. Easy stroll into town, Oak Bluffs Harbor and sandy beaches. Property is tied into the Town Sewer. TERRIFIC INVESTMENT OPPORTUNITY for the SAVVY BUYER.

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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 New York Avenue Oak Bluffs MA 02557

Oak Bluffs, MA90 New York Avenue

Price$1,500,000

Est. Mortgage: $/month

Pending

MLS Number 38556

  • Residential
  • Mls Status Pending
  • Bedrooms 7
  • Bathroom 2.5
  • Acreage 0.2572

Oak Bluffs Victorian Style Home within a short bike or walk to town! There are 7 bedrooms 2.5 bathrooms. The interior is spacious with many charming features. Many upgrades include newer porch, newer electric panels, plumbing, windows..

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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 Lagoon Road Oak Bluffs MA 02557

Oak Bluffs, MA45 Lagoon Road

Price$750,000

Est. Mortgage: $/month

Pending

MLS Number 38543

  • Residential
  • Mls Status Pending
  • Bedrooms 2
  • Bathroom 2
  • Acreage 0.3957

Open House Saturday and Sunday cancelled.....Lagoon Pond Access is nearby (600 feet) so bring your kayak, canoe, windsurfer, shellfishing equipment and bathing suit! Charming Comfortable Vineyard Cape is nestled on a peaceful 17,240 sq. ft. lot and boasts glowing wood floors, cathedral ceiling and a split bedroom design. There is extra sleeping space in the open loft that overlooks the great room below. The yard is partially wooded, finished with colorful plantings and includes a storage shed in the back yard. Inviting deck is accessed off the dining area. This is a home for those who won't "abide" by the ordinary!

Listed by Doug Reece of RE/MAX on Island

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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41 Bayes Hill Road Oak Bluffs MA 02539-4427

Oak Bluffs, MA41 Bayes Hill Road

Price$1,895,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38461

  • Residential
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.7699

CUSTOM DESIGN BUILD - exquisite craftsmanship and meticulously maintained - noted island architect, Phil Regan of Hutker Architects, brought his best when he designed this spacious, light filled home for family to enjoy. Character and charm is built into every room, from the glass doors and pantry cupboards of the "East Chop inspired" kitchen to the handwrought chandeliers and sconces by Vermont's Hubbardton Forge, and the fir, ash and maple hardwood accents throughout. Gracious sightlines and lofted ceilings complement airy living and sleeping spaces, including a first floor primary suite, plus spacious hallways that allow for special reading nooks and a kitchen office desk. Both the living and dining rooms open onto the large mahogany deck overlooking a serene park-like setting perfect for entertaining or relaxing at home. The grounds have been beautifully designed with the same care and creativity as the interior, orchestrating beautiful vistas on every side of the property from the lush lawns, hydrangeas, evergreens, ornamental trees, and Japanese maples, arranged for privacy and beauty. The privacy is enhanced by the common land and Land Bank conservation areas behind the property with miles of walking trails to enjoy. Granite steps and pathways, a pea stone drive and an ample one car garage built with the same sophisticated design as the main house, add the finishing touches to this enchanting home. Bayes Hill Association offers residents tennis and pickle ball courts plus easy access to Lagoon Pond for kayaking or swimming, plus immediate connection with the southern woodland trails and to Featherstone Center for the Arts.

Listed by Dawn Bellante Holand, 508.524.1601 of Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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37 Pocasset Avenue Oak Bluffs MA 02557

Oak Bluffs, MA37 Pocasset Avenue

Price$799,000

Est. Mortgage: $/month

Pending

MLS Number 38552

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 1
  • Acreage 0.16

Oak Bluffs Victorian Style home located across the street from Hiawatha Town Park. Corner lot with 4 bedrooms 1 bathroom.. Newer roof! Intown location short stroll to public sandy beaches! Circuit Avenue is a block away! INVESTMENT OPPORTUNITY for the SAVVY buyer!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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69 Brush Pond Road Oak Bluffs MA 02557

Oak Bluffs, MA69 Brush Pond Road

Price$1,799,000

Est. Mortgage: $/month

MLS Number 38490

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.41

New to market— Oak Bluffs 3 bedroom, 2 bathroom waterfront home. Home office, fireplace, expansive red brick patio, rooftop sundeck which affords one of the most spectacular sunset views on Martha’s Vineyard.

Listed by Barbara Twiss of Laer Realty Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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 Forest Hill Avenue Oak Bluffs MA 02557

Oak Bluffs, MA21 Forest Hill Avenue

Price$725,000

Est. Mortgage: $/month

MLS Number 38524

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.1899

Oak Bluffs Stylish COMPLETELY Renovated Bungalow Style Residence located within an easy short walk to town, sandy beaches, galleries and Oak Bluffs Harbor! Efficient and open floor plan with 2 bedrooms, 1 bathroom, and delightful landscaped yard. Well-kept throughout with many thoughtful upgrades that include newer plumbing, electrical, roof, windows, doors, exterior cedar shingles and maintenance free Aztek trim. Beautiful original hardwood flooring throughout! A full basement with lots of storage space. Outdoor shower! Easy to Show and includes most of the furnishings!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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46 Farm Pond Road Oak Bluffs MA 02557

Oak Bluffs, MA46 Farm Pond Road

Price$1,600,000

Est. Mortgage: $/month

MLS Number 38510

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.6899

Harthaven - Opportunity to become a member of the desirable Harthaven Community with 2 association beaches, a private small boat harbor, and tennis. The area is located 1.5 miles to Ocean Park with easy access to the bike path, Farm Neck Golf Course, and conservation land walking trails. This 3 bedroom, 2 1/2 bath home is waiting for you to make it your own. The first floor features a back entry into a mudroom off of the kitchen with a 1/2 bath. The kitchen needs some TLC but it has great spaces to work with. The dining area is open to the living room which features a wood-burning fireplace and cathedral ceiling. Two bedrooms and a bath complete the first level. Upstairs is a primary bedroom with a private bath. Drive around back to the 1 car garage that is under the house and part of the basement. Home is being lived in year-round but it needs updating and repairs. It is being sold ''as is''. Tenants in residence until Sept. 15th. Association dues are for road and beach. Additional fees for tennis and a slip at the dock.

Listed by Michele Moore of Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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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52 Pond View Road Oak Bluffs MA 02557

Oak Bluffs, MA52 Pond View Road

Price$1,399,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38400

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.7378

This beautiful turnkey 4 bedroom 3 bath home is complete with walking distance to the private association beach on the lagoon. It's exactly what a buyer is looking for with its new roof,new azak trim, newly painted deck, great rentals, turn key fully furnished everything home, Great light, two bedrooms on the first floor, two master bedroom suites on the second, a large bath on the first and a large open sunny kitchen,dining, living area that is open for everyone to be involved in conversations. There is also a large deck that opens up off the kitchen for the BBQ on the back deck! Meticulously decorated expressing beach and "Vineyard lifestyle" you feel at home with your turn key Vineyard Home!

Listed by Fred Mascolo of Jane Brown Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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 MA_LINKMV as of August 2, 2021 . 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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