Oak Bluffs Real Estate

Oak Bluffs is a classic beach resort town on the northeast shore of Martha's Vineyard. Real estate in Oak Bluffs includes condos, single family homes, homes with dock access, acreage, and more. Whether you’re looking for a permanent residence or a vacation home, Hancock Real Estate can help you find your island dream home.

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51 Head Of The Pond Road Oak Bluffs MA 02557

Oak Bluffs, MA51 Head Of The Pond Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 41818

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.517

Iron Hill, Centrally located with convenient access to Island villages. 3 Bedroom, 2 Bath Ranch on 1.5+ acres. An empty canvas with limitless possibilities. Mature landscaping designed for privacy, aesthetics, and low maintenance. Paved private road access, with generous setback for residence. Bike path, Bus stop, State Forest, & Walking Trails nearby. Association covenants allow up to two horses.

Listed by Bruce Stuart and Associates

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$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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 Windemere Road Oak Bluffs MA 02557

Oak Bluffs, MA45 Windemere Road

Price$1,489,000

Est. Mortgage: $/month

MLS Number 41770

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 1.5
  • Acreage 0.36

POND-FRONT - WATER VIEWS ABOUND - A treat for your senses! A wonderful location on Windemere Road abutting Doug's Cove Preserve and adjacent to the Land Bank Beach on the LAGOON. First time this property has been available for sale in over 60 years, having been enjoyed by the same family for the past few generations. This Quintessential Vineyard cottage abuts 4.6 acres of Martha's Vineyard Land Bank land on two sides including the Land Bank sandy beach on the Lagoon. Very well maintained, exceptionally well laid out Summer Cottage, surprisingly spacious, with a lovely pond-front yard. Living room, kitchen and dining areas are very light and bright with vaulted ceilings and a delightful sun room flanked by windows on three sides for beach, Lagoon or sunset views. So picturesque with a rare combination of views overlooking the Lagoon, the Land Bank Beach, the Drawbridge and Doug's Cove Preserve. There are two bedrooms, one with a Queen bed and one with twin beds along with a shared full bath. Additionally, there's a half bath outside off the deck and a separate Outdoor Shower. Mahogany Deck (22' x 12') ideal for gatherings, parties, dinners, sunbathing or to relax and watch sunsets, the Lagoon, beach activity, Doug's Cove and, the Drawbridge and nature flying by. Plenty of outdoor space on the deck, in the yard, in the water, not to mention the Lagoon being your swimming pool! Sail, paddle board, kite board on the Lagoon. Kayak and explore Brush Pond. Relax on the beach. Some Rentals in place for Summer 2024. Property is already connected to Town Sewer. Some expansion Possibilities. Good size shed with electricity for additional storage. Easy access to the Public Boat Landing, Eastville Beach, Ferry, VH, Oak Bluffs. Easy to show. Some contents may be purchased separately.

Listed by Alisan Lohan-Conway Properties

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$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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 Towanticut Avenue Oak Bluffs MA 02557

Oak Bluffs, MA41 Towanticut Avenue

Price$1,450,000

Est. Mortgage: $/month

MLS Number 41865

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.2299

What a wonderful opportunity to own a Contemporary Ranch style home on this beautiful Island of Martha’s Vineyard. It is well maintained with three bedrooms, two full baths, central a/c, and a full unfinished basement. Ideal location in a very quiet neighborhood, just a short distance to bike path, Town, ferry, restaurants, beaches, shops all that you could ask for. Living room is light, bright and airy with a lovely bay window flows to the eat in kitchen with table space, granite counters tops, small breakfast bar, Linoleum flooring, plus laundry area. There is glass slider off the kitchen area that opens to the back deck, to a beautiful manicured back yard which reflects alot of loving care. Mature Arborvitaes & small Alberta Spruces surround the property for screening privacy. Beautiful hydrangeas face the front of the house, that are just gorgeous in bloom. Master en-suite on one end, the other two bedrooms are on the other, both of which share the full bath. Full unfinished basement can be used for storage or get creative with a little imagination— you certainly can make additional usage. The inside has been freshly painted, and new carpeting has been installed. You must see it ! It can be your Happy Place!

Listed by Island Home Realty Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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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60 Prospect Avenue Oak Bluffs MA 02557

Oak Bluffs, MA60 Prospect Avenue

Price$1,449,000

Est. Mortgage: $/month

Open House

MLS Number 41939

  • Residential
  • Next Open House: Wed 07/17 1:00 pm. to 3:00 pm.
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2

OAK BLUFFS IMPROVED PRICE~ This home LIVES LARGE and offers 3 Distinct Structures situated on a BEAUTIFUL landscaped .34 Acre private lot ~EASY WALK or BIKE RIDE to OAK BLUFFS HARBOR, Town, Sandy Beaches, Ferry Ports and Town Parks! Tastefully renovated SPACIOUS Split-Level Home featuring a lovely and functional open floor plan. The main level displays beautiful hardwood floors, a bright open kitchen, and a charming dining area. The focal point in the family room is an attractive propane gas fireplace that creates the perfect space for entertaining. Step outside and enjoy the mahogany deck overlooking the expansive backyard surrounded by tall Leland Pines and many mature plantings. Sliders and large windows flood the interior with streams of sunlight. In addition, there are 2 delightful bedrooms each with custom "California Closets" and cabinetry. The lower level has one airy bedroom, a full bath, hobby room, laundry room, utility room and work out room. This property is a must-see treasure you will not want to leave. Features Central AC, lots of closets, garden shed, outdoor shower, cement driveway, and detached roomy garage. New Roof (2023) garden and hardscape. Whether enjoying indoor gatherings or outdoor activities, this home provides a perfect balance of comfort and versatility. The Two Story detached Studio is ideal for a Yoga, Art Studio or detached office! The Possibilities are endless!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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$1,425,000

Est. Mortgage: $/month

MLS Number 41535

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

The best value on East Chop, in pristine condition and just a short walk to the beaches, tennis courts, yacht club/harbor, downtown restaurants and the ferries. This property includes a contemporary style 2-bedroom main house, and a permitted and approved detached 1-bedroom/1-bathroom for overflow guests or family and which has expansion potential. 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 windows. The second floor features an ensuite master bedroom with its own balcony deck and outdoor shower. The level 10,000 sq ft lot includes a front and side yard and parking for 2-3 vehicles. New Title V septic installed 2022 (Title V Inspection passed Feb 2024) and new hot water tank. Being sold partially furnished. Unfinished walk out basement can be used as workshop or finished as a family room.

Listed by MV Luxury Homes

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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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11 Winemack Street Oak Bluffs MA 02557

Oak Bluffs, MA11 Winemack Street

Price$1,395,000

Est. Mortgage: $/month

MLS Number 42032

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

MOVE-IN READY! Don't miss this summer! Full dormered Cape situated on a quiet dead-end street. Nicely landscaped with flowering trees, white post rail fence in front and privacy fence, side & back. Within walking distance to beaches, hospital, downtown Oak Bluffs, library, parks, and more. Features an open living concept family room, sunny kitchen and dining area with access to a large private exterior deck, perfect for summer entertaining. A first fl. office with double closet could also be used as a game room or bedroom with adjacent new bath. Off the bright inviting front entry is a large formal living room with a double closet. Upstairs, the spacious front to back primary bedroom boasts a huge walk-in closet and full en suite. Also upstairs, 2 more roomy bedrooms with shared Jack-&-Jill full bath. Recent updates include new 1st fl. bath, roof, skylights, cedar trim, front porch - over $30K in improvements. Full dry basement/workshop. Plenty of parking. Great location, don't wait

Listed by Laer Realty Partners

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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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10 Lauras Way Oak Bluffs MA 02557

Oak Bluffs, MA10 Lauras Way

Price$1,395,000

Est. Mortgage: $/month

Active With Contract

MLS Number 42088

  • Residential
  • Bedrooms 1
  • Bathroom 3
  • Acreage 10346

Just what you've been waiting for…Peace and tranquility surround this light filled rose covered cottage on Martha’s Vineyard. This meticulously maintained home has been lived in and cared for year around by its original owners and is being offered to the market for the very first time! This property offers the convenience of being just a short walk to town center, the harbor, ferries, and shops, yet it is nestled on a private cul-de-sac paved road in an association with underground utilities. Quiet and close to everything! Built in 2002, this hidden gem shows like a new home. Upgrades include the following: Hardwood floors throughout, recessed lighting with dimmers, new exterior doors, updated hardware and light fixtures, a full house water filtration system, rebuilt deck and a brand-new pergola. Step inside and feel the warmth where every detail has been cared for. The first floor consists of a full bath, dining room and an open kitchen and living room. The newly renovated chef’s kitchen features custom cabinetry with lighting, Quartz countertops and sleek Monogram commercial-grade stainless steel appliances. French doors open to a pantry with a butcher block counter, beverage center and built in shelving for ample storage. The second floor features an en suite bedroom with walk-in closet, a third full bath as well as a flex space. Step outside onto the Mahogany deck with a brand-new pergola and experience the tranquility of an outdoor oasis. Rest and recharge among the beautifully landscaped and thoughtful outdoor spaces, including a zen perennial garden and a blue stone patio, perfect for entertaining. Outdoor features also include a charming garden shed and an outdoor shower. This is a place where time slows down and the hustle and bustle of daily life feels worlds away. Make this special Vineyard home your personal sanctuary.

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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 Waterview Road Oak Bluffs MA 02557

Oak Bluffs, MA46 Waterview Road

Price$1,350,000

Est. Mortgage: $/month

Active With Contract

MLS Number 42122

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.26

WATERVIEW FARM! Built in 1968, this property is one of the first seasonal cottages in this unique community of 55 homes with its own Association beach & dock. The sandy beach is the perfect launch area from which to enjoy all the recreational activities on Sengekontacket Pond --- everything from kayaking, paddle boarding, sailing and water access over to State Beach and Nantucket Sound. The Waterview Farm Association maintains architectural guidelines supportive of the "Menemsha Fishing Shack" appearance while recognizing that most all of these seasonal cottages have been upgraded to substantial, year-round dwellings. This 3 bedroom, two bath cottage is an exception and has been owned by the same family since its construction. It offers distant water views and has a casual, outdoorsy, summer camp vibe. The design consists of two pods connected by a screened porch with large decks, at front and rear. The pod to the left is the bedroom wing with bathrooms and the pod to the right consists of the living room, dining area, kitchen and loft, with a combined total of 1,160 square feet of structure. The property has been well maintained by the family and includes a recently built large garden shed, privacy fencing and a new three bedroom septic system design approved by the Board of Health. Seller will provide a credit at closing for the upgraded 3 bedroom system. New owners may continue its current use as a seasonal beach cottage, enjoying all of the Association amenities, while planning for the future of this well-preserved gem.

Listed by Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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 Dolly Lane Oak Bluffs MA 02557

Oak Bluffs, MA21 Dolly Lane

Price$1,295,000

Est. Mortgage: $/month

Active With Contract

MLS Number 42215

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.46

DEER RUN - SHOWINGS START JULY 2. This much-loved Cape-style home has had only one owner since being built in 1990. It is located in Deer Run, one of Oak Bluffs' most desirable communities. The house has been extremely well cared-for, and is neat as a pin. The neighborhood is quiet and this particular property backs onto an association "green belt," and behind that is the State Forest. There are three bedrooms and two baths, plus a basement that could easily be finished to provide more elbow room. There is a two-car garage to make this a complete package. The property is easy to show and buyers are encouraged to visit while the beautiful gardens are in bloom.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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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40 Hidden Cove Road Oak Bluffs MA 02557

Oak Bluffs, MA40 Hidden Cove Road

Price$1,225,000

Est. Mortgage: $/month

MLS Number 41807

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

The living comes easy at this three-bedroom Oak Bluffs condominium in the highly regarded Hidden Cove Association. This spacious unit offers a bright, open feel on all three levels- living, dining, and kitchen, which extends to an outdoor deck on the main floor, a primary suite with a private sitting area on the upper level, and two spacious guest rooms and a bath on the lower level. Amenities are plentiful and include enjoying the heated pool exclusive to condo owners, water access on Sengekontacket, and tennis courts. A fantastic opportunity to enjoy all the benefits of home ownership without the hassle!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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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123 Manchester Avenue Oak Bluffs MA 02557

Oak Bluffs, MA123 Manchester Avenue

Price$1,199,000

Est. Mortgage: $/month

Active With Contract

MLS Number 41742

  • Residential
  • Bedrooms 2
  • Bathroom 2
  • Acreage 0.2754

Classic Cape Style Home located in Oak Bluffs Lagoon Heights ~Immediate Investment Opportunity to move right into this attractive home that is cheery and bright with a flexible floor plan and great layout. Updates include newly painted solarium, and interior house painting and exterior power wash. Features include a Viessmann 200 boiler that provides radiant floor heat(OIL) throughout each room with a separate thermostat and zone. Built-ins in the primary and cedar closet! The exterior of the home includes many mature plantings and stone walls. There is an unfinished walk out basement with lots of storage! Ready for a new buyer! TITLE 5 is for 3 BEDROOMS PASSED SEE ATTACHED REPORT ..ROOM FOR EXPANSION with Town Approvals! Dead end road with privacy and close proximity to Oak Bluffs center, FarmNeck Tennis/Golf Club and downtown Vineyard Haven with quick access to both ferry ports!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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 Sea Glen Road Oak Bluffs MA 02557

Oak Bluffs, MA22 Sea Glen Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 42263

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 1.5
  • Acreage 0.4646

Welcome to 22 Sea Glen, a charming retreat nestled on a spacious lot with a gentle slope, offering the potential for both outdoor enjoyment and future expansion. This delightful home features 2 bedrooms and 1.5 bathrooms across 1642 square feet of living space. Upon entering, you'll find a well-appointed kitchen and an open living and dining room, creating a seamless flow for indoor and outdoor entertaining. Sliding glass doors allow for an abundance of natural light, illuminating the interior and providing a connection to the outdoor space. Please contact agent for a private tour. Seasonal rentals are in place.

Listed by Compass LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 2024
* 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 LINKMV as of July 15, 2024 . 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.