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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104 Winemack & 101 Park Streets Oak Bluffs MA

MLS Number 35562

  • Residential
  • Square Feet 2040
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.69

East Chop -- Meticulously maintained 5-bedroom/3-bathroom home on 0.69 acres, with water view, large open floor plan, beach stone fireplace, beautifully landscaped yard and 2-car garage. This fabulous home should be at the top of your list because of its close proximity to beaches, tennis courts, the Oak Bluffs harbor and downtown areas. Living room with beach stone fireplace opens to enclosed porch and exterior deck running the length of the house. First floor features living room, dining room, kitchen and bedroom with full bath. Rear enclosed porch opens to back deck and great backyard looking out across Crystal Lake to the Vineyard Haven outer harbor. Second floor has 4-bedrooms, two full baths. Home comes partially furnished and is partially insulated. Includes two car garage and outdoor shower, central heat pump A/C. Recent improvements have included new kitchen, AC/heat/insulation, new plumbing and electric wiring, new deck and porch windows, two remodeled bathrooms, garage door openers, and rebuilt fireplace. Title V septic design is being prepared.

Listed by RE/MAX on Island

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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 Tower Ridge Road Oak Bluffs MA

Price$1,795,000

Est. Mortgage: $/month

MLS Number 35358

  • Residential
  • Square Feet 3957
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.78

Incredible investment opportunity in the highly desirable Tower Ridge neighborhood. This lovingly maintained home has undergone many sensible upgrades and is ready for a new owner's stress-free enjoyment. The property is situated on a quiet and private street, and is located close to Farm Neck Golf Club, bike path and miles of hiking trails. New windows, renovated gourmet kitchen, copper gutters, red cedar siding, 2-sided granite fireplace, renovated tile baths, sun-room, sauna, fireplace in master bedroom, cathedral ceilings, finished basement, and plenty of outdoor space, are among the many features this home offers. A detached 2-car garage with 15ft ceilings is perfect for boat storage. Above the garage is a spacious studio with cathedral ceilings and private second floor deck. A picture-perfect garden shed was fully renovated and features a covered porch, wood detail throughout, loft storage space, updated windows and is set up for year-round use. This is an investment opportunity not to be missed!

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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112 Park Street Oak Bluffs MA

Price$1,789,000

Est. Mortgage: $/month

MLS Number 35058

  • Residential
  • Square Feet 2100
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.31

Year Round East Chop Home offers WATER VIEWS and SPECTACULAR SUNSETS. Nestled on a large double lot in this highly desirable neighborhood. This dazzling home offers classic charm with modern, luxury amenities. The 75 ft. wrap around deck and covered dining rotunda were built for enjoying true Island living. This home has 4 bedrooms and 3 full bathrooms with marble, custom tile and original hard wood floors. Incredible customized high end kitchen and cozy sun room have double french doors that opens onto a pergola covered deck creating a flowing indoor/outdoor living experience. Just completed ! An extensive addition and upgrade to the homes insulation as well as tree removal and trimming enhancing the view easement. If you are searching for your Island dream home or an investment property with over $80,000 a year of rental income this classic Vineyard home is a must see.

Listed by Laer Realty Partners

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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273 East Chop Drive Oak Bluffs MA

Price$1,695,000

Est. Mortgage: $/month

MLS Number 35374

  • Residential
  • Square Feet 1104
  • Bedrooms 3
  • Bathroom 1
  • Half Bath 1

Located on East Chop Drive, this unique offering provides the opportunity to own one of the Vineyard's quintessential beach cottages. The 1,100 sq ft, three-bedroom, 1.5-bath cottage is in immaculate condition with its restored original look, stone fireplace and wrap around porch. Enjoy the beautiful sunsets from your private waterfront, which is also perfect for a refreshing swim or family barbecue. The property could provide an existing MV property owner with a second location for perfect getaways, and with the property's strong rental history, a great investment.

Listed by Landvest MV

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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5 John Wesley Park Oak Bluffs MA

Price$1,649,000

Est. Mortgage: $/month

MLS Number 34510

  • Residential
  • Square Feet 2600
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

EAST CHOP - Have it all, top tier craftsmanship and a phenomenal location! With dedicated attention to detail, this 2,600 sq. foot home features exquisite luxury finishes with every possible modern convenience, and is nestled in a most coveted East Chop enclave. It's truly the best of both worlds, brand new construction, in an iconic Martha's Vineyard setting. This beautifully proportioned home offers 4 generous bedrooms and 4.5 baths, as well as a 1,000 sq. foot ground level finished basement that provides even more living space, with lots of storage. The spacious open floor plan with 9 foot high ceilings is perfect for entertaining. The gourmet kitchen has center island with seating and flows easily to the dining room with dramatic coffered ceiling. The living room has multiple seating spaces. The attached garage conveniently stores your island car. The sweet back yard area will be hardscaped to flow seamlessly from the ground level finished basement space. And of course, the perfect finishing touch in this neighborhood is the subtle and inviting front porch. Is there anything more quintessentially “east chop” than rocking in a chair and greeting your neighbors as they stroll through these quiet, timeless avenues? You and your guests will be walking to the beach (.5 mile), the harbor (.56 mile), the Lighthouse (.75 mile), and possibly spend just as much time in downtown Oak Bluffs as you will in this stunning home. Ready for summer 2019 occupancy.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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 Old Harbor Lane Oak Bluffs MA

Price$1,590,000

Est. Mortgage: $/month

MLS Number 35090

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1
  • Acreage 0.8

VIEWS, VIEWS, VIEWS! This wonderful summer vacation home offers views in every direction whether it's Sengy Pond, State Beach, Nantucket Sound, or natural preserve open space, you'll be captivated by each vista. This retreat boasts inviting, spacious, vaulted ceilings, light and bright bedrooms that each look to the water offering summer living at its best. Bask in the rising sun from one deck and the setting sun from the other deck! LOCATION! This parcel adjoins conservation land offering unobstructed views that reach all the way to Sengy Pond, State Beach and beyond. Waterview Farms is centrally located between three towns; Oak Bluffs, Vineyard Haven & Edgartown yet still very private being an exclusive community adjacent to Farm Neck Golf Course. This neighborhood provides beach access with boat storage and docking available. This spacious parcel is great for events & parties, or flying kites & out door games. Explore quaint nearby walking trails to Pecoy Point, or use your paddle board or kayak to enjoy Felix Neck & State beach! The MV biking trails access is at entrance to the community with an easy ride to town! Two adjoining build-able lots may be available for purchase, please inquire. Owner carry financing available. Agent holds interest in property.

Listed by Sierra Properties & Investments

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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33 Beach Road Oak Bluffs MA

Price$1,500,000

Est. Mortgage: $/month

MLS Number 35049

  • Residential
  • Square Feet 1622
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.1899

Smell it! Feel it! Taste it...the sea that is! Waterfront 3 season cottage looking westerly over Vineyard Haven Harbor. Sunsets and sailboats everyday plus a DEEPWATER DOCK for all your boating needs. Originally known as "Station #7" of the NY Yacht Club, this historic home was used "back in the day" to give club members a comfortable place to tie up their tenders and step ashore while sailing the waters around the Vineyard. Converted to the Classic 4 bedroom cottage it is today; in the not too distant past. Newer kitchen. Water views from most rooms. Off street parking. A one-of-a-kind property!

Listed by RE/MAX on Island

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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55 Worcester Avenue Oak Bluffs MA

Price$1,389,000

Est. Mortgage: $/month

MLS Number 35514

  • Residential
  • Square Feet 2446
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

NEW CONSTRUCTION - WALK TO WATER - Custom Three Bedroom, Three and a Half Bath Home with extensive interior trim including wainscoting, coffered ceilings and rustic beams. The entire ground floor is L-Shaped with two living areas on opposite sides of the house, the kitchen being the central point. The main Living Room will have a Coffered Ceiling, Hardwood floors, direct access to a huge deck and a propane Fireplace. The Custom Kitchen will have Quartz counters, Stainless Steel Appliances and Rustic Beams. Two dining areas, one formal, one informal provide a transition into each of the living areas. (See Floor Plans in Photos). Second living area with built-in bookcases. Shiplap clad entrance hallway with half bath. Wainscoting throughout the main living level. Upstairs, two story landing overlooks the entrance hallway. There are Two Master Bedrooms - they each have their own private bathrooms and private balconies. There's also a third living room upstairs which leads to a Third bedroom, sharing the full guest bathroom. Custom tile work throughout. Full size windows in part of the full basement. Forced Hot Air heat and Central Air-Conditioning. Huge mahogany Deck 12ft x 40ft.. Two Car Garage and off street parking. A short walk to the end of the road and you'll be at the Beach on the Lagoon - Great for swimming and boating - a Big Plus for renters! Minutes to bike or to drive to downtown Oak Bluffs and Ferry. Progress photos will be added regularly. Easy to Show! (Taxes only reflect land assessment.)

Listed by Alisan Lohan-Conway Properties

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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 Quail Run Oak Bluffs MA

Price$1,299,000

Est. Mortgage: $/month

MLS Number 34677

  • Residential
  • Square Feet 2877
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

Custom Contemporary Design!! ! This home shows like a new home! IMMACULATE Residence impeccably maintained is in the desirable Sengekontacket Community of Oak Bluffs! This Exquisite custom design, comfortably on one level, is situated on almost an acre of land with mature landscaping, stone walls and colorful perennial flower beds. Enter an impressive foyer into an OPEN BRIGHT living room highlighted with a beautiful stone European wood burning fireplace and 12 ft ceilings. CENTRAL AC ! The interior design is complemented by attractive furnishings that add to the graceful flow of the floor plan. Gracious Master Suite and 2 additional bedrooms are all spacious and inviting with custom closets, the kitchen is large with high end appliances, and there is a cozy separate den, and a dining room with sunsets. SURPRISE! There is a lower level, fully finished, offering a large media/rec room and multiple gathering spaces along with a full tiled bathroom & spacious workshop with walk out access! TERRIFIC LOCATION with private amenities that include access to both fresh and salt water ponds, community dock, mooring available, 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. MUST SEE HOME!

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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61 Bayes Hill Road Oak Bluffs MA

Price$1,225,000

Est. Mortgage: $/month

MLS Number 22464

  • Residential
  • Square Feet 2745
  • Bedrooms 5
  • Bathroom 3
  • Acreage 1

A must see in Bayes Hill! This spacious two story home on an acre of land with a fantastic backyard is the perfect place to call home. Traditional in style with formal and casual spaces that flow nicely to the multiple gathering areas. The dining room, kitchen and family room span the back of the house and all feature glass doors to the pool area. The outside spaces are amazing - heated gunite pool with pebble tec finish with patio surround and cabana for lounging in the shade. A screened porch offers more outside yet sheltered space, and the expansive decking unifies it all. Four great sized bedrooms occupy the second level including a grand master with walk-in closet and luxuriously appointed bath. A first-floor office/den can also serve as a fifth bedroom. The lower level is nicely finished and offers an additional 700+ square feet of space - perfect for movie watching and gaming. This home has it all - laundry room/mud room, two car garage, attic for storage and more. Bayes Hill is an attractive neighborhood with substantial homes and large parcels providing good privacy; and enjoy association tennis!

Listed by Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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27 Bayes Hill Road Oak Bluffs MA

Price$1,175,000

Est. Mortgage: $/month

MLS Number 34713

  • Residential
  • Square Feet 3500
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

A builder's own custom colonial home nestled in a private setting of the Bayes Hill Association in Oak Bluffs. A desirable community of substantial homes with private tennis and easy access to the Lagoon & Sailing Camp. This home is situated on a .76 acre lot with an abundance of mature landscaping offering privacy. This home comfortably accomodates multi-family living with its four floors of finished space. A spacious open kitchen with a eatin bar and lots of cabinetry and dining area leading to the a TV room which includes custom built-ins for storage. The first floor also has a gracious living room with woodburning fireplace and a formal dining room ( or could be a 1st fl bdrm) with glass doors that lead to the back deck and patio area. The second floor is comprised of a master bedroom suite , three guest bedrooms with a shared bath, and a separate wing that functions as a perfect “in- law suite” or 2nd master suite. The suite is complemented with a beautiful atrium window, wet bar and full bathroom. Designed for year around living, with gas FHA heating zones and central A/C,ample storage ,huge garage and laundry room with sink. In addition, the attic has been converted into a spacious and bright office space with large skylights and built in shelving. The basement is fully finished with a second washer / dryer & bath and plenty of storage. Well sited on the lot with a back deck, patio, big yard and garden.Surrounded by an abundance of mature trees and colorful rhododendroms & hydrangeas with irrigation. This home was thoughtfully designed to comfortably accommodate all the family and friends that will come to visit!

Listed by Martha's Vineyard Island-Wide Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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1 Bird Street Oak Bluffs MA

Price$1,159,000

Est. Mortgage: $/month

MLS Number 34308

  • Residential
  • Square Feet 2472
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.22

Location! Location! A short 5 minute walk to the ferry, movie theater, town, beach, harbor and library. Come view this private gorgeous newly renovated Cape style home featuring (4) bedroom (3) full baths, attached garage and over 2400 SF of living space. This pristine open concept home includes custom white kitchen cabinets with quartz countertops, center island with seating and a separate eat-in dining area. The kitchen space flows into an oversized family great room. The first floor includes 2 sunny bedrooms with glass patio doors that open onto a private relaxing side deck overlooking the side yard and custom Japanese gardens. The second floor is comprised of brand new construction that includes 2 master bedroom suites with large walk-in closets and 2 modern tiled bathrooms. The home radiates with morning and afternoon sun. Property includes a brand new private custom cedar outdoor shower and a new extra wide driveway with a cobblestone apron. The yard is surrounded by mature plantings that bring color all season long and plenty of privacy. This property is a the perfect investors dream or family Vineyard getaway!

Listed by Premier Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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