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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348 Sea View Avenue Oak Bluffs MA 02557

Oak Bluffs, MA348 Sea View Avenue

Price$5,995,000

Est. Mortgage: $/month

Pending

MLS Number 35291

  • MultiFamily
  • Mls Status Pending
  • Village State Beach
  • Bedrooms 13
  • Bathroom 6.5

150 Feet of PRIVATE BEACH at this WATERFRONT COMPOUND IN HARTHAVEN - Perched high on a bluff with 180 degree views of Nantucket Sound and beyond, this property offers a rare opportunity for a waterfront family compound or an investor's dream with a private beach. The three homes that make-up this unique 13 bedroom property are as follows: The "Main Deck" is a sprawling cape-style home with 5+ bedrooms, 2 1/2 baths, oil forced hot water heat, air conditioning, wood-burning fireplace, large covered deck overlooking the bluff and a screened-in porch. This home was updated in 1996. This home is considered the main house of the property because of its commanding location perched on the bluff. The "Captain's House" was rebuilt in 1996. It has a reverse-style floor plan to take full advantage of the sweeping water views. Featuring 2 master suites and 2 additional bedrooms that share a bath, this home is light-filled, open and airy. Wood-burning fireplace. The craftsmen that created this home gave extra attention to the wood details throughout and made the house worthy of the finest sea "captain". You will notice these details from the moment you walk into the foyer and move your way through the home to enjoy the beamed ceiling in the living room. The "Cottage" completes this property...almost. This home was also fully rebuilt in 1996. It consists of a living room with wood-burning fireplace, eat-in kitchen, first floor bedroom, first floor laundry and bath. The second floor bedroom has breathtaking views from its private deck. A second large deck runs along the back side of the house. All 3 homes have been created to be independent of each other and all feature air conditioning, outdoor showers and more. With plenty of storage with additional space above, bath and outdoor shower, there is lots of possibilities to to be creative. The garage nicely completes this property. All homes have a solid rental histories with repeat tenants. Sellers would consider a full "turn-key" option. Please view Video of the Property to get a full feel for this one of a kind waterfront property.

Listed by Island Real Estate

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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9 Crescent Road Oak Bluffs MA 02557

Oak Bluffs, MA9 Crescent Road

Price$3,650,000

Est. Mortgage: $/month

Pending

MLS Number 37888

  • Residential
  • Mls Status Pending
  • Village East Chop
  • Bedrooms 3
  • Bathroom 3

EAST CHOP: Dramatic WATER VIEW property features a refined open design with meticulous attention to detail integrating the highest quality materials that makes this offering soundly stand out from other fine homes in this price range. The exquisite landscaping surrounding the residence is an established arboretum of exotic trees, plantings, and stone work highlighted by a crystal clear Koi pond with a soothing waterfall. The interior, both comfortable and visual, flows from one intimate setting to another offering dreamy views of NANTUCKET SOUND complemented by the artistic combination of colors, materials and textures...gleaming Birch flooring throughout, imported marble accents in bathrooms and kitchen, Venetian Plaster ceilings and walls with inset railings in the stairways, broad commercial grade Fleetwood windows, Lutron lighting system, Viking and Sub Zero Appliances, the finest contemporary finishes and fixtures...SO MUCH MORE TO EXPERIENCE....Situated in a protective setting on the Bluffs of East Chop...an easy walk to Beaches, Harbor and Town Center.

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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89 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA89 East Chop Drive

Price$3,395,000

Est. Mortgage: $/month

MLS Number 37747

  • Residential
  • Mls Status Active
  • Village East Chop
  • Bedrooms 7
  • Bathroom 5.5

Move in ready for Summer! This spectacular direct oceanfront residence is located in East Chop an exclusive area of historic Oak Bluffs on Martha's Vineyard. With nearly one acre of land, there are endless opportunities to keep the home as is or build the new home of your dreams. Enjoy spectacular unobstructed and panoramic views of Nantucket Sound. Wake up to amazing sunrises, enjoy the daily "boat show" and watch the sun go down as you roast marshmallows on your own private beach area. An easy stroll takes you to the harbor, town, great restaurants, shops, and an abundance of other activities that make East Chop a very special place for the whole family to enjoy. In the market for more space for your home-based business or work from office - the finished lower level provides ocean views as well as its own entrance giving you the best of both worlds! This unbelievable setting must be seen to be appreciated. Don't miss out on the opportunity to acquire this generational asset! For those looking for an investment property, this beautiful home also has a great rental history. Video Tour: https://youtu.be/Qjn-BOGKzRk

Listed by New England Property Shoppe

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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 Dukes County Avenue Oak Bluffs MA 02557

Oak Bluffs, MA90 Dukes County Avenue

Price$2,195,000

Est. Mortgage: $/month

Pending

MLS Number 37831

  • MultiFamily
  • Mls Status Pending
  • Village Downtown
  • Bedrooms 5
  • Bathroom 5.5

Downtown Oak Bluffs – Entrepreneurs, savvy business owners, investors or those simply seeking downtown living, this property is a must-see to understand the opportunities it presents. Located in the Art’s District, this collection of boutique residences offers upscale and stylish interiors with hand-selected designer finishes. Carefully spaced to ensure privacy, each oasis is extended by intimate courtyards for open air dining or relaxation. The compound includes a highly-visible commercial/office space and plenty of parking for residents or customers. This dynamic embraces the work from home trend and is an income-producing opportunity. Zoned in B1 where flexibility exists to cater to alternative uses. Pedestrian-friendly where a stroll or bike ride will take you to the picturesque harbor, sandy beaches, shopping and eclectic eateries - all the best of Oak Bluffs is steps away.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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3 Pond View Drive Oak Bluffs MA 02557

Oak Bluffs, MA3 Pond View Drive

Price$1,950,000

Est. Mortgage: $/month

Pending

MLS Number 37052

  • Residential
  • Mls Status Pending
  • Village Lagoon/Harbor
  • Bedrooms 3
  • Bathroom 3

3 Pond View has a striking modern 3600 sq.ft home & 750 sq. ft. studio nestled in a private setting abutting a greenbelt of conservation land. The house and studio were designed by Vineyard architect, Bruce MacNelly. It is spacious with high ceilings, white oak floors, an open floor plan which enhances all of its light-filled spaces. The large high windows frame the outdoors, providing visual interest all year long. It is the perfect spot for entertaining and features large walls for exhibiting artwork. The main level offers a large dining room, galley kitchen, living room, large master bedroom, 1.5 baths, laundry & ample closets. Outside the kitchen, there is a bluestone terrace perfect for outdoor dining and entertaining. On the ground floor, there are two walk-out bedrooms, a bath, a large family room & two workrooms that open to a rice stone patio and gardens. The separate spacious studio is ideal for an artist, writer or anyone working remotely. The property has deeded access to 25 feet of beach on Lagoon Pond, a short walk from the residence. Owner's abutting parcel of land is available to purchase by the buyer.

Listed by Kendall & Kendall

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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220 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA220 East Chop Drive

Price$1,895,000

Est. Mortgage: $/month

MLS Number 37706

  • Residential
  • Mls Status Active
  • Village East Chop
  • Bedrooms 4
  • Bathroom 2.5

Prime home in desirable East Chop diagonally across from one of the Vineyard's most photogenic lighthouses, the East Chop Light. With dramatic views from this uniquely designed 4-bedroom, 2 ½ bathroom, year-round or vacation house, this property should be at the top of your list if you're looking for water views, sunsets over West Chop, and close proximity to beaches, tennis courts, the Oak Bluffs harbor and downtown areas. The home -- known locally as "Pilot House", was built true to its name to replicate the bridge of a ship's Pilot House to allow the Captain views of a wide sweep of the sea. Wrap around decks off the second floor provide panoramic water views, in addition to the roof-top Widow's Walk which boasts 180-degree water views of Nantucket and Vineyard Sounds. Built to take advantage of the views, the second floor’s open floor plan has walls of large windows in the living room, dining room and kitchen which provide ample water views, sunsets to the west, sunrises to the east and night-time starry evening viewing. A master bedroom and full bath complete the floor. First floor includes 3 bedrooms, and 1 ½ bathrooms, in addition to access to the basement storage areas and garage. Property includes outdoor shower, and parking for several cars on each side of the house. Title V septic certified 12/19/2020. Deck is in need of repairs/replacement and is the buyer's responsibility, as it can either be repaired or redesigned to suit the buyer's taste. The house is being sold fully furnished. The lot is large enough to allow for expansion of the house but please confirm any plans with appropriate town offices.

Listed by RE/MAX on Island

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%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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246 Newton Avenue Oak Bluffs MA 02557

Oak Bluffs, MA246 Newton Avenue

Price$1,750,000

Est. Mortgage: $/month

Pending

MLS Number 36905

  • Residential
  • Mls Status Pending
  • Village Lagoon/Harbor
  • Bedrooms 4
  • Bathroom 2

Four bedroom family home OVERLOOKING and FRONTING Lagoon Pond. Commanding views up and down the Pond, across to VH harbor, Vineyard Sound & beyond to Falmouth. A picture perfect setting with active views and outstanding sunsets. Plus your own DEEPWATER DOCK, extending 115ft for boating and swimming pleasure. The first floor of this residence has a dining area, galley kitchen, 2 bedrooms, bath & utility room. 2nd floor has two add'l bedrooms, bath, entry den & large, open living room with sliders to a spacious deck. The grounds and embankment are lush green providing privacy yet yielding to the vast view. 2 car garage to rear with lots of storage space. This homes comes mostly furnished.

Listed by Towne & Country Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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 Tower Ridge Road Oak Bluffs MA 02557

Oak Bluffs, MA21 Tower Ridge Road

Price$1,725,000

Est. Mortgage: $/month

MLS Number 35358

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

Located in the highly desirable Tower Ridge neighborhood offering, privacy, tennis, and easy access to Farm Neck Golf Club, the Island bike path and miles of hiking trails. This lovingly maintained home has undergone many sensible upgrades and recent renovations including, 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 incredible investment opportunity not to be missed!

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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319 Barnes Road Oak Bluffs MA 02557

Oak Bluffs, MA319 Barnes Road

Price$1,675,000

Est. Mortgage: $/month

Pending

MLS Number 37728

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.8

WATERFRONT OPPORTUNITY IN OAK BLUFFS! 4 BEDROOM WATER VIEW raised ranch style residence, renovated 2013, on commanding hilltop setting that rolls gently to private water frontage on Lagoon Pond....tastefully landscaped with stone patio and well maintained with sitting platform above a short stairway to the Lagoon. Ideal for all water sports and includes a 12'x12' seasonal anchored raft and mooring equipment.

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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10 Pequot Avenue Oak Bluffs MA 02557

Oak Bluffs, MA10 Pequot Avenue

Price$1,550,000

Est. Mortgage: $/month

Pending

MLS Number 37781

  • Residential
  • Mls Status Pending
  • Village Downtown
  • Bedrooms 4
  • Bathroom 2.5

Beautifully restored Vintage Victorian year-round home located less than a block to the Inkwell Beach and walk to town. Views of Nantucket Sound from the wrap-around front porch and the second floor master balcony. The exquisitely detailed front porch is made of solid mahogany with hand-turned mahogany posts. This home was taken down to the studs 5 years ago and finished to perfection. This home offers 4 bedrooms, 2.5 baths, a bright kitchen with granite counters and stainless steel appliances a large living room, dining room, full bath, laundry room, and first floor bedroom. The second floor contains 3 additional bedrooms and one full bathroom with access via two separate staircases, one via the living room and one via the dining room. There is a bonus living area attached to the rear of the home with a small living area and 1/2 bath...ideal for an in-law suite. Solid rental history of $50k per season with potential for more. Fully insulated with air conditioning and heating, along with a cozy gas fireplace makes this home perfect for year-round living. There is also a rear deck and enclosed outdoor shower. An in-town gem with some furnishings included, makes it virtually turn-key.

Listed by Ocean Park Realty Inc

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$
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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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11 Isaac Avenue Oak Bluffs MA 02557

Oak Bluffs, MA11 Isaac Avenue

Price$1,400,000

Est. Mortgage: $/month

MLS Number 38024

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.2513

New Construction Underway in Oak Bluffs! Just a short walk to the Lagoon or a quick bike or drive to downtown, this new home is conveniently located for year round or summer use. The property features an open concept kitchen and dining area with hardwood floors throughout the first floor. The kitchen has quartz countertops and a center island with induction cooktop and range hood. The dining area has access to the mahogany side deck for outdoor entertaining, and to the living room with pocket doors for added privacy. A home office, half bathroom and laundry/mudroom finish off the first floor living space. The second floor includes two guest bedrooms and a shared full bathroom with carrara marble double sink vanity, tile floors and tub/shower tile surround. The Primary Bedroom Suite includes a walk-in closet and private bath with carrara marble double sink vanity, walk-in shower, dual rain and hand held shower heads and tile floors. A functional and thoughtful floor plan with many of the features you're looking for in a home. Estimated completed construction date ~ end of August 2021.

Listed by Donnelly + Co

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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11 Sengekontacket Road Oak Bluffs MA 02557

Oak Bluffs, MA11 Sengekontacket Road

Price$1,399,000

Est. Mortgage: $/month

Active With Contract

MLS Number 37930

  • Residential
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.8199

WATER VIEWS – WATERFRONT COMMUNITY. Set upon the hill overlooking Fresh Pond, with water views from almost every room and ample space to gather friends and family. A premier location to enjoy your Vineyard lifestyle and all that the Sengekontacket community offers - access to both fresh and saltwater ponds, a community dock, clubhouse, tennis/pickleball courts, kayak storage, and boat ramp, walking trails. A central kitchen with island, hardwood floors, and dining area lead to a sunny living room/great room with a dramatic brick fireplace and large den with a cozy propane stove, both with soaring cathedral ceilings and wood beam detail. Stairs lead to an expansive enclosed loft space designed as the fourth bedroom or home office. The main living spaces all enjoy water views to the north and large glass doors to the south for easy access to over 750 s/f of deck designed for the best indoor and outdoor entertaining. A sunny primary bedroom with an en-suite bath and walk-in closet, along with two bedrooms with large windows to highlight the water views and a full bath, complete the first floor. The large glass doors of the walk-out basement let in natural light and invite expansion.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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"Based on information submitted to MA_LINKMV as of April 19, 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."