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: 2.96% last updated on Jun 10, 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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104 Winemack Avenue & 101 Park Street Oak Bluffs MA 02557
Pending

MLS Number 38203

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.6887

The Rose Cottage in East Chop - this bright and airy, waterview ca 1920 home with detached garage offers the perfect expanse to spread out in a highly desirable location. Spanning Winemack and Park streets, the property is perfectly set with a beautifully framed view of Vineyard Sound, including regular ferries and boats in passing by. The home is immaculate and deceptively spacious, with five bedrooms and open living areas graciously incorporated on two levels. Indoor and outdoor living is truly superb at this property, with upper and lower decks and a sun room complementing the exceptionally bright and positive interior. Recent renovations include all new siding on three sides, interior and exterior paint, new septic, hvac system upgrades and more. Come grab this rare opportunity in a prime East Chop location - conveniently located to town, beaches and more.

Listed by Compass

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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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168 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA168 East Chop Drive

Price$2,650,000

Est. Mortgage: $/month

MLS Number 38342

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.0002

Dramatic Vineyard Sound Views on East Chop Drive - Charming cottage on desirable East Chop Drive - Enjoy spectacular views of Vineyard Sound & boats passing by from your front deck of this cozy Martha's Vineyard retreat. The cottage is just under 1,000 Sf and sits on 12,256 SF of land, and currently features 2 bedrooms and 1 bath. Permits are being prepared for the potential of a new 4 bedroom septic system. This setting offers unbelievable views from a remarkable location in Oak Bluffs.

Listed by Wallace & Co. Sotheby's

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%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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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26 Pequot Avenue Oak Bluffs MA 02557

Oak Bluffs, MA26 Pequot Avenue

Price$2,250,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38143

  • Residential
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.2

The Cinderella Cottage is a glamorous Victorian Seaside home. Meticulously renovated, this Gingerbread style home on Pequot Ave, puts you just steps from Inkwell Beach & the village of Oak Bluffs. Colorful and decorative detailed gingerbread trim adorns all. A gracious wrap around porch with large side seating area overlooks the grassy green yard. A quiet back slate patio is enclosed with greenery and gardens. The upstairs covered balcony charms with more gingerbread trim. The two story fairytale turret has upper level water views. The etched glass French doors will bring you into a beautiful living room whose high ceilings & decorative trim, marble mantel and hardwood floors delight. The sunny separate dining room continues with tasteful bright colors, etched glass door, high ceilings and its own marble mantel. Double pocket doors open up a big family room off to the side with more high ceilings, decorative trim and arched bay window. The modern kitchen fills the back section of home w/ top-notch appliances and cabinetry, center counter top w/built in snack bar for 4, and designer painted diamond wooden floors. A separate Laundry room, additional half bath and small side enclosed porch to patio complete this floor. Upstairs are three large bedrooms with an additional Extra room turned into a bunkroom for kids. Two full baths (two have gorgeous marble tiles on floors, walls and ceilings, & bead board wainscoting (one w/ claw foot tub, one w/ oversized shower). Each spacious bedroom room is a wonder, professionally decorated with color and style, bay windows and all with hardwood flooring. Additional open study area plus sitting areas outside the rooms are perfect for a quiet break or reading-TV nook. The 2 story turret has what feels like a secret staircase leading up to a game room and up again to a private sitting area with water views. There's so much more with full basement, heat, lovely grounds. This is a home perfect for family and entertaining friends. Keep as a family home or rent weekly. Wonderfully maintained, highly sought after rental area. (Inquire for rental income figures). Turnkey except for personal items. Broker must accompany clients. Showings can be set up for Sat & Sun after 3PM

Listed by Austin R.E. Properties of MV

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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: 2.96% last updated on Jun 10, 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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60 Pennacook Avenue Oak Bluffs MA 02557

Oak Bluffs, MA60 Pennacook Avenue

Price$1,800,000

Est. Mortgage: $/month

MLS Number 38343

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 1.5
  • Acreage 0.06

Nestled in the heart of the Cottage City and Copeland Historic Districts, this antique home is within walking distance to everything. Beaches, Boats, Restaurants, Shopping, Playground, Basketball, Pickleball, Tennis, Parks, Bike Path and more. Watch the world go by as you laze on your shaded front porch after a day on the beach and a soak in the hot tub. This corner lot in a quintessential Victorian neighborhood offers much privacy overlooking Pennacook Park and much convenience with it's central location.

Listed by Anchor Realty of Martha's Vineyard

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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

Pending

MLS Number 35358

  • Residential
  • Mls Status Pending
  • 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: 2.96% last updated on Jun 10, 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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312 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA312 East Chop Drive

Price$1,695,000

Est. Mortgage: $/month

MLS Number 37959

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.2502

"The Doll House" is an iconic home on East Chop Drive with waterfront on Crystal Lake and views of Vineyard Sound. Once a quaint fishing cottage, this home has been carefully renovated and meticulously maintained over the years. With nearly 150 feet of waterfront on Crystal Lake, you can enjoy swimming, kayaking or paddling from your backyard. The main house features a comfortable sunporch, open living room with a stone fireplace, a sun filled master bedroom with waterviews, updated cook's kitchen and dining room both featuring stunning brick floors. French doors in the kitchen open to a spacious yard for outdoor entertaining and a charming "boathouse" that has been converted to a dining area. A modern spiral staircase takes you to an expansive rooftop deck where you can spend the day bathing in the sun and watching the Ferry boats come and go. A delightful guest cottage offers 2 additional guest bedrooms with high ceilings and a full bath. Other amenities include a private outdoor shower and a one-car garage with an attached artist studio. This wonderful location is also an easy bike ride to the East Chop tennis, beach and yacht clubs and to both downtown Oak Bluffs and Vineyard Haven. Truly a magical island home.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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 Narragansett Avenue Oak Bluffs MA 02557

Oak Bluffs, MA22 Narragansett Avenue

Price$1,595,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38237

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.08

IN-TOWN OAK BLUFFS: Classic Victorian STEPS from the Public Beach on Nantucket Sound and a few blocks to town center, popular Circuit Avenue, shopping, ferries, Oak Bluffs Harbor and town Parks! This gracious residence has been upgraded and carefully maintained over the years. Features a wrap-around porch with views to Nantucket Sound and an enclosed three season porch section on the other side, a welcoming parlor room, dining room with built-in china closet, completely modern kitchen with cozy breakfast nook and pantry, separate laundry room, upgraded full bathroom, a bedroom on the first floor, a small basement for utilities, and an outside shower. The interior is highlighted by bead board on ceilings and walls, and an attractive medley of Oak, Black Walnut and Pine flooring. There is ample off street parking in the driveway that includes a small garage. The second floor has 3 more bedrooms, a pass through bedroom, 2 private balconies, and another full bathroom. The house shows large with additional versatile spaces that have been used for overflow of guests. Tastefully furnished, this offering is turn key and ready for occupancy. Excellent rental history.

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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 Hidden Cove Road Oak Bluffs MA 02557

Oak Bluffs, MA3 Hidden Cove Road

Price$1,550,000

Est. Mortgage: $/month

MLS Number 38324

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.2899

Located within the desirable Hidden Cove Association- A WATER ACCESS COMMUNITY created on over 65 acres with homes privately nestled with direct access to Sengekontacket Pond and Nantucket Sound. A lovely area with private boat dockage, walking trails and tennis all within the outskirts of Oak Bluffs with easy access to other towns. This inviting contemporary residence is designed to comfortably accommodate a large family with many special high-end touches throughout. The main floor greets you with a gracious living room anchored by a maple wood buring fireplace and high wood-beamed ceilings. There is lots of natural light from floor to ceiling windows, skylights and doors that lead to the deck connected to a chef’s kitchen with marble counters and backsplash with wood paneled Décor appliances seamlessly integrating the custom cabinetry. The upper level is dedicated as the Principal suite with room for a sitting area and office space with access to a private balcony and a stylish bathroom en-suite with a deep soaking tub and a separate glass shower stall. The garden level comfortably separates all the bedrooms and bathrooms with bonus area with California Closet's murphy bed for an overflow of guests. The sliders lead to an enchanting private yard with lush green grounds, mature plantings, an irrigation system, the requisite outdoor shower and invisible fence.  A blue-stone patio with spacious outdoor dining and grill area is an inviting spot to gather and entertain with family and friends.The attached one car garage has room for storage, beach gear and the summer car. This is a special property not to be missed.

Listed by Martha's Vineyard Island-Wide Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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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105 Eastville Avenue Oak Bluffs MA 02557

Oak Bluffs, MA105 Eastville Avenue

Price$1,450,000

Est. Mortgage: $/month

MLS Number 38275

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.45

Located near Eastville Beach and the hospital you will enjoy the large yard with wrapping deck. Walking into this restored Antique home you will find wide plank wood flooring while you take-in the large light filled livingroom with fireplace in pristine condition. The first floor also offers a den with fireplace, mudroom with side entry from the driveway parking, full bath and a separate half bath tucked under the stairs, a spacious bedroom with wall storage and closet, gorgeous dining room with built-in china cabinets and doors to the deck area and outdoor shower. Continue through this main floor to find a vaulted ceiling in the kitchen with sky light and exposed beams. The laundry with another exterior door to a garden patio and wrapping deck complete this room. While in the home, take note of the woodwork moldings of years gone by. The second floor offers a bathroom with claw foot tub/shower and 3 spacious bedrooms. The attic is a great space for storage. Come and enjoy this truly unique Vineyard home and create new memories for years to come. Winter peak views of the water.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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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20 Pequot Avenue Oak Bluffs MA 02557

Oak Bluffs, MA20 Pequot Avenue

Price$1,450,000

Est. Mortgage: $/month

Pending

MLS Number 37618

  • Residential
  • Mls Status Pending
  • Bedrooms 15
  • Bathroom 4
  • Acreage 0.2

Welcome to The Towers! OPPORTUNITY KNOCKS- WITH THIS VERY RARE AND UNIQUE PROPERTY. Located just one block from the beach and several blocks to Ocean Park, the ferry and downtown Oak Bluffs. This 15 Bedroom property has been utilized for the past handful of years as a licensed lodging house for employee housing. Commercially licensed to operate as: an INN/MOTEL/B&B/LODGING HOUSE. The possibilities abound with this classic Victorian home on an oversized lot for the area. Don't miss out on this very rare offering!

Listed by Martha's Vineyard Island-Wide Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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 June 15, 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."