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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3 Canonicus Avenue Oak Bluffs MA 02557

Oak Bluffs, MA3 Canonicus Avenue

Price$2,300,000

Est. Mortgage: $/month

MLS Number 41509

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.0899

WATER VIEWS!!! Steps to the Beach - walk along the most scenic drive on Martha's Vineyard! This stunning property is a true gem, offering an exceptional combination of classic charm, modern amenities, and an ideal location for enjoying the island's relaxed lifestyle. Nestled in the heart of Oak Bluffs, this home is a short stroll to beaches, restaurants, and shops. The scenic harbor and parks are also just moments away, making it perfect for experiencing the best of the Vineyard. This renovated antique home boasts timeless architectural features and a welcoming front porch creating an inviting and picturesque curb appeal. The interior is a blend of elegance and modern convenience offering an inviting atmosphere for family and friends to gather. Enjoy the serene outdoor spaces, including a patio area for outdoor dining and rooftop deck (widow's walk) that features panoramic ocean views! With its prime location and strong rental income history, this property can serve as both your idyllic vacation retreat and a smart real estate investment. Don't miss the garage and surprise bonus area. Come experience the timeless allure of Martha's Vineyard, and make this extraordinary property your island haven. Summer leases are in place and income will transfer to the buyer. OWNER FINANCING IS AVAILABLE.

Listed by Compass | Point B

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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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28 Rogers Way Oak Bluffs MA 02568

Oak Bluffs, MA28 Rogers Way

Price$2,100,000

Est. Mortgage: $/month

MLS Number 40849

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 0.2299

READY FOR THIS SUMMER! NEW CONSTRUCTION, contemporary farmhouse style home with wrap around deck and outdoor shower. This home features a first floor en-suite bedroom with a full bath, a half bath off the foyer entry, an open kitchen/dining and living room area with a gas fireplace, a wall of glass with windows and sliding glass doors from the dining area and living room area. There is a well designed mudroom area with a first floor laundry, a large overflow pantry and a built in bench seating area. The second offers two en-suite bedrooms, a large second floor living room area and a second laundry area. A full poured foundation with a walk out door completes this new construction offering. The property location offers close proximity to the center of town, beaches, and bike paths. This quiet location, with attractive homes, is convenient to everything that Oak Bluffs has to offer. Come and enjoy NEW CONSTRUCTION with COASTAL STYLE!

Listed by Vineyard Village Realty

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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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19 Wendall Avenue Oak Bluffs MA 02568

Oak Bluffs, MA19 Wendall Avenue

Price$1,999,000

Est. Mortgage: $/month

MLS Number 40661

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 1.5
  • Acreage 0.307

LOCATION LOCATION LOCATION!!! EAST CHOP OAK BLUFFS! Set high on the hill with refreshing sea breezes this exclusive four bedroom three season home has existing detached garage boasts expansion options. Currently four bedrooms, sleeping for ten, in R2 zoning has 20' setbacks that allow for expansion of an addition or another structure. A wonderful peaceful neighborhood surrounded with multiple parks and conservation lands. This home holds relaxing timeless charm and original design with high vaulted ceilings abundant natural light beach stone wood burning fireplace wood flooring with built in cupboards and closets throughout. Quiet and peaceful set high on The Bluff the large 13,372SF lot is sheltered by additional 12,197SF of East Chop Conservation land, surrounded with a lovely moat of mature flowering rhododendron plantings adding even greater privacy. On Island Time with sounds of the sea the buoy's chime and the ferry blasts close to the beach! Enjoy the wonderful breeze while entertaining and relaxing on the front porch with morning coffee and afternoon festivity! Your MV beach retreat for generations to come. Navigate with quick access just moments away, OB harbor, beaches, EC Tennis, EC Beach Club, Downtown, restaurants, shopping, and multiple Ferry Terminals. A rare and highly coveted Property.

Listed by Seacoast Properties

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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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34 Paddock Road Oak Bluffs MA 02557

Oak Bluffs, MA34 Paddock Road

Price$1,950,000

Est. Mortgage: $/month

MLS Number 40763

  • Land
  • Mls Status Active
  • Acreage 2.059

The Preserve at the Woodlands - A terrific opportunity to build in this beautiful and prestigious neighborhood in Oak Bluffs. The Preserve has matured into an enclave of significant residences and offers excellent privacy, with convenience to downtown, harbor and beaches. The orientation of this parcel is prime with southern exposure for backyard pool and patio, and it is abutting dedicated open space on two sides. The lot has been perk tested and is ready for you to build your ultimate Vineyard compound.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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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2 Farm Path Oak Bluffs MA 02557

Oak Bluffs, MA2 Farm Path

Price$1,950,000

Est. Mortgage: $/month

MLS Number 41356

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.89

"Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard and a pool! The large detached two-bay garage has a new attached studio with full bath, laundry, kitchen and a private deck. Newer exterior cedar shingles and trim, and a new 4 bedroom septic installed. Equidistant to each down-Island village, it resides within a mature neighborhood with attractive curb appeal.

Listed by Landmarks at TODAY Real Estate

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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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37 Circuit Avenue Oak Bluffs MA 02557

Oak Bluffs, MA37 Circuit Avenue

Price$1,900,000

Est. Mortgage: $/month

MLS Number 41996

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 2

Downtown Oak Bluffs- 2 Penthouse Condominiums being sold together. Located in the heart of Oak Bluffs on Circuit Ave. with easy access to beaches, shops, and restaurants. These two units with a combined 1787 square feet of interior space come and an amazing rooftop deck were you can see panoramic views of the Vineyard Sound and Oak Bluffs harbor. This large deck with multiple seating areas is an ideal place to gather with family and friends and relax above it all. As you enter the first unit you'll notice the beautiful hardwood floors and custom-made cabinetry throughout, with a kitchen and breakfast bar leading into a dining area. A Ship's ladder takes you the the rooftop deck which gives you a birds eye view of downtown Oak Bluffs and the surrounding water. The spacious living room is a great place to gather with an electric fireplace for cozy nights. Off the living area is a private sleep alcove for overnight guests. The bedroom is large and inviting with plenty of closet space. A tiled bathroom has a glass enclosed shower surround. --- The second unit has the same hardwood floors, with the kitchen and dining area are divided with custom cabinetry. An wooden staircase leads to the rooftop deck creating a nook with storage and a daybed on the other side. Take a step down to the comfortable living area. The spacious bedroom has an alcove with pull down skylight, ideal for an exercise area or office. A tiled bathroom with full tub and shower can be entered off the hall or bedroom. Both of the units have their own entrances to the amazing rooftop deck exclusively for their use only. A connecting door in the living rooms between the units can be opened up or lock depending on your desired use. A separate Laundry room is available on the second floor.

Listed by Anchor Realty of Martha's Vineyard

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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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53 Carol Lane Oak Bluffs MA 02557

Oak Bluffs, MA53 Carol Lane

Price$1,795,000

Est. Mortgage: $/month

MLS Number 42042

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.17

Welcome to Oak Bluffs! This classic colonial style 4-bedroom, 2.5-bathroom house has just undergone a complete interior renovation, promising contemporary comfort and style. As you step inside, you'll be greeted by a spacious living room adorned with a cozy gas fireplace. The open layout seamlessly connects the living room to the dining area, creating an ideal space for entertaining. The newly updated kitchen features modern appliances, sleek countertops, and ample storage space. An office, half-bath and laundry room complete the first floor. Upstairs, the primary bedroom suite awaits with plenty of natural light and a luxurious en-suite bathroom. The second-floor features 3 additional bedrooms and a guest bathroom. Outside, the newly landscaped fenced-in yard boasts a stone patio and plenty of outdoor entertaining space. An oversized screened porch completes this welcoming outdoor oasis. Located on the bike path, this location is convenient to Downtown Oak Bluffs, and nearby beaches.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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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25 Hampson Avenue Oak Bluffs MA 02557

Oak Bluffs, MA25 Hampson Avenue

Price$1,775,000

Est. Mortgage: $/month

MLS Number 42036

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.27

Fantastic Oak Bluffs downtown location! Walk to ferry, Circuit Avenue, beach, harbor and library. Investor's dream with outstanding seasonal rental income. This pristine Cape style, 4 bedroom 3 bath home is being offered fully furnished. The property was newly renovated in 2018. The renovations include; new appliances, interior paint, refurbished kitchen cabinets, granite stone countertops, solid hardwood floors, new home furnishings, refurbished front deck and stairs, outdoor shower, redefined crushed stone 6 car driveway, and an electric heat pump 5 zone HVAC system. The first floor is an open concept plan, with a large peninsula island, plenty of storage closets, a large dining area, a nicely appointed family room, a queen bedroom with a full bathroom and a generous size primary king bedroom en-suite. The second floor boasts a large second living or study area, 2 large bedrooms with a full bathroom. This home radiates with morning and afternoon sun. The basement is partially renovated with high ceilings. It is clean and dry and has a concrete poured bulkhead. This 1400SF basement could easily become a very large finished space. The yard includes mature trees, grass front lawn, irrigation system, a large crushed stone driveway, an oversized front porch and a back deck that accommodates a grill and dining. A perfect turnkey solution, for the savvy investor and/or family to enjoy this charming walk to town home.

Listed by Premier Properties

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$
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$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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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51 Head Of The Pond Road Oak Bluffs MA 02557

Oak Bluffs, MA51 Head Of The Pond Road

Price$1,600,000

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.

Listed by Bruce Stuart and Associates

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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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17 School Street Oak Bluffs MA 02557

Oak Bluffs, MA17 School Street

Price$1,599,000

Est. Mortgage: $/month

MLS Number 41611

  • Land
  • Mls Status Active
  • Acreage 0.6
  • Bedrooms 4
  • Bathroom 1

Exceptional In-Town Opportunity: A Canvas for Luxury Living in Oak Bluffs. Discover a rare opportunity in the heart of Oak Bluffs, on Martha's Vineyard – a sprawling .6-acre lot offering a serene blend of natural beauty and prime location. This property presents a unique opportunity to create a luxury residence with a design that honors the island's charm and your personal taste in upscale living. Key Highlights: Prime Location with Natural Splendor: Experience the best of both worlds - a peaceful oasis boasting picturesque views of gardens, pine woods, and wetlands stretching to Sunset Lake and Oak Bluffs Harbor, while being just moments away from the vibrant harbor life, exquisite dining, entertainment, and sandy beaches. Approved Plans for a Dream Home: Included in the sale are approvals and plans for a breathtaking 2,500 sq ft home, masterfully designed by Breese Architects. The proposed 4-bedroom, 3-bathroom residence has received the nod from the Martha’s Vineyard Commission, Oak Bluffs Historic Commission, and Conservation Commission, ensuring a seamless transition from vision to reality. Innovative Design and Elegance: The architectural plans showcase a home elevated above natural grade, providing stunning water views from a second-floor balcony. The design cleverly incorporates two garage spaces beneath the raised floor levels, merging functionality with style. Historic Charm Meets Modern Elegance: While the exterior echoes the historic character of the original house, the interior proposes a bright, open concept with a striking vaulted ceiling in the great room and upper-level windows that bathe the kitchen and dining area in natural light. Seamless Indoor-Outdoor Living: Envision life in a space where the transition from indoors to outdoors is effortless, featuring a screened porch, open porches, and a balcony, perfect for savoring the tranquil surroundings. This property represents more than just a home; it's a lifestyle choice for those who appreciate the blend of historical reverence and modern luxury. With demolition approval already in place for the existing structure, your vision for a distinguished living experience is ready to be realized. Connect with me to explore how this property can be the canvas for your dream home, where luxury, location, and natural beauty converge.

Listed by eXp Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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$1,499,000

Est. Mortgage: $/month

MLS Number 41939

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.3399

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! MORE PHOTOS COMING SOON ..

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 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 May 27, 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.