Oak Bluffs Homes for Sale

If you are looking to purchase a home the town of Oak Bluffs, Breakwater is here to assist you along the way. You will find listings in the famous Martha's Vineyard Camp Grounds "Gingerbread cottages",  along Ocean Park, or on East Chop as well as other areas within the Village.  Purchasing a home in this classic beach town can range from a small summer cottage to a luxury waterfront home.   

Find Homes For Sale in Oak Bluffs

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348 Sea View Avenue Oak Bluffs MA

Oak Bluffs, MA348 Sea View Avenue

Price$5,995,000

Est. Mortgage: $/month

MLS Number 35291

  • Multi-Family
  • Village State Beach
  • Location 41.436238,-70.555927
  • Bedrooms 12
  • Bathroom 6

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: 3.07% last updated on Jul 2, 2020
* 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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395 Barnes Road Oak Bluffs MA

Oak Bluffs, MA395 Barnes Road

Price$4,350,000

Est. Mortgage: $/month

MLS Number 36053

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 4330
  • Bedrooms 4
  • Bathroom 4

RARE OPPORTUNITY ON THE LAGOON WITH A DEEP WATER DOCK - It is rare to find a home in a setting like this on Martha's Vineyard. Tucked away just off Barnes Road, it feels as if you are in a remote locale, yet you are so close to all the Island has to offer. Invite your friends and family. This home boasts room to absorb many people without feeling crowded and has plenty of private retreats for the generations to come. West facing views and glorious sunsets help make this a perfect place to spend - and end - a day. Entertaining is a breeze throughout the open concept main floor. Take in a glorious sunset from the screened porch or out near the dock. Clams and scallops are within your reach just offshore. A ball game or two have been known to erupt on the front yard. Sit back and soak in the natural setting - the fish and fowl will keep you entertained. A deep water dock and deep water access, with the added comfort of the protected location. Come for a visit. You will want to stay for a lifetime.

Listed by Point B Realty LLC

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$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Old Harbor Lane Oak Bluffs MA

Oak Bluffs, MA19 Old Harbor Lane

Price$3,850,000

Est. Mortgage: $/month

MLS Number 35849

  • Residential
  • Village Sengy
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

!!!Visit our interactive Link: http://www.analogstudioinc.com/temp/MV/index.html Rare Opportunity to build 3 separate dwellings or to build your dream home near the water with private beach access and .3 miles to Farm Neck Golf Club! These properties are currently 3 individual lots which can be combined to offer a large estate lot. A summer home is already in place on lot 7, but is not winterized for year-round living. Renderings shown in photos are for visualization purposes and do not necessarily reflect the HOA specifications for Waterview Farms. For Information regarding 4th lot shown please contact listing agent. Two of these parcels adjoin conservation land offering unobstructed views of Sengy Pond, State Beach and beyond. Waterview Farms provides beach access with boat storage and docking available. Explore quaint nearby walking trails to Pecoy Point, or use your paddle boards or kayaks to enjoy Felix Neck & State beach! The MV biking trails access is at entrance to the community with an easy ride to town! This listing includes 7 Old Harbor Lane which is also listed separately.

Listed by Sierra Properties & Investments

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$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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18 Paddock Road Oak Bluffs MA

Oak Bluffs, MA18 Paddock Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 36170

  • Residential
  • Village Central
  • Square Feet 4329
  • Bedrooms 5
  • Bathroom 5

Your luxury oasis awaits in Oak Bluffs' most sought after enclave, “The Preserve At The Woodlands.” This new construction luxury home sits on over two acres, surrounded by generous setbacks that provide added privacy among tall pines and oaks. This property truly accommodates the Vineyard lifestyle in a distinctive and beautifully maintained setting perfect for entertaining in the summer and beyond. For the sports and outdoor enthusiast, The Preserve is just a minute from the renowned Farm Neck Golf Club and connects to walking and biking trails that lead to the three down island beaches. With more than 4200 sq. ft., five-bedroom/bathroom ensuites, and 10 ft. ceilings, this stunning home defies expectations! Nestled at the end of a softly curving driveway, hidden from the road by a stretch of mature trees, the house provides coveted privacy coupled with a spacious modern interior that boasts high-end amenities, top of the line appliances, and all the requisites for a home to be enjoyed year-round. Specific features include: First and second-floor master bedroom suites, guest suite, chef's kitchen with Thermidor appliances, hardwood floors, custom tile bathrooms, multiple balconies and patios, luxe closets and storage throughout the home, spacious third-floor loft, massive unfinished basement with 10-foot ceilings, expansive outdoor entertaining spaces, and lush landscaping. As the home approaches the last stages of construction, the new buyers may opt to have the developers oversee the addition of an already-permitted 16'x34' inground pool and/or customize closets and basement. Completion of 18 Paddock is set for September 2020. With few lots remaining in this exclusive neighborhood, don't miss out on this incredible opportunity to fulfill the dream of luxury homeownership on the Vineyard.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Sengekontacket Road Oak Bluffs MA

Oak Bluffs, MA3 Sengekontacket Road

Price$1,999,000

Est. Mortgage: $/month

MLS Number 36665

  • Residential
  • Village Sengy
  • Square Feet 3400
  • Bedrooms 5
  • Bathroom 4

SENGEKONTACKET A WATERFRONT COMMUNITY: Situated on almost 2 acres of land, gently south sloping, abutting conservation land, this sun-filled Vineyard design has all of the features for a gracious year round or vacation lifestyle. The very special Sengekontacket community offers 2 tennis courts, a clubhouse on a spring fed freshwater pond, and a private salt water dock with easy access to Vineyard Sound. The house design has a cheerfully engaging great room with lots of windows, granite and quartz counters, a black granite gas fireplace highlights the built-in cabinetry, beautiful wide oak flooring, and access to a stone patio, and a sweeping back yard meadow. Also, on the first floor, is a convenient mud room with separate laundry room, a half bathroom and at the other end is en suite master with private deck. The second floor, with brilliant Caribbean Pine flooring, has 4 more spacious bedrooms serviced by 3 more tiled bathrooms. Accessed from the mudroom is a stairway to a 6th unfinished bedroom/full bath over the garage. With high end appliances, irrigation, central AC, and exquisite custom detail, this is a property of exceptional value. PERFECT SETTING FOR A BACKYARD POOL! EXCELLENT RENTAL HISTORY!

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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24 Paddock Road Oak Bluffs MA

Oak Bluffs, MA24 Paddock Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 35641

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 3450
  • Bedrooms 4
  • Bathroom 3

New custom home built by Dubin Construction. House includes upstairs and downstairs master bedrooms as well as upstairs and downstairs living rooms. Second floor includes two additional bedrooms with a shared bath. Custom kitchen and cabinets throughout. Hardwood flooring with tile in side entrance, laundry and bathrooms. Large luxurious bathrooms, large deck off living room and dining room. Stone patio off first floor master. Outdoor shower. Still time to customize landscaping.

Listed by Dubin & Reardon

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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24 Paddock Road Oak Bluffs MA

Oak Bluffs, MA24 Paddock Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 36525

  • Residential
  • Square Feet 3450
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

BEST VALUE IN THE PRESERVE!!! New Custom Built Residence, 2019, by Dubin Construction situated in OAK BLUFFS' most desirable Community that features large home sites and lots of conservation land with a pond. Contemporary design offers upstairs and downstairs master bedroom suites as well as a first and second floor living room and includes two additional bedrooms with a shared bath. Kitchen has gorgeous cabinetry with high end appliances, there is wide oak flooring throughout and gleaming marble tile detail in entrance, laundry and bathrooms. Other highlights include luxurious bathrooms, large deck off living and dining room, stone patio off first floor master, and a very special stone fireplace anchors the great room. Call for an appointment to view this wonderful property!

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Blueberry Path Oak Bluffs MA

Oak Bluffs, MA7 Blueberry Path

Price$1,800,000

Est. Mortgage: $/month

MLS Number 36036

  • Residential
  • Village Sengy
  • Square Feet 3770
  • Bedrooms 4
  • Bathroom 4

The Tower House - Sengekontacket, Oak Bluffs Water views of Sengekontacket Pond and the Nantucket Sound from almost every room in the unique hilltop contemporary. This large-bright 4+ bedroom/4.5 bath house has almost 4,000 sq/ft of living space with 2 master suites, multiple living areas and six private decks including a rooftop deck that provides 360-degree views of the Island. The original section of the house has been completely renovated and has a master suite with private balcony, two other bedrooms with a shared bath and a large open modern kitchen with Bosch appliances and Quartz countertops and large deck with lovely Vineyard views. The new section has two living areas and dining area, a master suite that spans the entire floor that includes a huge master bedroom with private office, walk-in closet and bathroom. The third floor provides another living or sleeping area with half bath and a private deck. A custom stainless-steel staircase brings you to a rooftop deck that provides a 360-degree view of the Island. Enjoy the great amenities that the Sengekontacket Association which offer walking trails, tennis/pickleball courts, a member clubhouse with large mahogany deck, private beach and kayak/canoe launch.

Listed by The Vineyard Life Brokered by eXp Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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232 Massachusetts Avenue Oak Bluffs MA

Oak Bluffs, MA232 Massachusetts Avenue

Price$1,799,000

Est. Mortgage: $/month

MLS Number 36118

  • Residential
  • Village East Chop
  • Square Feet 5269
  • Bedrooms 5
  • Bathroom 4

East Chop -- Expansive 5-bedroom/4-bathroom (3-ensuite) home, looks out over Mill Square Park, with peeks of water in the distance, and surrounded by the best amenities East Chop has to offer -- beaches, yacht club, and tennis club. This graceful home features a large living room with paneled ceiling and beach stone fireplace, large dining room with Dutch tiled fireplace and, two large, sun-filled, family rooms (one upstairs and one downstairs). Ideally located with just a 7-minute walk to the beaches, tennis courts and harbor during the day, and 12-minutes walk to downtown restaurants and night life in the evening, this vacation home is ideal for those extended family stays! Upgraded to a 220 electrical system/circuit breakers '88-'89.

Listed by RE/MAX on Island

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Pennacook Avenue Oak Bluffs MA

Oak Bluffs, MA7 Pennacook Avenue

Price$1,690,000

Est. Mortgage: $/month

MLS Number 33956

  • Multi-Family
  • Village Downtown
  • Bedrooms 8
  • Bathroom 4
  • Half Bath 1

**Unoccupied and easy to show virtually or in socially-distant person.** In the coveted Copeland District, steps from beach and town: An unparalleled palace of a property awaits the fortunate investor. Dunmere-by-the-Sea, a soaring, three-story edifice was once an elegant hotel of Oak Bluffs' heyday as a swinging Victorian resort. For the past 40-plus years, this "wedding cake" with panaromic views of Nantucket Sound has served its owners well as a three-unit apartment building. Vacation tenants hail from as near as Boston and as far as Budapest, including many longtime repeaters. Updates over the years have spared many elements of period charm -- the mansard roof, substantial "gingerbread" trimmings, the serpentine interior stairway. Each unit enjoys bright and spacious floor-through living, with open common areas, full kitchens and baths, two-plus bedrooms and water views. They share use of a laundry, a deep wraparound porch, four parking spaces and generous yard space for lounging and cookouts. The raised finished basement, inclusive of full bath and laundry, has full windows and both indoor and outdoor entries. The opportunities abound: Glamorously upgrade or simply refresh the "old school" cottage ambience. Continue the lucrative landlord tradition. Create condominiums (subject to town permitting). Or go rogue and transform the building into your personal, palatial single-family domain. Property is eligible for tie-in to the town sewer.

Listed by Coldwell Banker Landmarks

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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

Oak Bluffs, MA273 East Chop Drive

Price$1,645,000

Est. Mortgage: $/month

MLS Number 36707

  • Residential
  • Village East Chop
  • Square Feet 1104
  • Bedrooms 3
  • Bathroom 1

Little Jaws - Aptly named after the cinematic classic, this quintessential Vineyard retreat exudes charm. Located at the water's edge, this 1930's cottage is centered around the vaulted living room with large beach-stone fireplace. Original hardwood floors and detail throughout. The first floor offers 2 bedrooms with full bath along with kitchen, dining area and sun-room, perfect for an afternoon nap or to catch up with a great book. The second floor is comprised of the Master Bedroom with powder room. The large covered porch is the perfect spot to listen to the waves and watch the activity in Vineyard Sound. Enjoy incredible sunsets, boating, paddle-boarding, fishing, etc, just steps away.

Listed by Donnelly + Co

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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

Oak Bluffs, MA21 Tower Ridge Road

Price$1,595,000

Est. Mortgage: $/month

MLS Number 35358

  • Residential
  • Village Central
  • Square Feet 3957
  • Bedrooms 3
  • Bathroom 4

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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