Oak Bluffs Houses for Sale

/22
$1,250,000
- 2 Beds
- 1 Bath
- 742 Sq Ft
47 Winemack St, Oak Bluffs, MA 02557

Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a

Lisa Lucier

Anchor Realty of MV

(508) 403-9601

47 Winemack St, Oak Bluffs, MA 02557
Explore Oak Bluffs
/21
$1,650,000
- 3 Beds
- 1 Bath
- 1,033 Sq Ft
9 Brunswick Ave, Oak Bluffs, MA 02557

PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively updated inside and out. Enjoy peace of mind with a new septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a

Alice Pierce

Coldwell Banker Realty - Hingham

(508) 715-6242

9 Brunswick Ave, Oak Bluffs, MA 02557
/42
$5,995,000
- 3 Beds
- 6 Baths
- 3,608 Sq Ft
385 Barnes Rd, Vineyard Haven, MA 02568

Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

Wendy Harman

Compass

(508) 205-8817

385 Barnes Rd, Vineyard Haven, MA 02568
/34
$2,500,000
- 6 Beds
- 2.5 Baths
- 1,666 Sq Ft
34 Massasoit Ave, Oak Bluffs, MA 02568

This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to

Lisa Lucier

Anchor Realty of MV

(508) 348-7972

34 Massasoit Ave, Oak Bluffs, MA 02568
/27
$1,200,000
- 2 Beds
- 2.5 Baths
- 1,500 Sq Ft
70 Carol Ln, Oak Bluffs, MA 02557

Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot this ranch home with a finished basement has been recently renovated. The first floor has 1500 sq feet with of a large open kitchen, dining area, and living room with plenty of room for large gatherings. The primary bedroom has a bathroom on suite. Another bedroom has easy access to the hall bath. The

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 456-5742

70 Carol Ln, Oak Bluffs, MA 02557
/34
$3,450,000
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
6 Brewster Ave, Oak Bluffs, MA 02557

Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

Katherine Donahue Sandpiper Realty Inc

6 Brewster Ave, Oak Bluffs, MA 02557
/40
$1,825,000
- 4 Beds
- 4 Baths
- 3,927 Sq Ft
44 Tiffany Dr, Oak Bluffs, MA 02557

Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted

Nora Jardin Island Real Estate

44 Tiffany Dr, Oak Bluffs, MA 02557
/42
$1,895,000
- 3 Beds
- 4 Baths
- 2,558 Sq Ft
35 Tower Ridge Rd, Oak Bluffs, MA 02557

Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just as inviting, with an oversized deck overlooking mature plantings and a generous side yard--perfect for

Katherine Donahue Sandpiper Realty Inc

35 Tower Ridge Rd, Oak Bluffs, MA 02557
/46
$2,395,000
- 5 Beds
- 3.5 Baths
- 3,873 Sq Ft
50 Hidden Cove Rd, Edgartown, MA 02539

Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The

Sean Federowicz Landmarks at TODAY Real Estate

50 Hidden Cove Rd, Edgartown, MA 02539
/26
$2,150,000
- 2 Beds
- 2.5 Baths
- 2,137 Sq Ft
30 Franklin Ave, Oak Bluffs, MA 02568

Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

Stacy Ickes Donnelly + Co

30 Franklin Ave, Oak Bluffs, MA 02568
/55
$1,830,000
- 4 Beds
- 4 Baths
- 1,600 Sq Ft
12 & 14 Maple Ave, Oak Bluffs, MA 02557

Two Historic Oak Bluffs Cottages - Prime Location – Deeded SeparatelyPerched atop a gentle hill, surrounded by lush, established gardens in one of the island’s most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history—just a short distance to the harbor, downtown, and the beloved Winston’s takeout.Built at a time when

Leslie C. Floyd Portfolio Real Estate, Inc.

12 & 14 Maple Ave, Oak Bluffs, MA 02557
/39
$2,495,000
- 5 Beds
- 2.5 Baths
- 2,577 Sq Ft
16 Atlantic Ave, Oak Bluffs, MA 02557

East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most

Katherine Donahue Sandpiper Realty Inc

16 Atlantic Ave, Oak Bluffs, MA 02557
/44
$2,699,000
- 6 Beds
- 4 Baths
- 2,400 Sq Ft
111 Eastville Ave, Oak Bluffs, MA 02557

Motivated Seller!! Steps to the beach- Minutes to downtown Oak Bluffs and Vineyard Haven. This is a perfect location.FULLY FURNISHED, TURNKEY, with an impressive rental history. Situated on an oversized lot that is two parcels away from the beach. This home offers six bedrooms and four

Ed Charter Arrowhead Homes

111 Eastville Ave, Oak Bluffs, MA 02557
/19
$2,295,000
- 4 Beds
- 5 Baths
- 2,820 Sq Ft
71 Netock Ave, Oak Bluffs, MA 02557

On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor

Ellen Valentgas Sotheby's International Realty

71 Netock Ave, Oak Bluffs, MA 02557
/30
$2,195,000
- 4 Beds
- 2.5 Baths
- 1,825 Sq Ft
4 Dempster Park, Oak Bluffs, MA 02568

This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. First floor includes large living room with dining area and Rumford wood burning fireplace that opens out to a front porch and deck running the length of the house and which wraps around to the rear patio.

Perry Patterson MV Luxury Homes LLC

4 Dempster Park, Oak Bluffs, MA 02568
/37
$2,240,000
- 3 Beds
- 2 Baths
- 1,608 Sq Ft
22 Greenleaf Ave, Oak Bluffs, MA 02557

Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect

Jennifer O'hanlon Compass

22 Greenleaf Ave, Oak Bluffs, MA 02557
/39
$2,240,000
- 3 Beds
- 2 Baths
- 1,608 Sq Ft
22 Greenleaf Ave, Oak Bluffs, MA 02539

Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coastal living on Martha’s Vineyard. From the highest vantage point on Greenleaf, enjoy sunrises that fill

Jen O'Hanlon Compass | The O'Hanlon Group

22 Greenleaf Ave, Oak Bluffs, MA 02539
/21
$3,100,000
- 3 Beds
- 1 Bath
- 1 Sq Ft
23 Circuit Avenue Extension, Oak Bluffs, MA 02557

Rare Opportunity with Endless Possibilities - Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound--a setting that captures the very

Rene Ben David Ocean Park Realty, Inc.

23 Circuit Avenue Extension, Oak Bluffs, MA 02557
/37
$1,995,000
- 4 Beds
- 3 Baths
- 3,058 Sq Ft
2 Farm Path, Oak Bluffs, MA 02557

"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

Sean Federowicz Landmarks at TODAY Real Estate

2 Farm Path, Oak Bluffs, MA 02557
/24
$2,195,000
- 4 Beds
- 3 Baths
- 2,262 Sq Ft
30 Sengekontacket Rd, Oak Bluffs, MA 02557

Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main

Cassie Bradley Wallace & Co. Sotheby's International Realty

30 Sengekontacket Rd, Oak Bluffs, MA 02557
/24
$2,150,000
- 2 Beds
- 2.5 Baths
- 2,137 Sq Ft
30 Franklin Ave, Oak Bluffs, MA 02568

Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

Stacy Ickes Donnelly + Co.

30 Franklin Ave, Oak Bluffs, MA 02568
/25
$1,500,000
- 4 Beds
- 2 Baths
- 1,248 Sq Ft
23 Laurel Ave, Oak Bluffs, MA 02557

LOCATION! YEAR ROUND HOUSE!INVESTMENT PROPERTY!STARTER HOME!A comfortable home in an established, East Chop neighborhood, this four bedroom, two bathroom house is located within walking distance to the Harbor, downtown Oak Bluffs, and the Oak Bluffs Ferries. There is easy access to shops, family entertainment, and the beach. This home provides a welcoming porch and a spacious backyard patio

Sandra Grymes Martha's Vineyard Island-Wide Realty

23 Laurel Ave, Oak Bluffs, MA 02557
/11
$915,000
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
8 Hitchings Cir, Oak Bluffs, MA 02557

Nestled in a quiet Oak Bluffs neighborhood, less than a mile from the harbor, beaches, shops, and restaurants, this Cape-style home offers the perfect balance of convenience and tranquility. The interior features an open kitchen and living room, plenty of space for guests, and a full unfinished basement. The two bedroom Title V septic system has passed inspection. Outside, the property features a

Peyton Wallace Studio Realty

8 Hitchings Cir, Oak Bluffs, MA 02557
/39
$1,470,000 Open Thu 11AM - 12PM
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
26 Winne Ave, Vineyard Haven, MA 02568

Welcome to your dream home just a short walk to the lagoon. This home offers easy access for dropping a kayak or taking a refreshing afternoon dip from a public access point. Discover this charming home nestled on a corner lot within a serene neighborhood. This beach home has an updated kitchen and bathrooms. The kitchen is equipped with new appliances and gorgeous quartz countertops, making it a

Joe & Nicole Holland Vineyard Dream Realty LLC

26 Winne Ave, Vineyard Haven, MA 02568
/33
$839,000
- 2 Beds
- 1 Bath
- 954 Sq Ft
16 Cottage Park, Oak Bluffs, MA 02557

Just steps from the iconic Tabernacle and Trinity Park, this charming cottage is nestled in the heart of the historic Martha's Vineyard Camp Meeting Association--a designated National Historic Landmark District. Surrounded by colorful gardens and picturesque pedestrian walkways, it offers an easy stroll to Oak Bluffs Harbor, beaches, ferries, art galleries, restaurants, and all the vibrant charm

Marilyn Moses Ocean Park Realty, Inc.

16 Cottage Park, Oak Bluffs, MA 02557
/47
$5,450,000
- 4 Beds
- 5.5 Baths
- 3,300 Sq Ft
8 Paddock Rd, Oak Bluffs, MA 02557

Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of a tranquil pond and surrounding grasslands, this beautiful residence offers a masterful blend of traditional coastal architecture and modern luxury. Located in the prestigious enclave of The Preserve, this sprawling home is designed for effortless elegance, privacy, and indoor-outdoor living.At the heart of

Lesley Heidt Sandpiper Realty Inc

8 Paddock Rd, Oak Bluffs, MA 02557
/15
$845,000
- 2 Beds
- 1 Bath
- 624 Sq Ft
60 -R Carol Ln, Oak Bluffs, MA 02557

Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

Sheila Morse Island Real Estate

60 -R Carol Ln, Oak Bluffs, MA 02557
/14
$845,000
- 2 Beds
- 1 Bath
- 624 Sq Ft
60R Carol Ln, Oak Bluffs, MA 02557

Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

Nora Jardin Island Real Estate

60R Carol Ln, Oak Bluffs, MA 02557
/28
$1,325,000
- 3 Beds
- 2 Baths
- 1,764 Sq Ft
170 Barnes Rd, Oak Bluffs, MA 02557

Calling water and boating enthusiasts. Solid Cape-style home one block from Sailing Camp Park, water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back

Christine Rose Martha's Vineyard Island-Wide Realty

170 Barnes Rd, Oak Bluffs, MA 02557
/44
$6,395,000
- 6 Beds
- 5.5 Baths
- 7,000 Sq Ft
400 Barnes Rd, Vineyard Haven, MA 02568

Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

Jennifer DaSilva Compass | Point B

400 Barnes Rd, Vineyard Haven, MA 02568
/43
$5,800,000
- 6 Beds
- 5.5 Baths
- 3,214 Sq Ft
15 Tamarack Ln, Oak Bluffs, MA 02557

FARM NECK: The original 1780 Farm House was tastefully restored in 1985 to honor the land and legacy of Farm Neck. This serene 3.7 acre oasis of rolling greenery with a variety of mature trees and lots of natural privacy has an up Island feel with the down Island convenience to fine dining, shopping, ferry, airport, bike paths and includes Stockholder Membership in the popular Farm Neck Golf

Michael Schweikert Ocean Park Realty, Inc.

15 Tamarack Ln, Oak Bluffs, MA 02557
/34
$1,495,000
- 4 Beds
- 1.5 Baths
- 1,305 Sq Ft
46 Kennebec Ave, Oak Bluffs, MA 02557

Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs' allure as a premier summer destination on Martha's Vineyard. This delightful three-season cottage has been carefully modernized over the years, offering a rare investment opportunity. Located

Michael Schweikert Ocean Park Realty, Inc.

46 Kennebec Ave, Oak Bluffs, MA 02557
/11
$1,350,000
- 3 Beds
- 1.5 Baths
- 1,496 Sq Ft
44 Iron Hill Rd, Oak Bluffs, MA 02557

Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca Farm. This property at the end of a cul de sac on Iron Hill Road is filled with possibilities. This 1.6-acre has 60,000 sq ft+ and can therefore accommodate up to 6 bedrooms with the 10,000 sq ft per bedroom rule. Intended to be a guest house to a future-built main house, the current home is 3-bedrooms

Cheri Mason LandVest MV

44 Iron Hill Rd, Oak Bluffs, MA 02557
/16
$1,350,000
- 3 Beds
- 1.5 Baths
- 1,496 Sq Ft
44 Iron Hill Rd, Vineyard Haven, MA 02568

Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca Farm. This property at the end of a cul de sac on Iron Hill Road is filled with possibilities. This 1.6-acre has 60,000 sq ft+ and can therefore accommodate up to 6 bedrooms with the 10,000 sq ft per bedroom rule. Intended to be a guest house to a future-built main house, the current home is 3-bedrooms

Cheri Mason Landvest MV

44 Iron Hill Rd, Vineyard Haven, MA 02568
/46
$1,795,000
- 3 Beds
- 2.5 Baths
- 1,406 Sq Ft
17 John Wesley Ave, Vineyard Haven, MA 02568

Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor

kyle Neyer Tea Lane Associates

17 John Wesley Ave, Vineyard Haven, MA 02568
/18
$899,000
- 1 Bed
- 1 Bath
- 960 Sq Ft
1 Onondaga Ave, Oak Bluffs, MA 02557

Charming Single Story Cottage on a Beautiful Oak Bluffs Lot - Perfect for Your Vineyard Retreat! Discover the timeless appeal of this cozy 1-bedroom, 1-bath home nestled on a spacious 0.31-acre lot in the heart of Oak Bluffs. Built in 2000 and lovingly owned by the same family since its inception, this property offers a fantastic opportunity for both comfortable living and future expansion.

Leslie Floyd Portfolio Real Estate Inc.

1 Onondaga Ave, Oak Bluffs, MA 02557
/23
$1,090,000
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
54 Towanticut Ave, Oak Bluffs, MA 02568

Living is Easy in this 3-bedroom 2 bath air-conditioned Ranch located 1 mile from the Center of Oak Bluffs. Features include a spacious living room with a wood-burning fireplace and lovely built-ins, an updated kitchen with granite countertops and stainless-steel appliances. The dining area has sliders leading to a spacious deck and outdoor shower overlooking the yard space with plenty of room

JoJo Lambert Island Home Realty Inc.

54 Towanticut Ave, Oak Bluffs, MA 02568
/39
$1,399,000
- 2 Beds
- 3 Baths
- 1,632 Sq Ft
35 Stevens Ave, Oak Bluffs, MA 02557

Nestled in a quiet Oak Bluffs neighborhood, this colonial-style home and its surrounding area gives the feel of being up-Island. The well-kept home was built in 2008 and is move-in ready. Located 1 mile to Circuit Avenue, and less than a mile to both the Oak Bluffs School and the Oak Bluffs Library, the property is also conveniently close to a bus stop and the bike path. Its many features include

Paul Thoutsis Dockside Real Estate

35 Stevens Ave, Oak Bluffs, MA 02557
/41
$9,900,000
- 8 Beds
- 9 Baths
- 8,560 Sq Ft
150 E Chop Dr, Oak Bluffs, MA 02557

Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast

Moira Lown Coldwell Banker Realty - Wellesley

150 E Chop Dr, Oak Bluffs, MA 02557
/15
$1,149,000
- 3 Beds
- 2 Baths
- 1,596 Sq Ft
96 Manchester Ave, Oak Bluffs, MA 02557

Nestled in a quiet neighborhood less than two miles from the heart of Circuit Avenue, this contemporary cape-style home is ready to welcome you. A charming farmer's porch invites you into a spacious living area with cathedral ceilings and an open-concept design that seamlessly connects the kitchen, dining, and living spaces--perfect for gathering with family and friends. The main level features a

Michele Moore Island Real Estate

96 Manchester Ave, Oak Bluffs, MA 02557

Showing Results 1 - 40, Page 1 of 2

Massachusetts Dukes County Marthas Vineyard Oak Bluffs

Why Live in Oak Bluffs

Oak Bluffs, located in the northeast of Martha’s Vineyard, is renowned for its whimsical gingerbread houses and historical significance as a summer haven for Black Americans. This down-island town is a bustling port of entry during the summer season, where tourists disembark from ferry boats and explore attractions like Circuit Avenue, known for its T-shirts and fresh doughnuts. The town features gray-shingled beach houses overlooking the Nantucket Sound, and the commercial district offers pizza parlors, ice cream shops, and clothing stores. Oak Bluffs is home to the oldest platform carousel in the U.S., the Flying Horses Carousel, and hosts the Martha’s Vineyard African American Film Festival and a fireworks show every August. The Ritz Café provides nightlife with live music and karaoke, while the Sweet Life Café offers upscale dining year-round. Ocean Park, with its rolling hills and Victorian homes, and the Martha’s Vineyard Camp Meeting Association, with its brightly colored gingerbread houses, are notable landmarks. The town also has gray-shingled beach cottages, Cape Cods, and farmhouses. Martha’s Vineyard Regional High School, a highly rated institution, serves the island’s students. Health care is accessible at Mass General Brigham Martha’s Vineyard Hospital, which offers comprehensive services. Residents and visitors can enjoy sandy pathways along the Nantucket Sound, beaches like Inkwell Beach, and a skate park near the high school. Oak Bluffs is 10 minutes from Vineyard Haven, 15 minutes from Edgartown, and 15 minutes from Martha’s Vineyard Airport.

Learn more about living in Oak Bluffs

Home Trends in Oak Bluffs, MA

On average, homes in Oak Bluffs, Marthas Vineyard sell after 103 days on the market compared to the national average of 52 days. The median sale price for homes in Oak Bluffs, Marthas Vineyard over the last 12 months is $1,295,000, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,295,000

Median Single Family Sale Price

$1,590,000

Median 2 Bedroom Sale Price

$1,490,000

Median 1 Bedroom Sale Price

$1,495,000

Average Price Per Sq Ft

$1,122

Number of Homes for Sale

Last 12 months Home Sales

136

Months of Supply

5.60

Median List Price

$1,575,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

11%

How to Buy a Home How to Finance a Home How to Sell a Home

In Oak Bluffs, there are currently 58 houses for sale, offering a variety of options for prospective buyers. With houses ranging from $829,000 to $10,500,000, there's something for every budget. As of September, 2025 the median home price in Oak Bluffs, Marthas Vineyard is $1,575,000, while the average sale price is $1,412,220, providing insight into local market trends. On average, houses spend 103 days on the market before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options available to suit every lifestyle. Browse properties and houses for sale in Oak Bluffs, Marthas Vineyard and find the perfect place to call home.

Oak Bluffs Types of Homes for Sale

More About Living in Oak Bluffs

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage