Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio—creating an inviting connection between indoor comfort and outdoor living. The first floor also includes a bedroom with a full bath, offering ideal flexibility for guests or remote work. Upstairs, two spacious bedrooms share an updated tile bath, providing comfortable accommodations with timeless appeal. The detached studio is a great bonus offering a living area, modern kitchenette and full bath! A spiral staircase leads to an additional upper-level space, offering even more versatility for guests, creative use or a private retreat. Strong rental history!
Your Vineyard summer begins the moment you arrive. This rare, fully furnished waterfront retreat offers 175' of private shorefront on Lagoon Pond — one of Martha's Vineyard's most coveted settings. Taken to the studs in 2022 and reimagined by architect Ramsay Gourd, this bright coastal escape features soaring vaulted ceilings, white shiplap, and painted beams. Glass sliders open to bluestone terraces where water views take center stage. The open kitchen offers custom cabinetry, stainless appliances, and casual dining perfect for summer entertaining. The primary suite includes a tiled ensuite, loft, and separate entrance to patio and beach path. Two additional bedrooms with cathedral ceilings share a glass-shower bath. Outside: mahogany shower, rolling lawns, and hydrangea beds complete the quintessential Vineyard setting. Turnkey and move-in ready — kayaks included. Strong rental history with 2026 leases in place. 4-bedroom septic. Lot is elevated out of flood plain with sweeping views
Refined Vineyard living in The Preserve. Set on a knoll overlooking the pond and sweeping grasslands, this exceptional home blends classic coastal architecture with modern luxury. The expansive great room showcases cathedral ceilings, rich millwork, and abundant natural light, with three sets of French doors opening to a bluestone patio with multiple sitting areas and a heated saltwater pool. The chef’s kitchen flows seamlessly into the dining and living spaces. One wing offers a den/study and a luxurious primary suite with spa-like bath and dressing room, while the opposite wing features three guest bedrooms, each with ensuite baths and walk-in closets. Additional highlights include a propert mudroom and a finished lower level with media room, full bath, and storage. Surrounded by mature landscaping, with easy access to trails, the bike path and Farm Neck Golf Club. The Preserve is a private enclave of luxury homes and is arguably one of Oak Bluffs most exclusive neighborhoods
Set along 125 feet of private Lagoon frontage, this beautifully designed home offers over 5,400 sq. ft. of light-filled living space across three levels. High ceilings, skylights, and walls of glass capture sweeping water views, while a decorative stone fireplace anchors the main living area. The chef’s kitchen features stainless appliances, stone counters, custom cabinetry, and a large island, complemented by a wet bar and casual dining area. Three ensuite bedrooms include a primary suite with water views, a sitting area, walk-in closet, pool access, and a spa-like bath. The walk-out lower level offers a game room, media area, kitchenette, wine storage, and bonus room. Outdoors, enjoy a heated pool, spa, bluestone terrace, and direct access to calm waters for swimming, boating, and some of the best steamers, littleneck, and cherry stones on the Island. Offered furnished with strong rental history.
Courtesy: Anchor Realty of MV
508-696-7777
In the heart of Downtown Oak Bluffs walk to everything from this Circuit Avenue location Unit #5 comes with an amazing roof top deck that is only shared with one other condo (#4). This well appointed sleeps 4 with custom wood features and a staircase to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area,, large bedroom with alcove, a sleep nook, a tiled bathroom with tub shower enclosed shower. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic views overlooking the town of Oak Bluffs and the surrounding waters. Enjoy watching the boats in the harbor or having diner under the stars, Leave the car behind you don't need it.
Courtesy: Anchor Realty of MV
508-696-7777
In the heart of Downtown Oak Bluffs this Restless Winds Penthouse condominium Unit #4 on 2nd floor comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a nautical feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom with glass enclosed shower, and a large primary bedroom that's over 16'x21'. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic views overlooking the town of Oak Bluffs and the surrounding waters. Enjoy watching the boats in the harbor or having diner under the stars, Leave the car behind you don't need it.
Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath with in-suite laundry, plus its own separate exterior entrance, perfect for added privacy or guest flexibility. Two additional guest bedrooms and a full hall bath complete the interior layout. Outdoor living is equally inviting, with a charming front deck featuring built-in bench seating, a stone patio for entertaining, and a convenient storage shed. Recent upgrades include a new roof, updated flooring, and energy-efficient mini-split systems for heating and cooling. Move-in ready and perfectly suited for enjoying the Vineyard lifestyle.
Courtesy: Island Real Estate
508-693-4800
Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live music are just a short walk from your condo.This is an end unit with beamed wood ceilings, a comfortable living room with a gas fireplace and sliders that lead to the patio. The primary bedroom has a half bath and a generous closet with extra storage space. The kitchen has been updated with granite counter tops. The recently updated full bathroom has a walk-in shower. A bonus 'sleep alcove' has twin beds (with new mattresses) and both a closet and owners closet. Picturesque grounds include gardens and green areas, a heated community pool, 3 clay tennis courts, bbq areas with fire pits, a children's playground, and a management office with resident manager apartment. This association is pet friendly. Shared washers and dryers and function rooms. There is ample parking on the property for owners. Gulph Creek Hotel management, on site, provide exceptional rental and management services for guests and owners. Their responsibilities include housekeeping, maintenance and rental bookings. Live or rent - the options are yours. There is an assessment. Please inquire. The Island Inn is seasonal, welcoming guests from April through October.
Nestled in a quiet Oak Bluffs neighborhood, this charming, sun-filled four-bedroom, two-bath home sits on a spacious corner lot and offers an ideal opportunity for both seasonal and year-round living. The home features a functional layout with a cozy wood burning stove and abundant natural light throughout. The main level offers a spacious living area open to a kitchen, both with wide plank flooring, as well as two comfortable bedrooms and access to a screened-in porch, perfect for relaxing summer evenings. Upstairs, you’ll find two extra large bedrooms and a shared bath, providing flexible space for family and guests.The enclosed backyard is well suited for gardening, entertaining, or simply enjoying the outdoors, while the nearby Lagoon town landing offers easy access for kayaking, canoeing, or launching a small boat. Ideally located walking distance to the Lagoon, less than one mile to Farm Neck, and under two miles to the heart of Circuit Ave and all Oak Bluffs has to offer.
Charming, custom-built, 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, year-round ferries, and miles of ancient way trails through acres of conservation land. Well-maintained with many decorative details, features include a large primary bedroom, a convenient first-floor bedroom, and an open kitchen dining area flowing to a spacious wooden deck and outdoor shower—perfect for indoor-outdoor living. Beautifully maintained with wood floors, skylights, and natural light throughout, this move-in-ready home blends comfort, character, and charm. The floor plan offers privacy between the 3 oversized bedrooms. Ideal for year-round living or a seasonal retreat. 4 bedroom septic system in place invites expansion.
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 & extensively UPDATED INSIDE AND OUT. Enjoy peace of mind w/ NEW septic system, siding, windows, water line from the street, & upgraded electrical & plumbing. Interior boasts new flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new heat/AC systems for year-round comfort. Recently installed professionally landscaped grounds offer curb appeal & outdoor enjoyment, complete w/ shower & patio furniture for al fresco dining & relaxing. Also included are ALL FURNISHINGS & handy owner’s shed for extra storage. An exceptional value just moments from downtown Oak Bluffs and Beaches. 5 minute walk to HARBOR. AIRBNB HISTORY $89,000 already booked Summer '26!
Courtesy: Coldwell Banker Realty
508-862-8021
RENOVATED 2 bedroom 1 full bath with laundry mobile home is located in The Park at Pocasset. Enjoy a sunlit living room and a NEW kitchen with gas range, refrigerator, sink, and cabinetry. The open floor plan has uniform NEW flooring and NEW windows enhancing the home's inviting atmosphere. Bedrooms are tucked at the back for privacy, with easy access to the bathroom and laundry area. Primary bedroom has a large walk in closet. The park is located in the village of Pocasset offering restaurants, beaches nearby and walking trails across the street. Park application requires a 700+ credit score for all residents and owners. All ages are welcome and so are your pets.
A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, this 3-bedroom, home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, new kitchen, baths, windows, doors and basement with stylish finishes throughout. Originally crafted in the Victorian era and thoughtfully restored for contemporary living, this home enjoys an unbeatable setting and is steps to beaches, ferries, restaurants, galleries, and all the conveniences of downtown Oak Bluffs.Whether cherished as a year-round residence summer retreat, or a high-demand rental, this Ocean Park home offers exceptional walkability and an unrivaled island lifestyle in one of Oak Bluffs’ most coveted locations. This listing is for Parcel One of the current Deed. The assessed value is yet to be properly recorded.
Courtesy: Ocean Park Realty, Inc.
508-693-4210
NEW CONSTRUCTION ~Welcome to Lagoon Ridge, Oak Bluffs' newest and most sought-after neighborhood. Build your 3-bedroom dream home in this elevated enclave, set 95 feet above Lagoon Pond and capturing sweeping sky views, colorful sunsets, and refreshing sea breezes. This exceptional home site represents one of the final opportunities in this thriving new community.To be built -- The Naushon -- features 3 bedrooms, 3.5 bathrooms, and over 2,400 square feet of thoughtfully designed living space. A grand wrap-around covered porch provides a welcoming entry and the perfect place to enjoy morning coffee or cool evening breezes. Inside, the open-concept floor plan connects the chef's kitchen with spacious living and dining areas, ideal for entertaining family and friends. Each bedroom suite includes a tiled en-suite bath with customizable fixtures and finishes, and the second-floor suites may offer private balconies for added relaxation. Classic Oak Bluffs cottage architecture meets modern comfort and energy efficiency, making The Naushon an ideal year-round or seasonal retreat. Lagoon Ridge offers direct access to conservation lands with walking and biking trails, and nearby Lagoon Pond invites kayaking, sailing, and shell fishing. All utilitieselectric, town water, and a private, state-of-the-art Amphidrome wastewater systemare located at the street. This innovative system serves the entire neighborhood, providing convenience and peace of mind. Lagoon Ridge is a covenant-protected community with architectural review and professional management by First Property Management Co. This beautiful home site is ready for the construction of your Vineyard dream home. Eleven lots have soldonly two remain available. Call for details!
Courtesy: Island Real Estate
508-693-4800
Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to the beach, town, bike path, and more, this home sits in a special location. It is also part of both the Cottage City and Copeland Districts. The property is over 100 years old but not on the MACRIS registry. Buyers should research the process for making major renovations.Home is being sold ''as is''. Septic is a functioning cesspool but it will need to be upgraded. Basic engineering is being completed and a septic plan is being drawn up. It will be the Buyer's responsibility to have the plan approved and complete the installation as part of the overall plan for the property. Buyers should consult an architect about the process for completing major renovations.
Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home’s original charm. Tucked privately at the rear of the property, the guest cottage offers a peaceful retreat ideal for hosting family and friends or creating a flexible living space. Located in the heart of East Chop, a close-knit and distinguished community, this property is just moments from beaches, the lively harbor, and the vibrant shops and restaurants of downtown Oak Bluffs.
Courtesy: Sandpiper Realty Inc
508-627-3737
Meadowview Farms -- This home is ideal for those who love to host lively gatherings! Set at the end of a quiet cul-de-sac, this spacious Colonial offers over 3,200 sq ft designed for comfortable living and easy entertaining. The home features four bedrooms and 2.5 baths, including a primary suite with walk-in closets and private bath. The main living area flows from a living room with fireplace into the kitchen and dining space, while a large screened-in porch creates an exceptional setting for gatherings and outdoor enjoyment. A huge second-floor bonus room provides flexible space for media, recreation, or home office use. Additional highlights include a full basement, attached two-car garage, landscaped lot, association tennis courts, and convenient access to the bike path. Just minutes to Farm Neck Golf Club and all that Oak Bluffs has to offer. shops, restaurants, beaches, harbor and all the enjoyment Oak Bluffs has to offer.
Experience the elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime 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 finest beaches. Clad in red cedar clapboard siding with an asphalt roof, the residence sits quietly above and across from Lagoon Pond, where you can enjoy water views and access to fishing, boating, kayaking and paddleboarding. The home is a harmonious balance of indoor comfort and outdoor connection. Inside, the thoughtful spacious design layout includes multiple private suites ideal for guests or multigenerational living, cherry floors and Douglas Fir doors and trim. Elevator, media room, wine cellar, fully equipped gym, lush landscaping, infinity pool, spa and waterfall - this luxury property has it all!
Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor shower, parking, and mini-split climate control; its upstairs bedroom enjoys views from Farm Pond to Nantucket Sound. Completing the property is the charming Lilac House, a fun open-concept bunk house with a full bath, water-view deck, and private outdoor shower. A wraparound porch captures sweeping ocean views, while beaches, shops, restaurants, Circuit Avenue, and the Harbor are moments away. An established rental history further enhances this rare opportunity in one of Oak Bluffs’ most iconic locations.
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 room flow seamlessly into the great room and screened porch. Spectacular dining room, reading room, laundry and 1st floor bedroom suite.The primary suite features panoramic water views, a private balcony, fireplace, outdoor shower, spa-like bath, and two dressing rooms. Seven additional bedrooms, create ample space for guests to luxuriate and relax. Lower level includes game room and gym. Outside, enjoy a sprawling lawn, decks, lush landscaping, and two outdoor showers. Close to East Chop Beach Club, Tennis Club, Yacht Club, Ferry, and Oak Bluffs shops. Be the envy of all you see!
Oak Bluffs is located in Massachusetts. Oak Bluffs, Massachusetts has a population of 5,284. Oak Bluffs is more family-centric than the surrounding county with 39.56% of the households containing married families with children. The county average for households married with children is 27.66%.
The median household income in Oak Bluffs, Massachusetts is $94,545. The median household income for the surrounding county is $77,392 compared to the national median of $69,021. The median age of people living in Oak Bluffs is 40.4 years.
The average high temperature in July is 78.9 degrees, with an average low temperature in January of 22.7 degrees. The average rainfall is approximately 47.4 inches per year, with 24 inches of snow per year.
