Oak Bluffs, MA Real Estate Search

Oak Bluffs, MA Homes for Sale

The Charm of Oak Bluffs Real Estate

Oak Bluffs, MA is a charming coastal town on the island of Martha's Vineyard known for its vibrant culture and historic architecture. The real estate in Oak Bluffs reflects the town's unique character, with many beautiful Victorian homes and cottages lining the streets. From waterfront properties with stunning views of the harbor to quaint cottages tucked away in the woods, there is a diverse range of options for buyers looking to settle down in this picturesque town.

The Investment Potential of Oak Bluffs Properties

Investing in real estate in Oak Bluffs can be a smart financial decision, as the town is a popular vacation destination with a strong rental market. Many buyers choose to purchase properties in Oak Bluffs as vacation homes or rental properties, knowing that they can generate income from short-term rentals during the busy summer months. With its prime location on Martha's Vineyard and its charming appeal, Oak Bluffs properties have the potential to appreciate in value over time, making them a sound investment.

The Amenities and Attractions of Oak Bluffs

In addition to its beautiful homes and properties, Oak Bluffs offers a wide range of amenities and attractions for residents to enjoy. From beautiful beaches and scenic walking trails to charming shops and restaurants, there is no shortage of things to see and do in Oak Bluffs. The town is also home to the historic Flying Horses Carousel, the oldest platform carousel in the country, as well as the iconic Gingerbread Cottages, a colorful historic district that is a must-see for visitors and residents alike.

Choosing a Real Estate Agent in Oak Bluffs

When it comes to buying or selling a home in Oak Bluffs, it is important to work with a knowledgeable and experienced real estate agent who understands the local market. A qualified agent can help buyers find their dream home in Oak Bluffs, negotiate the best price, and navigate the complexities of the real estate process. Sellers can also benefit from working with an agent who can help them market their property effectively and attract qualified buyers. By choosing the right real estate agent, buyers and sellers can make the process of buying or selling a home in Oak Bluffs as smooth and successful as possible.

Conclusion

Whether you are looking for a vacation home, rental property, or permanent residence, Oak Bluffs offers a wide range of real estate options to suit your needs. With its charming homes, beautiful scenery, and rich history, Oak Bluffs is a unique and desirable place to live. By investing in real estate in Oak Bluffs, buyers can not only enjoy the many amenities and attractions of the town, but also benefit from the potential financial rewards of owning property in this sought-after location.

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Oak Bluffs, MA Homes for Sale

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Newest Oak Bluffs, MA Homes for Sale

$1,575,000
3 Beds ⋅ 4 Baths ⋅ 73299369 MLS
UNLOCK THE POTENTIAL WITH THIS SUPERB LOCATION. Meadow View Farms is close to Farm Neck Golf Course, just minutes from the vibrant downtown, and the islands best beaches. This charming colonial is an incredible opportunity for those looking to put their personal touch on a Martha's Vineyard property. The home features a private entrance to the third bedroom with a private bathroom offering excellent rental or guest suite options. Whether you are looking for additional income through seasonal rentals or for extended family and guests, this set up provides fantastic opportunities for flexible living arrangements. The expansive manicured yard has abutting conservation land with walking and biking trails. A large garage offers extra space for a workshop or studio.

13 W Meadow Ln, Oak Bluffs

Listing courtesy of Listing Agent: Hourihan Group from Listing Office: Coldwell Banker Realty - Plymouth.
$1,199,900
3 Beds ⋅ 2 Baths ⋅ 73291232 MLS
Welcome to 2 Nahomon St., Oak Bluffs, MA! Set on a private 1/4-acre level lot at the end of a quiet cul-de-sac, this home offers tranquility and convenience. The first floor features an ensuite bedroom for easy single-level living. Recent upgrades include a new septic system, upgraded electrical panel, new washer and dryer, and an outdoor shower. The spacious bonus room has potential to become a 4th bedroom. Within close proximity (1 mi) to Oak Bluffs Harbor, restaurants, attractions, and beautiful beaches, this home is perfect for enjoying everything Martha’s Vineyard offers. Plentiful parking and a cozy gas fireplace complete the picture, making it an ideal year-round residence or vacation getaway! NOT IN A FLOOD ZONE! Open House Saturday October 12 10:00 AM - 12:00 PM and Sunday October 13 11:00 AM - 1:00 PM. Best and final offers due by Tuesday October 15 by 12:00 PM.

2 Nahomon St, Oak Bluffs

Listing courtesy of Listing Agent: Jarrod Smith from Listing Office: Romano Real Estate.
$1,050,000
3 Beds ⋅ 3 Baths ⋅ 73282757 MLS
Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor with sliders to the deck. The spacious primary suite occupies the entire upper level, and two bedrooms and a full bath occupy the lower level with access to a patio. There is also a 1-car garage that includes additional storage for bikes and outdoor furniture. This is an opportunity to design and create your dream space on MV.

40 Hidden Cove Unit 15, Oak Bluffs

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$999,000
3 Beds ⋅ 3 Baths ⋅ 73282756 MLS
Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor with sliders to the deck. The spacious primary suite occupies the entire upper level, and two bedrooms and a full bath occupy the lower level with access to a patio. There is also a 1-car garage that includes additional storage for bikes and outdoor furniture. This is an opportunity to design and create your dream space on MV.

40 Hidden Cove, Oak Bluffs

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$979,900
3 Beds ⋅ 2 Baths ⋅ 73282754 MLS
Great opportunity to purchase your Vineyard home. This 3-bedroom, 1.5-bath home is ready for your vision. The kitchen and living room are at the back of the house with slider doors to the deck, overlooking the spacious yard. A bedroom and half bath with laundry hook-up complete the first floor. There are two bedrooms and a full bath on the second floor. The unfinished basement offers room for storage. Located in the heart of Oak Bluffs, this home offers easy access to local shops, restaurants, the ferry, and nearby beaches and hiking trails. The property is being sold “as is”. The sale of the property is subject to approval from the Dukes County Probate and Family Court.

195 County Road, Oak Bluffs

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$2,275,000
5 Beds ⋅ 4 Baths ⋅ 73281158 MLS
Welcome to a lovely post and beam home nestled in the serene enclave of Tower Ridge which offers both privacy and an abundance of natural beauty.Upon entering the home, you are greeted by the grand living space adorned with a majestic wood-burning fireplace, serving as the focal point for large gatherings and cozy evenings alike. The property boasts both a primary home and a garage apartment ensuring comfort and convenience for all family, residents and guests.The property is graced with an oversized deck and more than 25 mature trees, including delightful fruit-bearing varieties, creating a picturesque landscape that invites relaxation and the perfect setting for entertaining. The expansive grounds provide several locations for a pool, perfect for those seeking to enhance their outdoor living experience.An exceptional feature of this property is the garage apartment which provides a rental income opportunity or offers an ideal space for guests. Nearby bike and hiking trails

35 Tower Ridge Road, Oak Bluffs

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.
$2,900,000
3 Beds ⋅ 2 Baths ⋅ 73279143 MLS
OAK BLUFFS BEACHFRONT WITH DOCK - This beautifully renovated 2024 beachfront cottage offers panoramic views of Vineyard Haven Harbor, along with a private dock and an additional parcel for extra privacy and water frontage. The three-bedroom, two-bath home combines modern upgrades with classic Vineyard charm, featuring original wood floors, beadboard walls, and a cozy gas fireplace. The living room's picture window frames stunning harbor views, while the adjacent dining area and sunroom provide ideal spaces for relaxation and entertainment. The updated kitchen is a chef's dream with new appliances, double ovens, butcher block countertops, and a farmhouse sink. The first-floor bedroom opens to an expansive deck with seating, a gas grill hookup, and an outdoor shower. Upstairs, two charming bedrooms offer designer wallpaper, beadboard accents, and refinished floors. With every detail meticulously updated, this pristine property is move-in ready for immediate enjoyment of Vineyard life.

17 Beach Road, Oak Bluffs

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$2,275,000
2 Beds ⋅ 4 Baths ⋅ 73262533 MLS
New Construction To Be Built~The Homes at Lagoon Ridge is a subdivision in Oak Bluffs of stylish, new construction properties. The "Naushon" home design is an elegant 2 bedroom, 3 full and 1 half bath home with over 2500sf of living space. Just off the foyer, the Great Room is open to the kitchen and dining area, offering an ideal space to entertain. The smart kitchen design includes stainless steel Bosch appliances and quartz countertops. For privacy, the main level guest bedroom and en suite bathroom are on the opposite side of the foyer. The spacious primary bedroom suite, on the second level, features a private bathroom with Kohler soaking tub and a tiled walk-in shower. A full bath, laundry room and loft complete this space. Enjoy the spacious backyard from your deck or covered porch and enjoy your perfect Vineyard home. *Renderings are for illustrative purposes only. Construction details are governed by builder specifications and final construction agreement with Builder.

35 Double Ox Rd, Oak Bluffs

Listing courtesy of Listing Agent: Theresa Geary from Listing Office: Donnelly + Co..
$2,350,000
2 Beds ⋅ 3 Baths ⋅ 73260532 MLS
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 baths, including a spa room, this residence offers both comfort and relaxation. The bright living room offers a gas fireplace with built-in shelving, and access to a wrap around porch and stone patio. The 2-car garage provides ample storage space. Located just minutes from downtown Oak Bluffs, this home offers convenience and charm. Don't miss the opportunity to own this fantastic property.

30 Franklin Ave, Oak Bluffs

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..
$235,000
1 Baths ⋅ 73256642 MLS ⋅ ['Island Inn'] BLDG.
Island Inn is the quintessential “condotel,” for buyers who want their vacations and easy income too! The popular Island Inn offers grassy grounds, tennis, pool, charcoal grills, fire pits, playground, and event hall. Easy access to State Beach and in-town Oak Bluffs. There’s no need to worry about caretaking from afar. Vacasa, the on-site management company, takes care of bookings, cleanings and routine maintenance to ensure the best experience. The compound is open six-plus months, from April-October. Unit 12 is a fully equipped studio with easy ground level access and is located at the more peaceful end of the compound. The unit is offered fully furnished. Kick back on your patio with a beverage at the end of a long day of play or run the toddler about the lawn till bedtime. For a livelier evening, hang out at family-friendly Noman’s, just across the lawn. Showings inside the unit are scheduled only between tenants.

27 Island Inn Rd Unit 12D, Oak Bluffs

Listing courtesy of Listing Agent: Kristin Buck from Listing Office: Donnelly + Co..
$1,695,000
3 Beds ⋅ 2 Baths ⋅ 73249801 MLS
Welcome to 12 Mae Avenue, a 3-bed, 2-bath home with 1,700sf of Martha's Vineyard charm. Nestled in Oak Bluffs' sought-after Lagoon area, this gem offers panoramic Lagoon views from almost every angle. The first floor features a full bathroom and three generous bedrooms, including a primary bedroom with its own ensuite bathroom. The rear door leads to a covered porch with two roomy swings. The second floor boasts a spacious living room with vaulted ceilings, a dining room, and a kitchen with stunning views. Step outside to the upper porch, where automatic awnings provide shade for outdoor dining and entertainment. With its ideal location near the Lagoon and downtown Oak Bluffs, this home is the quintessential Martha's Vineyard retreat, offering a classic charm with a touch of vintage allure. Don't miss your chance to make this island paradise your own and take advantage of its solid rental history.Furnishings available for separate purchase / negotiation.

12 Mae Avenue, Oak Bluffs

Listing courtesy of Listing Agent: David Dickinson from Listing Office: Compass.
$2,490,000
3 Beds ⋅ 2 Baths ⋅ 73246461 MLS
Nestled in Oak Bluffs on Martha's Vineyard, this cherished family home on Greenleaf Avenue blends historical charm with coastal serenity. With only ten homes in this exclusive locale, it's a rare find. Enjoy panoramic views from the rooftop deck, the highest point on Greenleaf Ave, overlooking Lakeside Park, Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. Architecturally designed to echo local cottages, it seamlessly integrates with Oak Bluffs' aesthetic.For 27+ years, this residence has been a source of family memories, featuring 3 bedrooms, a finished basement, and a multipurpose building. Situated on a tranquil side street, it's close to Oak Bluffs' vibrant community life yet offers a peaceful retreat. Embrace the town's traditions like Illumination Night and fireworks while enjoying a quiet oasis. This property isn't just a home; it's a gateway to the enchantment of Oak Bluffs—a rare chance to continue a legacy of memories in Martha's Vineyard's embrace.

22 Greenleaf Avenue, Oak Bluffs

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$13,200,000
8 Beds ⋅ 9 Baths ⋅ 73245479 MLS
Welcome to your dream retreat in Oak Bluffs. A magnificent 8 br oceanview estate. This property is designed to accommodate family and friends with ease while offering an elegant and serene enviroment for all to enjoy.The open floor plan of the main living areas ensures a seamless flow between the living room, dining room, and kitchen, making it perfect for entertaining. High ceilings and large windows flood the space with natural light and provide spectacular water view from every angle. The state-of-the-art kitchen is a chef's delight, featuring high-end appliances, ample counter space, and a large island that doubles as a breakfast bar. Custom cabinetry and elegant finishes complete this culinary haven. Most rooms feature ensuite baths and large windows that offer stunning water views. In addition to the main living room, the property includes several sitting areas, a media room, and a game room, ensuring there's always a perfect spot for relaxation and entertainment.

150 East Chop Drive, Oak Bluffs

Listing courtesy of Listing Agent: Reciprocal Reciprocal from Listing Office: Cape Cod Reciprocal.
$1,595,000
1 Beds ⋅ 1 Baths ⋅ 73241592 MLS
East Chop Harbor Front Luxury Condominiums -- Location, location, location -- This 1-bedroom, waterfront condominium unit, the "Captain's Quarters", features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40’ T at the end for a 9th boat. Each condo unit includes a designated parking space for one vehicle. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations.

47 East Chop Drive Unit 5, Oak Bluffs

Listing courtesy of Listing Agent: Perry Patterson from Listing Office: MV Luxury Homes LLC.
$2,095,000
2 Beds ⋅ 1 Baths ⋅ 73240524 MLS ⋅ ['East Chop Harborfront Apts/Condominiums'] BLDG.
East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condominium, the "Tivoli", features outstanding water views of the harbor and the sound beyond all the way to Chappaquiddick. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living and dining areas and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include a private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40’ T at the end for a 9th boat. Each unit includes a designated parking space for one vehicle. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, and dredged dockage.

47 East Chop Drive Unit 4, Oak Bluffs

Listing courtesy of Listing Agent: Perry Patterson from Listing Office: MV Luxury Homes LLC.
$2,095,000
2 Beds ⋅ 1 Baths ⋅ 73240350 MLS ⋅ ['East Chop Harborfront Apts/Condominiums'] BLDG.
East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, waterfront condominium, the "Highlands", features outstanding water views of the harbor, the sound and the Cape beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 2nd floor unit includes new kitchen with Bosch appliances, living and dining areas and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include a private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40’ T at the end for a 9th boat. Each unit includes a designated parking space for one vehicle. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, and dredged dock.

47 East Chop Drive Unit 3, Oak Bluffs

Listing courtesy of Listing Agent: Perry Patterson from Listing Office: MV Luxury Homes LLC.
$1,595,000
1 Beds ⋅ 1 Baths ⋅ 73240214 MLS ⋅ ['East Chop Harborfront Apts/Condominiums'] BLDG.
East Chop Harbor Front Luxury Condominiums -- This 1-bedroom, waterfront condominium, "Cottage City", features outstanding water views, cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 1st-floor unit includes new kitchen with Bosch appliances, living room with fireplace, dining area and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40’ T at the end for a 9th boat. Each condo unit includes a designated parking space for one vehicle. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, and dredged dockage.

47 East Chop Drive Unit 2, Oak Bluffs

Listing courtesy of Listing Agent: Perry Patterson from Listing Office: MV Luxury Homes LLC.
$1,595,000
1 Beds ⋅ 1 Baths ⋅ 73240160 MLS ⋅ ['East Chop Harborfront Apartments/Condomi'] BLDG.
East Chop Harbor Front Luxury Condominiums -- Location, location, location -- This 1-bedroom, 1st floor, waterfront condominium, "Oak Bluffs", features outstanding water views of the harbor and sound beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock with water/electric for 8 slips and a 40’ T at the end for a 9th boat; Each condo unit includes a designated parking space for one vehicle. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations. Occupancy beginning 11/1/24.

47 East Chop Drive Unit 1, Oak Bluffs

Listing courtesy of Listing Agent: Perry Patterson from Listing Office: MV Luxury Homes LLC.
$14,000
5 Beds ⋅ 3 Baths ⋅ 73209866 MLS
Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and hardwood throughout. First floor bathroom and bedroom. Updated bathrooms. Fans and flatscreen TVs in each of the five-guest rooms. PRICES REFLECT PRIME SUMMER WEEKLY RATES. Weekly Prime Rates $14,000-$17,000/wk. Available for 3-Night Weekend Fall/Spring. Tax, Cleaning and Deposit required. INQUIRE.

55 Samoset Ave, Oak Bluffs

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.
$28,500
9 Beds ⋅ 7 Baths ⋅ 73193364 MLS
**PEAK SUMMER WEEKLY RATE** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and distinctive design. TV lounge, two first floor bedrooms one queen, one bunk queen/full, shared full bathroom, powder room and laundry. 2nd level features king primary ensuite with vaulted ceilings, secondary primary with rooftop deck and fabulous water views, two additional queen guest rooms and one shared full bath. Expansive covered porch, rocking chairs, outdoor dining, private patio, BBQ grill, outdoor shower, parking for four. Internet, A/C and cable TV. Guest house; three bed, two full bath and two kitchens. Prices vary weekly $28,00-$40,000/wk plus tax and security. Inquire for availability.

9 Tuckernuck Ave, Oak Bluffs

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.
$6,750
3 Beds ⋅ 3 Baths ⋅ 73190837 MLS
***PRICE REFLECTS WEEKLY SUMMER RATE*** 3 Bed, 3 Bath home located close to downtown Oak Bluffs; shopping, restaurants and beaches. Enjoy spacious living and enjoyment with dining for 8 guests. Two adjacent living areas invite gathering and relaxation and features large flat screen TV with cable, board games and pullout sofa. Hi-speed WIFI throughout. Full kitchen highlighted by stainless appliances, dishwasher, oven, microwave, keurig coffee maker and all cooking essentials. First floor laundry and powder room. Second level features three spacious guest rooms each with flat screen TV's and mini split climate control. Shared full bath with shower/tub. Primary ensuite full bathroom and walk-in closet Hardwood flooring throughout. Lush lawn and outdoor shower (new this season!!). Large deck affords living and dining and cooking on the Weber BBQ grill. Parking for 4 cars. Inquire for availability. Rates vary. Cleaning, Taxes and Security Deposit additional.

18 Hampson Ave, Oak Bluffs

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.
$1,995,000
3 Beds ⋅ 2 Baths ⋅ 73186012 MLS
Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the covered porch. Watch the ferries come and go and delight in the dazzling colors of the setting sun. Recent renovations include raising the house and the pouring of a foundation offering an additional 930 square feet of lower level living area. Experience true Vineyard living at its best, just steps away is easy access to the Lagoon with clamming, swimming, and boating. Bring your vision to the open and airy studio/ bunkhouse that is included in this offering at 60 Bay View Avenue and features the same wonderful vistas. Two unbuildable lots abut this property so you will never lose sight of the b

2 East Side Road, Oak Bluffs

Listing courtesy of Listing Agent: Carol Shore from Listing Office: Donnelly + Co..
$20,000
5 Beds ⋅ 3 Baths ⋅ 73126946 MLS
THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone patio, private cobblestone driveway, comfortable beds, pillows and mattresses encased in (non-vinyl) water and allergen proof protectors. COVID-19-conscious cleaning and disinfecting are done regularly. *Bathmats and kitchen towels are supplies.AVAILABLE ALL YEAR ROUND, CHECK THE CALENDAR FOR RATES.

55 Samoset Ave Ob503 Unit 1, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$1,999,000
3 Beds ⋅ 4 Baths ⋅ 73120084 MLS
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!

28 Rogers Way, Oak Bluffs

Listing courtesy of Listing Agent: Michele Casavant from Listing Office: Vineyard Village Realty.
$11,000,000
7 Beds ⋅ 6 Baths ⋅ 73112884 MLS
East Chop waterfront – Once in a lifetime, a property of this caliber becomes available, with an on-the-water East Chop location, a wide range of amenities, and multi-functional use! Uses include -- 1.) Currently operated as East Chop Harborfront Apartments (6 units), a pre-existing non-conforming use for the past 40+ years, 2.) Use it as a residential home or family compound, or live in a portion and rent a portion, 3.) Potential to convert to condominiums, paperwork presently in process but would be a buyers choice. Located directly on the harbor, this property features outstanding water views of the harbor and sound beyond and is just steps from the tennis club, beaches, ferries to the mainland and downtown. In pristine condition, this 6-unit property includes a 106 ft dock with water/electric for 8 slips and a 40’ T at the end for a 9th boat. Parking for 6-7 vehicles at street in front. Built in 1952, the property has had extensive top to bottom renovations.

47 East Chop Drive, Oak Bluffs

Listing courtesy of Listing Agent: Perry Patterson from Listing Office: MV Luxury Homes LLC.
$6,500
2 Beds ⋅ 2 Baths ⋅ 73087124 MLS
**NOW BOOKING SUMMER 2024** Charming pond front home sleeps 6 guests comfortably. Open living/dining with hardwood flooring, cathedral ceilings, stainless appliances, island eatery, dining for 6. Deck with pond views, outdoor seating, dining and BBQ grill. Living room with comfortable wrap around couch and large flatscreen TV. 2 Full bathrooms with shower/tub combo. Lower level with; one king bedroom w/Lg Flatscreen TV, direct access to covered bluestone patio w/chaise lounges, additional guest bedroom with twin/double bunk. BONUS SLEEPING SPACES include loft with full bed,TV and mini fridge, and detached finished building with queen bed, seating area, refrigerator and dining area. Gorgeous gardens, expansive lawn and a fabulous children's play structure on site. PRICE REFLECTS WEEKLY SUMMER RATES. Rates Vary Weekly $5,500-$6500 per week. Taxes and Fees apply. Inquire for availability.

4 Elisha Lane, Oak Bluffs

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.
$12,500
4 Beds ⋅ 2 Baths ⋅ 72423911 MLS
THIS IS A SUMMER RENTAL ONLY. This antique Vineyard home is thoughtfully styled with classic country-chic interior decor. The wraparound porch has plenty of room to enjoy people watching or sipping ice cold tea, perfect for a hot summer day. Alternatively, you can enjoy peering down the street from the master bedroom which opens up to a charming porch with plenty of room for two to enjoy coffee or drinks. This house is just a hop skip and a jump from Circuit Ave. and right next to Niantic park which has basketball, pickle-ball, tennis courts and a playground that are open to the public.

11 Wamsutta Ave, Ob540, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$40,000
4 Beds ⋅ 3 Baths ⋅ 72419593 MLS
THIS IS A SUMMER RENTAL ONLY. Gracious 4 bedroom home with private beach access and tennis. This home has a reverse design that has been fully renovated and thoughtfully decorated. There is a large deck overlooking gardens and a peep of the water. A separate studio is attached by the deck. You are a short distance from town, less than a mile to the public beach and a minutes to a beautiful private beach.

38 Farm Pond, Ob524, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$20,000
3 Beds ⋅ 1 Baths ⋅ 72420544 MLS
THIS IS A SUMMER RENTAL ONLY. 1900 Oak Bluffs Victorian. Ten minute walk to Nancy’s restaurant/downtown OB and 1/2 mile walk to Jetty beach in East Chop. The house was purchased empty in 2018 so all furnishings are new and the house is freshly painted. On the second floor, there are 3 bedrooms and a full bathroom, which connects to hall and master bedroom. Two bedrooms include queen beds and one bedroom includes a full bed and a set of twin bunks. On the first floor, there is a large living room connected to a sleeper den, which provides great common area for playing board games and relaxing after a day at the beach. The living room includes a 50” tv with cable and x-box, which can be used as a dvd. Small bathroom with shower on the first floor connects to the kitchen which has an eat in kitchen, with seating for 6. Great covered front porch for your morning coffee or a glass of wine under the outdoor lights.

67 New York Ave Unit OB536, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$21,000
3 Beds ⋅ 2 Baths ⋅ 72420585 MLS
THIS IS A SUMMER RENTAL ONLY. Centrally located to Edgartown, Vineyard Haven and Oak Bluffs. Just a short drive will take you to any of the town beaches and the Sailing Camp Park is a quick bike ride away. The home is located on over a 1/2 acre of landscaped property in a beautiful, private, neighborhood, with private roads great for biking and is wonderful for families, friends or even a romantic getaway. The community is exclusive to guests and is tranquil and quiet. The bike path and bus route is located right off of the community and is a breeze to get to. Within a very short walk is the State Park with jogging trails and places to explore.

24 Deer Run Rd. Unit OB521, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$24,000
3 Beds ⋅ 2 Baths ⋅ 72849969 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include high-speed wifi, Sonos, cable, HBO, Netflix and Hulu. Updated appliances and a fully equipped, modern kitchen complete this wonderful home. This is a perfect place to fully experience all the possibilities of Oak Bluffs. Circuit Avenue and town favorite Jetty Beach are each just 1/2 mile away. Enjoy expansive outdoor space: relax in a large, shaded backyard.

5 Laurel Ave Ob532, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$13,000
4 Beds ⋅ 3 Baths ⋅ 71721689 MLS
PRICES ARE WEEKLY NOT MONTHLY. Located in Waterview Farms, this four bedroom home features a private beach on Sengekontacket Pond, private dock access to Land Bank boat launch and several walking trails. Just minutes to Farm Neck Golf Course, beaches and town.

14 Pulpit Rock Drive, Ob501, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$20,000
3 Beds ⋅ 3 Baths ⋅ 72850076 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms on the first and third floors. Nicely decorated and just a great place to enjoy yourself.

40 Hidden Cove 5 Ob537, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$40,000
6 Beds ⋅ 3 Baths ⋅ 71303478 MLS
THIS IS A SUMMER RENTAL ONLY. Watch the boats come and go from the harbor while you picnic and relax on your beach. This fabulous waterfront three bedroom main house and three bedroom guest house also offers your own dock and mooring.

120 Eastville Ave Ob520, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$20,000
4 Beds ⋅ 2 Baths ⋅ 72849934 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

291 Barnes Rd Ob516, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$21,000
6 Beds ⋅ 2 Baths ⋅ 72430053 MLS
THIS IS A SUMMER RENTAL ONLY. EAST CHOP LOCATION!! Located across from the historic Baptist Temple Town Park. This charming 1885 Victorian cottage is original to days gone by and a significant part of the Vineyard Highlands. Six bedrooms and two full bathrooms allow for friends and family to visit along with a cozy, bright vintage kitchen. This is a house of distinctive "Carpenter Gothic" construction built by the architect G.A. Rice on one of the highest points of Oak Bluffs.

12 John Wesley Ave Ob519, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$56,000
4 Beds ⋅ 3 Baths ⋅ 71298769 MLS
THIS IS A SUMMER RENTAL ONLY. This home offers a spacious open floor plan providing a comfortable yet elegant retreat, truly an upscale surprise, perfect for relaxing or entertaining. With an expansive mahogany wraparound deck, sweeping views and a screened-in porch, enjoying the evening sunsets while grilling and dining al fresco or try a nearby bistro or 5 star restaurant----the choice is yours.

337 Barnes Rd, Ob526, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$6,500
3 Beds ⋅ 3 Baths ⋅ 72420641 MLS
THIS IS A SUMMER WEEKLY RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Victorian Cottage located on Ocean Park in the heart of Oak Bluffs with fully equipped and updated kitchen, five bedrooms and three baths, cozy living spaces and multiple amenities will accommodate your family and friends. Smell the sea air and watch the waves break from your front porch. This charming beach house is steps away from Circuit Avenue, a plethora of restaurants, Flying Horses carousel, The Strand movie theater, Steamship Authority ferries and of course the beach overlooking Nantucket Sound.

23 Ocean Ave. Unit OB539, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$64,000
4 Beds ⋅ 7 Baths ⋅ 72850038 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in dining overlooking the pool. The first floor has a master bedroom with waterviews and private bath. There are two additional en suite bedrooms on the second floor with an open sitting area looking over the main floor living area out towards the water. The lower level is a great entertaining space with a pool table, poker table and kitchenette. The fourth bedroom is also on this level with a private bath. On the other side of the bedroom there is a small exercise room. Enjoy the outdoor heated pool or take a walk down to the small beach on the lagoon. The outdoor kitchen is non-functioning .

385 Barnes Rd Ob534, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$12,000
3 Beds ⋅ 2 Baths ⋅ 71296098 MLS
THIS IS A SUMMER RENTAL ONLY. This irresistible home is a 3-minute walk away from a deeded, sandy, sheltered beach and only a 5-minute drive to the center of Oak Bluffs and all the fun activities that Circuit Avenue has to offer. The casual getaway has wonderful ambiance enhanced by its soaring ceilings, a wood-burning fireplace, and delightful furnishings.

8 Beach Plum Path, Ob525, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$14,200
3 Beds ⋅ 2 Baths ⋅ 72845556 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

59 Prospect Ave Ob502, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
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