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18 Sylvan Avenue, Tisbury
$2,095,000
4 Beds ⋅ 4 Baths ⋅ 73571249 MLS
Welcome to 18 Sylvan Avenue, a delightful, custom-crafted four-bedroom, four-bath, contemporary-style home set at the end of a quiet neighborhood road in Vineyard Haven. Surrounded by eight acres of conservation land, the property offers a peaceful setting with a spacious wraparound deck overlooking the natural landscape. It truly feels like its own private enclave, both inside and out. The home is in pristine, move-in-ready condition and has been thoughtfully renovated and meticulously maintained by the current owners. A welcoming entry leads directly into the open-concept space where a well appointed living room with fireplace flows into the dining area and kitchen. Positioned to the right of the entry is the primary bedroom suite, while two additional bedrooms and two bathrooms are tucked beyond the kitchen on the opposite side of the home, creating a functional and well designed layout which maximizes privacy. A finished lower level with a full bathroom and laundry provides additional flexible living space or a fourth bedroom. Skylights and sliders throughout the home fill the interior with natural light and create an easy connection to the multiple decks, beautiful mature gardens and woodlands. With an impressive rental history, this unique property is offered turnkey, making it an ideal opportunity as a year-round residence, Island retreat, or investment property. A true gem, conveniently located only 1.5 miles to Vineyard Haven’s Main Street shops, restaurants and ferry terminal, and only 5 miles to all that downtown Oak Bluffs has to offer! Please note there is ducted HVAC and mini splits for both heat and AC as well as radiant heat in the floors throughout both levels. Property is located in the Lagoon Pond Watershed, septic will require an upgrade after transfer. Seller will include a four bedroom septic design.

18 Sylvan Avenue, Tisbury

no property photo
$389,000
1 Beds ⋅ 2 Baths ⋅ 22604260 MLS
Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommodating up to six guests, the unit features one bedroom with a queen bed, a separate sleeping area partially divided by a 4' wall with two single beds, a sofa bed, 1.5 baths, and a small kitchen with a two-burner cooktop. The Island Inn is a seasonal resort community, open April-October, with beautifully maintained grounds, heated pool, three association clay tennis courts, outdoor fire pits, and easy access to downtown Oak Bluffs, beaches, restaurants, shops, ferries, golf, and boating. The popular Noman's outdoor family restaurant is directly next door, offering dining, cocktails, lawn games, live entertainment, and a pet-friendly atmosphere. Gulph Creek Management is conveniently located on site and handles rentals, bookings, cleaning, repairs, and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required

21 Island Inn Road, Oak Bluffs

no property photo
$287,500
1 Beds ⋅ 1 Baths ⋅ 22604264 MLS
Welcome to 27 Island Inn, Unit 9C, an inviting Martha's Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-bath suite accommodating up to four guests with a queen bed, sofa bed, cozy living area, well-equipped kitchenette with 2-burner cooktop, and patio/deck. Units 9C and 10C can be enjoyed separately or together through the adjoining door. Each is being offered for sale separately, with the opportunity to purchase both together—ideal for additional family, guests or expanded rental possibilities. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular and pet-friendly Noman's, offering outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, you're minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required.

27 Island Inn Road, Oak Bluffs

no property photo
$310,000
1 Beds ⋅ 1 Baths ⋅ 22604263 MLS
Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha's Vineyard retreat offering an ideal combination of personal enjoyment and rental opportunity. Accommodating up to four guests, 10C features a queen bedroom, sofa bed, cozy living area, well-equipped kitchenette. A unique feature is the adjoining door to Unit 9C, a studio with two double beds, full bath and kitchenette. Units 9C and 10C are being offered for sale separately, with the opportunity to purchase both together—perfect for extended family, guests, or expanded rental possibilities while still allowing each unit to be used independently. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular pet-friendly Noman's, featuring outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, just minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required.

27 Island Inn Road, Oak Bluffs

no property photo
$260,000
1 Beds ⋅ 1 Baths ⋅ 22604259 MLS
Welcome to 27 Island Inn, Unit 25F, a comfortable studio offering the perfect combination of a Martha's Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular pet-friendly Noman's, featuring outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, just minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance, making ownership easy and convenient. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required.

33 Island Inn Road, Oak Bluffs

24 Towanticut St, Oak Bluffs
$789,000
73568028 MLS
OAK BLUFFS - EIGHT (8) BEDROOM LOT. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time. Convenient access from both Towanticut Avenue and Oak Avenue, increases flexibility for design options, access and privacy. Walking distance to Oak Bluffs Harbor, Oak Bluffs Library, Sunset Lake, Campground cottages, shops, restaurants, Oak Bluffs Ferry, beaches and local entertainment. This property is ideal for seasonal enjoyment, multigenerational living, or a strong rental in one of Martha’s Vineyard’s most desirable markets. A chance to acquire a ready to build lot with tons of potential, substantial bedroom capacity, options for two structures, offering long-term and enduring value & BUILDING PERMIT in place for an ADU. This could be yours! Ready to go.

24 Towanticut St, Oak Bluffs

21 Vickers Street, Edgartown
$3,075,000
3 Beds ⋅ 2 Baths ⋅ 73567342 MLS
Katama at its best ~ WITH A POOL! Set in one of Martha’s Vineyard’s most coveted locations, 21 Vickers Street is a classic beach home with an effortless connection to everything that makes Katama so special. Just one mile from South Beach, with the bike path, Katama General Store, and Edgartown Village close by, this updated, move-in-ready home puts the best of the Island within easy reach. A newly installed pool and expansive yard create a private setting for summer days and long afternoons outdoors. Inside, the kitchen features an inviting banquet dining area and opens to a spacious cathedral-ceilinged family room with sliders to the back deck, outdoor shower, pool, and yard. A separate living room provides another gathering space, while a first-floor bedroom and full bath offer flexibility for family and guests. Upstairs, two generous bedrooms share a full bath. The full basement provides ample storage for bicycles, beach chairs, paddleboards, and all the essentials of Vineyard life. With the ability to tie into town sewer for up to six bedrooms, the property also offers exciting possibilities for the future. The very best of Katama comes together here with a coveted location, a classic Vineyard home, and an easy way to enjoy everything that makes summer on Martha’s Vineyard so special. Sale is contingent on seller finding another home.

21 Vickers Street, Edgartown

no property photo
$2,875,000
3 Beds ⋅ 3 Baths ⋅ 22604139 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 96 at 131 N. Water Street is a beautifully appointed 1061± sq. ft., second and third-floor condominium featuring 3 beds and 3 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cooktop, microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits,.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 96 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

131 N Water Street, Edgartown

no property photo
$1,975,000
2 Beds ⋅ 2 Baths ⋅ 22604140 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 94 at 131 N. Water Street is a beautifully appointed 730± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 94 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

131 N Water Street, Edgartown

no property photo
$2,595,000
2 Beds ⋅ 2 Baths ⋅ 22604141 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 22 at 131 N. Water Street is a beautifully appointed 960± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. An in-unit washer/dryer, outdoor shower, and elevator access add everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. A rare opportunity to own a luxury residence at one of Martha's Vineyard's most celebrated destinations. Harbor View Hotel retains a Right of First Refusal as outlined in the Master Deed. An owners caged-in storage area is in the basement.

131 N Water Street, Edgartown

no property photo
$2,425,000
2 Beds ⋅ 2 Baths ⋅ 22604138 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 62 at 131 N. Water Street is a beautifully appointed 865± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cook-top stove, microwave, and refrigerator/freezer. An outdoor shower adds to everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Harbor View Hotel retains a Right of First Refusal as outlined in the Master Deed. Washer/Dryer and dedicated storage area located in Cottage #5.

131 N Water Street, Edgartown

53 Circuit Avenue, Oak Bluffs
$5,500,000
6 Baths ⋅ 73566891 MLS
Exceptional mixed-use property in the heart of Oak Bluffs thriving high-foot-traffic Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, this distinctive building combines sophisticated commercial and residential spaces with outstanding craftsmanship and state-of-the-art systems. The street level is 2,320 sf and offers exceptional flexibility for restaurant-bar and/or retail operators (a commercial kitchen and bar remain intact) and includes three handicapped accessible half baths and a covered rear exterior loading area. A very large newly excavated 1,717 sf basement provides rare clean, dry storage and auxiliary operational space. The second-floor with 1,669 sf, features two residential apartments, totaling six bedrooms and three full baths for income potential or owner flexibility. Formerly housing an A&P grocery store (The Great Atlantic & Pacific Tea Company) and 99-occupancy restaurants, the property presently houses an upscale retailer while retaining its restaurant-bar infrastructure for future use.

53 Circuit Avenue, Oak Bluffs

no property photo
$2,500,000
4 Beds ⋅ 3 Baths ⋅ 22604104 MLS
Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

9 Codman Spring Road, Edgartown

59 Hagerty Drive, Tisbury
$6,150,000
6 Beds ⋅ 7 Baths ⋅ 73565263 MLS
Tucked away on a quiet street in coveted West Chop, this pristine property offers exceptional privacy, stunning scenery, and easy access to downtown Vineyard Haven. Designed for effortless indoor-outdoor living, this sophisticated compound combines timeless charm with every modern amenity. The first floor features an inviting open-concept layout ideal for both relaxed family living and entertaining. The kitchen overlooks the dining area, an intimate sitting area, and a versatile game and reading area beyond. The spacious TV and family room features custom built-in bookcases and French doors that open onto a bluestone patio and the pool area beyond. A generous screened porch provides additional living space. Completing the first floor is a large guest bedroom with an ensuite bath, along with a powder room, pantry, mudroom, and laundry room. Upstairs, the gracious primary suite features vaulted ceilings, a sitting area, and a luxurious bath with a soaking tub. There are two additional guest bedrooms, each with an ensuite bath. A private sun deck overlooks the pool and beautifully landscaped grounds, offering a wonderful spot to relax and enjoy distant water views. A dedicated office with water views toward Woods Hole and the Elizabeth Islands provides an inspiring setting for work or quiet retreat. Above the garage, a separate one-bedroom apartment offers a full kitchen, bath, and laundry, with convenient interior and exterior access. The living space in the apartment is currently being used as the sixth bedroom. Outside, the property transforms into a private oasis. The upper garden patio features an inviting sofa seating, while a stone staircase leads down to the heated 20' x 40' pool with spa. The expansive pool terrace is furnished with comfortable loungers and the pool cabana provides additional seating and a welcome retreat from the sun, all surrounded by lush, mature plantings. Other amenities include a gym, two enclosed outside showers and a pool powder room. With its exceptional privacy, generous living spaces, water views, pool and cabana, guest accommodations, this stunning property is truly one of the Grand Dames of West Chop.

59 Hagerty Drive, Tisbury

no property photo
$2,850,000
6 Beds ⋅ 2 Baths ⋅ 22604053 MLS
Two side by side cottages built in 1945 Directly Pondfront on Sengekontacket with 180 degree views over the pond out to the Causeway, State Beach, Nantucket Sound and beyond. A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beach, Nantucket Sound and beyond. Set along the Boulevard, behind a traditional white picket fence, this .66 acre property features two side-by-side cottages dating back to the 1940s and captures the relaxed character of an earlier Vineyard. The larger cottage is a quintessential Vineyard retreat with beautiful direct waterviews from the Main living areas, dining area and porch. Upstairs, a sitting area and small upper deck provide exceptional views across Sengekontacket Pond to State Beach extending out towards Cape Cod. The porch and the spacious lush side yard with lawn and lovely plantings, offer an inviting setting for morning coffee, summer dinners, entertaining, or simply enjoying the changing light and activity on the water. The larger cottage has an established rental history. An attractive option for seasonal rental income. The second smaller cottage offer the opportunity for a new owner to renovate and make the space their own as additional living space, a guest cottage or studio, subject to applicable approvals. Another compelling option is to explore removing the cottages and combining the existing square footage together with a percentage of additional square footage as allowed, to create one larger residence to take full advantage of this extraordinary waterfront setting. Any renovations, expansion or redevelopment would be subject to all applicable approvals and zoning regulations. Additionally, just a stone's throw away, the nearby boat landing provides convenient access to the pond, with openings into the Nantucket Sound, for launching kayaks, paddleboards and trailered boats. putting one of the Vineyard's most beautiful waterways practically at your doorstep. With two cottages, acreage, established rental history, convenient boating access and remarkable views.#49 The Boulevard offers a special opportunity to enjoy a classic Vineyard property today while imagining and planning its possibilities for the future.

49 The Boulevard, Edgartown

8 Turkeyland Cove Road, Edgartown
$3,650,000
73565039 MLS
Set in the heart of Katama, this exceptional 5.5-acre building lot offers a rare opportunity to create a private island retreat surrounded by nature and conservation land. The property is bordered by 87 acres of Sheriffs Meadow conservation land and an additional 75 acres of town-owned land, providing an extraordinary sense of privacy and protected open space. Located in a well-established Katama neighborhood, the property captures the essence of the island lifestyle, with the sights, sounds, and salt air of the Atlantic Ocean close by. Just minutes from South Beach and Wilson’s Landing, easily enjoy swimming, boating, fishing, and long summer days by the water. A remarkable opportunity to build in one of the Vineyard’s most coveted settings, with expansive protected land and the beauty of Katama all around.

8 Turkeyland Cove Road, Edgartown

no property photo
$2,200,000
2 Beds ⋅ 2 Baths ⋅ 22604013 MLS
This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious Studio with fireplace. A gunite swimming pool, gardens, expansive lawn areas, outdoor shower, and one-car garage complete the setting. Renovated in 2013 and equipped with central air conditioning, the property feels wonderfully secluded while remaining centrally located for convenient access to both up and down Island destinations. The current septic system meets all regulations and is designed for four bedrooms. Converting the Studio into an ADU is possible, and the permitting path forward has been identified by the building inspector. Enjoy effortless access to Lambert's Cove Beach, 7a Foods, State Road Restaurant, and all the iconic West Tisbury landmarks.

99 Oak Lane, West Tisbury

99 Oak Lane, West Tisbury
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 73564420 MLS
This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious Studio with fireplace. A gunite swimming pool, gardens, expansive lawn areas, outdoor shower, and one-car garage complete the setting. Renovated in 2013 and equipped with central air conditioning, the property feels wonderfully secluded while remaining centrally located for convenient access to both up and down Island destinations. The current septic system meets all regulations and is designed for four bedrooms. Converting the Studio into an ADU is possible, and the permitting path forward has been identified by the building inspector. Enjoy effortless access to Lambert’s Cove Beach, 7a Foods, State Road Restaurant, and all the iconic West Tisbury landmarks.

99 Oak Lane, West Tisbury

no property photo
$1,289,000
2 Beds ⋅ 2 Baths ⋅ 22604010 MLS
Discover the charm of West Tisbury with the perfect blend of country living and village convenience. Ideally located just a short stroll from the heart of town, you'll enjoy easy access to all the West Tisbury Village has to offer. Set on a lovely lot, the home features a spacious southeast-facing deck overlooking a sunny yard. Four detached outbuildings. A generous south-facing living room is filled with natural light and offers peaceful views of the surrounding landscape. The kitchen provides an opportunity to create a space tailored to your vision. Off the kitchen is a large dinning area with a beautiful custom cabinet. The primary suite includes a sitting area and sunroom, while a second bedroom off the front entry features a half bath and access to the outdoor shower. Although the home is currently configured as a two-bedroom residence, it is served by an existing four-bedroom Title V septic system. This property presents an exceptional opportunity for buyers looking to renovate and make a home their own. Heating is provided by a mini-split systems. The expansive outdoor living areas blend seamlessly with the natural surroundings. The house is being sold in as-is condition.

29 Scotchmans Lane, West Tisbury

no property photo
$2,995,000
5 Beds ⋅ 2 Baths ⋅ 22604007 MLS
WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock.

27 Beach Road, Oak Bluffs

9 Codman Spring Road, Edgartown
$2,500,000
4 Beds ⋅ 3 Baths ⋅ 73564299 MLS
Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

9 Codman Spring Road, Edgartown

258 Edgartown-Vineyard Haven Rd, Edgartown
$3,875,000
5 Baths ⋅ 73564126 MLS
EXCEPTIONAL MIXED-USE INVESTMENT AND OWNER-OCCUPANT OPPORTUNITY JUST MINUTES FROM HISTORIC EDGARTOWN ON BEAUTIFUL MARTHA'S VINEYARD! This meticulously maintained 6,712 SF property offers three commercial units plus a residential apartment with an additional side attic future expansion potential to add an additional apartment. Commercial spaces include a dental practice with finished lower level (full bath, kitchenette, living area & bedroom, and storage room), a Pilates studio with reception area, two studios & half bath, and a commercial catering kitchen with a full basement prep/expansion kitchen and half bath. The spacious 1+ bedroom condo features open-concept living, kitchen, bonus room (area with built in couch/bed) & full bath. Unfinished attic includes architectural plans for a second residential apartment - enhancing future value and income potential. Ideal for medical, dental, restaurant, wellness, professional offices, retail, creative studios or investors. Property has town water and sewer - a great bonus. Ample on-site parking, flexible layout, and an outstanding Edgartown location just outside the Historic District.

258 Edgartown-Vineyard Haven Rd, Edgartown

36 Hines Point Rd, Tisbury
$2,995,000
3 Beds ⋅ 1 Baths ⋅ 73564072 MLS
HINES POINT WATERFRONT GEM with 85 feet of frontage on the Lagoon, offering ever-changing water views and the perfect vantage point to watch the Steamship Authority ferries arrive in Vineyard Haven Harbor. Enjoy the charming, timeless cottage with a one-car garage as an idyllic summer retreat, or bring your Vineyard vision to life with beautiful architectural plans by Sullivan +Associates Architects. Perched atop a gentle embankment, this exceptional property captures expansive views of the Lagoon, harbor, and town. A private staircase leads to the water's edge, where you can launch a kayak, paddle board, or small boat and explore the Lagoon and beyond. Just a short stroll to the Martha's Vineyard Museum, downtown Vineyard Haven, shops, restaurants, and the ferry, this is a rare opportunity to own in one of the Island's most coveted waterfront locations.

36 Hines Point Rd, Tisbury

no property photo
$1,095,000
3 Beds ⋅ 2 Baths ⋅ 22603994 MLS
Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you'll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping, restaurants, and all the attractions that make this area of Martha's Vineyard so special. Martha's Vineyard Hospital is also just a short two-minute drive away. Built in 1988, the home offers approximately 1,456 square feet of living area, with prefinished wood flooring in the living room and bedrooms. The roof is approximately 10 years old, and recent improvements have focused primarily on the basement, where the space has been transformed to expand the home's usable living and recreational area. Whether you envision a TV room, game room, home office, exercise area, or a combination of uses, there are plenty of possibilities. A newly completed "doghouse"-style exterior basement entry provides convenient direct access to the lower level. The first and second floors would benefit from a little TLC and personal touches to brighten and refresh the space, providing a great opportunity for the next owner to make the home their own. Outside, the property offers a small, manageable yard with off-street parking, along with a classic Vineyard outdoor shower—a favorite feature after a day at the beach and something many consider a must-have for Island living. Set on a 5,000-square-foot lot, the property offers the best of both worlds—a quieter location at the Eastville side of Winemack Street while still being just minutes from downtown Oak Bluffs. Title 5 System failed, Seller is offering a credit at closing to help with costs (to be determined). Prequalification letter from your lending source or proof of funds required. Owner and tenants currently occupy the home; 24-hour notice for showings is preferred.

2 Winemack Street, Oak Bluffs

no property photo
$1,255,000
3 Beds ⋅ 2 Baths ⋅ 22603967 MLS
Charming Oak Bluffs Ranch on a Peaceful Cul-de-Sac Welcome to this inviting 3-bedroom, 1.5-bath ranch-style home nestled on a generous .35-acre lot at the end of a peaceful cul-de-sac in Oak Bluffs, Massachusetts. Ideally located near the beach and town center, this property offers a wonderful blend of privacy, convenience, and classic island living. The comfortable single-level layout features three bedrooms and one-and-a-half baths, offering plenty of space for family, guests, or a relaxing Martha's Vineyard getaway. Step outside onto the sunny deck, an ideal spot for morning coffee, outdoor dining, or unwinding after a day at the beach. The lovely, spacious yard provides plenty of room for outdoor enjoyment, while the storage shed is perfect for beach equipment, bicycles, gardening tools, and seasonal belongings. Set on a quiet cul-de-sac with a desirable .35-acre lot, this home combines the tranquility of a residential setting with the convenience of being close to Oak Bluffs beaches, restaurants, shops, and the town center. A wonderful opportunity to create your own island retreat in one of Martha's Vineyard's most beloved communities.

11 Stanley Street, Oak Bluffs

528 Main Street, Tisbury
$1,600,000
4 Beds ⋅ 4 Baths ⋅ 73563290 MLS
Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, and bedroom—perfect for extended family or guests. There are two driveways. The home also features a garage and a finished basement offering excellent storage or future expansion potential. A detached studio at the rear of the property provides wonderful overflow space for a home office, art studio, or guests. The property is only 2/10ths of a mile to the town beach at the end of Grove Ave, and half a mile to the town beach on Owen Little Way. Ready for a new owner's vision and updates, this well-located property presents an exceptional opportunity to enjoy the convenience and charm of this desirable neighborhood. This property is being offered "as-is." *Please note there is only AC in the primary bedroom wing addition.

528 Main Street, Tisbury

139 Chappaquiddick Road, Edgartown
$12,250,000
7 Beds ⋅ 4 Baths ⋅ 73563263 MLS
You truly can have it all—just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village yet set along one of the most spectacular stretches of beach, with a 190' private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartown Lighthouse. A gentle slope leads to the sandy shore, where days unfold along the pristine waters of the harbor. Inside, casual elegance defines the home, with a seamless blend of gracious formal spaces and inviting areas for relaxed gatherings. The grounds are equally captivating, made even more exceptional by the inclusion of 75 Landing Place Road, with the availability of an additional conforming lot further elevating this offering — providing the opportunity to create a one-of-a-kind family compound and enduring legacy estate. Cherished by the same family for generations, this extraordinary waterfront compound is a truly special place.

139 Chappaquiddick Road, Edgartown

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$1,095,000
1 Beds ⋅ 2 Baths ⋅ 22603763 MLS
This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or proven income-producing investment. The home features a bright, open-concept kitchen, dining, and living area with beautiful hardwood floors that create a warm and inviting atmosphere. A first-floor den, complete with a daybed, provides flexible space for two additional overnight guests, while a full bathroom on the main level adds convenience. Sliding glass doors from the dining area open to a spacious deck overlooking the beautifully landscaped gardens, creating the perfect setting for outdoor dining, entertaining, or simply relaxing. Additional outdoor amenities include a hot tub and an outdoor shower, allowing you to fully enjoy the Vineyard lifestyle. Upstairs, you'll find a spacious primary bedroom, a large open loft that can serve as an additional living or sleeping area, and a second full bathroom. Adding even more value, the home is equipped with transferable solar panels .

323 County Road, Oak Bluffs

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$1,525,000
4 Beds ⋅ 3 Baths ⋅ 22603890 MLS
A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you will find two large bedrooms, a full bathroom with walk-in shower and plenty of attic storage. Set on a picturesque two-acre parcel, the property also features a detached 384-square-foot studio, which sits privately from the main house, with a private parking area, yard, and septic system, it presents wonderful possibilities for hosting family and friends or creating a private artist's studio or home office. Ideally located just minutes from Nip 'n Tuck Farm, Up-Island Cronig's Market, Conroy's Apothecary, and Main St. in Vineyard Haven. As a W. Tisbury resident, you'll also enjoy access to the coveted Lambert's Cove Beach with a resident permit, one of Martha's Vineyard's most treasured shoreline beaches. Main house cesspool will need to be upgraded. Septic design included with the sale. *Estate Rules Apply

150 Field View Lane, West Tisbury

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