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$2,195,000
4 Beds 3 Baths 73542433 MLS
A cherished coastal classic, this vintage gem stands just a block from Main Street, its covered front porch and intricate carved wood details a gracious nod to a more elegant era. Step inside to a grand foyer and three levels of light-filled living, where hardwood floors, rich millwork, and timeless craftsmanship set the tone throughout. Four large bedrooms and tile baths — including a double vanity and step-in shower — blend vintage charm with modern comfort. Major interior renovation in 2008, the kitchen was thoughtfully designed for entertaining: featuring custom cabinetry, stone countertops, stainless steel appliances, double wall ovens, gas range, and wine fridge, plus a wet bar and half bath. A partially finished basement and third-floor home office add 500 sq ft +/- of flexible bonus space. A/C. Outside, beautiful gardens unfold behind arched garden gates with a deck, bluestone patio, and double-car barn. Two blocks to the VHYC, Owen Little or Grove Street Beach. 5-bed septic.

30 Daggett Avenue, Tisbury

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..

$775,000
2 Beds 1 Baths 73503536 MLS
Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance is the newly renovated Tisbury School! The interior delivers classic warmth, showcasing mellow wide pine floors in the living areas. Enjoy the convenience of an efficient kitchen with deck access to the back yard, a cheerful updated bathroom, and comfortable carpeted bedrooms. The full, dry basement is a blank canvas, offering massive potential. This is your affordable opportunity to settle on Martha's Vineyard! Schedule your showing! Property being sold as-is. Seller providing a 3 bedroom septic design. Buyer is responsible for installation and payment of the new system.

51 Lantern Ln, Tisbury

Listing courtesy of Listing Agent: Idalyn Macchia Gilstad from Listing Office: Wallace & Co. Sotheby's International Realty.

$800,000
3 Beds 2 Baths 73502474 MLS
This home has been patiently awaiting its next chapter in Vineyard living. Built in 1983, it offers a functional center-entrance layout with efficient use of space and modern systems already in place. The generously sized lot, both wide and deep, presents an excellent opportunity to expand the home's footprint and tailor it to your vision. Located in the Spring Hill neighborhood of single-family homes, just one mile from the heart of Vineyard Haven and moments from Lake Tashmoo. This property provides easy access to downtown amenities while remaining close to peaceful water views and natural surroundings for which Martha's Vineyard is known. Please note, this property is being sold in "as-is" condition, and a new septic system is needed at the buyer's expense. Possibility of a 5-bedroom septic allowed. Ring cameras on the property. Please don't walk the property without an appointment.

17 Mariner Rd, Tisbury

Listing courtesy of Listing Agent: Karl Olsen from Listing Office: Carlson & Company, LLC.

$2,000,000
4 Beds 4 Baths 73449959 MLS
The Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to a peaceful and private deck. Living room offers a comfortable space for TV and relaxing. There is also nice size first floor primary with walk-in closet and spacious en-suite bathroom. The grand entryway takes you to the second floor which offers a second primary bedroom with walk-in closet and en-suite bath. There are two guest rooms that share bath and second floor laundry. Wood and tile floors throughout, propane FHA with A/C. The walkout basement offers almost 10' of ceiling height and is ready to be finished off for additional living space, workshop or office.

151 Tashmoo Ave, Tisbury

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

$2,448,000
3 Beds 4 Baths 73470913 MLS
Welcome to this fabulous property, within close proximity to the ferry, downtown shops, restaurants, galleries, Owen Park Beach, and the MV Playhouse. This beautifully designed home has been lovingly maintained and offers the ideal balance of Vineyard charm and modern convenience. Designed across multi-levels of living spaces, the home provides a flexible layout that works beautifully for entertaining, relaxing, and hosting guests. The main floor welcomes you to an inviting open floor plan living room filled with natural light and open to the dining area with direct access to the wrap-around deck, perfect for outdoor entertaining. The fabulous kitchen with a custom bar and cabinetry by Ryan Dillon Designs, and a bedroom with ensuite bath complete this floor. The second-floor features the primary ensuite and another ensuite bedroom and half bath. A third-floor retreat and finished lower-level offer plenty of flexible bonus space. For added convenience there is a two-car garage.

61 Causeway Road, Tisbury

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$1,225,000
4 Beds 2 Baths 73472920 MLS
This move-in ready four-bedroom, being offered fully furnished, delivers effortless living, simply bring your swimsuit and settle in. Featuring an open and inviting layout, the living space seamlessly extends to the large deck and heated pool, perfect for relaxing or entertaining. Conveniently located just one mile from the shops and restaurants of downtown Vineyard Haven and less than two miles from the sandy shores of Tashmoo public beach. With a strong rental history, it's perfectly suited as a year-round residence, vacation retreat, or investment property. The property is located within the Tashmoo Watershed District, and the septic system will require upgrades to comply with denitrification requirements.

344 Greenwood Ave, Tisbury

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

$1,300,000
3 Beds 2 Baths 73459283 MLS
Located on a cul-de-sac in a serene neighborhood, this classic Cape-style home is less than 1.5 miles from Main Street, Vineyard Haven. The location is ideal—close to restaurants, shopping, and the ferry. The three-bedroom home offers a comfortable and functional layout. The first floor features a spacious living room with a wood-burning fireplace, an adjacent dining room, and a fabulous three-season room off the kitchen, filled with an abundance of natural light. A bedroom and a full bath with laundry complete the main level. Upstairs, there are two generous bedrooms and a shared full bathroom. One bedroom includes a flexible bonus area suitable for a den, office, or overflow. The other bedroom enjoys an oversized walk-in closet. With classic Cape charm, hardwood floors, a full unfinished basement, and a two-car garage, this home presents an excellent opportunity in a desirable location. Located outside the Lagoon Pond Watershed, this property does not require a septic upgrade.

169 Clover Hill Drive, Tisbury

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$1,500,000
5 Beds 4 Baths 73410472 MLS
128 Spring Street—just moments from the Tisbury School and downtown Vineyard Haven. Built in 2013 and sited on an ample 1/4-acre lot, the house features four bedrooms and two-and-a-half bathrooms, along with a separate first floor one-bedroom in-law apartment complete with a full bath—ideal for extended family, guests, or added rental flexibility. The central location offers convenience to schools, ferry, shops, and beaches, while the layout allows for privacy, adaptability, and long-term value. Few properties on Martha’s Vineyard offer this level of space, flexibility, and opportunity in such a walkable, well-connected neighborhood. Note: This property is also being marketed as part of compound with the abutting 1BR/1BA home located at 136 Spring Street.

128 Spring St, Tisbury

Listing courtesy of Listing Agent: David Dickinson from Listing Office: Compass.

$2,500,000
5 Beds 5 Baths 73418565 MLS
BEAUTIFUL CUSTOM-BUILT RETREAT – LAMBERT’S COVE This impressive 4,900+ sq ft home offers privacy with easy access to downtown and James Pond Reserve at Lambert’s Cove Beach. Featuring 5 bedrooms, 4.5 baths, and a stunning chef’s kitchen, perfect after trips to local farm stands. Enjoy multiple living areas—oversized family/media room, dining room, sunny living room, and game room. Outdoor amenities include an oversized deck with a hot tub, 2 outdoor showers, a lower patio, an expansive lawn, and a Bocce Court. The 2-acre lot allows a pool or an ADU (with permitting). A private attached apartment with a separate entrance offers guests plenty of privacy. An attached two-car garage and shed provide ample storage space. Surrounded by conservation land and trails, it’s ideal for nature lovers. Whether year-round, a vacation, or an investment with a proven rental history, this fully furnished home delivers.

79 David Ave, Tisbury

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..

$1,800,000
3 Beds 4 Baths 73336163 MLS
This pristine hidden gem, recently developed home is located downtown, a short walk from shops, the lagoon, the beach, the harbor,and the MV Museum.S et back from the road, the home offers a quiet and peaceful luxury living experience. The property boasts solid hw floors, ducted heating and AC, a gas fireplace, quartz countertops, tiled baths, an open floor plan, a 1st-floor primary bedroom, 2 living rooms, 2 laundry areas, and custom blinds throughout. This home is filled with light from all sides and features views of mature oak trees. The generous raised deck is perfect for outdoor entertainment and relaxation. Below, you’ll find a bluestone patio, an outdoor shower, a storage shed, and well-designed lawn and landscaping. The exterior of the property is very low maintenance due to the hardscapes and natural trees. The driveway can accommodate five vehicles. Additionally, the newly developed walk-out lower level could be converted into an accessory apartment with town approval.

82 Skiff Ave, Tisbury

Listing courtesy of Listing Agent: Lenny Altieri from Listing Office: Premier Properties.

$1,735,000
3 Beds 4 Baths 73417770 MLS
POOL & LUSH GARDENS — Nestled on 3 acres beside 25 acres of conservation land, this 2,500+ sq. ft. home offers tranquility and convenience. The sun-filled living room with fireplace flows to the kitchen, dining area, screened porch, and sunny deck—perfect for enjoying serene views. The main floor hosts a spacious primary suite with en-suite bath; upstairs offers two large bedrooms, a full bath, and ample storage. A bonus room above the 2-car garage is ideal for an office, media room, or guest space. Outdoors, enjoy a poolside oasis, mature gardens, a fenced flower/vegetable garden with a shed. Offering the best of “Up Island” peace with “Down Island” amenities.

56 Bridle Path Rd, Tisbury

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..

$1,750,000
3 Beds 2 Baths 73283096 MLS
Nestled in a private neighborhood in Vineyard Haven conveniently located to the ferry and town for plenty of shopping and dining, this renovated home is move-in ready and sited on 1.5 generous acres. There are two entrances to the home. Offering separation from the main part of the home is a dramatic cathedral-ceiling Great Room with a wood-burning stove where you will occupy most of your time. There is an office area set aside in this room and a cleverly designed spiral staircase with a loft perfect for overflow. Entering the opposite side of the home you will enjoy the open floor plan with a fully renovated kitchen, dining room, and living room with another wood-burning stove. A renovated full bath with laundry and a first-floor bedroom complete this floor. There are two large bedrooms with skylights for great natural light and another large fully renovated full bath on the second floor. You will love the stunning professionally landscaped yard + patio with room for a pool.

97 Snake Hollow, Tisbury

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$1,265,000
3 Beds 2 Baths 73206867 MLS
A must see property located in the heart of Vineyard Haven. This three-bedroom, two bath, colonial style condo boasts expansive living spread over three floors. Completed in 2019, this energy efficient 1682 sq ft home includes a 5 KW solar PV system. The open layout of the first floor includes a modern, galley style kitchen with stainless steel appliances and extensive counter space. The three bedrooms located on the second floor include the primary bedroom with an amazing third floor loft. The loft spans the length of the home and offers distant water views of Lagoon Pond and Vineyard Haven Harbor at opposite ends. The house is surrounded by unbelievable, professionally landscaped yards with ornamental trees, a grape arbor, herb garden, planting beds, cobblestone walls, front and back lawns, and over 1500 sq ft of brick paver walkways and patio spaces. The property is fully fenced and provides the owners with a private oasis in the heart of downtown Vineyard Haven.

62 Lagoon Pond Road Unit B, Tisbury

Listing courtesy of Listing Agent: Allison Fisher from Listing Office: Donnelly + Co..

$1,300,000
2 Beds 2 Baths 73283023 MLS
This Recently Constructed Carriage House in Vineyard Haven is the epitome of thoughtful planning with custom details and exceptional finishes throughout. The sunny second level has an open floor living and kitchen area with vaulted ceilings. Highlights include a farmer’s sink and quartz countertops. There are two bedrooms, one is ensuite and both have been outfitted with California style closets. There is a full bath in the hall. Separate laundry area is off the living room. The oversized walk out garage offers ample storage or possible expansion of living space. Constructed with efficiency in mind which translates to lower energy costs and outfitted with hurricane windows, AZEK deck and trim, and 30-year asphalt shingles, this property is BUILT TO LAST. Take advantage of all the Vineyard living has to offer – easy access to Lake Tashmoo is close by as well as town tennis courts.Whether you are searching for a year-round home or vacation getaway, this home is a true island gem.

22 Briarwood Lane, Tisbury

Listing courtesy of Listing Agent: Carol Shore from Listing Office: Donnelly + Co..

$2,695,000
4 Beds 3 Baths 73305459 MLS
Rare opportunity to own one of the largest wooded properties in West Chop. This 1.86 acre property includes over an acre of undeveloped wooded land, a beautiful historic colonial home that has been meticulously renovated and a newly developed adorable detached studio. The main house features an open floor plan with a brand new kitchen with a center island that opens into a living room and a gorgeous glass enclosed dining space. The main floor boasts a second living room with a fireplace, a first floor primary bedroom with a full bathroom, a third living room or study and open concept foyer. The second floor includes a second primary bedroom with a private seating a bathroom and 2 additional bedrooms that share a bathroom. This home includes ducted AC system throughout. Enjoy the privacy and the quiet of this property while grilling and entertaining on the backyard bluestone patio. Marvel at the extremely large circular driveway that surrounded by a forest of evergreens. The home includ

484 Main St, Tisbury

Listing courtesy of Listing Agent: Lenny Altieri from Listing Office: Premier Properties.

$1,560,000
3 Beds 4 Baths 73267654 MLS
With nearby access to the Lagoon and Sheriff’s Meadow, this delightful home is nestled in a private enclave with natural landscaping offering an idyllic retreat. Designed with an open layout on the main floor, the home features a spacious kitchen any chef will enjoy. Enjoy the natural sunlight and dramatic cathedral ceiling living room with sliders to the expansive deck. The adjacent dining room also has a set of sliders with direct access to the deck. A bedroom and newly renovated full bath complete this floor. The luxurious primary suite is on the second floor. There is a newly renovated full bath with a walk-in shower, a soaking tub, and a huge walk-in closet. A guest bedroom and another recently renovated full bath complete this floor. You will be pleasantly surprised by the finished walkout lower level with a full kitchen, living room, bonus space, and full bath + laundry offering endless opportunities. There is plenty of storage room too!

30 Hillside Path, Tisbury

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$900,000
3 Beds 1 Baths 73206856 MLS
Enjoy easy condo living right in the heart of the village of Vineyard Haven. This home is less than 0.2 miles (4 min. walk) from the Steamship Authority ferry terminal with all-island access via the Vineyard Transit Authority. This well-maintained, three-bedroom bungalow style home has been in the same family since it was built, and it is just a short stroll to the MV Museum, and all the shops and restaurants Vineyard Haven has to offer. There are many modern updates, yet the house still maintains much of its original period-charm. The home has a wood burning fireplace, 4 kW solar PV system, and central AC. The property includes off-street parking, and it is directly across from Veterans Park with ample additional town parking. There is a private fenced in backyard area with a wood deck and brick paver patio, along with additional side and front lawn areas. The manicured grounds have been professionally landscaped for seasonal outdoor living and entertaining. The property is located wi

62 Lagoon Pond Road Unit A, Tisbury

Listing courtesy of Listing Agent: Allison Fisher from Listing Office: Donnelly + Co..

$1,500,000
5 Beds 4 Baths 73226115 MLS
LOCATED IN THE HEART OF VINEYARD HAVEN, This classic home boasts 5 bedrooms and 4 bathrooms across over 3,200 sq ft of living space. Nestled in the perfect in-town Vineyard Haven neighborhood, this residence offers unparalleled convenience. Main Street, Owen Park, the Ferry, Owen Little Way Beach, and the Vineyard Haven Yacht Club are within walking distance. This historic home exudes timeless charm and potential. The property includes a 400 sq ft heated studio. The possibilities are vast. The property sits on a large lot with numerous opportunities, including the potential for subdividing and adding a guest house. Preliminary engineering has already been completed for the subdivision, but town approval is required. 70 TASHMOO IS NOT SITUATED IN THE TISBURY WATERSHED! Title V inspection has passed. Make your vision a reality with a spacious family retreat or a prime investment opportunity.

70 Tashmoo Ave, Tisbury

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Compass.

$2,250,000
3 Beds 3 Baths 73235222 MLS
Privately located alongside the first and second hole of the Mink Meadows Golf Club golf course, this architectural home in coveted Mink Meadows on 2.12 acres, is in close proximity to the West Chop Club, MINK MEADOWS PRIVATE ASSOCIATION BEACH ACCESS, and the Mink Meadows Golf Club. Recently updated by the owner/accredited architect for Hutker Architects, ample attention to detail was taken into account for each meticulous and thoughtfully designed upgrade. The property is attractively adorned with established plantings and a mix of aesthetically maintained trees and flower beds. Main house consists of 3-bedrooms, 2.5 bathrooms with an open floor plan and expansive screened in porch with built in high end heaters for year-round use and enjoyment. A second annex structure accompanies the property which can be used as a yoga studio, office or creative space with a loft above. An oversized garage allows for one car and a small boat, with storage space above, offers a well rounded property

338 Bigelow Road, Tisbury

Listing courtesy of Listing Agent: Emily Flake from Listing Office: Viewpoints; Bobbi Flake Reed, Inc..

$820,000
2 Beds 1 Baths 73179775 MLS
Discover this Martha's Vineyard gem, a charming cottage nestled near the town and bike paths, yet serenely situated down a country lane. With deeded Lagoon Pond access, enjoy kayaking, boating, and swimming at your leisure. The home features two bedrooms, a flexible additional room, and an inviting open-plan living and dining area. Highlighting the property is a 320 sq ft three-season room, offering extra space for relaxation. Practical amenities include a full walk-out basement for storage or expansion, plus a walk-up attic space. Outdoors, a spacious lawn and shed await your personal touch. Sold as-is; septic system upgrade required by the buyer. Embrace the chance to make this tranquil retreat your own on Martha's Vineyard.

7 Elm Street, Tisbury

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.

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