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$2,295,000
4 Beds ⋅ 4 Baths ⋅ 73575143 MLS
Nestled on an acre of beautifully landscaped grounds in a tranquil, park-like setting, this home is tucked away on a quiet lane within an established neighborhood. Located just a quarter mile from miles of Land Bank walking trails and less than two miles from Main Street, it offers the perfect opportunity to embrace the Vineyard lifestyle, just minutes from the vibrant center of Vineyard Haven. Thoughtfully designed for both everyday living and entertaining, the main level boasts hardwood floors, high ceilings, and lots of windows that bathe the living areas and bedrooms in natural light. The kitchen serves as the heart of the home, featuring a center island and a dining area that opens onto a deck and attached gazebo—ideal for outdoor dining and gatherings. The inviting living room, complete with a propane fireplace, provides a warm and welcoming space. Three bedrooms—including a primary with ample closet space and a newly refinished bath are all located on the first floor. Additional highlights include new stainless-steel appliances, a Bertazzoni stove, Andersen windows, renovated baths, fresh paint, refinished floors, custom window treatments, plantation shutters, and a generator. This turnkey property is ready for immediate occupancy, allowing you to settle in and enjoy from day one. On the garden level, you'll find versatile space for additional living, relaxation, or exercise. The family room includes a half-bath and sliders that open to the patio and outdoor shower. A separate guest suite complete with bedroom, den, full bath, and kitchenette provides flexible accommodations for visitors. Meticulously maintained inside and out, this home is ready to welcome its next owner.

125 Mayflower Ln, Tisbury

Listing courtesy of Listing Agent: Courtney Marek from Listing Office: Sandpiper Realty, Inc..
$2,095,000
4 Beds ⋅ 4 Baths ⋅ 73571249 MLS
COMING SOON! 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! Showings begin on September 25th. 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

Listing courtesy of Listing Agent: Madelyn Silvia from Listing Office: Wallace & Co. Sotheby's International Realty.
$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

Listing courtesy of Listing Agent: Madelyn Silvia from Listing Office: Wallace & Co. Sotheby's International Realty.
$2,695,000
5 Beds ⋅ 4 Baths ⋅ 73560291 MLS
Historic Water View Elegance Meets Modern Luxury in Vineyard Haven: Step into a piece of Martha's Vineyard history with this exceptionally charming antique Cape, originally dating back to 1808. While the home proudly retains its authentic historical character, boasting exquisite period details, rich moldings, and wide-pine floorboards, it has been thoughtfully updated to offer the ultimate in contemporary living. There are 5 total bedrooms, 2 on the first floor and 3 on the second floor. There are 2 en suite bedrooms, 1 on the first floor and 1 on the second floor. In addition, there are 4 full bathrooms (3 newly renovated), and a light-filled, spacious kitchen, designed to blend old world charm with modern needs. Additional updates include central air conditioning, 3 lined chimneys, and an upgraded septic system. A bluestone patio is ideal for al fresco dining and summer barbecues. And a lovely, professionally maintained backyard and garden complete the storybook picture. Perfectly positioned right across from picturesque Owen Park, this property places you at the very heart of Vineyard Haven culture and coastal convenience. Take in water views and the boat activity of scenic Vineyard Haven Harbor. Enjoy front-row access to Owen Park with the newly built town dock and the historic bandstand where you can enjoy the Vineyard Haven Band play Sunday evenings in the summer. When you want to explore further, you are a short walk from the village where there are several exciting new restaurants, a multitude of shops, and the historic Playhouse. Whether you are looking for a gracious year-round island residence, a seasonal getaway, or a desirable vacation rental income producer, this historic gem delivers on every front. Schedule your private tour today and experience the magic of Vineyard Haven living. Offer mostly furnished and equipped with some exclusions.

124 Main St., Tisbury

Listing courtesy of Listing Agent: Idalyn Macchia Gilstad from Listing Office: Wallace & Co. Sotheby's International Realty.
$3,295,000
5 Beds ⋅ 4 Baths ⋅ 73554212 MLS
Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking. 33 Lagoon Pond Road is a newly constructed, thoughtfully designed three bedroom, three bathroom home where luxury meets sophisticated coastal charm. Featuring an open floor plan, a designer kitchen with quartz countertops, custom tile bathrooms, and seamless indoor-outdoor living, the home enjoys water views from the living room, bedrooms, and inviting front porch. A private backyard, spacious rear deck, and attached two car garage provide both privacy and convenience, while the property's impressive rental history adds outstanding investment appeal. Complementing the main residence is 29 Lagoon Pond Road, a beautifully renovated two bedroom, one bath cottage offering its own private retreat with a charming rear patio and outdoor shower. Ideal for extended family, guests, employee housing, or additional rental income, the cottage provides flexibility for a variety of ownership opportunities. A true standout feature of this offering is the oversized rear parking lot at 29 Lagoon Pond Road, accommodating approximately ten vehicles. Parking of this scale is exceptionally rare in downtown Vineyard Haven and significantly enhances the property's versatility. Whether you're seeking a family compound, an income producing investment, or a premier in town property with unmatched flexibility, 29 & 33 Lagoon Pond Road represent a truly one of a kind opportunity in downtown Vineyard Haven. Tenants in place. Showings are limited to turnover days - please inquire with listing agent.

29 and 33 Lagoon Pond Road, Tisbury

Listing courtesy of Listing Agent: Madelyn Silvia from Listing Office: Wallace & Co. Sotheby's International Realty.
$2,195,000
5 Beds ⋅ 4 Baths ⋅ 73511187 MLS
Tucked back from scenic Lake Street, this distinctive home offers privacy and charm on a landscaped 0.7 acre lot with mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm, inviting feel. The four-level design provides flexibility and character. The main level features a spacious kitchen with a center island open to the dining area, and a sunken living room with floor-to-ceiling windows overlooking the trees. A large screened porch extends the living space outdoors. Two bedrooms, a full bath, and laundry complete this floor. Upstairs, a dramatic hallway leads to a generous primary suite with a spacious bath and additional laundry. The third level offers a private guest suite with living area and bath. The finished lower level includes added living space, bath, and walkout. Convenient to the public boat landing on Lake Tashmoo, the Lake Street tennis and pickleball courts and just a short distance to Downtown Vineyard Haven.

159 Lake Street, Tisbury

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
$32,000
4 Beds ⋅ 4 Baths ⋅ 72853514 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in kitchen with top of the line appliances that include a Viking gas stove, two dishwashers, a wine refrigerator and butler's pantry. There is a separate diningroom for entertaining and a family room with fireplace, large TV screen and entertainment equipment. There is a separate office with high speed internet access, fax machine and TV. The master bedroom has it's own private bath with jetted tub, separate shower, guest bedroom with it's own bath and two bunk rooms with a shared bath.LINENS PROVIDED $150. EXTRA!!!!!!

37 Mempremagog Ave Vh410, Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$25,000
4 Beds ⋅ 4 Baths ⋅ 72852696 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living room and den. Laundry room is on the first floor just off the kitchen along with an automatic ice machine conveniently located just off the pool deck, a two car garage with bonus studio/office above. Nicely landscaped backyard with many gardens, an in-ground HEATED pool. Association amenities include private association beach and opportunity to join the Golf Club. Also, just a short distance to West Chop Woods, Land Bank Beach.

100 Connie's Way Vh401, Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$10,800
2 Beds ⋅ 4 Baths ⋅ 72853588 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has to offer from this cozy conveniently located property.Dogs considered with agreement to pet addendum, $725. in security deposit and $275. cleaning fee.

256 Sandpiper Lane Vh417, Tisbury

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

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