Vineyard Haven Real Estate

Welcome to Vineyard Haven, a picturesque gem nestled on the enchanting Martha's Vineyard, located in Dukes County, Massachusetts. As the bustling port town of Tisbury, Vineyard Haven offers both residents and visitors a unique blend of coastal charm, rich history, and vibrant community spirit.

Picture yourself strolling along the scenic harbor, where the gentle lapping of waves meets the lively chatter of local shops and eateries. Vineyard Haven is renowned for its stunning waterfront views, making it a haven for boating enthusiasts and nature lovers alike. The town's historic architecture, including beautifully preserved 19th-century homes, adds to its quaint allure, inviting exploration at every turn.

The heart of Vineyard Haven is its thriving downtown area, filled with an eclectic mix of boutiques, art galleries, and gourmet restaurants. Whether you're seeking fresh seafood, artisanal pastries, or unique gifts, you'll find an abundance of delightful options right at your doorstep. The town also hosts a variety of cultural events throughout the year, from art shows to music festivals, ensuring there's always something exciting happening.

For outdoor enthusiasts, Vineyard Haven boasts access to stunning beaches and nature trails, perfect for hiking, swimming, or simply soaking in the sun. The nearby Tisbury Great Pond offers opportunities for kayaking and paddleboarding, immersing you in the region's natural beauty.

With its welcoming community and idyllic surroundings, Vineyard Haven is not just a destination; it's a lifestyle. Experience the charm of this coastal haven and discover why so many choose to call Vineyard Haven home. Whether you're looking for a serene retreat or an active coastal lifestyle, this enchanting town has it all.

Newest Listings in Vineyard Haven

$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

$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

$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

$1,595,000

5 Beds ⋅ 3 Baths ⋅ 73476994 MLS

Located in a quiet enclave off Main Street, Vineyard Haven and just a half-mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical, evidenced by the well-appointed kitchen which offers direct access to the expansive deck. With separate finished living quarters on the garden level, the home easily accommodates guests and multi-generational living. Mature plantings bloom on stone-scaped retaining walls and evergreen trees provide ultimate privacy. Moments from the harbor, shops, and ferry, and yet this property also offers seclusion and privacy, a rare combination at this price point. Offered partially furnished.

22 Old Lighthouse Road, Tisbury

$1,500,000

73471111 MLS

Prime commercial opportunity in Vineyard Haven, Martha's Vineyard's vibrant year-round community! This 2,614± sq. ft. corner commercial condominium in popular Woodland Center Marketplace —one of the largest in a well-managed association—offers outstanding visibility and versatile space. Currently configured for a tile and flooring business, Unit 8 features a showroom with office area, a workroom/warehouse storage section, kitchenette, and half bath. The flexible layout easily adapts for retail, design, or professional use. With ample parking, professional management, and a high-traffic location, this property is a standout investment. The successful Karpet Kare tile and flooring business is also available separately for those seeking a turnkey operation in a thriving commercial hub.

455 State Rd Unit 8, Tisbury

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