Vineyard Haven Homes from $1M-$3M

Scroll down to find $1,000,000-$3,000,000 homes for sale in Vineyard Haven. Contact Sandpiper Realty if you have questions or would like to schedule a showing.

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92 Main Street Vineyard Haven MA

Price$2,100,000

Est. Mortgage: $/month

MLS Number 34789

  • Residential
  • Square Feet 6330
  • Bedrooms 7
  • Bathroom 6
  • Half Bath 1

The Captain Dexter House, ca. 1843, has a storied history. Originally owned by one of the Island whaling captains, this home has had several iterations, including the most recent in 2004 when a 3 story addition completed the restoration of this charming historic residence set in the heart of the seaside village of Vineyard Haven. The restoration included the preservation of the original architectural details while bringing the home into the present century with the addition of the country kitchen including a large center island and top of the line appliances, informal dining area and family room with a fireplace and access to the garden patio. Conveniences include a walk-in pantry, powder room and full bath, and laundry room. Formal and informal living areas can be found throughout the house as well as seven bedrooms and six and one-half baths. There are five working fireplaces including the master bedroom suite. All mechanical systems have been completely updated including central AC. Exterior living areas feature a balcony off the second floor sitting area, covered porch with views of the harbor, newly fenced bluestone patio with mature plantings, tiered perennial gardens and private parking for 3 cars. Theater, restaurants, boating and the beach are within footsteps of this gracious in-town residence. Walk to the library and elementary school. Offered fully furnished with a list of exclusions, attached. Substantial rental history.

Listed by Coldwell Banker Landmarks

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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484 Main Street Vineyard Haven MA

Price$1,495,000

Est. Mortgage: $/month

MLS Number 34754

  • Residential
  • Square Feet 2755
  • Bedrooms 5
  • Bathroom 3
  • Acreage 1.87

It is RARE to find a charming, traditional home with nearly 2 ACRES of land - AND be walking distance to all that down town Vineyard Haven has to offer - the movie theater, restaurants, shops, and the Playhouse! Located on a lovely, coveted stretch of Main St. equal distance between the village and West Chop, the discerning buyer will see that opportunity abounds at this exceptional find. Outside features park-like grounds offering tranquility and privacy. A bonus vintage structure encompassing a single garage and 405 square foot wood shop/studio is in the rear. Inside the appealing front door is a welcoming foyer and stairs to the second floor. On the right is a den (or bedroom) with shelving. On the left are double pocket doors leading into the expansive living room with wood-burning fireplace. Off the living room is a first floor bedroom and bathroom. Also off the living room is a large light-filled dining room with a lovely bank of windows overlooking the park-like grounds. The mudroom, kitchen and pantry are at the back. Upstairs has a master bedroom and bath plus two more bedrooms that share a hall bathroom. Other bonus spaces include two unfinished attics. The boiler, electrical service, insulation, sheet rock, and oak floors were updated in recent years. You could live in this house now with all its period charm, or renovate to your personal tastes. Septic is designed for five bedrooms and passed Title 5 inspection. There is enough land for a guest house and/or pool. It is a quick walk to Grove Ave. beach, just perfect for a morning dip. Also, it is near the Yacht Club where the kids can have lunch with their buddies after the morning sailing lesson. Don't miss out on this singular beauty just waiting for the buyer with vision.

Listed by Viewpoints

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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26 William Street Vineyard Haven MA

Price$1,499,000

Est. Mortgage: $/month

MLS Number 34742

  • Residential
  • Square Feet 2395
  • Bedrooms 3
  • Bathroom 2
  • Half Bath 1

CLASSIC VINEYARD VICTORIAN. Walk to restaurants, stores, the Playhouse, VH Library, the Ferry, in fact anywhere in the Village, from this lovely, bright, comfortable home, complete with white picket fence, on much sought after William Street. This charming vintage home is a perfect combination of old and new. It was renovated in 2000, has had numerous updates, including the most recent improvement of a new roof, yet maintains the appearance and atmosphere of a traditional William Street Home. Entrance hall leads past a lovely sunny sitting room, or parlor and continues on to the main living room which has numerous windows and a covetable Mantle Framed wood burning fireplace and surround - the hearth and the heart of the home! Beyond, there's a third living area, currently used as a dining room, with built in shelving and french doors that take you out to a side yard, shaded by a wooden pergola. The dining room leads to a very large eat-in kitchen, with a wonderful O'Keefe & Merritt propane stove. The eat in kitchen comes with a built in sideboard buffet or workspace. Access to side yard via one door or take another set of Frence Doors to the back yard and outdoor shower. The main living level has oak floors throughout and a neutral color scheme. Generous laundry room and half bath are located off the kitchen. There are two staircases in this Greek Revival home leading up to three large bedrooms. The Master Bedroom is very spacious with vaulted ceilings, soft carpeting, bead board clad ceiling, ceiling fan, a sitting area, a full ensuite bathroom and second dressing/grooming area with a vanity. Very large guest room at the rear of the house, additional guest room in center of house, with a shared bathroom. Carpet throughout the second story provides a very comfy feel. Forced Hot Air heat and Central Air Conditioning throughout. Additional updates including but not limited to; Interior Painting, Landscaping; New roof over entire building in Autumn 2018; new gutters; cobblestone border added to the new gravel driveway and also form the new apron providing off street parking for two cars. Full basement with exterior access. Street parking is also available. TITLE 5 CERTIFICATION IN PLACE.

Listed by Alisan Lohan-Conway Properties

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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184 Franklin Street Vineyard Haven MA

Price$1,100,000

Est. Mortgage: $/month

MLS Number 34614

  • Residential
  • Square Feet 1788
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.39

Quintessential in-town living: A classic home, circa 1930, with substantial 21st Century updates. On a corner lot so generous, it allows for a future second dwelling. And with a four-bedroom septic already in the ground, why not? In the meantime, enjoy: Abundant light streaming through multiple glass sliders, windows and skylights. Restored wood floors. An updated marble-and-stainless kitchen. A farmer's porch, period oak front door and expansive mahogany rear deck. Central heat and AC. An accessibility ramp. For your outdoor pleasure: Professional landscaping, with irrigation. Stone patios, lampposts and a charming fountain. A kitchen garden enclosure. Detached garage and plenty of on-site parking to spare. All these comforts lie within a hop of Friday night lobster rolls, a skip of Owen Park and a jump of downtown. The home comes fully and tastefully furnished. Move-in or rent-out ready. NOTE: See property upgrades under Documents.

Listed by Coldwell Banker Landmarks

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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77 Checamo Road Vineyard Haven MA

Price$1,395,000

Est. Mortgage: $/month

MLS Number 34357

  • Residential
  • Square Feet 2801
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

Centrally Located. Privacy abounds in this 2,800 sq. ft. home on 4+ acres on a partially cleared lot. Miles of walking trails or horseback riding trails abuts this property making it a perfect place for keeping a horse or farm animals. This 3+ bedroom 4 bath home has been lived in year round and offers warm radiant heat, fireplace, artist room, finished basement, two car garage, loft area, office space and a sunroom for extensive outdoor living space! A builders home with many extras!

Listed by Carroll & Vincent R.E.

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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125 Main Street Vineyard Haven MA

Price$1,900,000

Est. Mortgage: $/month

MLS Number 33936

  • Residential
  • Square Feet 2770
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.18

Downtown Vineyard Haven home with harbor views. This historic 3-bedroom home is perfectly located on the outskirts of Downtown Vineyard Haven, next to Owen Park. The outside is well maintained and the two-story deck allows for unobstructed views of Vineyard Haven Harbor, while the inside is just waiting for a buyer to make it their own.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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229 State Road Vineyard Haven MA

Price$1,295,000

Est. Mortgage: $/month

MLS Number 34012

  • Residential
  • Square Feet 3304
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 2

SMART MOVE: HIGHLY VISIBLE LIVE-WORK OR RENTAL OPPORTUNITY. Set behind a handsome stone wall, this beautifully appointed craftsman-style home offers the perfect combination of luxurious in-town living and high visibility for an in-home business, successful rental property and/or multi-generational home. Built in 2008, this custom-crafted home integrates reclaimed architectural details with modern, state-of-the-art construction features including energy efficient insulation, multi-zoned heating and air conditioning, Lutron® lighting as well as superior quality details such as custom milled wood paneling, built-ins, crown molding and wainscoting. In addition, the current owners have made further upgrades to the property (see attached summary). Tisbury zoning bylaws allow for an in-home office/business for a professional services business, tradesperson or artisan -- with visible on-street signage. There is a detached, heated 800-square-foot garage/office/workshop with separate driveway entrance off Martin Road-Foster Road, providing nice separation and privacy from the house. There is also parking for up to six vehicles. This gorgeous property is currently being used as a successful rental property, generating over $85,000+/year in annual income. The property is ideally located within a 10-minute walk to Vineyard Haven village and ferries. Tasteful furnishings and contents are available for separate purchase/negotiation for a TURNKEY OPPORTUNITY. Come and see firsthand how this property can be a smart move toward your personal, business or investment goals!

Listed by Point B Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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108 William Street Vineyard Haven MA

Price$3,000,000

Est. Mortgage: $/month

MLS Number 31993

  • Residential
  • Square Feet 5534
  • Bedrooms 7
  • Bathroom 6
  • Acreage 0.657

Location, Location, Location in the historic seaside village of Vineyard Haven. This majestic property offers living at its best in a vibrant area of year round, well maintained, preserved period homes, one block to Main Street and steps to Owen Park with deep water dock, beach, bandstand, and large mooring field. Watch sunrise and moon rise over the ocean. Mere steps to all the shops, stores, restaurants, theaters, post office, and service providers in this quaint New England village setting.The Steamship Authority ferry dock is ultra convenient for commuters and excursions to the mainland. Walk to everything. This majestic single family water view residence plus guest cabin is located in the heart of the William Street Historic District with Bracketed-Italianate style and known as the Captain Benjamin Cromwell House and later as the Clough House. With with perfectly proportioned cross gable and cupola, impeccably renovated and maintained, amenities include 6 bedrooms, 5 baths, oil heat, a/c,1100+/- s.f. third floor loft, cupola, plus cabin/guest house, cathedral ceiling studio with kitchenette, full bath, closet, a/c, and Rinnai heat. The two car garage, out house, and his and hers outside shower complete the .66 acre manicured grounds. As the captain of the Island Line transportation service between New Bedford, Martha's Vineyard, and Nantucket with steam-powered side-wheelers, the Eagle's Wing and later the Monohansett, this property was an emblem of Captain Cromwell's success and enhanced by its prominent physical setting with surrounding ornate caste iron fencing. The architecture, water views, spacious front veranda 440+/- s.f., interior spaces with 9' and 10' ceilings, crown molding, gleaming antique wood floors, and history will captivate the attention of the most discerning buyer. The original village of Holmes Hole became the Town of Vineyard Haven in 1871 and later Tisbury. William Street was the second street originally laid out by the village in approximately 1831. The William Street Historic District is unique in that it has consistently maintained its look with its historic 19th century homes. Truly a rare, in-town opportunity with clay tennis courts and the elementary school and playground only steps away. In summary, this property needs to be seen to be fully appreciated. Please read floor descriptions for more details.

Listed by Viewpoints

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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77 Massabesic Avenue Vineyard Haven MA

Price$1,525,000

Est. Mortgage: $/month

MLS Number 33393

  • Residential
  • Square Feet 3540
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

Enjoy stunning water views from every room of this charming three bedroom Vineyard Haven home. Tucked away off lower Lambert's Cove Road, this post and beam styled house is nestled on over three acres in Lower Makonikey and boasts substantial views of Vineyard Sound from the first and second level. There are many sweet interior details including three fireplaces, a loft space, and a fully finished walk out basement which provides additional living space. The property also offers access to the association's private North shore beach. The house has been thoughtfully maintained by the current owner including new skylights, roof, downspouts, red cedar shingles and new roof. The graceful trees behind the home have been regularly topped and pruned to maintain the broad, deep view. The property offers ample outdoor spaces with deck and patio overlooking gently wooded land, open lawn space, as well as lovely plantings .

Listed by Tea Lane Associates

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$
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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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655 Herring Creek Road Vineyard Haven MA

MLS Number 33187

  • Residential
  • Square Feet 928
  • Bedrooms 2
  • Bathroom 1
  • Acreage 1.26

It's all about the beach, stunning sunrises, epic sunsets and the sound of the waves lapping on the shore. Live the Island life in this classic style summer house perched waterfront between Lake Tashmoo and Vineyard Sound. Kayaking, paddle boarding sailing just steps away. Designed for casual vacation living, it's a perfect summer home for generations to come.

Listed by Conroy & Company R.E., Inc.

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$
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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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48 Sandpiper Lane Vineyard Haven MA

Price$1,299,000

Est. Mortgage: $/month

MLS Number 32353

  • Residential
  • Square Feet 2260
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

WEST CHOP - Elegant and uniquely styled home in desirable Tashmoo Woods, on the last remaining lot within view of Mink Meadows Golf Course. This home has tremendous curb appeal. Front entrance via a vestibule, creating a nice transition into the home. Main living level has an Open Floor Plan, 9 foot high ceilings, striking 'two over two' oversized windows, Custom Trim Detail, Wood Burning fireplace and Wide Oak flooring throughout. Living room flows seamlessly to the dining area and kitchen. Large Custom Kitchen with Cream Cabinets (including oversized upper cabinets and numerous roll out shelves) beautiful mink colored Quartz counter tops, complementary Sea Glass backsplash and Stainless Steel appliances with a Cook's gas stove. Kitchen looks out over back yard and woodlands towards Mink Meadows and is adjacent to the garage for ease of access with groceries! Ground Floor Master Suite with Custom Trim and Wainscoting throughout, Walk in Closet, Double Vanity, Large Custom Tiled shower with Seamless Glass door. Upstairs to the Second Master Bedroom Suite, also with a Double Vanity, Quartz counters, Custom Closets, Custom Tiled floors and Shower with Seamless Glass Enclosure, Separate Water Closet and Custom Trim Detail! Two additional guest bedrooms share a bathroom with Tiled Tub and Wainscoting. Access to large storage area over garage. Second floor also has Wide Oak Flooring throughout, not a carpet in sight!! Multi zone Central Air-conditioning and forced hot air Heat. Full Basement. Front porch with Mahogany deck and Blue Stone Patio in rear yard off dining area. Mahogany clad Outdoor shower. Tashmoo Woods has numerous amenities including Association Tennis, Swimming Pool, Clubhouse, Dock and Private Beach Access. Minutes to Lake Tashmoo, Mink Meadows Golf, West Chop Club, Vineyard Haven Yacht Club, Restaurants, Shopping and Ferry. Move in ready. Empty and easy to show!

Listed by Alisan Lohan-Conway Properties

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$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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135 Bigelow Road Vineyard Haven MA

Price$1,695,000

Est. Mortgage: $/month

MLS Number 31850

  • Residential
  • Square Feet 2556
  • Bedrooms 4
  • Bathroom 4
  • Acreage 2.62

MINK MEADOWS ~ A true oasis nestled among the oaks on over 2.5 acres of land. Uniquely designed and crafted with the finest materials and highest level of workmanship. The custom contemporary home and guest cottage offer a quiet and warm environment that entrances, calms, and intrigues while providing comfort that flows from the carefully thought out design and exquisite surroundings. Mink Meadows golfing and beautiful association beach are just a walk away. Truly spectacular and must be seen to be fully appreciated.

Listed by Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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593 Herring Creek Road Vineyard Haven MA

MLS Number 28442

  • Residential
  • Square Feet 1104
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.89

With Lake Tashmoo in your front yard and all of Vineyard Sound at your back door, this is the perfect setting to recreate the summers of our childhoods - digging clams to cook & eat on the beach - swimming 'til our lips were blue while Dad fished - reading under beach towel "tents" until we were allowed back in the water. This enchanting beach house has a front-to-back living/dining room, offering views of both the Sound and Lake Tashmoo. The master bedroom is generous in size and its vaulted ceiling and views out to the Sound make it light and airy. The guest bedroom is just delightful with windows on three sides offering incredible views of the Sound and the lulling effect of the waves lapping against the shoreline is irresistible. The 2003 renovations of the home kept its vintage appeal while including all new Anderson replacement windows, updated kitchen, new exterior shingles and interior beadboard. At the same time, the owners undertook a complete rebuild of the separate studio/bunkhouse which has insulation, electricity and cable, oak flooring, all new drywall and skylights. There are two built-in couches/day beds, creating plenty of sleeping space for 6 - and the generous number of windows look out to big views of Lake Tashmoo. Come - be a kid again.

Listed by Karen M. Overtoom R.E.

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$
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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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585 Herring Creek Road Vineyard Haven MA

MLS Number 26173

  • Residential
  • Square Feet 704
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.42

This cottage sparkles, this environment enchants. You'll find a charming, waterfront beach cottage nestled above the dunes on Vineyard Sound. The beach is right out front and Lake Tashmoo is on the opposite side. There are sweeping views of both from the open plan living area and you can see the sun setting across the water every night. Sliding glass doors on either side allow for maximum views, beautiful natural light, and access to two decks, perfect for outdoor meals or relaxing in the sun or shade. The house has been renovated from top to bottom, including new hardwood hickory floors, a designer kitchen with new appliances, mahogany countertops, and subway tile backsplash. The new bathroom has heated tile floors. There are boating and swimming options aplenty. You can't find a better place for a lifetime of special Vineyard memories.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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24 Vincent Way Vineyard Haven MA

Price$1,295,000

Est. Mortgage: $/month

MLS Number 16794

  • Residential
  • Square Feet 1160
  • Bedrooms 3
  • Bathroom 1
  • Acreage 1.43

Watch sunsets from the deck plus wide angle views of Tashmoo --Riparian rights allow a mooring

Listed by The Island Group

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$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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36 Vincent Way Vineyard Haven MA

Price$1,295,000

Est. Mortgage: $/month

MLS Number 16793

  • Residential
  • Square Feet 1550
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.49

A waterfront home with panoramic filtered views of Lake Tashmoo on a nicely kept site with mature trees that canopy the entire site--Riparian rights allow a mooring

Listed by The Island Group

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$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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