Vineyard Haven Real Estate

Vineyard Haven, a community in Tisbury, is the main port of entry to Martha's Vineyard. The town is home to one of the most beautiful harbors on the island. Types of homes in Vineyard Haven include townhouse style condos, vineyard style homes, cottages, contemporary homes, Cape Cod style homes, and vacation homes.

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794 & 690 Chappaquonsett Road Vineyard Haven MA 02568
Pending

MLS Number 41193

  • Residential
  • Mls Status Pending
  • Bedrooms 10
  • Bathroom 10
  • Acreage 20.34

Chip Chop is the legendary 20-acre beach compound set on Vineyard Sound. The property has lived large in Martha’s Vineyard lore since the 1940s when it was built for celebrated Broadway star Katharine Cornell. For many decades it has hosted a broad spectrum of well-known figures from the worlds of literature, theater, cinema, and politics. There are two separate lots – one 17.4 acres and the other 2.84 acres. A mile of private shoreline surrounds the property, including 2000 feet of sandy beach on the exquisite swimming waters of Vineyard Sound, and a large swath of sandy beach on Lake Tashmoo. There are no fewer than 4 homes - a 3-bedroom main house, a 2-bedroom caretaker’s cottage, and 2 elegant beach houses built in 2007 which offer some of the most astonishing water views on Martha’s Vineyard. The Pond Pavilion and the Ocean Pavilion are 2 separate, detached bedroom suites. The swimming pool overlooking Vineyard Sound with views of the mainland beyond is simply stunning. A Har-Tru tennis court is discretely nestled in a private corner of the property. Supremely stylish and yet consummately casual, this famed Martha's Vineyard property is a unique offering and could never be recreated.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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103 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA103 Main Street

Price$12,700,000

Est. Mortgage: $/month

MLS Number 40823

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 5
  • Acreage 1.7

Welcome to your dream waterfront oasis on Vineyard Haven Harbor! This exceptional custom home offers an unparalleled blend of luxury, serenity, and captivating water views. Situated on a sprawling beach front parcel, this residence boasts an array of incredible features that epitomize coastal living at its finest. Step inside and be greeted by the seamless flow of the open-concept living space, designed to maximize both comfort and style. The interior is bathed in natural light, courtesy of the expansive windows that showcase panoramic views of Vineyard Haven Harbor. The gourmet kitchen is a chef's delight, featuring top-of-the-line appliances, custom cabinetry, and a spacious island. The adjacent sitting area features a fireplace and French doors leading to a screened porch. The primary bedroom suite boasts stunning water views, a spacious walk-in closet, and a luxurious en-suite bathroom. The additional guest bedrooms are generously sized, each offering its own unique view of the harbor or the lush surroundings. For those seeking relaxation and recreation, this property offers an outdoor paradise. Step outside to discover meticulously landscaped grounds, an expansive stone patio and pool, perfect for lounging or al fresco dining, while relishing the breathtaking scenes of the ferry passing by. One of the true highlights of this remarkable residence is its private beach, providing exclusive access to the pristine shoreline on Vineyard Haven harbor and allowing for easy boating access. A two-car garage offers ample storage for vehicles and outdoor equipment. Located on Main Street, you'll have easy access to the charming shops, galleries, and restaurants in Downtown Vineyard Haven. Live the waterfront lifestyle you've always dreamed of in this extraordinary home.

Listed by Wallace & Co. Sotheby's

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%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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1115 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA1115 Main Street

Price$9,950,000

Est. Mortgage: $/month

Pending

MLS Number 40330

  • Residential
  • Mls Status Pending
  • Bedrooms 11
  • Bathroom 8.5
  • Acreage 0.3145

Built in 1893 and representing one of the classic Grand Dames of the Chop, lies this 4-story, 11-bedroom, 7,000 sq ft residence. The home is permanently situated atop a gentle bank with a magical path through the vegetation to the beach. A sensitive and well thought-out renovation was completed honoring all of the home’s character and charm, while complementing the flow of the house and adding appropriate freshened finishes. The home offers amazing living spaces with tall ceilings, graced with period ceiling beams, a gourmet kitchen, original fireplaces, and large windows everywhere with “of course” the most incredible North Shore sunset views. There are expansive water views from nearly every room in the house as well as a wrap around porch and balcony. The wonderfully manicured grounds offer rolling grass lawns, stone walls, a stone terrace, mature plantings, and gardens. All of this located within close proximity to the West Chop Club, Mink Meadows Golf Course and downtown Vineyard Haven. This is a rare opportunity to acquire a classic, Martha’s Vineyard waterfront home that felt as wonderful in 1920 as it does 100 years later.

Listed by Landvest MV

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%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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31 Lamberts Cove Road Vineyard Haven MA 02568

MLS Number 35174

  • Residential
  • Mls Status Active
  • Village Tashmoo
  • Bedrooms 6
  • Bathroom 7.5

Why would you need to leave home? this extraordinary estate offers everything one needs for privacy and seclusion. This Historic property has been meticulously and tastefully restored to preserve the historic character and grandeur yet offers all of today's modern amenities. This gracious home is in pristine condition and now features 6 bedrooms, 5 full baths, 3 half baths, several sitting rooms, a more formal living room, dining room, family room and home office. All new heating and A/C. The newly renovated kitchen includes 2 Sub Zero refrigerators, a Bosche dishwasher, Thermador double ovens and a five burner stove top. Many complimenting features include original moldings, 7 fireplaces, wide pine and fir floors and all new windows. A har-tru tennis court, gunite pool and a delightful pool house were added in the late 1990's. The pool house is accessible to both tennis and pool through oversized doors that lead to private patios covered by a pergola. It is well equipped with grill area and wet bar, a changing room and full bath. Beautifully landscaped grounds with expansive lawns overlooking rolling meadows, extensive perennial gardens surrounded by stone walls offering exceptional privacy. New Roof on Main house and Pool house, new trim boards and exterior painting this past Fall/2022. Looks like new! Access to Lake Tashmoo, association dock and several walking trails. Additional 3.30 acre parcel. Please inquire. BUYER'S BROKER MUST BE PRESENT AT ALL SHOWINGS AND APPOINTMENTS.

Listed by Karen M. Overtoom R.E.

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$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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14 East Sound Lane Vineyard Haven MA 02568

Vineyard Haven, MA14 East Sound Lane

Price$4,995,000

Est. Mortgage: $/month

MLS Number 39980

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 4
  • Acreage 4.12

This hypnotic retreat on 4+ acres is sited on a north-facing bluff above 1300 feet of beachfront in Pilot Hill Farm, off Lambert's Cove Road. The Farm is comprised of 200 acres, about 1/2 of which is conserved woodlands, beach, fields and trails. Buy your fresh eggs and produce right at the Farm! The exciting contemporary home is comprised of 3 "pods" connected by 1600 sq.ft. of decking. All have dramatic cathedral ceilings and walls of windows that bring in the water views and flood the home with light. The core of the house has an open floor plan with a central fireplace in the living room, a spacious dining area and two bedrooms, each with their own baths. The primary suite is set apart unto itself and has a lovely sitting area, walk-in closet with floor to ceiling built-ins and a handsome bath. The two-story guest suite across the deck has a large ground-floor sitting room with wood stove, a bath beautifully updated in 2016, a walk-in closet and a loft bedroom. All three structures are wrapped in the most gorgeous gardens. Full basement, drive-under garage and a generator. Enjoy a beach at your doorstep, magical gardens and mesmerizing ocean views at this idyllic property. JUNE 2023 UPDATE: Installation of A/C just completed; home refreshed and redecorated; all new storm/screen doors; all exterior trim newly painted and whole property power washed.

Listed by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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 Burts Way Vineyard Haven MA 02568

Vineyard Haven, MA36 Burts Way

Price$3,995,000

Est. Mortgage: $/month

MLS Number 40619

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 6
  • Acreage 2.9654

Inviting waterfront property, just a half mile from town and ferry, is comprised of 3 contiguous parcels and a 6000+ sq.ft. waterfront lot totaling almost 3 acres of land with stunning views down the Lagoon toward the drawbridge. The spacious, 3,640 square foot home was sited and designed to take advantage of those views. The home has multiple gathering spaces on all three floors including an additional 700 sq. ft. in the finished lower level. A comfortable patio with pergola at the front provides outdoor seating with an unobstructed view to the water where you can moor your boat. The large deck at the rear, with a hot tub and a stonewalled garden area with lighted koi pond, completes the experience. In addition to the lot with the home, included with this package is a separate buildable parcel, the access road to the property itself, and a small waterfront parcel on the Lagoon. The property has a substantial rental history. This area, upper Lagoon Pond Road to Hines Point and Weaver Lane, has seen significant upgrades and investment in recent years and that is ongoing at this time. This is a wise investment opportunity. It is truly a safe harbor!

Listed by Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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137 Massasoit Avenue Vineyard Haven MA 02568

Vineyard Haven, MA137 Massasoit Avenue

Price$3,900,000

Est. Mortgage: $/month

Pending

MLS Number 39426

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 0.87

Start your day off viewing magnificent sunrises from the sun-dappled porch, set within the West Chop “loop"...the perfect setting to relax and watch the ferries sailing back and forth to Martha’s Vineyard. Inside, the soaring great room with vaulted ceiling, exposed beams, hardwood floors, expansive windows, and views out to the Nantucket Sound, offers a warm and welcoming gathering space. 5 bedrooms, 3.5 bathrooms, an eat-in kitchen with adjacent dining room, and spacious great-room, allow this much-loved home to accommodate a swell of visiting family and friends. Two 1st floor bedrooms share one full bath, with a half bath off the foyer. The bright and airy primary suite on the 2nd floor has magnificent northeast views over the water, with a cathedral ceiling, sitting area, dressing room, and full bath. Two adjoining rooms connect to this expansive primary suite where you can create a private at-home workspace and/or bonus room. A 4th bedroom and full bathroom complete this floor. Amenities include mini-splits, gas furnace, irrigation, and an outdoor shower, create comfortable for year-round living and well-suited for holiday gatherings. Tucked away from Main Street on 0.87 acres, this quiet, partially wooded, property sits atop a beautiful sloping lawn overlooking the stonewall, flowering meadow, and Sound. Rarely do you find homes with these magnificent views in West Chop, it is an opportunity not to be missed.

Listed by Viewpoints

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$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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232 Lagoon Pond Road Vineyard Haven MA 02568

Vineyard Haven, MA232 Lagoon Pond Road

Price$2,990,000

Est. Mortgage: $/month

Pending

MLS Number 40713

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathroom 4
  • Acreage 0.4843

WATER VIEWS from almost every room in this home. Mooring permit transferred with home sale (current waitlist 6 years) The full service "Safe Harbor Vineyard Haven Marina" is 1/4 Mile down the road (See website link). The potential is endless with this ranch boasting 5/4 bedrooms and 4 full bathrooms. All furniture included so move in immediately. Estate sale so needs a little TLC. This Vineyard Haven home is situated on Lagoon Pond less than 1 mile from town. You can arrive by ferry even with your own car, stroll down Main Street and walk to your new home if you want. This incredible home has 2,276 square feet of living space, an attached garage, a wood burning fireplace and a deck overlooking Lagoon Pond. Lagoon Pond is a saltwater navigable bay off of Vineyard Haven Sound. Don’t miss the opportunity to live on the water in Vineyard Haven. One of the most up and coming towns on the Vineyard.

Listed by Grade A Realty

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$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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89 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA89 Main Street

Price$2,975,000

Est. Mortgage: $/month

MLS Number 41117

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 5
  • Acreage 0.07

Generations have admired the elegant facade of this waterview home tucked into a corner of Vineyard Haven village, and the flower gardens in front are fully deserving of the oohs and aahs from passersby. The quaint exterior disguises what greets the visitor upon entering - a sophisticated combination of traditional and modern design within a completely renovated home (most recently in 2008-2010 and then in 2019). Consider the fact that the house has four large bedrooms all with modern ensuite bathrooms PLUS an office PLUS a separate den PLUS an extra bathroom. The primary bedroom with its private deck occupies the entire third level of the home and enjoys spectacular 120-degree harbor views of the multitude of wooden sailboats on their moorings and the ferries coming and going. This is a home for entertaining friends and family thanks to its open floor plan that opens onto a large deck. The home is located at the far end of Main Street in what is a bustling part of the village, and yet when one steps inside, the hubbub disappears as the door closes behind you. The cobbled driveway fits two cars and there is also a grassy driveway that leads to a detached two-car garage. The garage is currently configured to accommodate one car in the off-season. The other half of the garage is an art studio that could be used as is or repurposed as an office or gym. Tucked between the house and garage is a peaceful area with bluestone pavers that lead to an outdoor shower - the perfect place to rinse off after a day at the beach or out kayaking or paddle-boarding The house conveys with an easement to walk down to the harbor.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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201 Lagoon Pond Road Vineyard Haven MA 02568

Vineyard Haven, MA201 Lagoon Pond Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 40666

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.3445

This unique property offers three distinct structures and the additional waterfront lot! A charming four bedroom two bath home with spectacular views of Lagoon Pond waiting for your personal touch. Adjacent to the Main House a detached Barn beckons creativity with it's generous space and loft above it's an ideal spot for an art studio, workshop or office. The detached garage provides convenient parking plus added storage for your island adventures and watersports kayaks, beach equipment and bikes. Sit back and relax on your front porch and revel nature and your breathtaking water views!!! This property includes the additional waterfront land elevating the allure to a new level. This waterfront land gives you the potential for private Town mooring rights. See mooring application in 'documents'. A coveted perk grant you exclusive access and resident preference for a mooring in the picturesque Lagoon Pond with approval. Convenient to the scenic beauty of the Island, Downtown, shopping, dining, beaches with easy access to the Vineyard Haven Ferry Terminal.

Listed by Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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 Ferro Way Vineyard Haven MA 02568

Vineyard Haven, MA36 Ferro Way

Price$2,175,000

Est. Mortgage: $/month

MLS Number 41255

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 0.3494

Discover the pinnacle of luxury living in Vineyard Haven with this exceptional 5-bedroom, 3.5 bath home, now enhanced by a brand-new farmer's porch. Only 3 years old, this residence seamlessly marries modern sophistication with timeless charm, providing an idyllic retreat for families seeking the finest in comfort and style. From the moment you step inside, you'll be captivated by the expansive eat-in kitchen, boasting a gas stove, double ovens and a free-standing refrigerator as well as a free-standing freezer that cater to your storage needs while showcasing premium cabinetry and countertops. This culinary haven effortlessly flows into the dining area, perfect for daily life and entertaining. For easy clean up, enjoy the central vac system and 2 large pantries in the kitchen. The main floor bedroom, walk-in closet and main bath are an enchanting retreat away from the second-floor bedrooms which provide comfort and seclusion for family members and guests alike. Endless possibilities with the finished attic space which offers versatility to suit your family's evolving needs. Whether you desire a play area for youngsters or a productive home office, this space can be tailored to your preferences. Outdoor living reaches new heights with the addition of a freshly constructed farmer's porch. This charming space provides an inviting entryway and a welcoming spot to enjoy the surroundings. Thoughtfully designed outdoor lighting casts a warm glow over the outdoor spaces, setting the stage for enchanting evenings. The irrigation system ensures that the lawn and gardens remain vibrant and lush year-round. Set in the sought-after Vineyard Haven locale, convenience and elegance converge seamlessly. Local amenities, schools, parks and the delightful downtown area are all within easy reach. Whether you 're spending a leisurely day at the beach or exploring nearby boutiques, this location offers an array of options.

Listed by Compass LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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82 Skiff Avenue Vineyard Haven MA 02568

Vineyard Haven, MA82 Skiff Avenue

Price$2,090,000

Est. Mortgage: $/month

MLS Number 41096

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.2402

Downtown pristine recently developed 3 bedroom 2 1/2 bath home: provides privacy with a convenient short walk to shops, beach and ferry. Set back for quiet and peaceful luxury living, it's a hidden gem. This property boasts; solid hardwood floors, ducted heat/AC, gas fireplace, quartz counters, tiled bathrooms, an open concept floor plan, a first floor master bedroom, two living rooms and custom blinds throughout. This home is filled with light from all sides and views of mature Oak Trees, the generous raised deck is perfect for outside entertainment and relaxation. Below is a bluestone patio, outdoor shower, storage shed and well designed lawn and landscaping. It is move in ready with all furnishing available for purchase. The driveway supports 4 vehicles. Town approval in place to add a full bathroom and wet bar on the first floor. Agent is the owner.

Listed by Premier Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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Based on information submitted to LINKMV as of September 21, 2023 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.