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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1115 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA1115 Main Street

Price$11,950,000

Est. Mortgage: $/month

MLS Number 39443

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

Step back in time as you explore the old-world charm of this West Chop waterfront grande dame overlooking Vineyard Sound, the Elizabeth Islands, and Woods Hole. Built in 1893 and meticulously maintained and updated over the past century, the much-loved 7,026-sf Victorian home includes many original hand-crafted architectural details. The expansive great room with exposed beams and windows on three sides offers panoramic water views with truly magnificent sunsets, and the adjacent reading room faces a cozy wood-burning fireplace with a door to the covered porch. Flooded with morning light, the kitchen – convenient to the entry mudroom and butler’s pantry/laundry room – features a six-burner Wolf stove, soapstone counters, and sunny breakfast area. Each of the three floors includes a spacious main bedroom with an en-suite bath and expansive water views, for a total of three primary bedroom suites. The fully renovated basement addition – with an underground hallway and door leading to the beach path – also includes two bedrooms, totaling eleven throughout the house. Two bedrooms have fireplaces, and custom built-ins provide plenty of storage. Outside, beautifully crafted stone walls, a south-facing stone terrace, and mature perennial landscaping create a tranquil seaside retreat on .31 acres, with convenient proximity to the West Chop Club and Mink Meadows Golf Club. There’s no shortage of nearby things to do, from tennis and golf to swimming and sailing, but perhaps this property’s greatest appeal is its sense of timelessness, the charm and allure of a bygone era. With only a handful of owners over the generations, now is the rare opportunity to make summers at “Pierside” a part of your family’s history. *Stone Pagoda not included in sale of property*

Listed by Viewpoints

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$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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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1005 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA1005 Main Street

Price$9,900,000

Est. Mortgage: $/month

MLS Number 38460

  • Residential
  • Mls Status Active
  • Bedrooms 9
  • Bathroom 7
  • Acreage 0.8333

At the northernmost tip of Martha’s Vineyard sits one of the prestigious region’s most beautiful homes. Spectacular 270-degree ocean views await, completely unobstructed thanks to its ideal location. The estate is a feast for the eyes itself: a sweeshinglesping 5,050 square foot escape of traditional and countless windows, most framing the endless Atlantic beyond. Elegant and spacious without sacrificing any of its unique character, it presents the perfect venue for entertaining both indoors and out. An incredible painted deck, positioned between the house itself and the private beach below, gives the incomparable impression of total privacy with a maximized oceanfront view. Verdant landscaping extends the pocket of paradise to the entire 0.83-acre parcel. Start each morning in the bright and airy kitchen, by the generous island or in the cozy breakfast nook. Wander the length of the pristine beach below as the waves play against sand and stone. Enjoy an alfresco lunch, made seamless by the outdoor dining area with its unbeatable views. Come sundown, find a front-row seat to a vibrant show as the sun paints the horizon with its golden glow. Welcome to true coastal paradise!

Listed by Rovi Homes

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$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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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23 Bailey Lane Vineyard Haven MA 02568

Vineyard Haven, MA23 Bailey Lane

Price$6,750,000

Est. Mortgage: $/month

Open House

MLS Number 39266

  • Residential
  • Next Open House: Thu 08/11 12:00 pm. to 2:00 pm.
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 4

Overlooking the outer harbor with views of the East Chop Lighthouse and Nantucket Sound beyond, this delightful contemporary possesses a casual elegance. The open design fosters a convivial ambiance as each living area flows into another. Three levels provide an abundance of living space yet fosters pockets of privacy throughout. Beamed ceilings, the warm patina of mellow hardwood floors, plenty of light and air entering through several French doors opening onto screened porches enhance the enjoyment of living in this charming home. Work and pleasure knit seamlesly together. The library/home office with full bath is sequestered at one end of the house away from all of the daily activities of a busy household. This could easily be converted to a first floor bedroom. On the second floor luxury awaits in the spacious master suite complete with a private balcony offering views across the harbor to East Chop, a sitting area with a fireplace, ensuite bath, and walk-in closet. At the opposite end of the house two bedrooms and a shared bath complete the upper floor. The lower level provides an entertainement area, game room, wine closet, cedar closet, half bath and laundry. French doors lead to the covered bluestone patio and barbecue area bordered by the rolling lawn stretching to the private beach. An attached garage, stone walls and gardens provide the finishing touches. Located in the R 25 zoning area the oversize parcel could support a detached carriage house/guest space with town approvals. The driveway parcel, 5-J-4.3, is owned jointly and maintained with the abutter.

Listed by Landmarks at TODAY Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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. 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: 4.99% last updated on Aug 4, 2022
* 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$4,750,000

Est. Mortgage: $/month

MLS Number 39426

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

VIEWS galore from this spacious West Chop House loved and enjoyed by the same family for many decades. Start your day off viewing the magnificent sunrises from the huge, sun-dappled porch on this family-friendly house, set within the West Chop “loop," yet extremely private. It is the perfect spot to relax and watch the ferries sailing back and forth to Martha’s Vineyard. Just inside, the soaring great room with its vaulted ceiling, exposed beams, hardwood floors, expansive windows, and views out to Nantucket Sound – offers a warm and welcoming gathering space. Five bedrooms, three-and-a-half bathrooms, a spacious eat-in country kitchen with adjacent dining room, and plenty of sitting areas throughout allow this much-loved home to accommodate a swell of visiting family and friends with room to spare. A perfect place to work from home with privacy and separation. The bright and airy master suite upstairs has magnificent northeast views over the water, with a cathedral ceiling, comfortable sitting area, dressing room, and full bath. As a bonus, enjoy a walk-through study and den/bedroom, another full bath, and a light-filled bedroom. There are two spacious bedrooms downstairs, together with a third full bath and a half bathroom. Built in 1988 and renovated in 2002, the house has mini-splits, a gas furnace, irrigation, and an outdoor shower, comfortable for year-round living and well-suited for holiday gatherings. Tucked away from Main Street atop a beautiful, grassy slope overlooking the water, and the Sound beyond. The house is set on .87 acres of quiet woodland and open lawn bordered by a stone wall and flowering meadow plantings. It’s a rare offering in this location, right across the street from the West Chop Club’s Middle Pier and swimming beach. Close by are the West Chop Club, Vineyard Haven Yacht Club, Mink Meadows Golf Club, the 83-acre West Chop Woods nature preserve, and the classic 1891 West Chop lighthouse. Sailing, tennis, walking and running trails, biking fishing, children’s activities, and more are close at hand. Please note that 125 Massasoit, an abutting property, is also for sale at $2,950,000 offering a spectacular compound in the heart of West Chop. Rarely do you find homes with these magnificent views in West Chop, it is an opportunity not to be missed. Easy to show!

Listed by Viewpoints

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$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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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128 & 136 Spring Street Vineyard Haven MA 02568
Open House

MLS Number 39707

  • MultiFamily
  • Next Open House: Sat 08/13 10:00 am. to 12:00 pm.
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 4.5

Downtown Vineyard Haven Compound ~ two Lots/Properties being sold together in a Private 'Park Like' setting! This Compound currently boasts 6 bedrooms, 3 kitchens, 4.5 bath, 2 full basements with ability to construct another 3 bedroom structure and plenty of room for a large pool! A fantastic opportunity to Invest Purchase this In Town Property abundant natural light, hardwood flooring, tiled bathrooms, open concept, 3 kitchens, high ceilings. Large fenced in backyard safe for children and pets. Bluestone patio, fire pit and room for a pool. Just blocks to Main Street, the Ferry, Owen Park and Grace Lobster Rolls! Lot #1: 128 Spring Street is a 4 bedroom 2.5 bath Main House a 1 bedroom 1 bath In Law Apartment attached with a breezeway with separate entry. Partially finished basement with office and gym built 2014. Lot #2: 136 Spring Street is a 1 bedroom 1 full bath Guest House with a full unfinished walkout basement built in 2017. This existing two structures/two lot Property with 24,829 SF has ability to build another three bedroom Main House/Pool House!!! Must See in person schedule a showing!

Listed by Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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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87 Bellevue Avenue & 0 Howard Street Vineyard Haven MA 02568
Pending

MLS Number 39481

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathroom 3
  • Acreage 2.96

Sited on a bluff with expansive views overlooking the beautiful Lagoon Pond is this uniquely classic Victorian style cottage. The property is comprised of 2 adjacent parcels totaling 3 acres, a beautiful landscaped lawn, lush gardens, and mature plantings. Also featured is 270 feet of beachfront on Lagoon Pond. Built in the 1870's, this extraordinary home was once a part of the Innisfall Inn, which was a summer resort for actors, opera singers, and musicians. With many renovations and updates over the years, the original Victorian details have been thoughtfully preserved and the details of the new construction have been carefully matched. There is a charming detached bedroom/guest cottage, complete with water views, that has an attached storage shed. The location of the property affords one to easily access downtown Vineyard Haven by foot, bike, or boat . The private 270 waterfront beach is perfect for sailing, swimming, kayaking, paddling, etc. The property upon which the house is located is 1.57 acres, with a 5 bedroom septic system. The adjacent parcel is 1.39 acres, and has a 4 bedroom septic system installed to facilitate the permitting of a second home. Many options exist for this truly "one of a kind" property.

Listed by Match Point Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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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68 Hilltop Road Vineyard Haven MA 02568

Vineyard Haven, MA68 Hilltop Road

Price$3,300,000

Est. Mortgage: $/month

Pending

MLS Number 39691

  • Residential
  • Mls Status Pending
  • Bedrooms 9
  • Bathroom 6
  • Acreage 2.16

This exceptional contemporary is perfect for the extended family and guests with 8 bedrooms, 5 full baths in the main residence, detached bedroom and bath over the 2-car garage, a heated 52 x 20 pool, and pool house with 2 showers and a half bath. Professionally landscaped grounds, enclosed garden and dog run. A short distance to the private association beach. Preferred membership to join the Mink Meadows Golf Club. Closing to take place post Labor Day. Two weather vanes excluded from sale. 360 Virtual Tour link: https://360.mvweb.com/tours/q5-L58o7l

Listed by Landmarks at TODAY Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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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128 Spring Street Vineyard Haven MA 02568

Vineyard Haven, MA128 Spring Street

Price$3,200,000

Est. Mortgage: $/month

MLS Number 39962

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 0.25

Incredible In Town Location!!! 128 Spring Street is a large Colonial style home in an amazing location close to Town, Ferry and Main Street. There are many great features including high cathedral ceilings, open concept kitchen to living room, wonderful natural light, and many gathering spaces inside and out. Enjoy rocking on the front porch to relax and watch the world go by. Built with a large group in mind this home has 5 bedrooms and 3.5 bathrooms. The In Law Apartment is attached with a breezeway/mudroom with private separate entry, partially finished basement with office/media/gym. Included in this home is wonderful Central Air, wood flooring, large windows and transom windows, gas fireplace and plenty of room for family and friends to visit and enjoy. Options include a single family home or investment property. Pool permit in hand ~ add your pool and rent weekly/seasonally/employee housing. This property has many wonderful options contact me for a showing! The abutting Lot 136 Spring Street is also for Sale purchase both for a discounted price.

Listed by Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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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242 Herring Creek Road Vineyard Haven MA 02568

MLS Number 38926

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 4.1

122 ft private Dock & Mooring & House, on Lake Tashmoo on over 4 acres. its a beautiful stroll down an "old country rd" to the dock (with power & water). 1.5 story Home, located off Herring Creek Rd, features living space primarily on the first level, including kitchen, screened in porch, dining room, living room, laundry, 10+ closets, three bedrooms and two bathrooms (6 bedroom septic, plenty room for expansion). It's not often a house with a private dock & mooring, on Tashmoo comes from on the Market. Clamming & Fishing so close to home is what makes the Vineyard so special. Basement has a finished room with a rolling bar cart and a cozy sitting area for watching movies, entertaining or overflow guests. Roof is a few years old. The Unfinished 2nd Level has a lot of potential for expanded living space. A garden shed for storage and a huge clean basement. Come and make your own family memories on Lake Tashmoo- bring your boat, kayaks, clamming rakes and fishing poles. A truly exceptional location, with waterfront amenities. Less than a mile walk or bike ride to Tashmoo Town Beach and Wilfrid's Pond- Newly established walking trails on the right side of Herring Creek Rd. Mink Meadows Golf Course is a down a old country dirt road. This property is only about a 5 minute drive away from Downtown Vineyard Haven - the SSA, Restaurants and Shopping. A boater's paradise with superb potential. Being offered mostly furnished.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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 Massasoit Avenue Vineyard Haven MA 02568

Vineyard Haven, MA125 Massasoit Avenue

Price$2,975,000

Est. Mortgage: $/month

MLS Number 36566

  • Residential
  • Mls Status Active
  • Village West Chop
  • Bedrooms 5
  • Bathroom 3

One of a kind saltbox located in the heart of West Chop. Owned and loved by the same family since 1935, this home was erected on its current site in 1930 incorporating portions of an older (late 1700's) house which had been carefully dismantled and transported from Lambert's Cove to the current West Chop site. This is a wonderful opportunity for a new family to embrace a treasured home with peaks of water. This 5 bedroom, 3 bath home embodies simple summer life on Martha's Vineyard, rocking on the back porch, playing tag in the yard, or enjoying a morning or evening tide ride. Properties on "the Loop" rarely come on the market, this classic is not too be missed!

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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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27 William Street Vineyard Haven MA 02568

Vineyard Haven, MA27 William Street

Price$2,950,000

Est. Mortgage: $/month

MLS Number 39457

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.3869

Warm and welcoming sunlight interiors, a grand central staircase and multiple living spaces for guests and family to enjoy. Fully renovated to accommodate a modern lifestyle including SubZero and Wolf stainless appliances, first and second floor bedroom suites with tile and marble baths, all while carefully preserving the historic charm and character. Set among lush lawns and hydrangeas, a block to Vineyard Haven’s Main Street attractions, the ferry and Owen Park beach. Current septic has additional capacity and lot size should accommodate guest house or carriage house with proper permitting.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 2022
* 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 MA_LINKMV as of August 8, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_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."