Vineyard Haven, MA Homes

• 

  

  

  /28

  $550,000

  $49K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 725 Sq Ft

  124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568

  NEWLY RENOVATED ~ fully renovated exterior including a new roof, siding, shutters, trim, all new windows, doors, stairways, and decks. Outstanding move-in-ready, year-round two-bedroom ground-level condo with dedicated parking in an ideal Vineyard Haven location close to the ferry, Main Street shops, and restaurants. The beautifully maintained common grounds feature colorful landscaping, picnic

  Stephanie Roache Donnelly + Co

  124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
• 

  

  

  /27

  $1,735,000

  Sold Sep 29, 2025

  56 Bridle Path Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 4 Baths
  • 2,526 Sq Ft
  • Built 1996

  Last Sold Summary

  • 13% Below List Price
  • $687/SF
  • 2 Days On Market

  Current Estimated Value $2,166,208

  Last Listing Agent Tina Miller Donnelly + Co.

  56 Bridle Path Rd, Vineyard Haven, MA 02568
• 

  

  

  /30

  Est $2,535,298

  Not Listed For Sale

  41 Hidden Village Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 2,540 Sq Ft
  • Built 1981

  41 Hidden Village Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 335 Days On Market

  Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.
• 

  

  

  /5

  $639,000

  • Land
  • 12,998 Sq Ft
  • $2,141,421 per Acre

  52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568

  GOOD TO GO! This sunny 13,000-square-foot lot is ready for your Vineyard home. The property comes with a complete six-bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process.Conveniently located just

  Tina Miller Donnelly + Co

  52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
• 

  

  

  /15

  $1,000,000

  Sold May 13, 2026

  140 Midland Ave, Tisbury, MA 02568

  • 4 Beds
  • 4 Baths
  • 1,999 Sq Ft
  • Built 1974

  Last Sold Summary

  • 33% Below List Price
  • $500/SF
  • 2 Days On Market

  Last Listing Agent Tina Miller Donnelly + Co

  140 Midland Ave, Tisbury, MA 02568
• 

  

  /45

  Est $1,165,622

  Not Listed For Sale

  5 Rock Pond Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft
  • Built 1999

  5 Rock Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 145 Days On Market

  Last Listing Agent Kerry Quinlan-Potter Breakwater MV
• 

  /2

  $785,000

  $9K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 624 Sq Ft

  60R Carol Ln, Oak Bluffs, MA 02557

  Charming Oak Bluffs Retreat Near Town Tucked away down a quiet lane just moments from downtown Oak Bluffs, this charming home offers the perfect blend of simplicity, comfort, and convenience. Set on just over 8,400 square feet, the property provides easy, single-story living in a sought-after Oak Bluffs neighborhood. The bright, open-concept interior features a welcoming living area and kitchen

  Michele Moore Island Real Estate

  60R Carol Ln, Oak Bluffs, MA 02557
• 

  

  /28

  $1,400,000

  Sold Nov 26, 2025

  5 Scottys Ln, Vineyard Haven, MA 02568

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft
  • Built 1968

  Last Sold Summary

  • 22% Below List Price
  • $879/SF
  • 126 Days On Market

  Current Estimated Value $1,666,291

  Last Listing Agent Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  5 Scottys Ln, Vineyard Haven, MA 02568
• 

  

  /29

  Est $1,820,997

  Not Listed For Sale

  49 Oak Ln, Vineyard Haven, MA 02568

  • 4 Beds
  • 3.5 Baths
  • 2,576 Sq Ft
  • Built 1974

  49 Oak Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Wendy Harman Compass Massachusetts, LLC
• 

  

  /25

  $1,450,000

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  4 Lagrange Ave, Oak Bluffs, MA 02557

  New listing tucked away on a dead end road in Oak Bluffs ~Enjoy the best of Vineyard living from this beautifully renovated Oak Bluffs home, ideally located just a short walk from a private Lagoon beach—perfect for swimming, kayaking, paddleboarding and all your favorite water activities. The inviting living area features a dramatic vaulted ceiling and gas fireplace, creating a warm and spacious

  Marilyn Moses Ocean Park Realty Inc

  4 Lagrange Ave, Oak Bluffs, MA 02557
• 

  

  /34

  $3,746,925

  Sold Nov 14, 2025

  39 Sengekontacket Rd, Edgartown, MA 02539

  • 4 Beds
  • 3.5 Baths
  • 2,861 Sq Ft
  • Built 1974

  Last Sold Summary

  • 8% Below List Price
  • $1,310/SF
  • 114 Days On Market

  Current Estimated Value $3,668,740

  Last Listing Agent Jayne Isford Ocean Park Realty Inc

  39 Sengekontacket Rd, Edgartown, MA 02539
• 

  

  /22

  Est $1,219,176

  Not Listed For Sale

  41 Old County Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,264 Sq Ft
  • Built 1983

  41 Old County Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 216 Days On Market

  Last Listing Agent Jared Bicknell Compass LLC
• 

  

  /42

  $2,200,000

  Open Wed 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 2,420 Sq Ft

  61 Canonicus Ave, Oak Bluffs, MA 02557

  Location, location, location: This 1999 home with all the comforts of the 21 st Century isnestled on a landscaped lot within mellow surroundings. And yet ... it’s located withinmere moments of town, beach, bike path, bus line, parks, recreation, Farm Pond and aLand Bank trail. The situation hardly gets better. The 3BR/2.5BA house features adeep wraparound farmer’s porch, Brazilian

  Kristin Buck Donnelly + Co

  61 Canonicus Ave, Oak Bluffs, MA 02557
• 

  

  /37

  $1,705,000

  Sold Mar 24, 2026

  2 Farm Path, Oak Bluffs, MA 02557

  • 4 Beds
  • 3 Baths
  • 3,058 Sq Ft
  • Built 1992

  Last Sold Summary

  • 15% Below List Price
  • $558/SF
  • 347 Days On Market

  Current Estimated Value $1,733,576

  Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

  2 Farm Path, Oak Bluffs, MA 02557
• 

  

  /17

  Est $1,263,773

  Not Listed For Sale

  22 Briarwood Ln, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft
  • Built 2018

  22 Briarwood Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Carol Shore Donnelly + Co
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  /42

  $3,495,000

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft

  64 Christiantown Rd, Vineyard Haven, MA 02568

  This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home

  Karen Overtoom Karen M. Overtoom R.E.

  64 Christiantown Rd, Vineyard Haven, MA 02568
• 

  

  /23

  $1,500,000

  Sold Sep 25, 2025

  190 Longview Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1995

  Last Sold Summary

  • 15% Below List Price
  • $1,071/SF
  • 43 Days On Market

  Current Estimated Value $1,692,286

  Last Listing Agent Kathleen Kendrick Kendrick Real Estate

  190 Longview Rd, Vineyard Haven, MA 02568
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  /32

  Not Listed For Sale

  140 Merry Farm Rd, Vineyard Haven, MA 02568

  • 6 Beds
  • 7 Baths
  • 5,603 Sq Ft
  • Built 1995

  140 Merry Farm Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 238 Days On Market

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's
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  /38

  $5,995,000

  • 3 Beds
  • 3 Baths
  • 2,280 Sq Ft

  20 Sunnyside Ave, Vineyard Haven, MA 02568

  Waterfront Estate with Deep-Water Dock & Private Beach.Experience an exceptional Martha’s Vineyard waterfront lifestyle at this rare Lagoon Pond offering, ideally located just minutes from Vineyard Haven’s vibrant harbor, restaurants and shops. The property features a private deep-water dock—ideal for the avid boater—along with its own sandy beach for effortless access to the

  Peyton Wallace Studio Realty

  20 Sunnyside Ave, Vineyard Haven, MA 02568
• 

  

  /20

  $1,050,000

  Sold Jun 29, 2026

  12 Wheelhouse Way, Oak Bluffs, MA 02557

  • 3 Beds
  • 1.5 Baths
  • 1,487 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $706/SF
  • 125 Days On Market

  Current Estimated Value $1,068,435

  Last Listing Agent Dawn Bellante Sandpiper Realty, Inc.

  12 Wheelhouse Way, Oak Bluffs, MA 02557
• 

  /2

  Not Listed For Sale

  420 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • 7 Beds
  • 6 Baths
  • 4,125 Sq Ft
  • Built 1900

  420 Lamberts Cove Rd, Vineyard Haven, MA 02568
• 

  

  /37

  $1,150,000

  • 4 Beds
  • 3 Baths
  • 1,924 Sq Ft

  7 Fawndale Rd, Vineyard Haven, MA 02568

  Welcome to 7 Fawndale Road in Vineyard Haven. Located just 1 mile from Main St., this delightful property offers comfortable living and flexible spaces. The main level features offers single-story living featuring an open living and dining area with wood beams, a bay window, partial cathedral ceiling, skylight, and wood floors. The galley-style kitchen offers plenty of cabinetry and counter

  Michele Moore Island Real Estate

  7 Fawndale Rd, Vineyard Haven, MA 02568
• 

  

  /81

  $1,650,000

  Sold Jan 09, 2026

  209 Cove Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3.5 Baths
  • 2,194 Sq Ft
  • Built 1997

  Last Sold Summary

  • 15% Below List Price
  • $752/SF
  • 182 Days On Market

  Current Estimated Value $1,778,296

  Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

  209 Cove Rd, Vineyard Haven, MA 02568
• 

  

  /44

  Est $1,707,246

  Not Listed For Sale

  26 Manaquayak Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 2,320 Sq Ft
  • Built 1960

  26 Manaquayak Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate
• 

  

  /18

  $250,000

  • 1 Bed
  • 1 Bath
  • 331 Sq Ft

  27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568

  Island Inn ....tucked behind the ever-popular Noman's Restaurant. Located off the Beach Road in Oak Bluffs. Fully furnished and updated 2nd floor studio. New: floors, appliances, television, mini-split AC and two double mattresses, Fully furnished galley kitchen. Use the convenient bike path to State Beach and then further on into Edgartown ...OR a short distance north to Oak Bluffs center, ferry

  Patti Dean Wiggy's Pond Real Estate

  27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
• 

  

  /13

  $1,187,500

  Sold Jun 12, 2026

  54 Columbian Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 2 Baths
  • 1,764 Sq Ft
  • Built 1989

  Last Sold Summary

  • 8% Below List Price
  • $673/SF
  • 93 Days On Market

  Current Estimated Value $1,217,640

  Last Listing Agent Katrina Lima Donnelly + Co

  54 Columbian Ave, Oak Bluffs, MA 02557
• 

  

  /25

  Est $5,818,641

  Not Listed For Sale

  135 Capawock Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3.5 Baths
  • 2,921 Sq Ft
  • Built 2001

  135 Capawock Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jill Napior Tea Lane Associates
• 

  

  /5

  $789,000

  $68K PRICE DROP

  • Land
  • 16,892 Sq Ft
  • $2,034,554 per Acre

  24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568

  OAK BLUFFS - EIGHT (8) BEDROOM LOT. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time. Convenient access from both Towanticut

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
• 

  

  /24

  $3,050,000

  Sold Apr 15, 2026

  35 New York Ave, Oak Bluffs, MA 02568

  • 7 Beds
  • 5 Baths
  • 3,880 Sq Ft
  • Built 1884

  Last Sold Summary

  • 13% Below List Price
  • $786/SF
  • 23 Days On Market

  Last Listing Agent Emma Kennedy Sandpiper Realty, Inc.

  35 New York Ave, Oak Bluffs, MA 02568
• 

  /2

  Est $2,406,852

  Not Listed For Sale

  84 Cuttyhunk Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 4 Baths
  • 2,396 Sq Ft
  • Built 2001

  84 Cuttyhunk Ave, Vineyard Haven, MA 02568
• 

  

  /43

  $2,455,000

  $20K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,039 Sq Ft

  99 The Blvd, Edgartown, MA 02539

  Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddleboarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury.The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private

  Jennifer DaSilva Compass | Point B

  99 The Blvd, Edgartown, MA 02539
• 

  

  /13

  $1,250,000

  Sold Sep 18, 2026

  82 Pennsylvania Ave, Oak Bluffs, MA 02557

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • Built 1988

  Last Sold Summary

  • 4% Below List Price
  • $1,093/SF
  • 20 Days On Market

  Current Estimated Value $1,299,203

  Last Listing Agent Emma Kennedy Sandpiper Realty, Inc.

  82 Pennsylvania Ave, Oak Bluffs, MA 02557
• 

  

  /24

  Est $956,999

  Not Listed For Sale

  19 Speed Andrews Way, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,016 Sq Ft
  • Built 1972

  19 Speed Andrews Way, Vineyard Haven, MA 02568

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Grace Bishop Compass
• 

  

  /31

  $1,600,000

  $200K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,670 Sq Ft

  528 Main St, Vineyard Haven, MA 02568

  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

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  528 Main St, Vineyard Haven, MA 02568
• 

  

  /22

  $1,100,000

  Sold Apr 30, 2026

  14 21st St N, Edgartown, MA 02539

  • 3 Beds
  • 1.5 Baths
  • 1,304 Sq Ft
  • Built 1978

  Last Sold Summary

  • 8% Below List Price
  • $844/SF
  • 141 Days On Market

  Current Estimated Value $1,120,984

  Last Listing Agent Fran Agnoli The Agency

  14 21st St N, Edgartown, MA 02539
• 

  

  /54

  Est $5,171,503

  Not Listed For Sale

  14 E Sound Ln, Vineyard Haven, MA 02568

  • 4 Beds
  • 4 Baths
  • 2,470 Sq Ft
  • Built 1978

  14 E Sound Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 635 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate
• 

  

  /39

  $1,750,000

  • 3 Beds
  • 3 Baths
  • 1,932 Sq Ft

  14 High Meadow Ln, Oak Bluffs, MA 02557

  Welcome to this sun-drenched, reverse contemporary-style home located in the lovely Meadow View Farms community! This multi-level home has boundless potential. The second level features a bright, open floor plan with cathedral ceilings, living, dining, and kitchen areas, and 3 sliding doors that take you outside to the upper deck. Open the sliders to the expansive deck and you will almost double

  Jennifer B. DaSilva Compass

  14 High Meadow Ln, Oak Bluffs, MA 02557
• 

  

  /16

  $970,000

  Sold Dec 08, 2025

  6 Sachem Way, Oak Bluffs, MA 02557

  • 3 Beds
  • 1 Bath
  • 1,546 Sq Ft
  • Built 1973

  Last Sold Summary

  • 8% Above List Price
  • $627/SF
  • 4 Days On Market

  Current Estimated Value $1,062,214

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's

  6 Sachem Way, Oak Bluffs, MA 02557
• 

  

  /35

  Est $2,026,722

  Not Listed For Sale

  83 William Norton Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 1,907 Sq Ft
  • Built 1999

  83 William Norton Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Alexis Holden Tea Lane Associates
• 

  

  /26

  $925,000

  • 2 Beds
  • 1.5 Baths
  • 1,208 Sq Ft

  4 Quail Run Unit 21, Oak Bluffs, MA 02557

  Welcome to this FULLY FURNISHED, private, 2-bedroom, end-unit townhouse offering 1,208 sq ft of effortless coastal living. With seasonal rentals already in place this opportunity is the defenition of TURN KEY. Thoughtfully designed with both comfort and style in mind, this coastal retreat blends relaxed island charm with modern convenience—perfect for year-round living or as an established rental

  Emma Bryant Studio Realty

  4 Quail Run Unit 21, Oak Bluffs, MA 02557

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