Vineyard Haven, MA Homes

/38
$1,825,000
- 4 Beds
- 3 Baths
- 3,142 Sq Ft
7 S Meadow Ln, Oak Bluffs, MA 02557

Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort, and convenience in one of Oak Bluffs' most desirable locations. The main living area, filled with natural light and soaring ceiling, offers an open layout that is warm and inviting. A third floor den and exterior decks on all levels provide ample living space both indoors and out. Set within the

Katherine Donahue Sandpiper Realty Inc

7 S Meadow Ln, Oak Bluffs, MA 02557
Selling your home? Sell it faster and for more with a Homes.com Boost.
Learn More
/8
$6,000 total monthly price
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
- House for Rent
33 Kennebago Ave Vh414, Tisbury, MA 02568

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

Karen Overtoom Karen M. Overtoom R.E.

33 Kennebago Ave Vh414, Tisbury, MA 02568
/26
$1,600,000 Sold Nov 07, 2025
- 2,115 Sq Ft
- $757/SF
- 35 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2004
96 Pondview Dr, Oak Bluffs, MA 02536

This spacious fully furnished turn key four bedroom colonial style home is nestled on one half an acre of landscaped grounds with a quiet wooded backyard with a recently renovated back deck and outdoor shower. It's located in an excellent location off of Pond View Drive with access to conservation trails, bike path and local bus routes. A spacious design with 2,115 square feet of living space. A

Doug Burke Cronigs Real Estate

96 Pondview Dr, Oak Bluffs, MA 02536

/25
Est $1,984,778 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,636 Sq Ft
131 Shubael Weeks Path, Vineyard Haven, MA 02568

131 Shubael Weeks Path, Vineyard Haven, MA 02568

/61
$2,250,000
- 5 Beds
- 3.5 Baths
- 3,250 Sq Ft
28 Pine Tree Ln, Vineyard Haven, MA 02568

Enjoy beach-close living—just 0.2 miles to the shore—in sought-after West Chop. This welcoming 5BR/3.5BA colonial blends classic Vineyard character with modern comforts, including central air, an updated kitchen, and three fireplaces. Approximately 3,152± sq ft (expanded from 2,632± with a 520± sq ft finished space over the garage) offers flexible, easy flow to a large fenced backyard with a

Lisa Da Silva Compass | Point B

28 Pine Tree Ln, Vineyard Haven, MA 02568
/12
$15,000 total monthly price
- 5 Beds
- 6.5 Baths
- 4,137 Sq Ft
- House for Rent
41 Naushon Rd Wt116, Aquinnah, MA 02575

Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

Karen Overtoom Karen M. Overtoom R.E.

41 Naushon Rd Wt116, Aquinnah, MA 02575
/37
$2,100,000 Sold Nov 07, 2025
- 1,608 Sq Ft
- $1,306/SF
- 201 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
22 Greenleaf Ave, Oak Bluffs, MA 02557

Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect

Jennifer O'hanlon Compass

22 Greenleaf Ave, Oak Bluffs, MA 02557

/2
Est $1,698,838 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,102 Sq Ft
26 Old Coach Rd, Vineyard Haven, MA 02568

26 Old Coach Rd, Vineyard Haven, MA 02568

/9
$2,250,000
- 3 Beds
- 3.5 Baths
- 2,475 Sq Ft
35 Double Ox Rd, Oak Bluffs, MA 02557

Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase$700,000 and building contract $1,550,000.This 3-bedroom dream home is set in an elevated

Marilyn Moses Ocean Park Realty Inc

35 Double Ox Rd, Oak Bluffs, MA 02557
/8
$18,500 total monthly price
- 4 Beds
- 3.5 Baths
- 1,714 Sq Ft
- House for Rent
4 Windy Way Wt143, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

Karen Overtoom Karen M. Overtoom R.E.

4 Windy Way Wt143, West Tisbury, MA 02575
/39
$2,100,000 Sold Nov 07, 2025
- 1,608 Sq Ft
- $1,306/SF
- 197 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
22 Greenleaf Ave, Oak Bluffs, MA 02539

Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coastal living on Martha’s Vineyard. From the highest vantage point on Greenleaf, enjoy sunrises that fill

Jen O'Hanlon Compass | The O'Hanlon Group

22 Greenleaf Ave, Oak Bluffs, MA 02539

/45
Est $1,706,944 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,576 Sq Ft
38 Edgewood Dr, Edgartown, MA 02539

38 Edgewood Dr, Edgartown, MA 02539

/27
$2,400,000
- 3 Beds
- 3.5 Baths
- 1,884 Sq Ft
27 7th St N, Edgartown, MA 02539

27 SEVENTH STREET NORTH, EDGARTOWN offers NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2026; just in time to bring in the 2026 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers an island with

Michele Casavant Vineyard Village Realty

27 7th St N, Edgartown, MA 02539
/6
$6,000 total monthly price
- 3 Beds
- 2 Baths
- 2,213 Sq Ft
- House for Rent
16 Majors Cove Ln, Edgartown, MA 02539

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Light and spacious home in Major's Cove. Privacy, sunshine, spacious deck out back. Nicely maintained and convenient to all down island towns. Close to Oak Bluffs and Edgartown. Nestled privately in the Major's Cove association, this house is filled with light. It has cathedral ceilings in the living room, a gourmet kitchen open to a dining area or

Karen Overtoom Karen M. Overtoom R.E.

16 Majors Cove Ln, Edgartown, MA 02539
/18
$995,000 Sold Nov 06, 2025
- 990 Sq Ft
- $1,005/SF
- 5 Days On Market
- 3 Beds
- 1 Bath
- Built 1983
2 Flamingo Dr, Edgartown, MA 02539

Dodger's Hole - Traditional ranch style home with 3 bedrooms and 1 bath, set upon a half acre, corner lot located within a mature association neighborhood. A comfortable outdoor deck and outdoor shower completes the Vineyard experience. Convenient to the waters of Sengekontacket, and immediate access to bikes paths leading to the villages of Edgartown, Oak Bluffs and Vineyard Haven.

Sean Federowicz Landmarks at TODAY Real Estate

2 Flamingo Dr, Edgartown, MA 02539

/2
Est $1,321,507 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,400 Sq Ft
45 Pine Tree Ln, Vineyard Haven, MA 02568

45 Pine Tree Ln, Vineyard Haven, MA 02568

/36
$2,595,000
- 5 Beds
- 4 Baths
- 3,328 Sq Ft
159 Lake St, Vineyard Haven, MA 02568

Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy and charm on a beautifully landscaped 0.7 acre lot accented by mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm and inviting atmosphere. The home’s four-level design provides exceptional character and flexibility. The main level features a

Alyssa Halisky Wallace & Co. Sotheby's

159 Lake St, Vineyard Haven, MA 02568
/8
$4,800 total monthly price
- 3 Beds
- 3 Baths
- 3,279 Sq Ft
- House for Rent
165 Christiantown Rd, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

Karen Overtoom Karen M. Overtoom R.E.

165 Christiantown Rd, West Tisbury, MA 02575
/19
$835,000 Sold Nov 05, 2025
- 960 Sq Ft
- $870/SF
- 119 Days On Market
- 1 Bed
- 1 Bath
- Built 2000
1 Onondaga Ave, Oak Bluffs, MA 02557

Charming Single Story Cottage on a Beautiful Oak Bluffs Lot – Perfect for Your Vineyard Retreat! Discover the timeless appeal of this cozy 1-bedroom, 1-bath home nestled on a spacious 0.31-acre lot in the heart of Oak Bluffs. Built in 2000 and lovingly owned by the same family since its inception, this property offers a fantastic opportunity for both comfortable living and future expansion.

Leslie C. Floyd Portfolio Real Estate, Inc.

1 Onondaga Ave, Oak Bluffs, MA 02557

/36
Est $2,328,792 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,436 Sq Ft
377 State Rd, Vineyard Haven, MA 02568

377 State Rd, Vineyard Haven, MA 02568

/27
$1,800,000
- 3 Beds
- 3 Baths
- 2,293 Sq Ft
10 Trotters Ln, West Tisbury, MA 02575

Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

Rebecca V Conroy Conroy & Company R.E., Inc.

10 Trotters Ln, West Tisbury, MA 02575
/27
$18,840 total monthly price
- 3 Beds
- 2.5 Baths
- House for Rent
21 William St Vh430, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

Karen Overtoom Karen M. Overtoom R.E.

21 William St Vh430, Tisbury, MA 02568
/42
$1,700,000 Sold Nov 03, 2025
- 2,558 Sq Ft
- $665/SF
- 118 Days On Market
- 3 Beds
- 4 Baths
- Built 1986
35 Tower Ridge Rd, Oak Bluffs, MA 02557

Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just as inviting, with an oversized deck overlooking mature plantings and a generous side yard--perfect for

Katherine Donahue Sandpiper Realty Inc

35 Tower Ridge Rd, Oak Bluffs, MA 02557

/36
Est $1,179,160 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,780 Sq Ft
16 Rock Pond Rd, Vineyard Haven, MA 02568

16 Rock Pond Rd, Vineyard Haven, MA 02568

/26
$1,850,000
- 4 Beds
- 2.5 Baths
- 3,268 Sq Ft
7 Upper Meadow Ln, Oak Bluffs, MA 02557

Meadowview Farms - Tucked at the end of a quiet cul-de-sac, this spacious Colonial offers more than 3,200 square feet of comfortable living space. This home is ideal for those who love to host lively gatherings while providing ample accommodations. Inside, you’ll find four well-sized bedrooms and two and a half baths, including a generous primary suite with double walk-in closets and a private

Lesley Heidt Sandpiper Realty

7 Upper Meadow Ln, Oak Bluffs, MA 02557
/28
$32,000 total monthly price
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
- House for Rent
37 Mempremagog Ave Vh410, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

Karen Overtoom Karen M. Overtoom R.E.

37 Mempremagog Ave Vh410, Tisbury, MA 02568
/28
$1,260,000 Sold Nov 03, 2025
- 1,820 Sq Ft
- $692/SF
- 182 Days On Market
- 4 Beds
- 2 Baths
- Built 2002
11 Flamingo Dr, Edgartown, MA 02539

Located in the Dodger's Hole subdivision is this inviting four bedrooms plus office, two-bathroom cape style home. The property has been well cared for and is a delight to view. Sited on .5 acres of land with a pea stone driveway, wraparound deck, and outdoor shower with new enclosure. The antique garage is a great storage space for lawn equipment, garden supplies or small vehicle. The living

Skip Dostal, Jr Martha's Vineyard Real Estate

11 Flamingo Dr, Edgartown, MA 02539

/40
Est $1,720,934 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1 Sq Ft
179 Main St, Vineyard Haven, MA 02568

179 Main St, Vineyard Haven, MA 02568

/21
$1,999,999
- 4 Beds
- 3 Baths
- 2,730 Sq Ft
5 Pine Tree Ln, Vineyard Haven, MA 02568

Nestled at 5 Pinetree Lane, Vineyard Haven, MA, this single-family residence in Dukes County presents a unique opportunity to own a piece of classic American architecture. Built in 1927, this home offers a blend of vintage charm and comfortable living. The residence features three full bathrooms, providing convenience and privacy for all occupants. Imagine mornings where everyone can prepare for

Kristin Francoeur Gibson Sotheby's International Realty

5 Pine Tree Ln, Vineyard Haven, MA 02568
/18
$10,000 total monthly price
- 3 Beds
- 1.5 Baths
- 1,144 Sq Ft
- House for Rent
100 Franklin Terrace Vh411, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and

Karen Overtoom Karen M. Overtoom R.E.

100 Franklin Terrace Vh411, Tisbury, MA 02568
/16
$1,135,000 Sold Oct 31, 2025
- 1,344 Sq Ft
- $844/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 2002
30 Teaberry Ln, Edgartown, MA 02539

Well-maintained three bedroom, 2 bath home on a level .51 acre lot. Primary en-suite and open floor plan offers the best in first-floor living. Large unfinished basement, outdoor shower and recent Title V inspection of the four bedroom septic system. Deck overlooks the spacious backyard with room for a pool. Convenient to shellfishing or kayaking in Sengekontacket, Caroline Tuthill Preserve and

Dawn Bellante-Holand Sandpiper Realty

30 Teaberry Ln, Edgartown, MA 02539

/35
Est $1,162,460 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,368 Sq Ft
29 Dunham Ave, Vineyard Haven, MA 02568

29 Dunham Ave, Vineyard Haven, MA 02568

/135
$1,895,000
- 3 Beds
- 2 Baths
- 2,462 Sq Ft
129 Beach Rd, Tisbury, MA 02568

Unique, waterfront property with amazing, 180 degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Sellers have been actively making improvements to increase the commercial usage. Zoned both residential and commercial, rarely does such a unique property become available. Elevated above Beach Road and the lagoon, there are 2

Michele Moore Island Real Estate

129 Beach Rd, Tisbury, MA 02568
/25
$10,800 total monthly price
- 2 Beds
- 4 Baths
- 1,800 Sq Ft
- House for Rent
256 Sandpiper Lane Vh417, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

Karen Overtoom Karen M. Overtoom R.E.

256 Sandpiper Lane Vh417, Tisbury, MA 02568
/55
$1,100,000 Sold Oct 31, 2025
- 1,900 Sq Ft
- $579/SF
- 91 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1999
145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

Enjoy effortless island living in this beautifully renovated 3-bedroom, 2.5-bath condo, tucked within a quiet and well-maintained association. Thoughtfully updated with modern finishes and quality craftsmanship, this spacious unit offers comfort, style, and functionality. The open-concept living area features a cozy wood pellet fireplace, perfect for cooler evenings, and flows seamlessly into a

Emily Flake Viewpoints

145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

/23
Est $2,664,048 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,252 Sq Ft
5 Bold Meadow Cir, Edgartown, MA 02539

5 Bold Meadow Cir, Edgartown, MA 02539

/27
$1,695,000
- 3 Beds
- 2.5 Baths
- 2,236 Sq Ft
71 6th St N, Edgartown, MA 02539

Classic three-bedroom farmhouse offers the perfect blend of island charm and laid-back comfort. Located within walking distance to scenic Sengekontacket Pond, it’s an ideal retreat for nature lovers, kayakers, or anyone looking to enjoy the Vineyard lifestyle. The home features a welcoming front porch and back deck—perfect spaces to relax, dine, or entertain outdoors. Inside, you'll find a warm

Erin Leighton Compass

71 6th St N, Edgartown, MA 02539
/15
$7,500 total monthly price
- 2 Beds
- 1 Bath
- 800 Sq Ft
- House for Rent
83 Ashtons Way, Vineyard Haven, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be

Karen Overtoom Karen M. Overtoom R.E.

83 Ashtons Way, Vineyard Haven, MA 02568
/25
$1,125,000 Sold Oct 28, 2025
- 1,432 Sq Ft
- $786/SF
- 97 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1964
140 Longview Rd, Vineyard Haven, MA 02568

Nestled in the hills of Longview, less than 1 mile from beautiful Lambert's Cove Beach, this 3-bedroom retreat is a cozy year-round home or an airy summer getaway - whatever your needs might be. The vaulted ceilings throughout the home allow it to live much larger than its square footage - and the expansive front deck stretches the living space all through the spring, summer and even fall

Candy DaRosa Feiner Real Estate

140 Longview Rd, Vineyard Haven, MA 02568

/32
Est $4,566,360 Not Listed For Sale
- 5 Beds
- 8 Baths
- 5,305 Sq Ft
225 Bigelow Rd, Vineyard Haven, MA 02568

225 Bigelow Rd, Vineyard Haven, MA 02568

Showing Results 41 - 80, Page 2 of 18

Massachusetts Dukes County Vineyard Haven

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage