Homes in ZIP Code 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
• 

  

  

  /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
• 

  

  

  /40

  Est $1,938,772 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
• 

  

  

  /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
• 

  

  /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
• 

  

  /48

  Est $2,869,894 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  8 Coffins Field Rd, Edgartown, MA 02539

  8 Coffins Field Rd, Edgartown, MA 02539
• 

  

  /23

  $1,790,000

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  11 Beach Rd, Oak Bluffs, MA 02557

  Oak Bluffs: Waterfront Property at Vineyard Haven Outer Harbor**This is an exceptional opportunity to acquire a stunning white sandy beach property on Vineyard Haven Harbor. This charming Island cottage boasts breathtaking panoramic views of the harbor and sound, showcasing magnificent sunsets each evening over the West Chop Peninsula. You can enjoy the lively boating scene, with yachts from

  Alan Schweikert Ocean Park Realty Inc

  11 Beach Rd, Oak Bluffs, MA 02557
• 

  

  /34

  $25,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,334 Sq Ft
  • House for Rent

  100 Connie's Way Vh401, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

  Karen Overtoom Karen M. Overtoom R.E.

  100 Connie's Way Vh401, Tisbury, MA 02568
• 

  

  /17

  $1,200,000 Sold Oct 28, 2025

  • 1,680 Sq Ft
  • $714/SF
  • 209 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1987

  211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

  MULTIFAMILY OPPORTUNITYA wonderful compound on the outskirts of town. Set nicely back off the Edgartown Road, the existing home has 4/5 comfortable bedrooms and 2 baths on a nice 1-acre parcel with a good sense of privacy. Behind the home is a fire pit, a shed and another septic system already installed that will serve an additional 5 bedrooms! This property is on a trail to the Bare Hill

  Jim Feiner Feiner Real Estate

  211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
• 

  

  /49

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,092 Sq Ft

  670 State Rd, Vineyard Haven, MA 02568

  670 State Rd, Vineyard Haven, MA 02568
• 

  

  /37

  $1,995,000

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

  2 Farm Path, Oak Bluffs, MA 02557

  "Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

  Sean Federowicz Landmarks at TODAY Real Estate

  2 Farm Path, Oak Bluffs, MA 02557
• 

  

  /17

  $12,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • House for Rent

  223 Sandpiper Lane Vh405, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

  Karen Overtoom Karen M. Overtoom R.E.

  223 Sandpiper Lane Vh405, Tisbury, MA 02568
• 

  

  /39

  $1,470,000 Sold Oct 27, 2025

  • 1,620 Sq Ft
  • $907/SF
  • 23 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2007

  26 Winne Ave, Vineyard Haven, MA 02568

  Welcome to your dream home just a short walk to the lagoon. This home offers easy access for dropping a kayak or taking a refreshing afternoon dip from a public access point. Discover this charming home nestled on a corner lot within a serene neighborhood. This beach home has an updated kitchen and bathrooms. The kitchen is equipped with new appliances and gorgeous quartz countertops, making it a

  Joe & Nicole Holland Vineyard Dream Realty LLC

  26 Winne Ave, Vineyard Haven, MA 02568
• 

  

  /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
• 

  

  /24

  $2,150,000

  • 2 Beds
  • 2.5 Baths
  • 2,137 Sq Ft

  30 Franklin Ave, Oak Bluffs, MA 02568

  Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

  Stacy Ickes Donnelly + Co.

  30 Franklin Ave, Oak Bluffs, MA 02568
• 

  

  /40

  $32,500 total monthly price

  • 6 Beds
  • 4.5 Baths
  • 3,222 Sq Ft
  • House for Rent

  100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

  Karen Overtoom Karen M. Overtoom R.E.

  100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
• 

  

  /12

  $1,250,000 Sold Oct 23, 2025

  • Land
  • 4.12 Acres
  • $303,398 per Acre

  • 127 Days On Market

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

  This beautiful wooded 4.12 acre parcel of land is peaceful, serene and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. This is an opportunity to realize your vision and build a home that reflects your lifestyle. The large, flat building envelope offers many siting possibilities and, should you choose, the property is

  Abby Rabinovitz Tea Lane Associates

  25 Plum Bush Point Rd Unit 6, West Tisbury, 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
• 

  

  /26

  $1,950,000 Pending

  • 5 Beds
  • 3 Baths
  • 1,916 Sq Ft

  14 Rebekahs Way, Vineyard Haven, MA 02568

  Affectionately referred to as ‘The Treehouse', this property encompasses all the elements of a modern, sophisticated residence while providing the warmth and comfort of a private retreat. Professionally designed by Hutker Architects, this four-bedroom home, with a den/potential fifth bedroom, is sited in a private area, conveniently located with easy access to grocery store, pharmacy, and post

  Sheila Morse Island Real Estate

  14 Rebekahs Way, Vineyard Haven, MA 02568
• 

  

  /29

  $64,000 total monthly price

  • 4 Beds
  • 7 Baths
  • 3,600 Sq Ft
  • House for Rent

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557
• 

  

  /3

  $3,067,050 Sold Oct 22, 2025

  • 1,872 Sq Ft
  • $1,638/SF
  • 0 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1985

  114 Park, Oak Bluffs, MA 02557

  Not Listed in LINK

  LINK Email Cache LINK

  114 Park, Oak Bluffs, MA 02557
• 

  

  /36

  Est $2,466,989 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,791 Sq Ft

  225 Great Plains Rd, Vineyard Haven, MA 02568

  225 Great Plains Rd, Vineyard Haven, MA 02568
• 

  

  /24

  $2,195,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,262 Sq Ft

  30 Sengekontacket Rd, Oak Bluffs, MA 02557

  Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main

  Cassie Bradley Wallace & Co. Sotheby's International Realty

  30 Sengekontacket Rd, Oak Bluffs, MA 02557
• 

  

  /20

  $20,000 total monthly price

  • 3 Beds
  • 3 Baths
  • House for Rent

  40 Hidden Cove Rd, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

  Karen Overtoom Karen M. Overtoom R.E.

  40 Hidden Cove Rd, Oak Bluffs, MA 02557
• 

  /2

  $1,700,000 Sold Oct 20, 2025

  • 1,803 Sq Ft
  • $943/SF
  • 0 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1982

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  Not Listed in LINK

  LINK Email Cache LINK

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
• 

  

  /39

  Est $7,234,025 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 6,546 Sq Ft

  103 Main St, Vineyard Haven, MA 02568

  103 Main St, Vineyard Haven, MA 02568
• 

  

  /81

  $1,785,000 Pending

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

  209 Cove Rd, Vineyard Haven, MA 02568

  Wonderful Tashmoo Wood Association - West Chop. Welcome to this spacious and inviting home in the wonderful Tashmoo Wood Community. Rarely does a Single Family Home come on the market in this Private Association. This four (4) bedroom home, nestled on a private 1 acre lot with a tree lined driveway, abuts common land, is adjacent to Mink Meadows Golf Course and offers the ultimate in the

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  209 Cove Rd, Vineyard Haven, MA 02568
• 

  

  /25

  $24,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,257 Sq Ft
  • House for Rent

  5 Laurel Ave, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage decor and beautiful bamboo floors. Entertainment options include

  Karen Overtoom Karen M. Overtoom R.E.

  5 Laurel Ave, Oak Bluffs, MA 02557
• 

  

  /19

  $1,330,000 Sold Oct 17, 2025

  • 1,404 Sq Ft
  • $947/SF
  • 112 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1983

  32 MacHipscat Trail, Vineyard Haven, MA 02568

  This Cape Style home privately sited on 1.89 acres at the end of a cul-de-sac abutting conservation land with many walking trails. Nice features include spacious living spaces that include a well equipped kitchen with custom cherry cabinets, dining room, living room with fireplace, wood stove and french doors that lead you out to a private patio and backyard. Second floor offers two guest

  Brenda Galligan Karen M. Overtoom R.E.

  32 MacHipscat Trail, Vineyard Haven, MA 02568
• 

  

  /34

  Est $1,535,030 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  84 Christiantown Rd, Vineyard Haven, MA 02568

  84 Christiantown Rd, Vineyard Haven, MA 02568
• 

  

  /23

  $1,795,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,038 Sq Ft

  25 Hampson Ave, Oak Bluffs, MA 02568

  Location is everything. Fantastic Cape in a quiet neighborhood, just a 10-minute walk to harbor and downtown. The first-floor plan includes a spacious living-room that opens to an eat-in kitchen, large Master with full bath, and a second bedroom with a full bath. The second floor has a beautiful large open space area for a media room, study or playroom and 2 more large bedrooms with another full

  Lenny Altieri Premier Properties

  25 Hampson Ave, Oak Bluffs, MA 02568
• 

  

  /30

  $20,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • House for Rent

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

  Karen Overtoom Karen M. Overtoom R.E.

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557
• 

  

  /30

  $1,550,000 Sold Oct 16, 2025

  • 1,986 Sq Ft
  • $780/SF
  • 114 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  251 State Rd, Vineyard Haven, MA 02568

  This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. Abutting Land Bank property, the charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive

  Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
• 

  

  /36

  Est $2,202,915 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 2,705 Sq Ft

  9 Heather Trail, Vineyard Haven, MA 02568

  9 Heather Trail, Vineyard Haven, MA 02568
• 

  

  /26

  $2,150,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 2,137 Sq Ft

  30 Franklin Ave, Oak Bluffs, MA 02568

  Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

  Stacy Ickes Donnelly + Co

  30 Franklin Ave, Oak Bluffs, MA 02568
• 

  

  /14

  $14,200 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

  Karen Overtoom Karen M. Overtoom R.E.

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557
• 

  

  /30

  $1,226,500 Sold Oct 16, 2025

  • 1,637 Sq Ft
  • $749/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  9 Grovedale Rd, Oak Bluffs, MA 02557

  Welcome to a home full of character and charm in the heart of Oak Bluffs. This 3-bedroom, 2-bathroom property offers comfortable living with a sun-filled open kitchen and dining area featuring a picturesque bay window that flows seamlessly into a warm living room centered around a welcoming fireplace. Just a short distance from the Lagoon, the setting is enhanced by mature plantings that surround

  Bonnie Pierce Wallace & Co. Sotheby's International Realty

  9 Grovedale Rd, Oak Bluffs, MA 02557
• 

  

  /19

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,714 Sq Ft

  43 Look St, Vineyard Haven, MA 02568

  43 Look St, Vineyard Haven, MA 02568

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