Tisbury, MA Homes

• 

  

  

  /27

  $1,795,000

  • 3 Beds
  • 2.5 Baths
  • 1,740 Sq Ft

  27 Chapde Ln, Tisbury, MA 02568

  Classic Style Meets Timeless Charm - Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this residence provides a modern and spacious environment for comfortable island living. The home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen is a chef's delight that

  

  Wendy Harman

  Compass

  (508) 691-8993

  27 Chapde Ln, Tisbury, MA 02568
• 

  

  

  /16

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft
  • House for Rent

  100 Old Lighthouse Rd, Tisbury, MA 02568

  Property Id: 1831886Where memories are made! Come visit this newly renovated cottage (still working on furnishings) in the iconic West Chop neighborhood and experience them yourself! Walkable distance to everything for a fun filled, special vacation including downtown VH, Yacht Club and public beaches. Enjoy sunny days at the beach and starry nights on your own private bluestone patio.

  100 Old Lighthouse Rd, Tisbury, MA 02568
• 

  

  

  /30

  $1,837,500 Sold Apr 18, 2025

  • 1,654 Sq Ft
  • $1111/SF
  • 0 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1984

  55 Charles Neck Way, Vineyard Haven, MA 02568

  Long Point Beach Retreat - Privately set on 1.6 acres in the highly-coveted Long Point area of West Tisbury, this reverse style beach house is an idyllic island retreat. The open-designed Great Room features vaulted ceilings and a wall of sliding glass doors that open out to an expansive deck, perfect for indoor-outdoor summer living and entertaining. There are also screened porches on both

  Wendy Harman Compass

  55 Charles Neck Way, Vineyard Haven, MA 02568
• 

  

  

  /3

  Est $1,500,944 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,329 Sq Ft

  18 Towanticut Ave, Oak Bluffs, MA 02557

  18 Towanticut Ave, Oak Bluffs, MA 02557
• 

  

  

  /37

  $2,995,000

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  31 The Blvd, Edgartown, MA 02539

  Waterfront Charmer on Sengekontacket Pond - Perched on the shoreline, this contemporary cottage is enveloped by stone walls, lush gardens, and stunning water views. Inside, a bright, airy living space features an open dining area and a well-appointed kitchen. The all-white interior is complemented by hardwood floors, vaulted ceilings, skylights, air conditioning, and ceiling fans. Three sliding

  

  Wendy Harman

  Compass

  (508) 301-9323

  31 The Blvd, Edgartown, MA 02539
• 

  

  /41

  $8,750 per month

  • 4 Beds
  • 2.5 Baths
  • 1,811 Sq Ft
  • House for Rent

  11 High Meadow Ln, Vineyard Haven, MA 02568

  Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor full bath, plus additional half bath on main level. The

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  11 High Meadow Ln, Vineyard Haven, MA 02568
• 

  

  /42

  $865,000 Sold Apr 17, 2025

  • 1,208 Sq Ft
  • $716/SF
  • 2 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  4 Quail Run Rd Unit 17, Edgartown, MA 02539

  Luxurious Lifestyle Amenities: Renovated Townhouse With Tennis, Pickleball + Boating Access - This nicely appointed condominium in the exclusive Sengekontacket community offers a perfect blend of comfort and convenience. It features two walls of sliding glass doors that lead out to an expansive 288-square foot deck. The property was updated in 2023 with new Pella® sliding glass doors, new

  Wendy Harman Compass

  4 Quail Run Rd Unit 17, Edgartown, MA 02539
• 

  

  /23

  Est $1,301,237 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,184 Sq Ft

  4 Fowler Ave, Edgartown, MA 02539

  4 Fowler Ave, Edgartown, MA 02539
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  /16

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557

  East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Captain's Quarters'', features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living

  Perry Patterson MV Luxury Homes, LLC

  47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
• 

  

  /14

  $8,400 per month

  • 4 Beds
  • 3 Baths
  • 2,148 Sq Ft
  • House for Rent

  39 Old Coach Rd, West Tisbury, MA 02568

  Summer weekly rental only! June weekly rate is $8,400 and July weekly rate is $10,000/week - Sunday to Saturday. Recently renovated 4 bedroom, 3 bathroom home that sits on a private 2 acre lot in West Tisbury MA! This large cape house has just been update with new stainless steel appliances, new kitchen cabinets and countertops. Other updates include, new bathroom vanities and hardware,

  Joseph D'Amico Dee Development Company

  39 Old Coach Rd, West Tisbury, MA 02568
• 

  

  /35

  $1,875,000 Sold Apr 01, 2025

  • 3,841 Sq Ft
  • $488/SF
  • 47 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1994

  83 Dolan Ave, Vineyard Haven, MA 02568

  Beautiful Cape style home renovated over the years with an open floor plan, five bedrooms including a first-floor primary with en-suite, and a nicely finished walk-out lower level. There is a 7-bedroom septic system for additional bedrooms and a special permit for an apartment. Manicured yard with mature plantings providing excellent privacy. In-ground heated pool with blue stone patio and lots

  Courtney Marek Sandpiper Realty Inc

  83 Dolan Ave, Vineyard Haven, MA 02568
• 

  

  /36

  Est $2,496,817 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,470 Sq Ft

  28 Woodhaven Dr, Edgartown, MA 02539

  28 Woodhaven Dr, Edgartown, MA 02539
• 

  

  /12

  $1,995,000

  • 2 Beds
  • 1 Bath
  • 879 Sq Ft

  47 E Chop Dr Unit 4, Oak Bluffs, MA 02568

  East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condominium, the ''Tivoli'', features outstanding water views of the harbor and the sound beyond all the way to Chappaquiddick. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living and dining areas and a

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr Unit 4, Oak Bluffs, MA 02568
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  /27

  $21,700 per month

  • 5 Beds
  • 3 Baths
  • 2,168 Sq Ft
  • House for Rent

  97 3rd St N, Edgartown, MA 02539

  YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky

  Fine Homes Group Keller Williams Realty Boston-Metro | Back Bay

  97 3rd St N, Edgartown, MA 02539
• 

  

  /19

  $4,300,000 Sold Mar 24, 2025

  • 4,740 Sq Ft
  • $907/SF
  • 239 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 2024

  18 Bold Meadow Rd, Edgartown, MA 02539

  EDGARTOWN - NEW BUILD - Exceptionally stylish, wonderful curb appeal! Luxurious 4 bed, 6 bath home, timeless features, black windows, complimented by elegant neutral decor, peppered w/lovely details throughout. Abuts 32 acres Common land & 5,300 acres State Forest. Numerous entertaining areas, indoors & out. An entertainer's dream. Open floor plan - Living room, w/fireplace, breakfast area,

  Alisan Lohan - Conway Alisan Lohan - Conway Properties

  18 Bold Meadow Rd, Edgartown, MA 02539
• 

  

  /31

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,754 Sq Ft

  12 Fairway Dr, Vineyard Haven, MA 02568

  12 Fairway Dr, Vineyard Haven, MA 02568
• 

  

  /19

  $2,650,000

  • 4 Beds
  • 5 Baths
  • 2,820 Sq Ft

  71 Netock Ave, Oak Bluffs, MA 02557

  On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor

  Ellen Valentgas Sotheby's International Realty

  71 Netock Ave, Oak Bluffs, MA 02557
• 

  

  /20

  $14,000 per month

  • 5 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • House for Rent

  55 Samoset Ave, Oak Bluffs, MA 02557

  Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  55 Samoset Ave, Oak Bluffs, MA 02557
• 

  

  /23

  $1,115,000 Sold Mar 14, 2025

  • 1,286 Sq Ft
  • $867/SF
  • 237 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  496 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Two peaceful acres on coveted Lamberts Cove Road with access to Lamberts Cove Beach and proximity to West Tisbury Center and Conservation Land. This property boasts mature plantings, various trees, and much Mother Nature offers, including a small pond. The home has been completely renovated and enjoys hardwood floors, skylights, a wood stove, and other special features such as antique

  Stephanie Roache Donnelly + Co.

  496 Lamberts Cove Rd, Vineyard Haven, MA 02568
• 

  

  /13

  Est $1,220,833 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  33 Menahan St, Vineyard Haven, MA 02568

  33 Menahan St, Vineyard Haven, MA 02568
• 

  

  /17

  $1,995,000

  • 2 Beds
  • 1 Bath
  • 802 Sq Ft

  47 E Chop Dr Unit 3, Oak Bluffs, MA 02568

  East Chop Water Front Luxury Condominiums -- This 2BR, waterfront condominium, the ''Highlands'', features outstanding water views of the harbor, the sound and the Cape beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 2nd floor unit includes new kitchen with Bosch appliances, living and dining areas and a

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr Unit 3, Oak Bluffs, MA 02568
• 

  

  /30

  $28,500 per month

  • 9 Beds
  • 6.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  9 Tuckernuck Ave, Oak Bluffs, MA 02557

  **PEAK SUMMER WEEKLY RATE** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and distinctive design.

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  9 Tuckernuck Ave, Oak Bluffs, MA 02557
• 

  

  /19

  $1,265,000 Sold Mar 11, 2025

  • 1,682 Sq Ft
  • $752/SF
  • 350 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2010

  62 Lagoon Pond Rd Unit B, Vineyard Haven, MA 02568

  A must see property located in the heart of Vineyard Haven. This three-bedroom, two bath, colonial style condo boasts expansive living spread over three floors. Completed in 2019, this energy efficient 1682 sq ft home includes a 5 KW solar PV system. The open layout of the first floor includes a modern, galley style kitchen with stainless steel appliances and extensive counter space. The three

  Allison Fisher Donnelly + Co.

  62 Lagoon Pond Rd Unit B, Vineyard Haven, MA 02568
• 

  

  /34

  Est $2,431,655 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 1 Sq Ft

  248 Pond Rd, Vineyard Haven, MA 02568

  248 Pond Rd, Vineyard Haven, MA 02568
• 

  

  /13

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft

  47 E Chop Dr Unit 2, Oak Bluffs, MA 02568

  East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, ''Cottage City'', features outstanding water views of the harbor and sound beyond, a cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 1st-floor unit includes new kitchen with Bosch appliances, living room with

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
• 

  

  /10

  $20,000 per month

  • 5 Beds
  • 3 Baths
  • 2,352 Sq Ft
  • House for Rent

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

  Karen Overtoom Karen M. Overtoom R.E.

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
• 

  

  /24

  $917,500 Sold Mar 10, 2025

  • 1,898 Sq Ft
  • $483/SF
  • 138 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  40 Hidden Cove Rd Unit 15, Edgartown, MA 02539

  NEW PRICE. Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor

  Stephanie Roache Donnelly + Co.

  40 Hidden Cove Rd Unit 15, Edgartown, MA 02539
• 

  

  /30

  Est $1,169,275 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  54 Oklahoma Ave, Vineyard Haven, MA 02568

  54 Oklahoma Ave, Vineyard Haven, MA 02568
• 

  

  /12

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 731 Sq Ft

  47 E Chop Dr Unit 1, Oak Bluffs, MA 02568

  East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condominium, ''Oak Bluffs'', features outstanding water views of the harbor and sound beyond. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
• 

  

  /10

  $8,500 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

  Karen Overtoom Karen M. Overtoom R.E.

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
• 

  

  /25

  $917,500 Sold Mar 10, 2025

  • 1,898 Sq Ft
  • $483/SF
  • 139 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  40 Hidden Cove Rd, Edgartown, MA 02539

  NEW PRICE. Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor

  Stephanie Roache Donnelly + Co.

  40 Hidden Cove Rd, Edgartown, MA 02539
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  /40

  Est $1,742,557 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
• 

  

  /30

  $2,285,000

  • 4 Beds
  • 2.5 Baths
  • 1,825 Sq Ft

  4 Dempster Park, Oak Bluffs, MA 02568

  This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. First floor includes large living room with dining area and Rumford wood burning fireplace that opens out to a front porch and deck running the length of the house and which wraps around to the rear patio.

  Perry Patterson MV Luxury Homes LLC

  4 Dempster Park, Oak Bluffs, MA 02568
• 

  

  /8

  $11,800 per month

  • 4 Beds
  • 4 Baths
  • 2,612 Sq Ft
  • House for Rent

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

  Karen Overtoom Karen M. Overtoom R.E.

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
• 

  

  /38

  $2,860,000 Sold Mar 10, 2025

  • 3,752 Sq Ft
  • $762/SF
  • 290 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1836

  49 William St, Vineyard Haven, MA 02568

  Welcome to the timeless elegance of the Captain Swain House, nestled on the prestigious historic William Street in Vineyard Haven. This distinguished Greek Revival main residence and barn-style guest house seamlessly merges historical charm with modern luxury. Step into this meticulously updated 4-bedroom home and you will find a gourmet kitchen, a welcoming dining room, wet-bar and a screened

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  49 William St, Vineyard Haven, MA 02568
• 

  

  /48

  Est $3,207,386 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
• 

  

  /29

  $1,950,000

  • 1 Bed
  • 1 Bath
  • 524 Sq Ft

  61 Hines Point Rd, Vineyard Haven, MA 02568

  Tucked away on the serene shores of Lagoon Pond in Vineyard Haven, this cozy one-bedroom cottage offers the perfect island escape. Located on exclusive Hines Point, the home features stunning water views, direct access to a private beach, and the calming sounds of the tide just steps from your door. Inside, the cottage is thoughtfully designed for comfort and simplicity, with an open living area

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  61 Hines Point Rd, Vineyard Haven, MA 02568
• 

  

  /8

  $17,500 per month

  • 8 Beds
  • 4.5 Baths
  • 3,876 Sq Ft
  • House for Rent

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and

  Karen Overtoom Karen M. Overtoom R.E.

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
• 

  

  /6

  $776,500 Sold Mar 05, 2025

  • 768 Sq Ft
  • $1011/SF
  • 51 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1968

  32 Clark Ave, Vineyard Haven, MA 02568

  This two bedroom year-round home will afford you all the opportunities Vineyard Haven has to offer. This private lot is bursting with lilacs, forsythia, wisteria, raspberry canes, a mock orange bush and a peach tree. The home boasts natural light, cathedral ceilings, a comfortable kitchen and living area with two bedrooms and one full bath. There is a mudroom and a handsome, fully enclosed front

  Sheila Morse Island Real Estate

  32 Clark Ave, Vineyard Haven, MA 02568
• 

  

  /27

  Est $1,384,127 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,228 Sq Ft

  24 Alyssa Ln, Vineyard Haven, MA 02568

  24 Alyssa Ln, Vineyard Haven, MA 02568

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