Martha's Vineyard, MA Homes

/42
$3,395,000
- 3 Beds
- 3.5 Baths
- 2,527 Sq Ft
5 Katama Dr, Edgartown, MA 02539

Modern Coastal Retreat In Katama: Freshly reimagined and impeccably styled, this modern coastal residence in the heart of Katama offers a rare opportunity to own a newly renovated home just one mile from South Beach. This appealing retreat has been elevated with curated finishes, high-end systems, and a designer-selected furnishing package that perfectly embodies the relaxed luxury of Vineyard

Wendy Harman

Compass

(508) 546-9869

5 Katama Dr, Edgartown, MA 02539
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/10
$20,000 per month plus fees
- 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
/34
$2,475,000 Sold Sep 05, 2025
- 2,300 Sq Ft
- $1,076/SF
- 117 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1983
31 N Slope Ln, Chilmark, MA 02535

Located on a private lane along North Road in the heart of Chilmark, this hilltop four bedroom home was perfectly sited to enjoy fantastic water views of Vineyard Sound toward the Elizabeth Islands. Built in 1983 and lived in seasonally, this home has been meticulously cared for. There is a new forced air HVAC system, and recently upgraded electrical. In addition, there are three working

Bill Rossi Studio Realty

31 N Slope Ln, Chilmark, MA 02535

/12
Est $1,304,936 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,997 Sq Ft
3 Carole Ave, Vineyard Haven, MA 02568

3 Carole Ave, Vineyard Haven, MA 02568

/23
$8,995,000
- 11 Beds
- 8.5 Baths
- 6,289 Sq Ft
1 Louis Field Rd, Edgartown, MA 02539

SWEETENED WATER FARM ESTATE. Located just one mile from the heart of historic Edgartown Village, this compound in Sweetened Water Farm presents a rare opportunity to become the next steward of this extraordinary Martha’s Vineyard estate. Privately sited on 4.6 acres of exquisitely cultivated gardens, this remarkable property has been featured in several publications celebrating the island’s most

Wendy Harman

Compass

(508) 715-8610

1 Louis Field Rd, Edgartown, MA 02539
/12
$5,500 per month plus fees
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
- House for Rent
2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539

THIS PROPERTY IS A WEEKLY VACATION RENTAL PROPERTY. The home’s timeless interior offers a sitting room with a wood-burning fireplace, a hallway opening to a large, bright, modern kitchen featuring a Viking range and large dining table. Ample counter space and a wall of built-ins are the perfect complement to family and friends that enjoy cooking together. A gas grill and outdoor seating are only

Karen Overtoom Karen M. Overtoom R.E.

2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539
/7
$2,995,000 Sold Sep 04, 2025
- Land
- 3.01 Acres
- $995,017 per Acre
- 389 Days On Market
9 Turkeyland Cove Rd Unit 10.31430, Edgartown, MA 02539

TURKEYLAND COVE: 3-ACRE ESTATE-SIZED PARCEL IN KATAMA. This beautiful and private building site is one of the last remaining 3-acre parcels in Katama. The property offers a perfect opportunity to create a signature residence, multi-generational retreat, or equestrian dream, with possibilities for a Main House, Carriage House, pool, tennis court and/or barn. An idyllic Katama lifestyle awaits . .

Wendy Harman Compass | Point B

9 Turkeyland Cove Rd Unit 10.31430, Edgartown, MA 02539

/13
Est $1,256,744 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

/41
$9,495,000
- 4 Beds
- 6 Baths
- 4,605 Sq Ft
29 Slough Cove Rd, Edgartown, MA 02539

LUXURIOUS COUNTRY ESTATE IN KATAMA. Sited at the end of a long private drive, amid a bucolic 1.5-acre meadow setting with stone retaining walls and lush perennial gardens, this elegant country estate, designed by noted architect Patrick Ahearn, offers the epitome of luxurious living in Katama. The home’s timeless and charming character is highlighted by thoughtful, top-notch architectural details

Wendy Harman

Compass

(508) 691-8146

29 Slough Cove Rd, Edgartown, MA 02539
/10
$8,500 per month plus fees
- 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
/26
$965,000 Sold Sep 04, 2025
- 1,512 Sq Ft
- $638/SF
- 78 Days On Market
- 3 Beds
- 2 Baths
- Built 1998
62 Jernegan Ave, Edgartown, MA 02539

Charming 3-Bedroom, 2-Bath Ranch in Edgartown - Spacious, Private, and Conveniently Located. Discover this inviting 3-bedroom, 2 full bath ranch-style home set on a generous 1/2 acre lot in a quiet, private area of Edgartown. Featuring an open-concept layout, this home offers seamless flow between the living, dining, and kitchen spaces--ideal for both everyday living and entertaining. The

Jason Parisella Keller Williams Realty Beverly

62 Jernegan Ave, Edgartown, MA 02539

/14
Est $995,457 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,024 Sq Ft
51 Manchester Ave, Vineyard Haven, MA 02568

51 Manchester Ave, Vineyard Haven, MA 02568

/37
$9,995,000
- 6 Beds
- 7.5 Baths
- 7,205 Sq Ft
25 Lelands Path, Edgartown, MA 02539

Casual Elegance On Katama Bay - Welcome to 25 Leland’s Path on Katama Bay, a stunning property that embodies the perfect blend of casual elegance and serene waterfront living on Chappquiddick. This magnificent home offers over 7,200 square feet of living space, six bedrooms, all with en suite baths, and a three-room Owner's Suite with sweeping water views and a private second-floor deck. The

Wendy Harman

Compass

(508) 625-9706

25 Lelands Path, Edgartown, MA 02539
/8
$11,800 per month plus fees
- 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
/5
$2,995,000 Sold Sep 04, 2025
- Land
- 3.01 Acres
- $995,017 per Acre
- 2 Days On Market
9 Turkeyland Cove Rd, Edgartown, MA 02539

Turkeyland Cove: Three-Acre Estate-Sized Parcel In Katama - This beautiful and private building site is one of the last remaining 3-acre parcels in Katama. The property offers a perfect opportunity to create a signature residence, multi-generational retreat, or equestrian dream, with possibilities for a Main House, Carriage House, pool, tennis court and/or barn. The property offers easy access to

Wendy Harman Compass

9 Turkeyland Cove Rd, Edgartown, MA 02539

/30
Est $2,439,395 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,555 Sq Ft
10 Crow Hollow Rd, Vineyard Haven, MA 02568

10 Crow Hollow Rd, Vineyard Haven, MA 02568

/42
$5,995,000
- 3 Beds
- 6 Baths
- 3,608 Sq Ft
385 Barnes Rd, Vineyard Haven, MA 02568

Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

Wendy Harman

Compass

(508) 205-8817

385 Barnes Rd, Vineyard Haven, MA 02568
/8
$17,500 per month plus fees
- 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
/26
$1,500,000 Sold Sep 03, 2025
- 1,232 Sq Ft
- $1,218/SF
- 158 Days On Market
- 3 Beds
- 2 Baths
- Built 1972
37 Knoll Dr, Edgartown, MA 02539

TURNKEY KATAMA BEACH RETREAT - OWNER FINANCING POSSIBLETucked away on a quiet sandy road in the heart of Katama, this charming and surprisingly spacious home is move-in or rental-ready—offered fully furnished for immediate enjoyment or income. Featuring 3 bedrooms and 2 full baths, the home includes 1,232 square feet of main-level living plus 520 square feet of finished lower level—perfect for a

Josseph Barkett Compass

37 Knoll Dr, Edgartown, MA 02539

/2
Est $2,543,652 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,527 Sq Ft
230 Pond Rd, Vineyard Haven, MA 02568

230 Pond Rd, Vineyard Haven, MA 02568

/27
$1,695,000
- 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
/8
$16,000 per month plus fees
- 7 Beds
- 3.5 Baths
- 4,000 Sq Ft
- House for Rent
5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

Karen Overtoom Karen M. Overtoom R.E.

5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
/35
$1,295,000 Sold Sep 02, 2025
- 1,814 Sq Ft
- $714/SF
- 3 Days On Market
- 3 Beds
- 2 Baths
- Built 1980
35 7th St N, Edgartown, MA 02539

Welcome to this charming Cape-style home, just a short distance from the Village. Set on a spacious half-acre lot, this delightful property has been lovingly maintained. The home features an open layout that seamlessly blends comfort and functionality, making it perfect for both everyday living and entertaining. A sun-filled living room with cathedral ceilings and sliders opens to a multi-level

Stephanie Roache Donnelly + Co.

35 7th St N, Edgartown, MA 02539

/4
Est $2,911,900 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,789 Sq Ft
188 Pond Rd, Vineyard Haven, MA 02568

188 Pond Rd, Vineyard Haven, MA 02568

/42
$5,750,000
- 4 Beds
- 4.5 Baths
- 3,643 Sq Ft
4 Somerset Ln, Edgartown, MA 02539

New Construction: Reimagined Island Living At Somerset. Located in Katama, Somerset is an exclusive five-home luxury enclave perfectly located between Edgartown Village and South Beach -- and developed by Stanmar, owners of the Winnetu Oceanside Resort. The home sites have been designed to maximize outdoor living and entertaining around a spacious and private yard with expansive lawns and room

Wendy Harman

Compass

(508) 715-9594

4 Somerset Ln, Edgartown, MA 02539
/8
$3,300 per month plus fees
- 3 Beds
- 2 Baths
- 1,196 Sq Ft
- House for Rent
849 State Rd Unit 1, Aquinnah, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to both Philbin and Lobsterville beaches. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze. This sunny property is easily accessible as well as peaceful and relaxing. Owner is

Karen Overtoom Karen M. Overtoom R.E.

849 State Rd Unit 1, Aquinnah, MA 02535
/28
$1,320,000 Sold Aug 29, 2025
- 1,450 Sq Ft
- $910/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
10 Eagles Nest, Edgartown, MA 02539

Nestled in the serene setting of the Dodger's Hole community, this home is brimming with natural light, soaring ceilings and clean architectural lines.The open-concept layout features a generous living area with a seamless flow to the dining, kitchen and entertaining spaces, ideal for both everyday living and hosting guests.Kitchen has brand new stainless steel appliances! The spaces are

Jennifer B. DaSilva Compass

10 Eagles Nest, Edgartown, MA 02539

/34
Est $2,546,877 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

/32
$985,000
- 2 Beds
- 1 Bath
- 990 Sq Ft
37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.The interior

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 514-5238

37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
/8
$6,000 per month plus fees
- 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
/41
$2,590,000 Sold Aug 29, 2025
- 3,052 Sq Ft
- $849/SF
- 29 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2014
27 Watcha Path, Edgartown, MA 02539

STYLISH VINEYARD LIVING WITH EXCEPTIONAL OUTDOOR AMENITIES. This beautifully landscaped coastal-style home is set on three acres just off the bike path, offering easy access to all Island towns. The highlight? A heated salt water pool surrounded by expansive decking and outdoor gathering spaces—an ideal setup for Vineyard summers. Thoughtfully updated by the current owners, the home features four

Jen O'Hanlon Compass | The O'Hanlon Group

27 Watcha Path, Edgartown, MA 02539

/25
Est $2,091,937 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

/24
$935,000
- 1 Bed
- 1 Bath
- 797 Sq Ft
37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood

Lisa Lucier

Anchor Realty of MV

(508) 422-4131

37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
/4
$6,000 per month plus fees
- 3 Beds
- 2 Baths
- 1,608 Sq Ft
- House for Rent
836 State Rd, Aquinnah, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the

Karen Overtoom Karen M. Overtoom R.E.

836 State Rd, Aquinnah, MA 02535
/30
$1,995,000 Sold Aug 29, 2025
- 2,891 Sq Ft
- $690/SF
- 5 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1980
26 Box Turtle Ln, Oak Bluffs, MA 02557

This delightful home is on a scenic lot nestled within the Sengekontacket Association. Every room in the home is filled with natural light and beautiful views. It is a very short walking distance to the community boat dock and kayaking, as well as the walking trails of Sengy.Updated in 2008 by the architect owner, this home has 3 bedrooms in the main house and a lovely bedroom and bathroom in

Jayne Isford Ocean Park Realty Inc

26 Box Turtle Ln, Oak Bluffs, MA 02557

/43
Est $4,544,245 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,932 Sq Ft
12 Norton St, Edgartown, MA 02539

12 Norton St, Edgartown, MA 02539

/26
$2,795,000
- 3 Beds
- 3 Baths
- 2,750 Sq Ft
109 Herring Creek Rd, Edgartown, MA 02539

Coastal Retreat In Katama - Located in the heart of Katama, with the iconic Katama Airfield and the sandy shores of South Beach nearby, this contemporary coastal retreat is ideal for enjoying all the best of Katama. The reverse-style contemporary features a sunny, open-designed floor plan with vaulted ceilings that seamlessly combine an inviting Living Room with gas fireplace, a Game Room with

Wendy Harman

Compass

(508) 274-5363

109 Herring Creek Rd, Edgartown, MA 02539
/8
$13,600 per month plus fees
- 2 Beds
- 2 Baths
- 1,967 Sq Ft
- Condo for Rent
1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Enjoy this well appointed and immaculately clean two bedroom condo located just steps from the association pool and a short drive to South Beach with its gorgeous white sands. An open living room, kitchen and dining room with walk-out access to the deck and back yard offer plenty of gathering spaces to enjoy your company over meals, snacks and games

Karen Overtoom Karen M. Overtoom R.E.

1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539
/44
$1,890,000 Sold Aug 29, 2025
- 3,270 Sq Ft
- $578/SF
- 38 Days On Market
- 4 Beds
- 3 Baths
- Built 1981
1 Thames Ct, Edgartown, MA 02539

Welcome to this spacious and elegant 4- bedroom, 3-bathroom home nestled in a prime central Edgartown location. Offering over 3,200 sq ft of living space, this expansive property is perfect for a large family, accommodating guests, or serving as a lucrative income opportunity.Step inside to an inviting open-concept layout that seamlessly connects the living, dining, and kitchen

Jon Hartzband Martha's Vineyard Island-Wide Realty

1 Thames Ct, Edgartown, MA 02539

/45
Est $1,802,171 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

Showing Results 41 - 80, Page 2 of 18

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