Edgartown, MA Homes

/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
$19,000 total monthly price
- 5 Beds
- 5 Baths
- 3,137 Sq Ft
- House for Rent
19 Morse St, Edgartown, MA 02539

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, office/den and a full bath all

Karen Overtoom Karen M. Overtoom R.E.

19 Morse St, Edgartown, MA 02539
/2
$3,200,000 Sold Nov 18, 2025
- 960 Sq Ft
- $3,333/SF
- 40 Days On Market
- 2 Beds
- 2 Baths
- Built 1966
23 Manaca Hill Rd, Edgartown, MA 02539

Enjoy dynamic, panoramic views from this charming and thoughtfully updated single-story Chappaquiddick cottage. Designed for effortless living, the home features an expansive deck overlooking the outer harbor and iconic lighthouse, perfect for entertaining or relaxation. A rooftop observation area provides additional seating and even more breathtaking vistas. Deeded beach access is conveniently

Katherine Donahue Sandpiper Realty Inc

23 Manaca Hill Rd, Edgartown, MA 02539

/7
Not Listed For Sale
- 4 Beds
53 N Neck Rd, Edgartown, MA 02539

53 N Neck Rd, Edgartown, MA 02539

/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
/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
/34
$3,746,925 Sold Nov 14, 2025
- 2,861 Sq Ft
- $1,310/SF
- 114 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1974
39 Sengekontacket Rd, Edgartown, MA 02539

SPECTACULAR WATERFRONT home with stunning water views from every room. Situated in a private location in the Sengekontacket Association, this is an exceptional property in a rare setting. Completely renovated in 2014. In addition to the breathtaking water view of Major's Cove and of Felix Neck throughout the home, the front of the property faces serene pastoral views. This home offers four

Jayne Isford Ocean Park Realty Inc

39 Sengekontacket Rd, Edgartown, MA 02539

/14
Est $6,018,616 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,193 Sq Ft
100 Meetinghouse Way, Edgartown, MA 02539

100 Meetinghouse Way, Edgartown, MA 02539

/47
$5,500,000
- 4 Beds
- 2 Baths
- 2,808 Sq Ft
31 Butlers Cove Rd, Edgartown, MA 02539

This charming farmhouse lies on 3-acres of land overlooking the expansive fields and horse stables, inside the gates of the exclusive Herring Creek Farm Association. The home is in lovely original form and features a large living room with fireplace, dining room, 4 bedrooms and 2 baths. Built in 1910 as one of the first houses on the storied 200-acre farm with over 2,000 ft of private Atlantic

Gerrett Conover Landvest MV

31 Butlers Cove Rd, Edgartown, MA 02539
/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
/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

/36
Est $1,738,192 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,122 Sq Ft
62 Whalers Walk, Edgartown, MA 02539

62 Whalers Walk, 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
/29
$18,000 total monthly price
- 4 Beds
- 2.5 Baths
- 2,027 Sq Ft
- House for Rent
12 Cottle Lane Ed341, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This four bedroom Victorian home is located close to the Edgartown Village for shopping, theater or restaurants. Walk to Fulton Street Beach. All new appliances have been added recently as well as a number of room AC units throughout the house.

Karen Overtoom Karen M. Overtoom R.E.

12 Cottle Lane Ed341, 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

/36
Est $3,534,275 Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 3,902 Sq Ft
94 Marthas Rd, Edgartown, MA 02539

94 Marthas Rd, Edgartown, MA 02539

/23
$4,288,000
- 7 Beds
- 3.5 Baths
- 2,461 Sq Ft
69 School St, Edgartown, MA 02539

Located in the heart of Edgartown Village, this circa 1840 Greek Revival residence offers a rare opportunity to own a piece of island history on a coveted block. The property features a total of seven bedrooms across the main house and carriage house, making it a superb destination for family and guests. The main house features wide plank hardwood flooring and bright and sunny spaces with five

Peyton Wallace Studio Realty

69 School St, Edgartown, MA 02539
/40
$16,400 total monthly price
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
- House for Rent
20 Katama Bay Rd Ed350, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,100. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely Edgartown Bay Road area. This 3 bedroom newly decorated home is very close to South Beach. Easy access to town. Large grassy yard for the kids to play on.

Karen Overtoom Karen M. Overtoom R.E.

20 Katama Bay Rd Ed350, Edgartown, MA 02539
/30
$2,240,000 Sold Nov 06, 2025
- 1,764 Sq Ft
- $1,270/SF
- 27 Days On Market
- 3 Beds
- 2 Baths
- Built 1998
29 Pradas Way, Edgartown, MA 02539

THE PERFECT KATAMA RETREAT. Located just one mile from South Beach and steps from the bike path connecting Edgartown Village and the shoreline, this charming Katama property offers the ultimate Vineyard lifestyle. Beautifully built in 1998 by a respected Island contractor, this well-maintained home sits privately among soaring pines and welcomes you with a classic farmer’s porch. Inside, the

Wendy Harman Compass | Point B

29 Pradas Way, Edgartown, MA 02539

/20
Est $1,519,817 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,532 Sq Ft
39 Prices Way, Edgartown, MA 02539

39 Prices Way, Edgartown, MA 02539

/27
$5,250,000
- 4 Beds
- 3.5 Baths
- 3,018 Sq Ft
9 Fowler Ave, Edgartown, MA 02539

Edgartown Waterfront - Classic New England architecture meets the timeless allure of Martha’s Vineyard. This exceptional waterfront estate is set on the edge of Sengekontacket Pond, offering a sandy shoreline, panoramic water views, and a private mooring — the perfect setting for boating, paddle boarding, fishing, and clamming.A gated entrance opens to a beautifully landscaped property

Andrew McElhinney Compass LLC

9 Fowler Ave, Edgartown, MA 02539
/31
$50,000 total monthly price
- 5 Beds
- 5 Baths
- 2,975 Sq Ft
- House for Rent
17 Edgartown Bay Rd Ed328, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Private Beach, Waterfront, Mooring and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to

Karen Overtoom Karen M. Overtoom R.E.

17 Edgartown Bay Rd Ed328, Edgartown, MA 02539
/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

/23
Est $1,944,920 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,704 Sq Ft
31 Pulpit Ln, Edgartown, MA 02539

31 Pulpit Ln, Edgartown, MA 02539

/137
$4,175,000 Open House 12/13
- 6 Beds
- 3.5 Baths
- 3,397 Sq Ft
19 Kitts Field Cir, Edgartown, MA 02539

Old World Vineyard Charm Meets Modern Katama Living. Welcome to this beautifully crafted Katama family compound, a private, thoughtfully designed estate offering timeless elegance and exceptional amenities. Nestled near Edgartown Village, this stunning property includes a four-bedroom main residence with three levels of living space, a charming two-bedroom guest house, pool house, pool, spa,

Michele Casavant Vineyard Village Realty

19 Kitts Field Cir, Edgartown, MA 02539
/30
$20,000 total monthly price
- 4 Beds
- 3 Baths
- 2,226 Sq Ft
- House for Rent
54 Schoolhouse Road Ed330, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Perfectly located close to South Beach and Edgartown is this absolutely wonderful 3 bedroom home with a separate guest quarters that has one twin bed and one full bed, kitchenette and bath. The main house has a formal dining room right off of the kitchen, a bright sunny

Karen Overtoom Karen M. Overtoom R.E.

54 Schoolhouse Road Ed330, Edgartown, MA 02539
/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

/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

/52
$2,575,000
- 4 Beds
- 2.5 Baths
- 1,910 Sq Ft
76 Washque Ave, Edgartown, MA 02539

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends

Katherine Donahue Sandpiper Realty Inc

76 Washque Ave, Edgartown, MA 02539
/17
$48,000 total monthly price
- 4 Beds
- 3.5 Baths
- 2,675 Sq Ft
- House for Rent
9 Thaxter Lane Ed310, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Enjoy the pool with this Stunning custom designed and professionally decorated Tri Level contemporary home with open floor plan. Once inside you will be captivated by the dramatic open spaces, soaring ceiling and walls of glass. Located in a high end neighborhood within

Karen Overtoom Karen M. Overtoom R.E.

9 Thaxter Lane Ed310, Edgartown, MA 02539
/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

/52
Est $5,803,013 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,740 Sq Ft
12 Plantingfield Wood Cir, Edgartown, MA 02539

12 Plantingfield Wood Cir, Edgartown, MA 02539

/51
$3,995,000
- 4 Beds
- 4 Baths
- 4,920 Sq Ft
56 N Neck Rd, Edgartown, MA 02539

A RARE CHAPPAQUIDDICK LEGACY ESTATE w/BEACH ACCESS -- Privacy & Island Living at its finest. Step into a world where time slows, ocean breezes carry the scent of salt and cedar, and each day begins and ends with the relaxing sounds of the local fauna and the Vineyard Sound. This 18.4-ac. multi-residence estate, with 4 conforming size parcels, on Martha's Vineyard's treasured Chappaquiddick Island

Leslie Floyd Portfolio Properties

56 N Neck Rd, Edgartown, MA 02539
/23
$36,000 total monthly price
- 3 Beds
- 3 Baths
- 2,556 Sq Ft
- House for Rent
74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Less than 5 miles from the center of town, the property is a 3 bedroom uniquely-designed guest house which provides the space needed for a large family or visiting guests. Most of the living/entertaining space is on the second floor. The kitchen has granite countertops,

Karen Overtoom Karen M. Overtoom R.E.

74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539
/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

/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

/39
$2,950,000 Open House 12/14
- 3 Beds
- 3.5 Baths
- 2,268 Sq Ft
23 Thaxter Ln, Edgartown, MA 02539

OPEN AND AIRY COASTAL RETREAT WITH EASY ACCESS TO SOUTH BEACH and EDGARTOWN VILLAGE. Welcome to this tri-level contemporary home in the heart of KATAMA. This home offers the perfect blend of spacious indoor-outdoor living with three levels of outdoor decking nestled amongst mature vegetation and a quick stroll to South Beach. The home features vaulted ceilings, two first floor bedroom en-suites,

Michele Casavant Vineyard Village Realty

23 Thaxter Ln, Edgartown, MA 02539
/28
$29,300 total monthly price
- 3 Beds
- 2.5 Baths
- 1,871 Sq Ft
- House for Rent
76 Mattakesett Way Ed313, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,325. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This upside-down house was built in 2007. Sit out on the upper deck to panoramic ocean views or grill your favorite seafood while taking in the view. Watch the sun set to a new and beautiful aurora each night on either of the decks or while lazing on the porch swing.The

Karen Overtoom Karen M. Overtoom R.E.

76 Mattakesett Way Ed313, Edgartown, MA 02539
/12
$37,500,000 Sold Oct 30, 2025
- 16,209 Sq Ft
- $2,314/SF
- 0 Days On Market
- 9 Beds
- 9.5 Baths
- Built 2000
48 Witchwood Ln, Edgartown, MA 02539

Every nice town has an iconic property that is widely considered the most special and this property might just be it. From the moment one enters the driveway, you’re captured by the extraordinary landscaping, the expansive lawns and the general Gatsbyesque feeling that sweeps over you. The drive through carriage house, the symmetry of the classic architecture and courtyards and the spectacular

Gerrett Conover Landvest MV

48 Witchwood Ln, Edgartown, MA 02539

/42
Not Listed For Sale
- 6 Beds
- 8 Baths
- 4,617 Sq Ft
11 Cummings Way, Edgartown, MA 02539

11 Cummings Way, Edgartown, MA 02539

Showing Results 41 - 80, Page 2 of 18

Massachusetts Dukes County Edgartown

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