Edgartown, MA Homes

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  /45

  $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
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  /10

  $11,000 per month plus fees

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

  15 Price's Way Ed322, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools the downstairs. The

  Karen Overtoom Karen M. Overtoom R.E.

  15 Price's Way Ed322, Edgartown, MA 02539
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  /18

  $980,000 Sold Aug 11, 2025

  • 1,401 Sq Ft
  • $700/SF
  • 64 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 2005

  249 County Rd, Oak Bluffs, MA 02557

  This charming Cape-style home is ideally located just over a mile from downtown Oak Bluffs, offering the perfect blend of relaxed living and convenience. The open and inviting layout features spacious first-floor living areas, complemented by high ceilings and wood floors. A versatile second-story loft space provides an additional nook, perfect for a home office. Fronting the bike bath, enjoy

  Katherine Donahue Sandpiper Realty Inc

  249 County Rd, Oak Bluffs, MA 02557
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  /23

  Est $2,700,694 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
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  /63

  $4,295,000

  • 7 Beds
  • 6 Baths
  • 9,686 Sq Ft

  56 N Neck Rd, Edgartown, MA 02539

  A RARE CHAPPAQUIDDICK LEGACY ESTATE — 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-acre multi-residence estate, with 4 conforming parcels, on Martha’s Vineyard’s treasured Chappaquiddick Island is more than a

  Leslie C. Floyd Portfolio Real Estate, Inc.

  56 N Neck Rd, Edgartown, MA 02539
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  /21

  $14,000 per month plus fees

  • 4 Beds
  • 2 Baths
  • 1,505 Sq Ft
  • House for Rent

  175 Meetinghouse Way Ed321, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This updated contemporary is located in Katama area and a short bike ride to South Beach. There are 4 bedrooms, 1 down and 3 up, and a beautiful kitchen/dining which opens to a large living room. The house has a nice deck on the front and owners have added a deck off the

  Karen Overtoom Karen M. Overtoom R.E.

  175 Meetinghouse Way Ed321, Edgartown, MA 02539
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  /21

  $910,000 Sold Aug 08, 2025

  • 1,935 Sq Ft
  • $470/SF
  • 149 Days On Market

  • 1 Bed
  • 3.5 Baths
  • Built 1994

  119 Alpine Ave, Oak Bluffs, MA 02557

  Oak Bluffs Residence with guest house. Centrally located in Oak Bluffs, this property offers the rare opportunity to own a home in a prime residential location complemented with a detached cabin. The main house features, on the first floor, an inviting living/dining area, functional kitchen, and sun-filled parlor room with stunning floor-to-ceiling windows providing plenty of natural light and

  Michael Schweikert Ocean Park Realty Inc

  119 Alpine Ave, Oak Bluffs, MA 02557
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  /7

  Est $5,202,552 Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 6,783 Sq Ft

  3 Duarte Cir, Edgartown, MA 02539

  3 Duarte Cir, Edgartown, MA 02539
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  /39

  $3,200,000

  • 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

  Michele Casavant Vineyard Village Realty

  23 Thaxter Ln, Edgartown, MA 02539
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  /28

  $29,300 per month plus fees

  • 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
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  /49

  $3,250,000 Sold Aug 07, 2025

  • 3,665 Sq Ft
  • $887/SF
  • 33 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1978

  25 Beetle Swamp Rd, Edgartown, MA 02539

  Located at the end of Sweetened Water Farm and surrounded by conservation land, lies this beautiful nearly 5-acre property with incredible and expansive views back across the open fields to the horse pastures and barn. There is a 5-bedroom / 3-bath main house featuring an open floor plan, a screened porch and spacious decks. Additionally, there is a 6-stall horse barn with a one-bedroom apartment

  Gerrett Conover Landvest MV

  25 Beetle Swamp Rd, Edgartown, MA 02539
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  /32

  Est $2,812,695 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,101 Sq Ft

  10 Codman Spring Rd, Edgartown, MA 02539

  10 Codman Spring Rd, Edgartown, MA 02539
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  /45

  $2,895,000

  • 3 Beds
  • 3.5 Baths
  • 2,898 Sq Ft

  4 Pip'N Rd, Edgartown, MA 02539

  Chappaquiddick charm meets Edgartown elegance at this meticulously maintained property. No detail has been overlooked in this spacious custom home. The foyer entry greets you with a sizable dining room to your right which flows into an open eat in kitchen with a built in banquet, a granite kitchen island overlooking the masonry fireplace and wall of glass sliders in the living room. A wet bar

  Michele Casavant Vineyard Village Realty

  4 Pip'N Rd, Edgartown, MA 02539
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  /17

  $48,000 per month plus fees

  • 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
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  /20

  $1,525,000 Sold Jul 31, 2025

  • 1,411 Sq Ft
  • $1,081/SF
  • 34 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  467 Katama Rd Unit B2, Edgartown, MA 02539

  Mattakesett units continue to be in high demand and #B2 is the only unit currently on the market! Take advantage of all the Winnetu Resort amenities and a robust rental program which covers your fees and provides great revenue! This unit offers abundant views of the farm fields out front, open common space next to and behind, and is a short walk or bike to South Beach! There are 3 bedrooms, 2.5

  Cheri Mason Landvest MV

  467 Katama Rd Unit B2, Edgartown, MA 02539
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  /19

  Est $1,360,425 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft

  46 Windsor Dr, Edgartown, MA 02539

  46 Windsor Dr, Edgartown, MA 02539
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  /81

  $2,998,000

  • 3 Beds
  • 2 Baths
  • 2,558 Sq Ft

  12 Duarte Cir, Edgartown, MA 02539

  Nestled in the coveted Katama neighborhood of Edgartown, this stylish 3-bedroom, 2-bathroom contemporary home offers a perfect blend of comfort, location, and opportunity. Designed with an open and airy layout, the home features vaulted ceilings, abundant natural light, and a seamless connection to the outdoor living spaces. Set on a generous lot, the property presents a variety of expansion

  Jessie Holtham Wallace & Co. Sotheby's

  12 Duarte Cir, Edgartown, MA 02539
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  /11

  $12,500 per month plus fees

  • 4 Beds
  • 1.5 Baths
  • 1,413 Sq Ft
  • House for Rent

  11 Wamsutta Ave Ob540, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. This antique Vineyard home is thoughtfully styled with classic country-chic interior decor. The wraparound porch has plenty of room to enjoy people watching or sipping ice cold tea, perfect for a hot summer day. Alternatively, you can enjoy peering down the street from the master bedroom which opens up to a charming porch with plenty of room for two to enjoy

  Karen Overtoom Karen M. Overtoom R.E.

  11 Wamsutta Ave Ob540, Oak Bluffs, MA 02557
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  /22

  $1,000,000 Sold Jul 31, 2025

  • 768 Sq Ft
  • $1,302/SF
  • 96 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  130 Wing Rd, Oak Bluffs, MA 02557

  This well-maintained property is beautifully landscaped with gardens and generous lawn areas, offering incredible potential for growth and development. Conveniently located close to downtown Oak Bluffs, this property offers easy access to essential amenities and tourist destinations, whether you're driving, biking or relying on public transportation to restaurants, shops, beaches, bike paths and

  Lynn Buder Sandpiper Realty Inc

  130 Wing Rd, Oak Bluffs, MA 02557
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  /2

  Est $1,727,215 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  11 Deacon Vincent Way, Edgartown, MA 02539

  11 Deacon Vincent Way, Edgartown, MA 02539
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  /30

  $2,750,000

  • 3 Beds
  • 4 Baths
  • 2,830 Sq Ft

  42 Deacon Vincent Way, Edgartown, MA 02539

  Katama ~ Turnkey Retreat in Edgartown Estates. Located on a quiet, paved road in sought-after Edgartown Estates, this meticulously maintained home offers the perfect blend of privacy, space, and convenience. Ideally positioned equidistant to South Beach and downtown Edgartown, and just moments from the bike path, it’s an ideal Vineyard getaway or year-round residence. Thoughtfully designed for

  Stephanie Roache Donnelly + Co

  42 Deacon Vincent Way, Edgartown, MA 02539
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  /11

  $21,000 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,481 Sq Ft
  • House for Rent

  24 Deer Run Rd Unit OB521, Vineyard Haven, MA 02568

  THIS IS A SUMMER RENTAL ONLY. Centrally located to Edgartown, Vineyard Haven and Oak Bluffs. Just a short drive will take you to any of the town beaches and the Sailing Camp Park is a quick bike ride away. The home is located on over a 1/2 acre of landscaped property in a beautiful, private, neighborhood, with private roads great for biking and is wonderful for families, friends or even a

  Karen Overtoom Karen M. Overtoom R.E.

  24 Deer Run Rd Unit OB521, Vineyard Haven, MA 02568
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  /26

  $1,400,000 Sold Jul 10, 2025

  • 2,019 Sq Ft
  • $693/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1996

  73 Dodgers Hole Rd, Edgartown, MA 02539

  Situated on .5 acres in established Dodgers Hole, this well-maintained contemporary home has three bedrooms, including a primary ensuite on the first floor with a walk-in closet. Enjoy the cathedral-ceiling living room with a wood-burning fireplace and an adjacent light-filled sunroom with French doors to the deck. The eat-in kitchen is at the back of the house, with direct deck access. A

  Stephanie Roache Donnelly + Co.

  73 Dodgers Hole Rd, Edgartown, MA 02539
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  /30

  Est $2,468,232 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,404 Sq Ft

  10 Gerts Way, Edgartown, MA 02539

  10 Gerts Way, Edgartown, MA 02539
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  /47

  $5,450,000

  • 4 Beds
  • 5.5 Baths
  • 3,300 Sq Ft

  8 Paddock Rd, Oak Bluffs, MA 02557

  Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of a tranquil pond and surrounding grasslands, this beautiful residence offers a masterful blend of traditional coastal architecture and modern luxury. Located in the prestigious enclave of The Preserve, this sprawling home is designed for effortless elegance, privacy, and indoor-outdoor living.At the heart of

  Lesley Heidt Sandpiper Realty Inc

  8 Paddock Rd, Oak Bluffs, MA 02557
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  /16

  $40,000 per month plus fees

  • 4 Beds
  • 3 Baths
  • 2,748 Sq Ft
  • House for Rent

  38 Farm Pond Ob524, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. Gracious 4 bedroom home with private beach access and tennis. This home has a reverse design that has been fully renovated and thoughtfully decorated. There is a large deck overlooking gardens and a peep of the water. A separate studio is attached by the deck. You are a short distance from town, less than a mile to the public beach and a minutes to a beautiful

  Karen Overtoom Karen M. Overtoom R.E.

  38 Farm Pond Ob524, Oak Bluffs, MA 02557
• 

  

  /22

  $975,000 Sold Jul 07, 2025

  • 940 Sq Ft
  • $1,037/SF
  • 61 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 2025

  128 Manchester Ave, Oak Bluffs, MA 02568

  This delightful, modern cape-style home features thoughtful and impressive finish details. The covered porch welcomes you into the home where you will find well-appointed spaces. The kitchen has stainless appliances including a 5-burner gas range with pot filler, an LG French-door refrigerator and dishwasher. The kitchen area is finished with shiplap. There is an open dining and living area with

  Michele Moore Island Real Estate

  128 Manchester Ave, Oak Bluffs, MA 02568
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  /29

  Est $2,053,190 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  165 W Tisbury Rd, Edgartown, MA 02539

  165 W Tisbury Rd, Edgartown, MA 02539
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  /48

  $5,495,000

  • 3 Beds
  • 3.5 Baths
  • 4,131 Sq Ft

  36 Crocker Dr, Edgartown, MA 02539

  Stunning Katama Retreat ~ Welcome to this newly constructed architectural gem, nestled on half an acre in the heart of Katama. Perfectly positioned just blocks from the Field Club, close to South Beach, the bike path, and Edgartown Village, this home offers the ultimate indoor-outdoor Martha's Vineyard lifestyle. The elegant entryway sets the tone, leading into a spectacular vaulted living room

  Stephanie Roache Donnelly + Co.

  36 Crocker Dr, Edgartown, MA 02539
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  /12

  $17,000 per month plus fees

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  196 Vineyard Meadow Farms Wt130, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. Well appointed Farmhouse Colonial, on two private acres on private road. Conveniently located in Vineyard Meadow Farms abutting the entrance to Long Point Beach, considered by many to be the best beach on the Island. Home was built for families in mind, with three bedrooms upstairs, master with queen bed and ensuite bathroom. In addition there are two bedrooms, each

  Karen Overtoom Karen M. Overtoom R.E.

  196 Vineyard Meadow Farms Wt130, West Tisbury, MA 02575
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  /45

  $5,250,000 Sold Jul 02, 2025

  • 2,869 Sq Ft
  • $1,830/SF
  • 37 Days On Market

  • 3 Beds
  • 4.5 Baths
  • Built 1988

  14 Katama Farm S, Edgartown, MA 02539

  Katama Farm South - En route to this stellar location, enjoy scenic views while passing iconic Katama Farm. Less than a half-mile drive or a quarter mile walk from South Beach, this dynamic compound, which includes a spacious post and beam home and two-story barn, is privately situated on a large, beautifully landscaped, 1.6-acre parcel of land. The home is nearly 3,000sf in size and the multiple

  Courtney Marek Sandpiper Realty

  14 Katama Farm S, Edgartown, MA 02539
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  /14

  Est $1,859,540 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,519 Sq Ft

  2 Lexington Ave, Edgartown, MA 02539

  2 Lexington Ave, Edgartown, MA 02539
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  /44

  $6,395,000

  • 6 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  400 Barnes Rd, Vineyard Haven, MA 02568

  Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

  Jennifer DaSilva Compass | Point B

  400 Barnes Rd, Vineyard Haven, MA 02568
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  /15

  $30,000 per month plus fees

  • 3 Beds
  • 3 Baths
  • 2,888 Sq Ft
  • House for Rent

  101 Peasepoint Way Ed324, Edgartown, MA 02539

  THIS IS A SUMMER RENTAL ONLY. This grand and stately home is located in Starbuck Point in Edgartown. The home is elegantly furnished with traditional charm . The Captain's house is surrounded by neatly manicured lawns and the ocean is at the end of the street. It is a five minute walk to the Edgartown Village and Harbor for shopping, dining or theater.

  Karen Overtoom Karen M. Overtoom R.E.

  101 Peasepoint Way Ed324, Edgartown, MA 02539
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  /19

  $850,000 Sold Jul 02, 2025

  • 481 Sq Ft
  • $1,767/SF
  • 33 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1920

  68 Winter St, Edgartown, MA 02539

  Welcome to 68 Winter Street, a highly sought-after community of six, one bedroom condos located in Edgartown Village. Enjoy seasonal or year-round living at this sophisticated, garden level pied-a-terre. Elegant and well-appointed throughout, this stylish condo features open living with a nicely equipped kitchen, soaring ceilings, crown modeling, over-sized windows, and wood floors. Spacious

  Michele Moore Island Real Estate

  68 Winter St, Edgartown, MA 02539
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  /36

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,780 Sq Ft

  52 Marthas Rd, Edgartown, MA 02539

  52 Marthas Rd, Edgartown, MA 02539
• 

  

  /14

  $3,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  160 Katama Rd, Edgartown, MA 02539

  Gorgeous post-and-beam home built by a respected contractor. This spacious house plus detached guest quarters is on the outskirts of the village conveniently located on the way to South Beach. The property is at the end of a long driveway off Katama Road and is private and quiet. Upon arrival, you are greeted by beautiful landscaping with large beds of hydrangeas. There are 3 bedrooms in the main

  Bonnie Pierce Wallace & Co. Sotheby's

  160 Katama Rd, Edgartown, MA 02539
• 

  

  /13

  $27,000 per month plus fees

  • 4 Beds
  • 3.5 Baths
  • 1,962 Sq Ft
  • House for Rent

  20 Bay Lot Circle Ed323, Edgartown, MA 02539

  THIS IS A SUMMER RENTAL ONLY. Vacation by the beach in a relaxed contemporary home offering fabulous panoramic views of Edgartown Harbor, Chappiquidick, Katama Bay and South Beach. Our Katama Bay home is located off of Edgartown Bay Road at the quiet cul-de-sac,close to the beaches and boat launch access. For those who love the ocean breezes and sandy beaches, there is great sunbathing,

  Karen Overtoom Karen M. Overtoom R.E.

  20 Bay Lot Circle Ed323, Edgartown, MA 02539
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  /48

  $5,250,000 Sold Jul 02, 2025

  • 2,869 Sq Ft
  • $1,830/SF
  • 54 Days On Market

  • 3 Beds
  • 4.5 Baths
  • Built 1988

  14 Katama Farm Rd N, Edgartown, MA 02539

  Katama Farm South - En route to this stellar location, enjoy scenic pastoral views while passing iconic Katama Farm. A quarter mile from South Beach, this dynamic compound, which includes a spacious post and beam home and two-story barn, is privately situated on a large, beautifully landscaped, 1.6-acre parcel of land. The home is nearly 3,000 sf in size and the multiple outdoor living spaces

  Courtney Marek Sandpiper Realty Inc

  14 Katama Farm Rd N, Edgartown, MA 02539
• 

  

  /31

  Est $1,466,046 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft

  48 Puritan Dr, Vineyard Haven, MA 02568

  48 Puritan Dr, Vineyard Haven, MA 02568

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