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$2,950,000
4 Beds 3 Baths 73494371 MLS
Nestled on a private 1.7-acre parcel in the Bold Meadow neighborhood, this classic Cape offers a perfect blend of comfort and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from Edgartown. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a fireplace and a separate TV/family room. The kitchen includes stainless steel appliances, quartz countertops, and a breakfast bar. An eat-in area opens to a spacious mahogany deck, complete with outdoor seating and beautifully landscaped gardens. The first-floor primary suite features vaulted, beamed ceilings and offers a private retreat with an en-suite bath. An additional bedroom/office and a fully renovated hall bath are also located on this level. Upstairs, 2 guest bedrooms share a full bath, while a loft above the two-car garage provides a flexible bonus space.

2 Bold Meadow Road, Edgartown

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..

$2,225,000
3 Beds 3 Baths 73493917 MLS
Experience the ease of summer living in your own Martha’s Vineyard beach house. Perched atop a rise with sweeping views, abundant natural light, and star-filled skies, this furnished, move-in-ready home with four levels of lifestyle. A dramatic 30-foot vaulted foyer leads to a fully renovated chef’s kitchen with Sub-Zero refrigeration, premium stainless appliances, stone counters, and a custom banquette seating 10. The home features a formal dining room, oak floors, a wood-burning stone fireplace featured in Architectural Digest, and a view-facing living room with balcony. The primary suite includes a walk-in closet and en-suite bath with soaking tub and double vanity, plus two additional bedrooms. A spiral staircase leads to a loft lounge with private balcony and two bonus rooms. The walk-out lower level adds flexible space for a gym, office, or lounge. Expansion potential allows up to seven bedrooms, plus guest house, pool, and pool house. $25,000 credit at closing for sewer tie-in.

81 Whalers Walk, Edgartown

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..

$16,900,000
8 Beds 8 Baths 73485121 MLS
Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown’s historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house with full kitchen, and a two-car carriage house with additional living quarters. The property features a private backyard oasis with a 16' x 32' saltwater pool, spa, and pool cabana—an exceptional outdoor setting in Edgartown Village. With furnishings and window treatments included, the home is ready for immediate enjoyment. 114 North Water Street represents a turnkey Edgartown Village estate offering the scale, amenities, and setting that are seldom available in this iconic location.

114 North Water Street, Edgartown

Listing courtesy of Listing Agent: Erin Hegarty from Listing Office: Donnelly + Co..

$3,995,000
8 Beds 6 Baths 73483686 MLS
Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you’ll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures with grazing horses. Private guest quarters above the detached oversized garage offer additional comfortable accommodations. Sweetened Water Farm combines the tranquility of an up-island location with the convenience of being just moments from the boutiques, restaurants, and harbor of downtown Edgartown. A home for all generations in a setting like no other.

23 Beetle Swamp Road, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

$1,625,000
4 Beds 2 Baths 73483009 MLS
Turnkey Katama Home—Beautifully furnished and move-in ready, this updated coastal retreat offers relaxed Island living with a strong rental history and effortless ownership. Outdoor highlights include a 19-foot heated swim spa and Jacuzzi set on an expansive wood deck, an outdoor shower, bluestone fire pit patio, multiple lounging spaces, decks, and wooded privacy for serene entertaining. Inside, the light-filled kitchen, living and dining area features cathedral ceilings, stainless steel appliances, granite countertops, and modern finishes. Recent improvements include a new roof, renovated bathroom, new maple flooring, refreshed interior, and updated landscaping. The thoughtful layout includes a primary bedroom with private balcony, two first-floor bedrooms with a shared full bath, and town sewer allowing expansion up to six bedrooms. Ideally located near South Beach and just minutes to Edgartown Village and Morning Glory Farm, this is a rare opportunity in a sought-after neighborhood

58 Road To The Plains, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$3,100,000
1 Beds 1 Baths 73478796 MLS
3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach and Edgartown Village. Featuring a custom guesthouse built in 2018, with solid rental history and is outfitted with modern amenities. With a 6-bedroom septic system in place, there’s ample opportunity to build a main house or additional structures, pending necessary town approvals. Expansion to 8 bedrooms possible with septic upgrade. This unique opportunity allows the developer to enjoy Edgartown now while envisioning the full potential.

114 Meetinghouse Way, Edgartown

Listing courtesy of Listing Agent: Rose Ryley from Listing Office: Wallace & Co. Sotheby's International Realty.

$9,000,000
4 Beds 7 Baths 73476388 MLS
Behind its classic Village façade lies a home that reimagines Edgartown living, where timeless architecture meets bright, light-filled interiors and an effortless sense of modern luxury. Just moments from Main Street and the harbor, it offers the rare opportunity to enjoy the best of the Village from a residence designed for the way people live and entertain today. Exceptional craftsmanship and thoughtfully curated finishes define every level of the home. The backyard is a true extension of the home, anchored by a fully equipped cabana, heated saltwater pool, sunken fire pit, and striking custom glass wall. A strong rental history further enhances the property's appeal, offering exceptional flexibility as a private family retreat or a compelling investment opportunity. A home where exceptional quality meets effortless living, offering a fresh and relaxed interpretation of luxury in the heart of Edgartown Village.

43 Peases Point Way S, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

$2,399,000
4 Beds 3 Baths 73472929 MLS
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 modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shellfishing. Nearby, the Wasque Preserve offers over 200 acres. of pristine conservation land, with scenic trails, abundant wildlife, and direct ocean access. Whether you're seeking a serene coastal retreat, a multi-generational family home, or a proven investment property, 76 Washque has it all. With

76 Washque Ave, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

$2,700,000
4 Beds 5 Baths 73471802 MLS
Welcome to the opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a one-acre plot with a detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, living room featuring a wall of glass sliders. The gourmet kitchen is a chef’s dream, boasting Bosch appliances, a large quartz-topped island with seating for four.  The first floor hosts a primary suite with a luxurious private bath. Upstairs, you’ll find a cozy second living room and two spacious guest suites, each with private baths. The property includes a 900 sq ft detached accessory dwelling, complete with full kitchen, bath, and bedroom. With one acre of land, this property is poised for a future pool. Ready for your 2026 occupancy!  Note: This property is subject to M.G.L. Chapter 40A Section 6 of the Affordable Homes Act: Single-family residence not to exceed 1,850 sq ft of heated living area, min. 3 bedrooms, no short-term rentals.

6 Laura's Way, Edgartown

Listing courtesy of Listing Agent: Michele Casavant from Listing Office: Vineyard Village Realty.

$21,700
5 Beds 3 Baths 73313240 MLS
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 and shimmering sea. Grab bikes from the garage and hop on a path to visit picturesque Edgartown for boutique shopping and dining or head to historic Oak Bluffs for ice cream and carousel rides. Enjoy a day at the beach with boogie boards, chairs and cooler in tow before returning to the cottage for a barbecue where an additional first floor kitchen makes for effortless entertaining. Unwind in the primary bedroom and greet the sunrise with coffee on the balcony. Four more bedrooms and living areas easily accommodate everyone. WEEKLY RENTAL OPTIONS AVAILABLE

97 3rd St N, Edgartown

Listing courtesy of Listing Agent: Fine Homes Group from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.

$11,000
4 Beds 2 Baths 73193875 MLS
**SUMMER RATE$ 9,500-$11,000 WEEKLY** Freshly remodeled 4 bed, 2 full bath coastal cape with all new furnishings, flawless finishes, large private yard, close to South Beach, bike path and downtown Edgartown. Large family room with vaulted ceiling and large TV , gorgeous kitchen with all new stainless appliances, vaulted ceilings, sky lights, custom blue stone countertop, island eatery, and wine cooler. Formal dining for 8. First floor primary King suite with vaulted ceilings, fabulous closets and flat screen TV. Additional 1st floor queen guest room and shared bath with dual sinks, luxurious shower and power room. 2nd floor features two additional guest rooms; one queen with flatscreen TV and two twins and shared full bath. Internet, A/C and multiple flat screen TVs. Lush private rear yard, outdoor living/dining, wooden rocking chairs, BBQ grill and outdoor shower atop the rear deck. Off-street parking for 4. Prices vary weekly $9,500-$11,000/wk plus tax and security. Inquire.

29 Mercier Way, Edgartown

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.

$5,500
3 Beds 2 Baths 73125953 MLS
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 a few steps away from the kitchen. The adjacent family room features a gas fireplace, flat screen TV, generous seating and a unique wall of open shelving that defines the space into the spacious primary suite. Two large bedrooms and a full bath on the second floor round out this charming getaway. In true Vineyard style, two outdoor showers flank the home. This home is equipped with everything you need for a day on South Beach, State Beach or nearby Long Point. Perfect for a family vacation or a couples getaway, your home away from home awaits.

2 Fishermans Knot Rd Ed309 Unit 1, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$13,600
2 Beds 2 Baths 73120956 MLS
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 while you cool off inside in the air conditioning from a day of shopping and sun bathing. A small desk in the downstairs bedroom can be used as an office space with wifi connection throughout the condo and the basement offers one more gathering space where children can go enjoy a movie, work on a puzzle or play games. While there is no outdoor shower, there are two full bathrooms indoors: one upstairs and one downstairs, both have a shower and tub. We hope you will find it to be a place to return year after year.

1 Meetinghouse Village Way Unit 1 ED335, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$19,000
5 Beds 5 Baths 73007813 MLS
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 on the first floor. French doors lead out to a screened in porch. Five spacious bedrooms located on the second floor feature private or shared baths, and a spacious mahogany deck overlooking the landscaped backyard. This is an ideal in-town Edgartown vacation home.

19 Morse St Ed333, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$11,000
3 Beds 2 Baths 72843823 MLS
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 kitchen is fully equipped. The living and dining room are open concept with hardwood floors have cathedral ceilings with overhead fans. The main floor features a full bath, washer/dryer, and two bedrooms each offering a pair of twins. Each bedroom has it's own splitter A/C and plenty of fans to circulate the air. Upstairs there is a bedroom with a king size bed and a slider to a small balcony. Next to the king bedroom is a private sitting room.

15 Price's Way Ed322, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$56,800
5 Beds 4 Baths 72844897 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING.Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, lots of outdoor patio and deck space, Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool surrounded by meadows and lots of privacy. Take the Boston Whaler motor boat or kayak across Oyster Pond to private beach (used by Presidents Clinton and Obama in past summers.) Outdoor and indoor games galore to entertain..Crocquet, horseshoes, ping pong and a pool table in the finished basement... 2 master bedroom suites with king beds, and separate guest quarters with a king bedroom and bath. One bedroom with twin beds. Newly added hot tub for you to enjoy!

2 Nonamesset Rd Ed319, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$48,000
4 Beds 4 Baths 72843699 MLS
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 walking distance to South Beach. The yard is beautifully landscaped and has an 18x40 heated saltwater pool with blue stone surround and lounge chairs and fire pit. With three levels, multiple gathering spaces, four bedrooms and 4 1/2 baths is the perfect spot for large families. Three bedrooms are master suites with private baths. You will truly love this wonderful home for your next summer vacation on the Vineyard!! Pool Fee.

9 Thaxter Lane Ed310, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$36,000
3 Beds 3 Baths 72844888 MLS
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, updated appliances, and counter stools. Farmhouse style table with seating for eight provides the main dining space. The living room area has a gas fireplace, cozy furniture and two large sets of sliding glass doors which notably open to the second story deck. Adjacent to the open concept kitchen and living room is a charming sun room with a slate floor and lots of windows. The two king bedrooms are on the same floor down a corridor. The master suite has a sitting room/den, large king bedroom, sliding doors to a private deck.

74 Turkeyland Cove Rd Ed306, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

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