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105 Whalers Walk, Edgartown
$2,350,000
4 Beds ⋅ 3 Baths ⋅ 73567153 MLS
Renovated Edgartown Retreat With Pool, Terrace + Outdoor Entertaining Pavilions - Designed for relaxed indoor-outdoor living, this recently renovated four-bedroom, three-bath Edgartown home is set on just under an acre and centered around an exceptional new backyard retreat. From quiet mornings by the pool to leisurely dinners beneath the pergolas, the property offers a welcoming setting for enjoying the Vineyard lifestyle. The pool features a sun shelf and built-in seating and is surrounded by an expansive stone terrace with generous room for lounging and entertaining. Two pergola pavilions create a stylish open-air living area with dedicated lounge and dining spaces, while an outdoor shower completes the resort-like setting. An expanded rear deck provides an easy connection between the home and its impressive outdoor amenities. Inside, thoughtful renovations have created bright, comfortable spaces for everyday living and gathering. The redesigned kitchen features crisp white cabinetry, marble countertops, stainless-steel appliances, and an extended marble breakfast bar that connects the kitchen and dining areas while providing additional seating and workspace. Hardwood floors run throughout both levels, and air conditioning has been added for year-round comfort. The first floor also includes a renovated full bath and a new laundry room with front-loading appliances. Upstairs, a newly created primary suite offers privacy and a beautifully finished bath with a large custom-tiled shower. Two additional bedrooms feature new hardwood floors and fresh paint and share a completely renovated full bath. Further improvements include a new front stoop, Bluetooth-controlled irrigation, and a two-car garage with its own rear deck and outdoor shower, adding convenience for island living. Connected to town sewer with capacity for seven bedrooms, the property presents valuable future expansion possibilities. An established rental income history offers additional flexibility for buyers interested in combining personal enjoyment with income-producing potential. With its renovated interiors, exceptional pool setting, multiple outdoor gathering spaces, and room to envision what comes next, this distinctive Edgartown retreat is ready for memorable days and evenings on Martha's Vineyard.

105 Whalers Walk, Edgartown

Listing courtesy of Listing Agent: Ekaterina Brush from Listing Office: Compass.
58 Road To The Plains, Edgartown
$1,600,000
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..
24 Katama Bay View Road, Edgartown
$7,500,000
4 Beds ⋅ 6 Baths ⋅ 73504170 MLS
This classic New England home in Katama offers a refined blend of timeless architecture and modern comfort, set on a spacious, beautifully landscaped lot. The main house features three well-appointed bedrooms, including a light-filled primary suite and inviting guest rooms designed for comfort and privacy. The open-concept living area is ideal for entertaining, highlighted by a cozy fireplace and large windows overlooking the manicured grounds. French doors lead to a deck perfect for outdoor dining and relaxation. A state-of-the-art media room with plush seating and a large screen provides the ultimate space for movie nights or game days, with a wine cellar just steps away. The carriage house includes a three-car garage with a spacious one-bedroom apartment above. Located beside Sheriff’s Meadow Conservation land with public access to Katama Bay, and just minutes to South Beach and downtown Edgartown.

24 Katama Bay View Road, Edgartown

Listing courtesy of Listing Agent: Thomas Wallace from Listing Office: Wallace & Co. Sotheby's International Realty.
91 Plantingfield Way, Edgartown
$17,500,000
5 Beds ⋅ 5 Baths ⋅ 73544426 MLS
EDGARTOWN WATERFRONT — Located within one of Edgartown's most coveted waterfront enclaves, where properties are rarely offered, this exceptional 2.3-acre waterfront property encompasses over 240 feet of private sandy beach on Eel Pond and presents a rare opportunity to create a legacy family compound. The existing residence offers immediate enjoyment while providing an exceptional foundation for what comes next. With ample room for a pool, significant expansion potential, and a private mooring opportunity, the property offers the scale, flexibility, and setting to create one of Edgartown's premier legacy estates. Just minutes from downtown Edgartown, opportunities that combine significant acreage, private beach, protected waterfront, and extraordinary privacy are increasingly rare on Martha's Vineyard. Sellers to review any offers after 5pm July 7th.

91 Plantingfield Way, Edgartown

Listing courtesy of Listing Agent: Ralph Smith Jr. from Listing Office: Compass.
25 Harbor View Avenue, Edgartown
$1,495,000
3 Beds ⋅ 2 Baths ⋅ 73588980 MLS
Escape to the laid-back charm of Chappaquiddick, where easy summer living awaits in this inviting single-story contemporary home. Designed for relaxation and effortless entertaining, the bright and airy interior features an open floor plan, soaring vaulted ceilings, and an abundance of windows that fill the living spaces with natural light. Spend your days enjoying the calm waters of nearby Katama Bay, ideal for swimming, kayaking, and shellfishing, or head just down the road to the beautiful shores of Wasque Beach for sun, sand, and surf. Tennis enthusiasts will appreciate the neighborhood courts just a short stroll away. Whether gathering with family and friends or simply enjoying the peace and quiet of island life, this welcoming retreat offers the perfect setting to slow down, unwind, and savor all that a Vineyard summer has to offer.

25 Harbor View Avenue, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
19 Katama Point Road, Edgartown
$2,950,000
4 Beds ⋅ 3 Baths ⋅ 73586703 MLS
Set on a beautifully landscaped parcel in the heart of Katama, this four-bedroom home offers an exceptional opportunity in one of Martha's Vineyard's most coveted locations. Second-floor water views, a short stroll to Katama Landing, and easy access to both South Beach and Edgartown Village create the ideal backdrop for island living. Whether enjoyed as it is today or thoughtfully reimagined over time, the property offers a rare chance to establish a lasting family retreat in a setting where generations have come to create unforgettable Vineyard memories.

19 Katama Point Road, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
9 Martha's Road, Edgartown
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 73566610 MLS
Set on over a half an acre in Edgartown’s desirable Island Grove neighborhood, this three-bedroom, two-bath classic Cape offers an exceptional expansion opportunity in a convenient Katama location. The existing 1,560-square-foot home can be enjoyed as-is while plans are developed for a renovation, expansion, or new construction. With a connection to town sewer, the property can support up to seven bedrooms, creating potential for a substantial residence, pool, and accessory dwelling unit. Association tennis courts are located nearby, with Edgartown Village, South Beach, shops, restaurants, and the harbor all within easy reach. A rare opportunity to create a custom Vineyard retreat in an established neighborhood.

9 Martha's Road, Edgartown

Listing courtesy of Listing Agent: Rose Ryley from Listing Office: Wallace & Co. Sotheby's International Realty.
8 Woodhaven Dr, Edgartown
$3,225,000
3 Beds ⋅ 5 Baths ⋅ 73560514 MLS
Hidden behind a veil of privacy on a generous coastal sanctuary, an extraordinary property waits to be discovered. This custom masterpiece blends timeless architecture with a modern, elusive sophistication, offering comfortable finished living space within an impressive total structure. Cross the threshold onto rich hardwood floors where light dances beneath a dramatic cathedral ceiling, drawing you toward a luxurious modern kitchen and the quiet warmth of a central masonry fireplace. Secrets unfold across multiple levels, from a secluded bonus room to an expansive lower level offering basement space—including 624 square feet of finished living space perfectly suited for a private lounge, studio, or hidden sanctuary. Climate is effortlessly controlled through central air conditioning and gas forced hot air, ensuring year-round comfort. Yet the true mystery of this property lies just beyond the newly renovated exterior siding and doors: a private outdoor paradise completely shielded from the outside world. Here, summer days dissolve into long, twilight evenings around a pristine 18' x 38' in-ground gunite pool, framed by a sprawling entertaining patio, an intimate gazebo, a 693-square-foot wooden deck and an essential outdoor shower. Anchored by an attached two-car garage, a powered shed and a classic gravel driveway, this renovated haven isn't just a home—it is a private world waiting for those who live extraordinary lives.

8 Woodhaven Dr, Edgartown

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.
43 Peases Point Way S, Edgartown
$8,575,000
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. Property is being offered turnkey.

43 Peases Point Way S, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
17 Katama Point, Edgartown
$6,400,000
4 Beds ⋅ 7 Baths ⋅ 73542635 MLS
Coastal chic living with pool and pool house near Katama Bay. Perfectly positioned in the coveted Edgartown Bay Road area, moments from the Town Landing, this custom-built residence offers effortless Vineyard living with exceptional craftsmanship and turnkey convenience. Designed as a builder’s own home, the property features shiplap paneling, a custom fieldstone wall with wood-burning fireplace, designer finishes, and a fresh coastal palette. Offered fully furnished with contents valued at $200,000+, it is ready for immediate enjoyment, rental income, or summer living. Outdoor amenities include an inviting covered porch, expansive rear deck, custom gunite pool with PebbleTec®, detached pool house with wet bar and half bath, and outdoor shower. Launch kayaks or a boat nearby, enjoy Katama Bay, or head to South Beach. With rental income history averaging $225,000-$250,000 per year, this rare offering combines lifestyle, location, and investment appeal.

17 Katama Point, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
49 High Street, Edgartown
$3,650,000
5 Beds ⋅ 3 Baths ⋅ 73542542 MLS
A rare opportunity to create a premier in-town compound in one of Edgartown’s most desirable locations. Set on High Street, just moments from downtown Edgartown, this exceptional 16,000+ square foot lot offers tremendous potential to create a substantial five-bedroom residence while enjoying the convenience and charm of village living. The property currently features a 4 bedroom main house, attached 1 bedroom apartment, and an oversized garage with an attached 556-square-foot barn. The property provides a unique foundation for expansion, renovation, or a thoughtfully designed new build. With its generous lot size and coveted location, 49 High Street presents a rare opportunity to create a legacy property within walking distance of Edgartown’s shops, restaurants, harbor, and village amenities.

49 High Street, Edgartown

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
13 Plantingfield Way, Edgartown
$3,600,000
4 Beds ⋅ 3 Baths ⋅ 73494388 MLS
Set in the heart of Edgartown Village, this pristine Cape offers a wonderful blend of charm, comfort, and in-town convenience. Just moments from boutique shopping, galleries, dining, and the harbor, this four-bedroom, three-bath home captures the quintessential Vineyard lifestyle. A formal front entry opens to the inviting living room, while a side entrance leads to the bright kitchen with a built-in banquette dining area. The private primary wing features its own entrance, cathedral-ceiling bedroom, sitting area, full bath, kitchenette, and French doors opening to a pergola patio. The first floor also includes a guest bedroom, full bath, and laundry. Upstairs offers a large primary bedroom, another bedroom, and a full bath. The landscaped backyard features two patios for outdoor dining and entertaining. A full basement, storage shed, and one-car garage with additional parking complete this exceptional in-town offering near Sheriff’s Meadow trails and Fuller Street Beach.

13 Plantingfield Way, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
34 Tenth St S, Edgartown
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 73534315 MLS
Easy Edgartown living awaits in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout that works beautifully for everyday life, entertaining, or relaxed seasonal stays. The private primary suite includes its own bath, while two additional bedrooms share a full bathroom, creating a practical and comfortable floor plan. A full basement provides excellent storage and added flexibility, with room for bikes, beach gear, tools, or future possibilities. Step outside to enjoy the deck, fenced yard, and quintessential outdoor shower — the perfect Vineyard touch after a day at the beach. With the bus stop conveniently located at the end of the street, getting around the island is simple and stress-free. Just minutes from downtown Edgartown, bike paths, restaurants, shops, and some of the island’s most loved bea

34 Tenth St S, Edgartown

Listing courtesy of Listing Agent: Chrissie Teague from Listing Office: Insight Realty Group, Inc..
177 West Tisbury Road, Edgartown
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 73528549 MLS
Perched on an elevated half-acre lot, watch horses graze at Sweetened Water Farm from the front porch. This 3-bedroom, 3-bath Edgartown home is situated in a coveted location — less than a mile to Main Street. Easy access to the bike path, close to Morning Glory Farm, Great Pond, and South Beach. Renovate, expand, or reimagine. A connection to town sewer would unlock the potential for SIX BEDROOMS, a rare and valuable advantage in Edgartown. Whether a year-round residence or a summer retreat, this is your chance to create something truly special on Martha's Vineyard.

177 West Tisbury Road, Edgartown

Listing courtesy of Listing Agent: Emma Kennedy from Listing Office: Sandpiper Realty, Inc..
52 South Summer Street, Edgartown
$9,250,000
6 Beds ⋅ 7 Baths ⋅ 73497893 MLS

52 South Summer Street, Edgartown

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
471 West Tisbury Road, Edgartown
$2,595,000
4 Beds ⋅ 4 Baths ⋅ 73504062 MLS
COASTAL-STYLE CONTEMPORARY. Ideally located in central Edgartown, the property offers convenient access to the bicycle path, Morning Glory Farm, Edgartown Village and Katama/South Beach by way of Meetinghouse Way. This attractive home has been tastefully renovated and is a perfect island retreat for year-round and summer living. The open layout features vaulted ceilings, gorgeous hardwood floors and three walls of glass windows. French doors that open onto a three-season porch and an expansive wraparound mahogany deck, perfect for indoor-outdoor living and entertaining. The living area is anchored by a lovely gas fireplace and a beautiful kitchen which features stainless appliances, custom tile, countertops, wine cooler/beverage center and a center prep island/breakfast bar with counter seating. Mini split dual AC/heat units are located in every room and also in the basement. This property can be enjoyed as-is or expanded for up to seven bedrooms. Sale is subject to court approval.

471 West Tisbury Road, Edgartown

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.
17 Oakdale Dr, Edgartown
$2,210,000
3 Beds ⋅ 3 Baths ⋅ 73527361 MLS
Private Edgartown Retreat With Timeless Cottage Charm - Tucked away in a quiet and serene setting on the edge of Edgartown Village, this charming Vineyard retreat is ideally positioned halfway between town and State Beach, with the bicycle path nearby for easy access to both. Set along a private lane and bordered by classic Vineyard stonewalls, the property offers a rare sense of privacy with an expansive backyard and a wooded buffer between the property and the Edgartown Golf Club. Full of authentic island character, the home is loaded with charming cottage details and designed for effortless indoor-outdoor living. French doors open to an expansive south-facing deck and stone terrace with a pergola, creating an inviting setting for relaxing, dining, and entertaining. A screened-in porch, vegetable gardens, and ample room to add a pool further enhance the property’s easy Vineyard lifestyle. Inside, timeless charm blends with modern comfort, featuring two fireplaces and bright spaces.

17 Oakdale Dr, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
109 Litchfield Road, Edgartown
$1,600,000
3 Beds ⋅ 3 Baths ⋅ 73514894 MLS
CHAPPAQUIDDICK – Set back from the road on an oversized parcel, this spacious three-bedroom home offers both privacy and convenience, making it ideal for every season. A detached workshop provides exceptional versatility, offering ample space for storing boating and beach gear, fishing equipment, or serving as a creative workspace. Distant second-story water views and proximity to conservation land and hiking trails round out this property. Enjoy the property as is or take advantage of the generous acreage and its remarkable potential for expansion.

109 Litchfield Road, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
48 Turkeyland Cove Road, Edgartown
$5,700,000
3 Beds ⋅ 3 Baths ⋅ 73498507 MLS
Exciting Opportunity on Edgartown Great Pond - Encompassing 5.8 acres with more than 200 feet of direct pond frontage, the property offers a remarkable waterfront setting defined by expansive views and privacy. The existing three-bedroom, 2.5-bath home is ready for renovation or reimagining and is a valuable footprint close to the water—offering a unique starting point for future plans. The property presents extraordinary potential to create a Vineyard estate in one of the island’s sought-after pond front locations.

48 Turkeyland Cove Road, Edgartown

Listing courtesy of Listing Agent: Lesley Heidt from Listing Office: Sandpiper Realty, Inc..
2 Cosmos Way, Edgartown
$2,600,000
4 Beds ⋅ 3 Baths ⋅ 73525812 MLS
Tucked away on a private 1.5-acre parcel in Katama, this thoughtfully designed 4BR/2.5BA home offers the layout, amenities, and lifestyle buyers seek most in this coveted location. The open main living area features high ceilings, a fireplace, and French doors leading to a spacious deck overlooking the expansive yard with room for a pool. A screened porch adds to the effortless indoor/outdoor Vineyard living experience. The first floor includes a true primary suite, while upstairs offers three additional bedrooms, including a second potential suite with an ensuite bath already rough-plumbed. A full basement provides excellent storage and future expansion potential for media, recreation, or fitness space. Additional highlights include central air, generous storage, and a quiet setting near the bike path with easy access to South Beach and Edgartown Village. Privacy, acreage, convenience, and room to create the ultimate Vineyard retreat.

2 Cosmos Way, Edgartown

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
27 Knoll Drive, Edgartown
$4,700,000
4 Beds ⋅ 4 Baths ⋅ 73523238 MLS
Set the tone the moment you arrive with a dramatic first-floor foyer showcasing post-and-beam construction and warm architectural character. The heart of the home is an expansive great room anchored by a gas fireplace, seamlessly flowing through French doors that open to a sun-drenched pool area—perfect for indoor-outdoor living and entertaining. A generous dining area connects effortlessly to a well-appointed kitchen, highlighting double wall ovens, ample storage, built in beverage center and island seating for informal dining. The first floor also offers a versatile office or family room. The spacious primary bedroom is a true retreat with vaulted ceilings, featuring an ensuite bath with oversized shower with ample counter space including a seated vanity. Double closets plus a walk-in closet, and a wall to wall window seat with views overlooking the pool. Step outside to wraparound decks that extend the living space and invite you to unwind in a private, resort-like setting.

27 Knoll Drive, Edgartown

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..
4 Hye Ln, Edgartown
$1,700,000
5 Beds ⋅ 3 Baths ⋅ 73509658 MLS
Pristine and superbly maintained, this three-bedroom home and two-bedroom guest house has tremendous upside potential and a substantial rental history. This property is tied to town sewer and will allow for up to 7 bedrooms. One additional bedroom in the main house is possible within the existing footprint with appropriate town approvals. There is an additional 668 sq. ft. of finished space in the lower level that is not included in the ELA above. Potential buyers should consult with the town Building Department. This property has been freshly landscaped with extensive plantings and an irrigation system. The list of improvements is long, and the result is a stylishly updated property inside and out. It is conveniently located halfway between Morning Glory Farm and Meetinghouse Road, a primary access road to South Beach, 3.8 miles distant and only 8 minutes by car. Adjacent to the bike path, it is 2 miles to Main Street in Edgartown. It is being offered fully furnished.

4 Hye Ln, Edgartown

Listing courtesy of Listing Agent: Buder Team from Listing Office: Sandpiper Realty, Inc..
44 Plantingfield Way, Edgartown
$3,400,000
4 Beds ⋅ 3 Baths ⋅ 73460777 MLS
Post-and-beam style Edgartown home in a quiet, established neighborhood just minutes from downtown. This year-round property offers functional living spaces, a thoughtful layout, and generous outdoor areas ideal for relaxing or entertaining. The property is currently configured as a three-bedroom, 1-1/2 bathroom main house with a 1BR/1BA accessory apartment over a one-car, detached garage on a 1/2 acre lot. The garage structure also boasts a finished first floor studio space. The large, level lot also presents an excellent opportunity for those looking to start new and create a custom island retreat or private oasis complete with a pool. This property can be connected to town sewer and support up to six bedrooms with a grandfathered guest house. Located close to shops, restaurants, beaches, and the harbor, the home provides a perfect blend of convenience and privacy — ideal for year-round living, vacation use, or rental potential in one of Edgartown’s most sought-after areas.

44 Plantingfield Way, Edgartown

Listing courtesy of Listing Agent: David Dickinson from Listing Office: Compass.
99 Cooke St, Edgartown
$3,250,000
4 Beds ⋅ 4 Baths ⋅ 73484296 MLS
This updated classic cottage is located in the heart of Edgartown Village, less than a quarter mile from Main Street. Upon arrival, you are welcomed by a spacious front porch and elegant French door entry that lead into a dramatic foyer. The light-filled open floor plan seamlessly connects the kitchen, dining, and living areas, creating an inviting space for everyday living and entertaining. The first floor opens to a charming brick terrace and fenced backyard, an ideal setting for outdoor gatherings.The swimming pool serves as the centerpiece of this private outdoor retreat. This delightful cottage features four bedrooms, each with its own full bath, including a convenient first-floor primary bedroom suite. An elegant staircase leads upstairs to two spacious bedrooms with private baths. A charming balcony separates the bedrooms and is lined with a wall of ample storage closets, blending style with exceptional functionality.The partially finished lower level adds over 500 s.f.

99 Cooke St, Edgartown

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.
25 Bold Meadow Road, Edgartown
$3,381,000
4 Beds ⋅ 4 Baths ⋅ 73501677 MLS
This distinguished home in Edgartown’s Bold Meadow neighborhood features light-filled interiors highlighted by south-facing windows in a cathedral-ceilinged Great Room that flows into a new sunroom. The main house offers 3 bedrooms, complemented by a spacious detached 900-sf guest apartment above an oversized garage, ideal for hosting. Recent upgrades include a renovated kitchen, updated primary bath, and thoughtfully integrated sunroom. Set on 1.5 acres with greenbelt on three sides, the property offers privacy, expansion potential, and room for a future pool. A full-height basement provides additional possibilities such as a media room or gym. Located less than 3 miles to Edgartown Village and close to Morning Glory Farm, the home also benefits from 30 SunPower solar panels for energy efficiency. Move-in ready and meticulously maintained

25 Bold Meadow Road, Edgartown

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.
18 Windsor Drive, Edgartown
$1,150,000
3 Beds ⋅ 2 Baths ⋅ 73489567 MLS
Welcome to this light-filled Vineyard Cape brimming with potential, offering an open layout and abundant natural light. Vaulted ceilings enhance the spacious living and dining area, creating an airy setting for relaxing or entertaining. The kitchen flows seamlessly to an outdoor deck, ideal for summer gatherings and al fresco dining. Two bedrooms and a full bathroom with laundry complete the first floor. Upstairs, you’ll find a generous primary bedroom with abundant closet space, an additional full bathroom, and a cozy loft-style den overlooking the main living area. Centrally located just moments from the bike path, with easy access to Edgartown, nearby beaches, and all down-Island amenities, this property presents a wonderful opportunity to make it your own. With a 4-bedroom septic in place there is potential room for expansion. The property is being sold “AS IS”.

18 Windsor Drive, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
52 Windsor Drive, Edgartown
$1,125,000
3 Beds ⋅ 2 Baths ⋅ 73489622 MLS
Nestled on a wooded lot only 3.5 miles from Edgartown Village, this three-bedroom home offers a bright, open-plan main level with kitchen, dining, and living area flowing onto a private deck—ideal for outdoor dining, morning coffee, or enjoying the outdoors. A first-floor bedroom and bath add convenience, while two upstairs bedrooms and a bath provide flexible space for families or guests. The full basement offers generous storage and in-home laundry. BOH says four bedrooms are possible if septic is upgraded. Current three bedroom septic passed Title V. Easy access to multiple towns and Island beaches, this home puts the best of Martha's Vineyard at your doorstep.

52 Windsor Drive, Edgartown

Listing courtesy of Listing Agent: Emma Kennedy from Listing Office: Sandpiper Realty, Inc..
42 Deacon Vincent Way, Edgartown
$2,325,000
3 Beds ⋅ 4 Baths ⋅ 73494390 MLS
Katama ~ Easy Island Living in Edgartown Estates. Tucked away on a quiet paved road, this inviting home offers the best of Vineyard living, just minutes to South Beach, downtown Edgartown, and the bike path. Bright and comfortable, the interior features a vaulted living room with gas fireplace and an open kitchen/dining area that flows to a spacious back deck—perfect for outdoor dining and summer entertaining. An outdoor shower completes the beach-day routine. The first-floor primary suite includes cathedral ceilings, a walk-in closet, and private bath, while two second-floor bedrooms share a full bath. A bonus space with half bath above the garage is ideal for guests or a home office. Additional highlights include a mudroom/laundry area, oversized two-car garage, and full unfinished basement. Offered fully furnished and ready to enjoy.

42 Deacon Vincent Way, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
36 Smith Hollow Dr, Edgartown
$1,900,000
5 Beds ⋅ 3 Baths ⋅ 73472940 MLS
Tucked away behind association common land, this year-round compound offers the perfect blend of privacy, space, and flexibility. The post-and-beam main house features four bedrooms and combines timeless character with functional design, ideal for everyday living or seasonal enjoyment. A separate one-bedroom guest house with a welcoming farmer's porch is thoughtfully sited to ensure privacy and independence, complete with its own driveway and parking. The detached garage, with a loft above, adds even more versatility—ideal for storage or future finished space. Situated on one of the largest parcels in the Smith Hollow Association, the property enjoys a tranquil, park-like setting. With direct access to the bike path at the end of the road, you're just minutes from Edgartown and all down-island amenities. More than just a house—this is a place to call home.

36 Smith Hollow Dr, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
43 C Dark Woods Rd, Edgartown
$1,850,000
4 Beds ⋅ 4 Baths ⋅ 73357842 MLS
Welcome to Dark Woods – A Quiet Retreat, moments from the Village, bike paths, pristine beaches, and 27 acres of Sheriff’s Meadow conservation land. This meticulously maintained property is being offered fully furnished and is ready for your immediate enjoyment. The home offers an expansive layout that blends indoor and outdoor living. Step inside to find a spacious living room with a gas fireplace, a dining room, and an open eat-in kitchen overlooking a private backyard. The kitchen flows seamlessly outdoors to a two-tiered deck featuring a hot tub and outdoor shower. Above the two-car garage, a versatile bonus room offers the perfect space for a home office, media room, or private retreat. The primary ensuite enjoys a newly renovated bathroom. Two generously sized guest bedrooms and a full bathroom complete this level. The finished walk-out lower level includes an ensuite bedroom with a comfortable living and dining area. Tied to town water and sewer, you can expand up to 7 bedrooms.

43 C Dark Woods Rd, Edgartown

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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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