Edgartown, MA Real Estate | Edgartown, MA Recently Sold Homes for Sale

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.

$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..

$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.

$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.

$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..

$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..

$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.

$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.

$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..

$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.

$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.

$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..

$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..

$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..

$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.

$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.

$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.

$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..

$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..

$2,600,000

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.

$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..

$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..

$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.

$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.

$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.

$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..

$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..

$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..

$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..

$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..

$1,175,000

3 Beds ⋅ 2 Baths ⋅ 73439891 MLS

Nestled on a lush and private parcel close to The Boulevard, this contemporary three-bedroom, two-bath residence offers the perfect blend of style and comfortable living. Highlights include a gas fireplace, wood floors, an expansive deck to relax on, and established gardens. There’s even a shed to store all your summer gear. Enjoy this oasis as is or use as a foundation for future expansion.Explore the nearby walking trails of Felix Neck Wildlife Sanctuary. For those that love the water, the town landing is less than a mile away. Kayaking, paddleboarding and shell fishing await.Perfect as a year-round residence, summer retreat, or rental (with established history) this versatile home is being sold furnished (with a few exclusions) allowing for a smooth transition for the new owners- just bring your toothbrush.

112 Third Street North, Edgartown

Listing courtesy of Listing Agent: Kristin Buck from Listing Office: Donnelly + Co..

$1,775,000

3 Beds ⋅ 2 Baths ⋅ 73485519 MLS

A few blocks to historic Edgartown Village from this updated beach house in desirable Edgartown Estates. The open living area features decorative wood beams, a wood stove, designer tile flooring, and sliding doors to an expansive wraparound Trex deck (2018), creating seamless indoor-outdoor living. The expanded kitchen (2018) includes granite countertops, stainless steel appliances, ample storage, and natural light. Three bedrooms include a private primary suite with renovated en-suite bath, and comfortable guest accommodations. The finished lower-level bonus room with floating Pergo flooring is ideal for recreation or secure owner storage. Outdoor amenities include a classic Vineyard outdoor shower, storage shed, Belgian Block driveway accents, and mature landscaping. A four-bedroom septic system allows for future expansion. Offered turnkey, ideal for year-round enjoyment or strong seasonal rental income, all convenient to Edgartown Village, bike paths, and South Beach.

90 Schoolhouse Road, Edgartown

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

$1,500,000

4 Beds ⋅ 3 Baths ⋅ 73466772 MLS

This well-maintained custom Cape Cod–style home is ideally suited for year-round living, vacation getaway, or employee housing. Located at the end of a quiet street next to Pennywise Preserve conservation land, it enjoys extra privacy. The main level features an open layout with vaulted ceilings. There is a spacious den above an oversized two-car garage and an expansive deck for entertaining guests. The unfinished basement allows for future expansion. Notable highlights include two primary suites, central air conditioning, new furnace, and hardwood and tile flooring.

68 Twentieth Street South, Edgartown

Listing courtesy of Listing Agent: Carol Shore from Listing Office: Donnelly + Co..

$1,510,000

4 Beds ⋅ 3 Baths ⋅ 73445262 MLS

Edgartown Village Opportunity – Main House & New Guest Cottage Tucked just off Upper Main Street, this unique Edgartown property offers exceptional flexibility with two dwellings—perfect for personal use, rental income, or a combination of both. The main house has been thoughtfully updated with numerous improvements, including a new kitchen, renovated bath, upgraded electrical, and HVAC system for year-round comfort. The guest house, newly built in 2025, provides a fresh, turnkey space ideal for guests or rental potential. With a total of four bedrooms between both structures—and the ability to expand to six bedrooms thanks to town water and sewer connection—this property presents a rare opportunity in a sought-after location. Just moments from shops, restaurants, and all that Edgartown has to offer, this versatile property combines convenience, investment potential, and island charm.

10 Dory Circle, Edgartown

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

$2,475,000

4 Beds ⋅ 4 Baths ⋅ 73391522 MLS

Nestled on a generous corner lot in one of Edgartown’s sought-after neighborhoods, this beautifully maintained 4BD, 3.5BA home offers the perfect blend of comfort, convenience, and classic Vineyard charm. The home features a spacious and versatile floor plan, ideal for both year-round living and summer getaways. The light-filled living areas, anchored by a floor to ceiling wood burning fireplace, flow seamlessly into a well-appointed kitchen and dining area, perfect for entertaining. Step into the inviting screen porch-an ideal spot to enjoy your morning coffee or unwind with evening breezes. A partially finished basement and two-car garage provides ample storage, while the association tennis courts offer recreational opportunities just steps from your door. Outside, the expansive yard provides plenty of room for future expansion of a pool or ADU as the lot will support 6-bedrooms. With its prime location, community amenities, and room to grow, this property is a fantastic opportunity.

28 Martha's Road, Edgartown

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

$1,000,000

3 Beds ⋅ 3 Baths ⋅ 73423895 MLS

This rare multi-family residence offers a unique investment opportunity or the perfect island retreat. Whether you're looking to generate rental income, host guests, or settle into island life, this 3-bedroom, 3-bathroom property checks all the boxes. With numerous bonus spaces, off-street parking, a cozy backyard, and expansion potential (pending town approval), this is a truly exceptional find.Just steps from Edgartown’s shops, restaurants, and harbor, the home sits in one of Martha’s Vineyard’s most desirable locations.

48 West Tisbry Rd, Edgartown

Listing courtesy of Listing Agent: Mavis Francis from Listing Office: eXp Realty.

$2,470,000

4 Beds ⋅ 4 Baths ⋅ 73464407 MLS

CHARMING VINTAGE HOME IN THE HEART OF EDGARTOWN VILLAGE. Nestled within lush perennial gardens and surrounded by hedges and a classic picket fence, the Charles W. Crowell House is a delightful antique home that captures the essence of a bygone era. With its origins dating back to 1760, the home boasts beams crafted from trees that once grew on the property. These timeless timbers are prominently showcased throughout the home, adorning the ceilings and walls with their enduring presence. Renovated in 2010 to incorporate modern conveniences such as updated electrical, central air conditioning and refreshed kitchen and baths, the residence has seamlessly blended contemporary comfort with its original period charm. Noteworthy features include an open staircase, wide-planked pine flooring, two original fireplaces, and exquisite period millwork, as well as built-in cabinets and bookshelves. Comprising a total of four bedrooms and three and one-half baths, including a first-floor Primary Bedr

2 Green Ave, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$2,340,000

4 Beds ⋅ 5 Baths ⋅ 73433414 MLS

Nestled in the heart of Katama and tucked away on a generous sized lot sits this four-bedroom, four-and-a-half-bath home offering an exceptional opportunity for year-round living or investment potential. Ideally located, there is easy access to both Edgartown Village and South Beach The main level features an eat-in kitchen and a living room with a wood-burning fireplace. There is separate dining area, a spacious first-floor bedroom suite, powder room, and laundry closet for convenience. The upper floor includes a second primary bedroom suite with an oversized window allowing for lots of natural light, guest bedroom, sitting room, and hall bathroom. Additional potential awaits in the sizable unfinished basement. The grounds are meticulously landscaped. There is a stone patio with firepit and cozy front porch. The private backyard abuts association land, and no Vineyard home is complete without an outdoor shower. Completing this offering is a detached two car garage.

8 Old Dunhams Corner Way, Edgartown

Listing courtesy of Listing Agent: Kristin Buck from Listing Office: Donnelly + Co..

$2,590,000

4 Beds ⋅ 3 Baths ⋅ 73432815 MLS

Nestled just a short stroll from all the best of Edgartown Village, this beautifully renovated retreat offers the ideal balance of Vineyard charm and modern convenience. Designed across three levels of living spaces, the home provides a flexible layout that works beautifully for entertaining, relaxing, or hosting guests. The main floor welcomes you with an inviting living room and a custom bar area. The covered porch offers a perfect spot for enjoying al fresco summer dining and relaxation. A sun-filled eat-in kitchen features a Viking gas range, granite countertops with a hint of sea glass green. The primary bedroom offers private access to the pool terrace. On the second floor, two well-sized bedrooms share a full bath, while the Lower Level offers additional space for gathering or guests, including a large lounge with media area, a bedroom and full bath, and a laundry room. Step outside to your private backyard oasis, where a heated 8x19 saltwater pool is framed by a stone terrace.

2 Orchard Ln, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$3,120,000

4 Beds ⋅ 4 Baths ⋅ 73351506 MLS

Water views with a pool! This chic contemporary 4-bedroom home with a pool and 2-car garage enjoys the ever-changing water views of Sengekontacket Pond and Nantucket Sound on three levels. Fully renovated, this delightful home, being sold turnkey, marries a timeless Vineyard vibe with modern luxury. The mudroom entryway opens to the kitchen with a breakfast island, dining room, and living room with a gas fireplace and sliders to the heated pool. The fabulous family room is off the dining room, and beyond the kitchen is an office with sliders to the deck. A pantry, half bath, and laundry complete the first floor. There are 4 bedrooms on the second floor, including 2 primary suites with views, all with vaulted shiplap ceilings, a den, and a shared bath. The den and one of the suites both have private decks that capture the essence of the views. An outstanding spiral staircase provides access to the fabulous “Lookout Lounge,” with stunning views.

110 Fifth Street North, Edgartown

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

$4,750,000

3 Beds ⋅ 4 Baths ⋅ 73409409 MLS

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 Vineyard lifestyle. The open-concept living and dining areas flow into a gourmet chef’s kitchen. The adjacent covered patio, complete with a gas fireplace, is a true outdoor haven for relaxing or hosting guests. The first-floor primary suite offers a peaceful retreat, with dual walk-in closets, a spa-like bath, and direct access to a serene three-season room. Upstairs, discover a charming lounge loft with built-in beds and a desk. Two additional bedrooms each offer unique character: one features a private deck and en-suite bath, and the other boasts its own den/seating area, as well as access to a luxurious full bath with a double-sink vanity.

36 Crocker Drive, Edgartown

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

$3,075,000

4 Beds ⋅ 3 Baths ⋅ 73382296 MLS

Exceptional Opportunity in Down HarborRare chance to own in Edgartown’s exclusive Down Harbor community, known for its serene setting and access to Katama Bay. Enjoy deeded rights to a pristine sandy association beach, plus coveted mooring and dock privileges—benefits usually reserved for waterfront estates. This peaceful neighborhood is experiencing a wave of elegant new builds and renovations, enhancing its status among Martha’s Vineyard’s top locales.The existing home offers four bedrooms, three bathrooms, a two-car garage, and an artist’s studio above. With town approval, a six-bedroom septic system may be added, allowing for expansion.Set on a full acre of mature landscaping, the property offers privacy and tranquility. Whether enjoyed as-is or reimagined, it presents a unique opportunity for customization in one of the island’s most desirable settings.

3 Down Harbor Road, Edgartown

Listing courtesy of Listing Agent: Susie Pimpton-Wallo from Listing Office: Compass.

$3,695,000

4 Beds ⋅ 3 Baths ⋅ 73414840 MLS

Exceptional Opportunity to Create Your Signature Vineyard Compound. Behind a charming white picket fence with blooming hydrangeas, this beautifully renovated Edgartown property blends island charm with new construction. Renovated in 2024 by top-tier builders, the nearly new home offers immediate comfort and timeless style, with potential for expansion into a luxury compound. On a private double-sized one-acre lot, it supports up to 7 bedrooms, including a future guest house, carriage house, and space for a pool, hot tub, and outdoor entertaining areas. The main residence features hardwood floors, shiplap, custom built-ins, designer fixtures, and an inviting chef’s kitchen with premium appliances, stone countertops, and custom cabinetry. Seamless indoor-outdoor living includes a covered porch, screened porch, expansive deck, outdoor shower, and mature landscaping. Whether enjoyed as-is or expanded, this coastal chic property combines quality finishes with a prime Edgartown location

37 Road To The Plains, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$1,350,000

3 Beds ⋅ 2 Baths ⋅ 73360252 MLS

Nestled in the prestigious Majors Cove community, this lovingly maintained home offers the perfect blend of comfort, style, and Vineyard charm. Enjoy access to exceptional amenities, including tennis courts, a boat launch ideal for kayaking to State Beach, and proximity to the bike path for easy access to Edgartown, Oak Bluffs, and Vineyard Haven. Set on a pleasantly landscaped lot, this inviting home is filled with natural light. The heart of the home is the cathedral-ceiling living room. The open kitchen and dining area seamlessly connect to a spacious new deck, offering an ideal setting for outdoor entertaining. A mudroom with laundry is off the dining area, with access to the garage. Two comfortable bedrooms and a full bathroom complete the main level. The upper level is devoted entirely to the private primary suite with a generous bedroom, a dressing area, a walk-in closet, and a full bath with a soaking tub and separate shower. Offered furnished.

16 Majors Cove Lane, Edgartown

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

$2,240,000

3 Beds ⋅ 2 Baths ⋅ 73414894 MLS

The Perfect Katama Retreat - Just one mile from South Beach and steps from the bike path connecting Edgartown and the beach, this charming property offers the ultimate Vineyard lifestyle. Built in 1998 by a respected Island contractor, it sits privately among pines and welcomes you with a classic farmer’s porch. The traditional, relaxed floor plan features a sunlit open kitchen, dining, and living area with high ceilings and a cozy gas fireplace. The first floor includes a bedroom, full bath, and laundry—ideal for single-level living. Upstairs are two spacious guest bedrooms and a second full bath. Finishes include hardwood floors, beadboard wainscoting, and white-tiled bathrooms. Additional features: central air & heat, poured concrete basement, and glass doors to a back deck and private yard, perfect for entertaining. With a strong rental history, this home is a great investment or personal retreat, offering easy access to the best of Katama and Edgartown.

29 Pradas Way, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$15,725,000

6 Beds ⋅ 5 Baths ⋅ 73399803 MLS

Historic captain’s home circa 1850, brilliantly renovated by architect Patrick Ahearn in 2002, on coveted North Water Street. Enjoy sweeping 180° Edgartown Harbor views from bright, sunlit living spaces with heart pine floors and custom millwork. An open-concept first floor flows to an 18x29' mahogany deck, perfect for al fresco dining and entertaining. The rare double-wide lot offers a lawn reaching to the harbor’s edge, perennial gardens, arbor, and deep-water pier. Third-floor bonus living plus lower-level bonus rooms, laundry, and outdoor shower. Includes a detached guest house for additional accommodations. Timeless style meets modern luxury in one of Edgartown’s most sought-after addresses.

111 North Water Street, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$2,500,000

3 Beds ⋅ 2 Baths ⋅ 73351589 MLS

Waterfront Charmer on Sengekontacket Pond - Perched on the shoreline, this contemporary cottage is enveloped by stone walls, lush gardens, and stunning water views. Inside, a bright, airy living space features an open dining area and a well-appointed kitchen. The all-white interior is complemented by hardwood floors, vaulted ceilings, skylights, air conditioning, and ceiling fans. Three sliding glass doors open to a spacious mahogany deck, perfect for soaking in the views. The first floor offers two bedrooms and a stylish bathroom with laundry. An open staircase ascends to the second-floor primary suite, showcasing French doors, vaulted ceilings, a luxurious bath, and mesmerizing views. Designed for seamless indoor-outdoor living, this home provides magnificent vistas across Sengekontacket Pond to State Beach. Stone steps lead into the pond for boating and kayaking. Furnishings available and strong rental history, this property is a great investment opportunity.

31 The Boulevard, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$3,300,000

4 Beds ⋅ 6 Baths ⋅ 73355339 MLS

This beautifully renovated Katama retreat blends refined design, luxury amenities, and flexible living. The main house offers three bedrooms, including a peaceful primary suite with private deck, a second en suite, and a cozy bunkroom. The octagonal living room, skylit dining room with gas fireplace, and chef’s kitchen with quartz counters and high-end appliances are perfect for entertaining. Upstairs, a state-of-the-art theater features a 4K projector, 110" screen, and surround sound—also ideal as a family room or game space. A home office nook and powder room complete the level.The detached guest retreat includes a bedroom, sitting area, en suite bath, and its own projector and screen under soaring cathedral ceilings. A newly built exercise studio offers a 14-ft Endless Pool, gym space, and half bath. Outside, enjoy the bluestone patio, hot tub, and landscaped yard. With heated storage, a separate shed, and close proximity to South Beach, this is effortless Katama living.

28 Crocker Drive, Edgartown

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.

$1,450,000

3 Beds ⋅ 2 Baths ⋅ 73304703 MLS

In the heart of Katama, close to south beach and all that the area has to offer, is this traditional 3 bedroom cape with updates. The bright kitchen and dining area offer a modern space, perfect for entertaining. A vaulted ceiling makes the living room light and bright. Three bedrooms, one downstairs and two upstairs, share bathrooms on each level. An outdoor shower, screened porch and outdoor decks make the indoor / outdoor transition comfortable. This property has an excellent rental history, or make it your island getaway or year round home. Sold turnkey and as is.

6 Gerts Way, Edgartown

Listing courtesy of Listing Agent: Kathleen Dawson from Listing Office: Donnelly + Co..

$965,000

3 Beds ⋅ 2 Baths ⋅ 73372896 MLS

Charming 3-Bedroom, 2-Bath Ranch in Edgartown – Spacious, Private, and Conveniently Located Discover this inviting 3-bedroom, 2 full bath ranch-style home set on a generous .5 acre lot in a quiet, private area of Edgartown. Featuring an open-concept layout, this home offers seamless flow between the living, dining, and kitchen spaces—ideal for both everyday living and entertaining. The spacious primary bedroom includes a private en suite bath, providing a relaxing retreat. A large finished room in the full concrete basement adds valuable bonus space, perfect for a home office, gym, or media room. Enjoy the outdoors with a sizable backyard and a deck perfect for gatherings or peaceful mornings. Conveniently located just 15 minutes from the island’s main port, and close to local shops and dining, this property blends comfort, space, and accessibility—making it ideal for year-round living or a vacation getaway.

62 Jernegan Ave, Edgartown

Listing courtesy of Listing Agent: Nicholas Silvestri from Listing Office: Keller Williams Realty Evolution.

$1,500,000

3 Beds ⋅ 2 Baths ⋅ 73335892 MLS

TURNKEY KATAMA BEACH RETREAT - OWNER FINANCING POSSIBLETucked away on a quiet sandy road in the heart of Katama, this charming and surprisingly spacious home is move-in or rental-ready—offered fully furnished for immediate enjoyment or income. Featuring 3 bedrooms and 2 full baths, the home includes 1,232 square feet of main-level living plus 520 square feet of finished lower level—perfect for a media room, home office, or guest overflow. The sun-filled interior boasts hardwood floors, a wood-burning fireplace, and a stylish kitchen with stainless steel appliances and stone countertops. Step outside to a private backyard oasis with room for a pool and easy indoor-outdoor flow via a large deck. Recent updates include a 2022 roof, renovated baths, fresh interior paint (2025), and central air. Set on a generous 16,552-SF lot and just a short bike ride to South Beach, the Katama General Store, and downtown Edgartown. With strong rental potential, owner financing possible, and expansion op

37 Knoll Dr, Edgartown

Listing courtesy of Listing Agent: Joseph Barkett from Listing Office: Compass.

$1,295,000

3 Beds ⋅ 2 Baths ⋅ 73382625 MLS

Welcome to this charming Cape-style home, just a short distance from the Village. Set on a spacious half-acre lot, this delightful property has been lovingly maintained. The home features an open layout that seamlessly blends comfort and functionality, making it perfect for both everyday living and entertaining. A sun-filled living room with cathedral ceilings and sliders opens to a multi-level deck. The kitchen, dining area, and cozy sitting space with a wood-burning stove also offer direct access to the deck. The primary bedroom and a full bath are on the first floor, and a comfortable loft bedroom with built-in drawers occupies the second floor. There is an office in the basement and ample space for storage. Adding even more versatility to the property is a one-bedroom apartment above the detached garage. The abutting .5-acre lot, 27 Seventh Street North, is also available for sale, offering even more possibilities for expansion or investment.

35 Seventh Street North, Edgartown

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

$2,590,000

4 Beds ⋅ 4 Baths ⋅ 73396688 MLS

STYLISH VINEYARD LIVING WITH EXCEPTIONAL OUTDOOR AMENITIES. This beautifully landscaped coastal-style home is set on three acres just off the bike path, offering easy access to all Island towns. A heated saltwater pool, expansive decking, and outdoor gathering spaces create the perfect setup for Vineyard summers. The home offers 4 bedrooms and 3.5 baths, including two primary suites—one on each level. The open floor plan features a great room, updated kitchen with stainless appliances, maple cabinets, granite counters, island, and pantry. A cozy den with gas fireplace, mudroom, and laundry area enhance everyday comfort. Recent upgrades include the heated pool, finished 4th bedroom, improved driveway, and full interior repaint. The 2-car garage includes a Tesla charger. A 398 sq. ft. carriage house is under construction with major systems in place. A 6-bedroom septic allows for future expansion. Furniture is available for separate purchase for a turnkey experience.

27 Watcha Path, Edgartown

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.

$1,320,000

3 Beds ⋅ 2 Baths ⋅ 73396066 MLS

Nestled in the serene setting of the Dodger's Hole community, this home is brimming with natural light, soaring ceilings and clean architectural lines.The open-concept layout features a generous living area with a seamless flow to the dining, kitchen and entertaining spaces, ideal for both everyday living and hosting guests.Kitchen has brand new stainless steel appliances! The spaces are thoughtfully designed to foster tranquility and relaxation. The home's architecture and oversized windows and sliders to the brand new deck harmonize with its natural surroundings, offering a seamless indoor-outdoor lifestyle. This residence offers the perfect canvas for your design vision. Outside, enjoy a private backyard with room for gardening, recreation, or future expansion. The low maintenance yard sits on a private lot with a semi-circular driveway. Easily accessible to bike paths leading to Oak Bluffs, Edgartown and Vineyard Haven. Don't miss the chance to get your piece of the rock!

10 Eagles Nest, Edgartown

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.

$10,750,000

8 Beds ⋅ 8 Baths ⋅ 73207523 MLS

Unparalleled Chappaquiddick waterfront estate complete with deepwater dock, 300±-foot private beach, private 3-bedroom guest house and garage/barn, plus the unique added opportunity to acquire the private 17±-acre golf course adjacent, also suitable for horses or open space. Designed by award-winning Boston architects Albert-Righter-Tittmann and expertly crafted, this grand yet welcoming home, featured in numerous publications, is a refined modern take on traditional design. Harmonizing with the idyllic coastal scenery, the 5-bedroom main residence captures glorious wide-open views on Nantucket Sound taking in the sunset, legendary yachting regattas and July 4th fireworks. Comfortably styled and beautifully furnished, the inviting light-filled living/entertaining spaces open their doors to the breezy waterside porch. A worlds-away retreat, yet close to Edgartown village. Seller welcomes offers with requests for buyer concessions.

37 North Neck Road, Edgartown

Listing courtesy of Listing Agent: George Ballantyne from Listing Office: Gibson Sotheby's International Realty.

$1,450,000

3 Beds ⋅ 2 Baths ⋅ 73382313 MLS

Located in the sought-after Dodgers Hole neighborhood, this beautifully renovated home blends modern style with coastal ease. Sunlight fills the main living area, where cathedral ceilings and hardwood floors create a bright and welcoming space.The kitchen has been completely redone with fresh finishes and thoughtful design, and the brand-new baths add to the turnkey appeal. The finished lower level offers excellent bonus space—ideal for a media room, home gym, or overflow entertaining area.Set on a well-maintained lot just minutes from downtown Edgartown, South Beach, and island bike paths, 61 Dodgers Hole Road is a move-in-ready opportunity for year-round living, vacation enjoyment, or investment. Buyers and agents to verify all information herein.

61 Dodgers Hole Road, Edgartown

Listing courtesy of Listing Agent: Ellen Valentgas from Listing Office: Sotheby's International Realty.

$3,515,000

5 Beds ⋅ 5 Baths ⋅ 73372543 MLS

Located in the sought-after Island Grove neighborhood, this Edgartown home is near Morning Glory Farm, Downtown, and South Beach. Designed for entertaining, the first floor features a custom kitchen, dining and living rooms, den, screened porch, half bath, and a seamless flow to outdoor living and a new heated pool. A spacious first-floor primary suite includes a walk-in closet and full bath. Upstairs offers four bedrooms and two full baths. The finished lower level includes a living room with gas fireplace, wet bar, and full bath. Additional highlights: access to association tennis courts, two laundry rooms, two-car garage, four-zone HVAC, and mature landscaping. Recent updates include a heated pool with auto cover, outdoor shower, lighting, paint, and new appliances. The property is connected to town sewer which allows for up to six bedrooms.

7 Whistling Swan Circle, Edgartown

Listing courtesy of Listing Agent: Jarrett Hurwitz from Listing Office: Keller Williams Realty.

$1,400,000

3 Beds ⋅ 3 Baths ⋅ 73350872 MLS

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 half-bath completes the first floor. Two additional large bedrooms, one with a private balcony overlooking the pleasant yard, and a shared full bath occupy the second floor. With a full basement, a 4-bedroom septic, and many recent updates, including a new roof, shingling, skylight, furnace, and water heater, the property can be used in its current state or designed to fit your Vineyard vision. The community of Dodger's Hole is centrally located, enjoying easy access to the bike path and proximity to the Village and State Beach. Being sold furnished, this offering is ready for immediate use!

73 Dodgers Hole Road, Edgartown

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

$3,350,000

6 Beds ⋅ 6 Baths ⋅ 73316704 MLS

Nestled in the heart of Edgartown, is this historic residence known as The Lightkeeper’s Inn. This property has five bedrooms, five baths and a separate one bedroom, one bath cottage, on .20 acre. Beautifully decorated in ole Vineyard style, the residence has the island feel of old time Martha’s Vineyard. This 5BD/5BA home sits in the heart of Edgartown close to the waterfront. Known as The Lightkeeper’s Inn, this historic Inn was said to be home to Henry Lyman Thomas, one of the last lightkeepers of the Edgartown Lighthouse. The property is unique in that it offers onsite parking, which is a rarity on Martha’s Vineyard.Currently operated as an Inn, this property may be converted to a single family residence with the required proper permitting and approvals.Located close to Edgartown Ferry, Edgartown Lighthouse, and minutes from N. Water Street, which offers shopping and restaurants.

25 Simpson's Lane, Edgartown

Listing courtesy of Listing Agent: Greg Hartel from Listing Office: Hartel Realty.

$4,762,500

6 Beds ⋅ 6 Baths ⋅ 73340020 MLS

NEW CONSTRUCTION!! This gorgeous new home sits on a spacious lot in a new luxury private enclave of 5 homes with breathtaking views of the surrounding area. The property offers privacy, a serene and picturesque setting yet a convenient 1.6 mile distance to Edgartown Village. With meticulous attention to detail, this home boasts luxurious amenities and modern comforts, providing an exquisite living experience. Sewer connection permits expansion of up to 7 bedrooms! The first floor of this luxurious home features a grand living room with expansive windows overlooking a large 18X42 saltwater, gunite pool; gourmet kitchen is a chef's delight, equipped with top-of-the-line appliances, custom wood cabinetry and a spacious quartz island for culinary creations; dining area; walk-in pantry; den area; and primary en-suite bedroom and oversized bathroom. Second floor features a loft area, 5 additional bedrooms and 4.5 bathrooms. Don't miss the opportunity to make this stunning property yours!

69 Division Road, Edgartown

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.

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