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$4,200,000
4 Beds ⋅ 5 Baths ⋅ 73242178 MLS
NEW CONSTRUCTION. This EDGARTOWN COMPOUND offers it ALL! The Home has 5,763 square feet of high quality finished living space. There is a 14 X 40 ft. heated saltwater gunite pool with a waterfall feature and an 8 ft. round built in Spa. The Pool House features a half bath, kitchenette, cathedral ceiling, air conditioning and sliding glass doors. There is a detached garage with cathedral ceiling that can operate as another game room. The home sits on a flat 0.92acre of land that abuts a green belt of land. The homes entry opens to an expansive Open Floor Plan featuring two living rooms, both with gas fireplaces, one living room that features a soaring cathedral ceiling and a wall of sliding glass doors that lead to the outdoor entertaining area. The 1st floor bedroom has a glamorous bathroom, a walk in closet and home office. Three guests suites are on the second floor. The lower level offers finished space for a gym, media room or another lounge. Come and get it; ready for occupancy!

27 Bold Meadow Road, Edgartown

Listing courtesy of Listing Agent: Michele Casavant from Listing Office: Vineyard Village Realty.
$1,786,000
3 Beds ⋅ 4 Baths ⋅ 73301529 MLS
Move-In Perfect Bold Meadow Retreat - This charming expanded Cape greets you with delightful window boxes and a welcoming brick walkway, setting the tone for the warmth and character found within. The home boasts a well-thought-out open floor plan, featuring an inviting Living Room complete with wood-burning fireplace and custom built-ins and an adjacent Dining Room providing the perfect setting for gatherings with family and friends. The kitchen is a chef's delight, showcasing stone countertops, stainless steel appliances, and a convenient breakfast bar with counter seating. There are a total of three bedrooms, each with en suite bath, including a first-floor Primary Suite and a two-room bedroom suite on the second floor. The partially finished lower level offers a casual TV/Game Room and laundry area. With $350,000 worth of recent upgrades, this well-maintained home is also being sold TURNKEY with furnishings and contents, valued at $30,000, plus 2025 rental income.

15 Bold Meadow Ln, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$2,000,000
3 Beds ⋅ 4 Baths ⋅ 73289737 MLS
Welcome to this elegant haven nestled on a generous lot and gracefully buffered by the lush greens of the Edgartown Golf Course. Conveniently located approximately 2.5 miles from Edgartown Village and 1 mile from Morning Glory Farm.Upon entering, you are greeted by a refined living space that seamlessly blends classic charm with modern comforts.The heart of the home features an inviting living room, ideal for both intimate gatherings and grand multi-generational entertaining. The renovated kitchen is equipped with ample cabinetry and counter space, ensuring a delightful culinary experience. The oversized screened porch provides an enchanting space to enjoy family and friends while overlooking the verdant surroundings. A highlight is the finished basement, an additional 1,000 square feet. Step outside to the expansive deck. Large, professionally landscaped yard and a 2 car garage with unfinished framed out space above. Sewer connection permits expansion of up to 7 bedrooms!

16 Fisherman's Knot Road, Edgartown

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.
$1,860,000
3 Beds ⋅ 2 Baths ⋅ 73220582 MLS
Charming Saltbox Colonial With Pool + Association Tennis - Nestled in a serene and picturesque setting, this charming saltbox colonial is sited on a private wooded lot, surrounded by lush gardens and a beautiful outdoor living area with pool. The first floor welcomes you with an open and airy layout, featuring a sun-drenched Living Room adorned with vaulted ceilings, a cozy gas fireplace and an expansive wall of glass. Adjacent to the living area, you'll find a Dining Area and a cottage-style Kitchen. French doors lead out to a generous mahogany deck. Conveniently located on the first floor, one of the three Bedrooms offers comfort and privacy. Upstairs, the remaining two Bedrooms share another full bathroom. Step outside and into your very own oasis. The saltwater pool measures 14x30-feet and is surrounded by bluestone patio. Property has a solid rental history and is offered Turnkey with furniture and contents. The property also offers expansion potential for up to seven bedrooms.

3 Duncan Close, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$4,325,000
4 Beds ⋅ 5 Baths ⋅ 73276177 MLS
COMING SOON: MODERN COASTAL COTTAGE IN EDGARTOWN VILLAGE. Tucked away behind a picket fence and privet hedge, this charming, recently built custom home is within walking distance to Edgartown Village shops, restaurants and harbor, making it an ideal location for those seeking the vibrant atmosphere of downtown Edgartown. Step inside and be captivated by the fresh coastal décor and seaside-inspired palette, creating a bright and inviting interior. The open-designed Great Room is the heart of the home, featuring a spacious seating area with custom built-ins, and a gourmet cook’s kitchen equipped with Thermador® appliances, perfect for culinary enthusiasts. The adjoining sunroom with gas fireplace and French doors opens out to the beautifully landscaped backyard with bluestone terrace with pergola and built-in grill, offering ideal indoor-outdoor living and dining during the summer months -- while the Dining Room, complete with a wood-burning fireplace, provides a cozy space to share meal

106 Peases Point Way South, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 73298157 MLS
This 3BR, 1 & half BA salt box home in Dodger's Hole has been enjoyed by the same family for thirty years. First floor kitchen, dining and living are open concept with vaulted ceilings over the living and dining room. Also included on the first floor are a nice size bedroom and a half bath with laundry. Upstairs are two more bedrooms and a shared bath. Full unfinished basement. Recent upgrades include a new water heater, 40 year roof and skylights, MassSave insulation

4 Mockingbird, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$2,100,000
2 Beds ⋅ 1 Baths ⋅ 73306870 MLS
Waterfront Cottage

59 The Boulevard, Edgartown

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.
$2,580,000
4 Beds ⋅ 3 Baths ⋅ 73242341 MLS
CHARMING EDGARTOWN CAPE WITH GUEST COTTAGE + POOL. Step into this stylish in-town compound, featuring a charming Main House with a nicely updated kitchen and bathrooms, accompanied by a newly constructed, coastal chic Guest Cottage -- a perfect retreat for visiting family and friends. The two homes are centered around a spacious landscaped yard and a refreshing 16x34-foot gunite pool with a bluestone terrace, creating a private oasis for relaxation and entertainment. Nestled just a short distance from town, this home offers convenient access to Edgartown Village shops and restaurants while providing a serene retreat. Inside, the open layout welcomes you with an abundance of natural light and a seamless flow between the living spaces. With its desirable features and prime location, this charming compound presents a unique opportunity to embrace the quintessential Edgartown lifestyle. Note: Furnishings are available for purchase separately.

56 Pinehurst Road, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$2,994,000
4 Beds ⋅ 4 Baths ⋅ 73241127 MLS
This cape style home offers numerous gathering spaces for multi-generational living. The open kitchen/dining floor plan flows seamlessly into the cathedral ceiling family room which showcases a fireplace surrounded by stone. An additional first floor living room offers two separate seating areas. Both first floor living rooms sport french doors that lead to an inviting outdoor living space of decking, patio, garden views and an outdoor shower. There is a first floor and second floor primary suite. There are two additional guest bedrooms, with the capacity to expand with up to seven bedrooms. The first floor primary en-suite has a soaring cathedral ceiling and french doors that lead to outdoor decking. A lower level partially finished basement area offers two finished lounge areas, a laundry room and a large unfinished area for extra storage. The property offers a whole house generator.

5 Llewellyn, Edgartown

Listing courtesy of Listing Agent: Michele Casavant from Listing Office: Vineyard Village Realty.
$3,650,000
4 Beds ⋅ 6 Baths ⋅ 73263959 MLS
This stunning 4BD masterpiece has undergone a recent renovation, marrying timeless elegance with modern luxury. Step inside to discover a spacious interior adorned with premium finishes and thoughtful details at every turn. The main residence boasts 3BD, each offering a sanctuary of comfort and style. The primary and bath is found on the first level with an additional flex space used as an office. Two bedrooms with stylish barn doors are found on the upper level and are connected by a full bathroom. The gourmet kitchen has top of the line appliances with a large Quartz island. There is a DR and living area with TV and gas fireplace just off the kitchen. The spacious great room offers a second place to gather and watch TV. The expansive outdoor living areas feature a pristine pool surrounded by lush landscaping. The separate Carriage House offers a retreat of its own, complete with all the amenities needed for comfort including a bedroom, full bath and living room with gas stove.

14 Prices Way, Edgartown

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..
$5,300,000
4 Beds ⋅ 6 Baths ⋅ 73176717 MLS
Luxurious Living In Edgartown Village - Experience luxurious coastal living in the heart of Edgartown Village at this stunning home on Jordan Way. The spacious living area welcomes you with abundant natural light, creating a warm and inviting ambiance. An open floor plan seamlessly connects the living room, dining area, and kitchen, providing an ideal space for entertaining. The well-appointed kitchen boasts top-notch appliances, a center island with counter seating, and ample counter space and storage, catering to culinary enthusiasts. This beautiful home extends its living space to 5,400 square feet with a fully finished walk-out lower level featuring a Family/TV Room, billiards area, entertaining kitchen, game area, and in-home gym. The grand owner's suite offers a tranquil sanctuary with vaulted ceilings, a sitting area, and a luxurious spa-like bath with a double vanity, soaking tub, and walk-in shower. Three additional bedrooms, all with en suite baths, including a first-floor bj

1 Jordan Way, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$1,640,000
3 Beds ⋅ 2 Baths ⋅ 73264518 MLS
Welcome to your ideal Vineyard retreat with a heated pool! This pristine classic cape-style home features three bedrooms, two baths, and exquisite landscaping. The backyard is a stunning oasis with a fabulous pool, outdoor shower, grilling station, and an expansive deck perfect for outdoor entertaining. The home offers an open layout for comfortable living. The cozy living room flows into the dining area, with French doors to the deck and pool area, and the kitchen is easily accessible to all. The generous primary bedroom is on the first floor with direct access to a full bath. Two bedrooms with large closets and a full bath occupy the second floor. If you are looking for additional living space, a finished bonus room in the basement is currently used as an exercise room. Completing this fabulous property is an attached 1-car garage. Dodger's Hole is centrally located, enjoying easy access to the bike path and proximity to the Village and State Beach. Being sold partially furnished.

41 Dodgers Hole Road, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$1,975,000
4 Beds ⋅ 3 Baths ⋅ 73231131 MLS
Bold Meadow! This nicely maintained home is located in a well established neighborhood just outside of the Edgartown Village, close to Morning Glory Farm and South Beach. Many nice features throughout include a spacious living room with cathedral ceiling, wood burning fireplace and custom built-in cabinets. The Well equipped kitchen is open to the dining room with sliders to a deck with pergola overlooking a peaceful backyard. There is a first floor primary with en-suite bathroom and sliders to a private deck and outdoor shower. Coming in from the oversized 1-car garage is a mudroom, 1/2 bath and laundry room. Second floor includes 3 good size bedrooms, one with a window seat, that share a full bath. Potential for a second bath if one wanted. Wood, Tile and Carpet throughout. This home is immaculate inside and out.

29 Bold Meadow, Edgartown

Listing courtesy of Listing Agent: Brenda Galligan from Listing Office: Karen M. Overtoom R.E..
$4,555,000
5 Beds ⋅ 6 Baths ⋅ 73229874 MLS
Set over an acre of land, this beautiful setting offers privacy and breathtaking views of Morning Glory Farm + Land Bank meadows. Enjoy this ultimate compound with proximity to the bike path, the Village, and South Beach. The custom-built home + guest house boasts luxurious amenities centered around outdoor living spaces, including a large infinity edge heated pool + spa with beautifully landscaped + garden-lit grounds. With over 5,000 square feet of living space throughout the property, there is plenty of room for privacy + for all to gather comfortably. The 3-bedroom main house is thoughtfully designed. The focal point is the dramatic vaulted ceiling living room with a wood-burning fireplace, + slider doors to the expansive deck overlooking the pool, + outdoor kitchen. This property offers privacy and proximity to everything you need and is the ultimate in Vineyard living! Connected to town sewer, 7 bedrooms allowed.

29 Llewellyn Way, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$1,900,000
3 Beds ⋅ 3 Baths ⋅ 73228260 MLS
Charming Katama Retreat - Experience the ideal vacation home in Island Grove, just minutes from South Beach and Edgartown's delightful downtown. This property offers the perfect base for enjoying the island lifestyle, with close proximity to Morning Glory Farm and association amenities including tennis and pickleball courts. The home features an in-ground saltwater pool with waterfalls and spa, an outdoor bar, and stone fireplace for year-round entertainment. Inside, the updated kitchen opens to a sun-filled dining and living area, plus a four-season sunroom overlooking the pool. The second floor includes two bedrooms, a bonus room, and a primary suite with a luxurious bath, walk-in closet, and private balcony. The included photos with virtual staging and renovation possibilities, offer inspiration for your dream vacation retreat. Additional perks include a partially finished basement, versatile outbuildings, two-car garage and the ability to tie into town sewer, allowing up to 6 bdrms

18 Cormorant Circle, Edgartown

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$6,665,000
6 Beds ⋅ 8 Baths ⋅ 73219604 MLS
Coastal Charm With Edgartown Harbor And Lighthouse Views - Located in the heart of historic Edgartown Village, this exquisite property, designed by renowned architect Patrick Ahearn, captures the essence of village living. Spanning four floors of finished living space, totaling 6,340 square feet, the property features French doors that open out to multiple decks and porches, six bedrooms with en suite baths, plus a detached Carriage House with a private bedroom and full bath. The interior features beautiful heart pine floors, beaded board, raised paneling, custom built-ins, and millwork, adding a touch of sophistication to every room. The main level includes a formal living room and dining room, a gourmet kitchen, complete with a center island, top-grade appliances, and a separate butler's pantry. Cozy up by one of the four wood-burning fireplaces. Offered furnished plus the perfect beach cruiser, a rare and fully-restored Land Rover Defender, NATO model, valued at $150,000.

11 Cummings Way, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$1,099,000
2 Beds ⋅ 3 Baths ⋅ 73270636 MLS
This gem awaits your visions! Connected to town sewer for up to 4 bedrooms with expansion potential, the options are plenty. Just half a mile from the heart of Edgartown Village filled with shopping, restaurants, and beautiful Edgartown Harbor, you will love the location. If you are looking to head for the beach, State Beach is easily accessible and only 1.5 miles away. The interior offers wide-planked floors, a cathedral-ceiling kitchen and dining area, an adjoining living room, a 4-season sunroom, and a great mudroom. There is a full bath and 2 bedrooms. One of the bedrooms has a half bath and the other bedroom is open with direct access to the basement. The partially finished basement also enjoys wide-planked wood floors, a full bathroom, and interior and exterior access. A small studio and garden shed are in the backyard. This is an excellent opportunity for anyone who wants to be close to town on a tucked-away street. The property is being sold “as is”.

9 Hannah's Way, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$1,510,000
2 Beds ⋅ 3 Baths ⋅ 73240603 MLS
Privately sited in a quiet neighborhood on Oakdale Drive, abutting Edgartown Golf Club, this property offers a bright and spacious cathedral ceiling 1-bedroom, 1.5-bath home and a charming 1-bedroom, 1-bath cottage. The location is ideal with proximity to the bike path, State Beach, and the Village. The home features an open floor plan with beamed ceilings, skylights, and sliders to an expansive deck for extended outdoor entertaining. The cottage also embraces abundant natural light, with a vaulted ceiling and 2 sets of slider doors to a private deck, patio, and outdoor shower. Being sold furnished except for some personal items, this offering is a rare opportunity not to be missed. The septic system did not pass the Title V inspection. Sourati Engineering Group has been engaged to design and obtain Town approvals for a three-bedroom sewerage disposal system. Seller will contribute up to $20,000 at closing to the repair/execution of the Title V compliant system.

19 Oakdale Drive, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$2,125,000
4 Beds ⋅ 3 Baths ⋅ 73231439 MLS
The Perfect Package - If ever there was a property that truly delivers - here it is! With ease of location, systems and well planned spaces this expanded home offers abundant lifestyle comforts. Set back from the street, with a welcoming front entrance that reveals years of care and attention to details - blending luxury and coziness. RECENT UPGRADES include; Central AC, new windows, plantation shutters throughout, oak flooring on both levels, new exterior doors including rear slider to the expanded deck. This FOUR bedroom year 'round property is serviced by town water and town sewer allowing for permitted expansion up to 6 bedrooms. The 2019 built garage and rear patio balances this delightful offering. Front to back there's a lot to love about this Island Grove home with easy access to Katama, South shore beaches, Edgartown village as well as up island along the West Tisbury Road. Nearby amenities capture foodies and outdoor adventurers alike; Morning glory farmstand, Katama general

1 Old Squaw Circle, Edgartown

Listing courtesy of Listing Agent: Grace Bishop from Listing Office: Compass.
$3,140,000
3 Beds ⋅ 5 Baths ⋅ 73235344 MLS
Set privately in the heart of Chappaquiddick, this property offers a rare combination of exceptional landscaping with a refined home that exudes quality. While beaches, trails, and even downtown Edgartown are readily available, this property is a standalone oasis. On the exterior the home greets with high-end materials, including cedar shingle roof and siding, copper accent, and Azek trim. Multiple entrances lend naturally to indoor/outdoor living, allowing for enjoyment of bluestone patios, Ipe deck, flower and vegetable gardens, and open lawns. The interior of the home centers on a cathedral-ceiling great room, with fieldstone fireplace and chef’s kitchen at opposite ends. The primary suite is private, yet conveniently located, with a luxurious bathroom and walk-in closets. Two additional bedrooms are set on a separate wing of the house, each with private bathrooms. There is also a two-car garage and studio/workshop that is beautifully finished.

149 Litchfield Rd, Edgartown

Listing courtesy of Listing Agent: Peyton Wallace from Listing Office: Compass.
$2,315,000
4 Beds ⋅ 3 Baths ⋅ 73202293 MLS
Welcome to this well-maintained home, tucked away on a quiet street in the heart of Katama. The sunny and bright 3-season porch with gas fireplace greets you upon entry. This flows into an ample eat-in kitchen with granite prep island, top of the line appliances and a wet bar with wine refrigerator. The large open living room with cathedral ceilings, an abundance of natural light and gas fireplace is the focal point of the home. An en-suite primary and separate powder room complete the first floor. Upstairs you will find 3 large bedrooms with a shared bath. Impeccable grounds are fully irrigated with apple + pear trees. Oversized deck, outdoor shower, firepit, garden shed and large stone driveway with granite apron + border finish the exterior.

10 Gert's Way, Edgartown

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..
$1,300,000
1 Beds ⋅ 3 Baths ⋅ 73208122 MLS
Convenient to Edgartown center at the end of a private rd, you enter the lush, mature landscape that wraps around this surprising home. The well designed first level open floor plan with vaulted ceilings and three sets of sliding doors opens to an expansive deck that makes the home feel both light and spacious, with specimen plantings providing privacy on 1.4 acres. The primary en suite bedroom is also on the first floor. The surprises are the multi use intimate spaces on the second loft level, along with another full bath, and a full partially finished basement. A breezeway attaches the main entrance and the one car garage. Separate and private, but close to the house is a new, 2 car garage with a large finished space above, now used as a golf room with a golf simulator. Located in the Lily Pond district there is potential for a pool and expansion with town permits.

64 Jernegan Pond Rd, Edgartown

Listing courtesy of Listing Agent: Kathleen Dawson from Listing Office: Donnelly + Co..
$1,250,000
3 Beds ⋅ 2 Baths ⋅ 73214030 MLS
Live the lifestyle many only dream of in this fabulous 3 bedroom, 2 bathroom, Vineyard Contemporary with easy access to South Beach, Long Point, State Beach, and Morning Glory Farm. This sun-drenched home features hardwood floors, soaring skylit cathedral ceilings and generous spaces to gather with friends and family. Meticulously updated with new energy efficient Pella windows, six state-of-the-art heat pumps/air conditioning mini-splits, oversized water heater, finished basement with custom dehumidification system, and new kitchen appliances. Both bathrooms have been beautifully updated and the outdoor shower is ready to serve summertime guests. There's ample parking with a private driveway and a large shed for storage. An expansive deck & Juliet balcony overlook a backyard with space to relax or play. Whether you're looking for your next investment property or a seasonal retreat, make this Saddle Club gem your home away from home.

13 Saddle Club Rd, Edgartown

Listing courtesy of Listing Agent: Amy Rutkowski from Listing Office: A. Rutkowski Realty, Inc..
$1,900,000
3 Beds ⋅ 3 Baths ⋅ 73197918 MLS
Charming reverse-contemporary home in Katama – a fabulous beach getaway! Offering privacy from the crowds on a quiet street, yet proximity to the activity of South Beach. Located in the heart of Katama, with easy access to the bike path and proximity to the Village, Vickers Street is one of the most desirable spots on the Vineyard. The septic is for 3 bedrooms, but with the ability to tie into town sewer for up to 6 bedrooms, the options are endless. The main level offers an abundance of natural light and an open kitchen, dining room, cozy living room with wood-burning fireplace, half bath, and den/office. There are two accesses to the upper deck for extended outdoor entertaining. On the lower level, there are three bedrooms, including an ensuite primary with private access to the lower deck, another full bath, and laundry. The fully unfinished basement can be used for storage or the potential for additional living space. Being sold furnished.

28 Vickers Street, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$2,300,000
3 Beds ⋅ 4 Baths ⋅ 73137492 MLS
Introducing an outstanding property in Island Oaks, this perfectly maintained home offers an unparalleled combination of Vineyard charm, comfort, and the ultimate floor plan designed for entertaining. The first floor features a fabulous kitchen, dining room, and living room with a gas fireplace and sliders to the deck. The family room, with pocket doors, presents a quiet space to read or watch television. The primary suite occupies the entire left side of this floor with a walk-in closet, office space, an ensuite bath, and a private outdoor shower. There are two substantial bedrooms on the second floor, each with a full bath, and a cozy den at the top of the stairs. The 1977 sf unfinished basement enjoys 10’ ceilings and awaits your vision. Completing this offering is a garage with unfinished space above and newly installed solar panels. The home comes tastefully furnished.

28 Woodhaven Dr, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$2,409,000
2 Beds ⋅ 2 Baths ⋅ 73064627 MLS
Near the end of North Water Street, overlooking Edgartown’s picturesque harbor and steps from the iconic lighthouse, sits the most storied hotel on Martha’s Vineyard. Built in 1891 and after a top to bottom restoration in 2018 and extensive modernization again in 2021, this charming and sophisticated resort is offering the opportunity of fully managed residences with deeded ownership providing the splendor of Vineyard homeownership without the worry of maintenance and property management. The Harbor View Captain’s Cottages provide all of the hotel’s refined amenities. This all encompassing 2-Bedroom, 2-Bath second floor residence is located in the Captain Osborne Cottage and features fresh and inviting spaces. There is even a private outdoor shower and deck right off the primary bedroom! Owners enjoy a myriad of benefits including dining and lodging discounts at the hotel. There is also a fully managed rental program available. Enjoy carefree second homeownership!

131 North Water Street Unit 52, Edgartown

Listing courtesy of Listing Agent: Kimberly Naylor from Listing Office: Compass.
$3,800,000
6 Beds ⋅ 4 Baths ⋅ 73160542 MLS
Captain’s Quarters - Sitting up tall and proud at the crest of School Street, this iconic Edgartown village property has a lot to boast about. Surrounded by superb and historic architecture, the preserved town setting provides unmatched amenities. Nearby shopping, eateries, and harbor activities as well as Katama and stunning south shore beaches. The historic six-bedroom home has been thoughtfully restored and beautifully transformed. With design concepts, stylish renovations, upgraded systems, and rooms that multitask with ease – it all adds up to an appealing package. Serviced by town water and grandfathered with a six bedroom town sewer flow. Attached garage plus on-site parking for multiple vehicles. Side access through the gated arbor leads to the outdoor shower, private back yard with patio, and a useful shed too!

109 School Street, Edgartown

Listing courtesy of Listing Agent: Grace Bishop from Listing Office: Compass.
$1,100,000
1 Beds ⋅ 1 Baths ⋅ 73064625 MLS
UNPARALLELED LUXURY AWAITS AT THE HARBOR VIEW CAPTAIN’S COTTAGES - Built in 1891 and after a top to bottom restoration in 2018 and extensive modernization again in 2021, this charming and sophisticated resort is offering the opportunity of fully managed residences with deeded ownership providing the splendor of Vineyard homeownership without the worry of maintenance and property management. Sprinkled across the property, the Harbor View Captain’s Cottages provide all of the hotel’s refined amenities. This oversized 1-Bedroom, 1-Bathroom, first floor residence is located in Captain Collins Cottage and features fresh and inviting spaces with furnishings that evoke Vineyard style and life lived near the sea. The expansive living room has a pull out couch for extra guests. Ownership at the Harbor View Captain’s Cottages has been thoroughly contemplated to offer the finest service. Owners enjoy benefits including dining and lodging discounts.There is also a managed rental program available.

131 North Water Street Unit 21, Edgartown

Listing courtesy of Listing Agent: Kimberly Naylor from Listing Office: Compass.
$4,465,000
3 Beds ⋅ 4 Baths ⋅ 73180434 MLS
Stylish South Beach Retreat With Extraordinary Pool + Outdoor AreaNestled in the heart of Katama, this stunning contemporary tri-level home is thoughtfully designed for the ultimate indoor-outdoor living experience, with the soothing sounds of the nearby ocean adding to its allure. As you step into the dramatic Living Room, you'll be greeted by vaulted ceilings, a sleek tiled linear fireplace, and a full wall of 12-foot glass doors that seamlessly open out to an expansive mahogany deck. The open-concept Dining Room and gourmet cook's Kitchen are perfect for both intimate family meals. The outdoor living spaces are truly extraordinary, boasting a captivating gunite pool with a built-in whirlpool spa and a waterfall with a striking fire feature. An outdoor cabana with bar seating, two beverage refrigerators, and a 76" waterproof TV wall offers the perfect setting. Offered with furnishings and contents for a turnkey move-in or rental-ready property for Summer 2024.

7 Katama Dr, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$910,000
3 Beds ⋅ 2 Baths ⋅ 73146450 MLS
Seize the opportunity to own a slice of paradise! This adorable cape surrounded by a lush yard offers an expansive deck perfect for hosting gatherings or simply savoring the tranquil ambiance. This easy to maintain home features a first floor bedroom and bathroom, with 2 bedrooms and a shared bath upstairs. It's central location is proximate to Vineyard Golf Club and not far from Morning Glory Farm. Easy access to bike paths, the airport, Edgartown Village and beaches! Whether you're seeking a year-round residence or a seasonal escape, this property offers endless possibilities. Don't miss out. Home is being sold 'as is.'

10 Saddle Club Road, Edgartown

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

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