Chappaquiddick Luxury Homes

Find all luxury homes for sale in Chappaquiddick, Martha's Vineyard. You may also be interested in browsing listings for Martha's Vineyard luxury homes

Luxury Real Estate Chappaquiddick, Edgartown

Contact Sandpiper Realty if you have questions or would like to schedule a showing.

24 & 28 Litchfield Road Edgartown MA

Edgartown, MA24 & 28 Litchfield Road

Price$3,450,000

Est. Mortgage: $/month

MLS Number 35955

  • Residential
  • Square Feet 2146
  • Bedrooms 4
  • Bathroom 3
  • Acreage 6.3

Set splendidly on the waterfront in a treasured natural setting on Chappaquiddick, this home offers breathtaking views from its high perch above the protected cove of Caleb's Pond. Enjoy all that the area's pristine waters have to offer from this 6.3-acre property, comprised of two buildable lots of 3 and 3.3-acres. With the waterfront at your footsteps and rights to a nearby sandy beachfront adjacent to the Chappy Beach Club, you can enjoy boating, swimming, paddle boarding, fishing, clamming, scalloping, birding and more. Whether entertaining or having quiet respite, you'll experience dramatic water views and sparkling sunsets. The existing 4-bedroom home, known as “Clamalott” is charming and thoughtfully constructed with plenty of room for family or guests. Windows and decks provide light and views throughout, and the house offers a casual sense of ease and relaxation. The additional building lot provides the opportunity to create your own compound with many possibilities to include a pool, barn, 2nd home, and more. All this within 1 mile of the Chappy ferry, allowing for an easy stroll or bike to downtown Edgartown.

Listed by Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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58 North Neck Road Edgartown MA

Edgartown, MA58 North Neck Road

Price$1,400,000

Est. Mortgage: $/month

MLS Number 35897

  • Residential
  • Square Feet 2100
  • Bedrooms 4
  • Bathroom 2
  • Acreage 2.1

WATERVIEWS and shared PRIVATE WATER ACCESS to Edgartown Outer Harbor adds to the allure of this four bedroom Chappy home. Enter into the main foyer which features a split stairway. Upstairs is the main living area with cathedral ceiling, an open great room with combined dining and living room area, a wood burning fireplace, a two story wall of windows and sliding glass doors and an oversized kitchen. A master bedroom and full bath completes this floor. Off the Great Room is an expansive deck for additional dining and access to a roof top deck that offers views of the Edgartown Outer Harbor! The lower level of the home offers three bedrooms, two of which have sliding glass doors to a patio, a full bathroom and a laundry/utility room. The grounds have been lovingly planted and cared for with decorative flowering trees, plantings, stone patio and an entry stonewall. Recent additions to the home were the install of mini splits for heat and air conditioning in each bedroom. The crown jewel of the property is the shared private access to Edgartown Outer Harbor via a pathway easement that is across the street from the property. The beauty of the easement location is that it abuts Land Bank property and beach, a true delight! The entire property abuts 11.7 acres of Land Bank property, enhancing the peace and quiet of the setting. Strong rental history. Closing no sooner than November 1, 2020.

Listed by Vineyard Village Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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24 South Roger Road Edgartown MA

Edgartown, MA24 South Roger Road

Price$1,049,000

Est. Mortgage: $/month

MLS Number 35438

  • Residential
  • Square Feet 2406
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

This custom four-bedroom Chappaquiddick contemporary, unique in design with a highly functional layout, is the perfect place to call home. The light, bright and open living spaces and bedrooms are enhanced with direct access to the expansive outdoor decks, perfect for entertaining or a quiet retreat. There is more than meets the eye, with the newly installed solar panels and central air, making accommodations not only comfortable but efficient! The three-acre parcel, affording both privacy and future development opportunities, is located close to the ferry, Chappaquiddick Community Center and Slip Away Farm!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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77 Washque Avenue Edgartown MA

Edgartown, MA77 Washque Avenue

Price$895,900

Est. Mortgage: $/month

MLS Number 35392

  • Residential
  • Square Feet 1025
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.23

Chappaquiddick By the Sea- Step back, relax and unwind at this utterly charming three-bedroom cottage! Where the views across the neighboring Wasque preserve, 200 acres held in conservation, to the blue waters of Atlantic, will captivate and inspire. Enjoy the nearby ocean beach, or the calm waters and sandy shores of Katama Bay, located at the end of the road, which is perfect for swimming, boating, shellfishing. Located in one of the most special enclaves on Chappy, this is the definition of summer living!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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90 Pocha Road Edgartown MA

Edgartown, MA90 Pocha Road

Price$2,195,000

Est. Mortgage: $/month

MLS Number 34909

  • Residential
  • Square Feet 2692
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

Expansive protected views of Katama Bay and the Atlantic beyond are captured from almost every room of this perfectly appointed four bedroom home. Contemporary in style, with an open floor plan and expansive outdoor deck, this property lives large. Offering deeded beach access to the sandy shores and calm waters of the bay, perfect for shell fishing and endless water activities. An exceptional offering which can't be missed!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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22 Lelands Path Edgartown MA

Edgartown, MA22 Lelands Path

Price$12,900,000

Est. Mortgage: $/month

MLS Number 34890

  • Residential
  • Square Feet 10099
  • Bedrooms 8
  • Bathroom 9
  • Half Bath 2

Set on a commanding perch above the shores of Katama Bay, this luxurious 10,000 sf gambrel home, designed by renowned architect Patrick Ahearn, awaits the buyer searching for the best of coastal estates in New England. With nearly 6 acres private and over 40 acres of surrounding conservation parcels, peace and serenity are what define this Martha's Vineyard residence. Manicured lawns and meadows, comforting oak and pine trees, swans frolicking in nearby waters, sweeping water views, magical sunsets, and extensive sandy beaches combine to create relaxing outdoor environs. The interior of the home features a rarely achieved level of quality with views of the water readily available from every room. The master bedroom suite offers a breathtaking private outdoor space and luxurious bathroom, while guests can choose from multiple private bedroom suites with grand proportions. The home also features a beautifully appointed kitchen, extensive custom millwork, and smart home technology. Located on Chappaquiddick Island, the property sits in one of Martha's Vineyard's least travelled areas. Uncrowded, private and pristine, “Chappy”, as it is known locally, calls to those that move against the mainstream.

Listed by Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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126 Litchfield Road Edgartown MA

Edgartown, MA126 Litchfield Road

Price$1,200,000

Est. Mortgage: $/month

MLS Number 34229

  • Residential
  • Square Feet 2156
  • Bedrooms 3
  • Bathroom 2
  • Half Bath 1

CHAPPY- A CUSTOM BUILT GETAWAY IN A PARK LIKE SETTING- It is rare to find a home that suits both year round living and vacation getaway as well as this home. From the moment you enter this property it feels like home, yet the outdoor living on multiple decks, screened in porch and patio tips the scales towards a summer retreat. The custom interior replete with wood moldings, a Chef's kitchen, an open living and dining area with a large stone fireplace, vaulted ceilings, finished basement and three very large bedrooms leaves nothing to desire. Established gardens grace the exterior and a fenced in vegetable garden just a short distance from the house. Round out the offering with a two car garage that has an unfinished detached bedroom area above. Note: Title V septic allows for the 4th bedroom.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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56 Green Pastures Road Edgartown MA

Edgartown, MA56 Green Pastures Road

Price$2,490,000

Est. Mortgage: $/month

MLS Number 33881

  • Residential
  • Square Feet 1988
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3

Green Pastures- A private, residential enclave offering shared access to an association dock and waterfront on the calm waters of Katama Bay. Prominently positioned, amongst the large homesites and 18 acres of open community owned property, you'll find this delightful four bedroom, year round, home. A sizeable two-story garage, with plenty of storage for boats, beach and boating gear below and a detached bedroom with half-bath and deck above, is the perfect complement to this Chappaquiddick retreat. Plenty of space for a guest house and swimming pool -A fantastic offering in one of Chappy's loveliest communities!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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24 Manaca Hill Road Edgartown MA

Edgartown, MA24 Manaca Hill Road

Price$1,900,000

Est. Mortgage: $/month

MLS Number 33726

  • Residential
  • Square Feet 2096
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.34

Just a short walk from the Chappy Ferry sitting atop Manaca Hill, is this Chappy compound with sweeping water views over Edgartown Harbor on out to Cape Pogue. Deeded rights to a private association beach located just a short walk away. The Main House features an upside down layout with living spaces on the second floor designed to take advantage of the water views. The Living Area has a vaulted ceiling, and a wall of glass sliding doors and windows that open to a large, ocean-facing, wraparound deck. The Dining Area and Kitchen also open out to the living area for easy entertaining. The four Main House Bedrooms are on the first level and share a full bath with tub/shower. Upstairs, the TV/Family Room has a full bathroom. The separate Guest Cottage has a one Bedroom suite with full bath. The loft-style open layout has sleeping and dining areas, as well as an efficiency kitchen, and a deck. The entire Chappy Beach House Compound has large front and backyards, nicely manicured grounds. Please see documents for remodel plans by well known local designer to expand and update the house. These plans were previously approved by the town. This home has an established rental history.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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302 Chappaquiddick Road Edgartown MA

Edgartown, MA302 Chappaquiddick Road

Price$1,350,000

Est. Mortgage: $/month

MLS Number 33773

  • Residential
  • Square Feet 3743
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

Recently reduced and ready to go for summer 2019! Expansive four bedroom contemporary home convenient to all the wonderful amenities and beauty Chappaquiddick has to offer. Elegant by design, yet casual in nature, the open layout is ideal for entertaining. A large first-floor master suite, with recently renovated bath, requisite screened-in porch and swim spa are just a few attributes that make this property stand out amongst the rest. The full basement with extra high ceilings offers an additional 2,000s.f, which can be easily finished to create the ultimate workshop or rainy day rec room. The over-sized lot and a current septic system which can accommodate six bedrooms make expansion possibilities endless. Furnishings can remain, making your transition as seamless as possible for immediate enjoyment! Delightful and immaculate, you'll truly be Happy on Chappy!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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29 Road to the Gut Edgartown MA

Edgartown, MA29 Road to the Gut

Price$2,925,000

Est. Mortgage: $/month

MLS Number 33749

  • Residential
  • Square Feet 3230
  • Bedrooms 4
  • Bathroom 2
  • Acreage 5.57

Tucked between the calm waters of the bay and the Atlantic Ocean, under the guard of the Cape Poge Lighthouse, rests a retreat like no other. Lovingly restored and meticulously maintained, the three bedroom main house and one bedroom boathouse offer all the amenities one would expect, but not necessarily anticipate, from off the grid living. The ideal lifestyle choice for water sport and outdoor enthusiasts alike; with boating, kayaking, kite surfing, and shell-fishing at your doorstep, or for those seeking refuge and relaxation from the bustle of everyday life. Protected by the surrounding 500 acres of conservation, and accessed only over sand or by sea, this truly is the greatest escape.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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22 Lelands Path Edgartown MA

Edgartown, MA22 Lelands Path

Price$12,900,000

Est. Mortgage: $/month

MLS Number 33684

  • Residential
  • Square Feet 11677
  • Bedrooms 8
  • Bathroom 8
  • Half Bath 2

This spectacular estate was built in 2003 and offers over 11,000 sq. ft. of well designed living space with 8 bedrooms. Arguably the finest house on Chappaquiddick Island, highly situated and offering incredible views for 270. The house lies on 6-acres of manicured landscaping, rolling pastures and stonewalls. Surrounded by over 40-acres of unbuildable land adds to the majestic feeling of this world class estate setting and offers the ultimate seclusion and privacy, while just 3.5-miles to town.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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69, 75, 76 Bay View Avenue Edgartown MA

MLS Number 33590

  • Residential
  • Square Feet 1456
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.77

Expansive and protected views of Dow's Pond and Katama Bay are captured on every level of this Chappaquiddick contemporary. The oversized lot, a rarity in Wasque, allows flexibility for renovation and expansion including the potential for an additional bedroom. Thoughtfully designed, with multiple living areas, both inside and out and just a few hundred feet to the calm waters of the Bay… the epitome of a true Chappy summer experience.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

22 Lelands Path Edgartown MA

Edgartown, MA22 Lelands Path

Price$12,900,000

Est. Mortgage: $/month

MLS Number 33391

  • Residential
  • Square Feet 10099
  • Bedrooms 8
  • Bathroom 9
  • Half Bath 2

This exceptional Chappaquiddick estate is truly unique with breathtaking waterviews and stunning interiors. Designed by one of America's top classical architects, Patrick Ahearn, this custom residence is perched high on a hill on 5.95 acres with over 180 degrees of unobstructed water views of Katama Bay, Edgartown Harbor and the Atlantic Ocean beyond. Surrounded by acres of conservation land, this magical location offers unmatched privacy. Constructed with the utmost craftsmanship, this home features over 10,000 square feet of luxurious living space, 8 bedrooms and 11 baths. Dual master suites offer convenience, with the second level master suite featuring an expansive deck overlooking the ocean. Built for today's lifestyle and technology, the property has numerous amenities which include, an expansive living room for large family gatherings, 4 fireplaces, screened porch, wine cellar, gym, sauna, steam shower, roof top deck, custom woodwork, arched ceilings, 3 car garage and a top of the line gourmet kitchen with adjacent morning room. Truly a rare and unique opportunity to own and enjoy a generational quality estate.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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35A North Neck Road Edgartown MA

Edgartown, MA35A North Neck Road

Price$3,995,000

Est. Mortgage: $/month

MLS Number 30578

  • Residential
  • Square Feet 2486
  • Bedrooms 5
  • Bathroom 2
  • Acreage 4.3

North Neck… a truly spectacular setting with amazing, endless views from Edgartown Harbor, across Nantucket Sound and around to Cape Poge Bay. A casual and highly functional layout, a large common area complete with soaring ceilings and fireplace is flanked by two bedroom wings, ideal for easy summer living. The property includes 4.6+ acres of land,nearly 500' of private sandy beach and dock - swimming, boating and fishing are just steps away!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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