Chappaquiddick Luxury Homes

Find all luxury homes for sale in Chappaquiddick, Martha's Vineyard. Contact Sandpiper Realty if you have questions or would like to schedule a showing.

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90 Pocha Road Edgartown MA

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: 4.06% last updated on May 23, 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

Price$14,900,000

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: 4.06% last updated on May 23, 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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26 Caleb Pond Road Edgartown MA

Price$3,200,000

Est. Mortgage: $/month

MLS Number 34664

  • Residential
  • Square Feet 1194
  • Bedrooms 3
  • Bathroom 2
  • Half Bath 2

Remarkable waterfront property with deepwater dock on the Chappy side of Edgartown Harbor. Distance is less than a mile to the Chappy ferry. The water views extend from the village waterfront across the inner then outer harbor all the way to South Beach. Everything in-between is a front row seat to one of the most scenic waterscapes on the eastern seaboard. This is an incredibly active view and you can watch multimillion dollar wooden boats under full sail, teens taking the Whaler for a ride with their friends, kayakers and paddleboarders weaving between the moorings, and oystermen harvesting their catch. You might also spot your spouse or one of the kids returning from the village - taking the short cut by just motoring across the harbor instead of driving or biking to the ferry. The draft at the end of dock at low tide is 5'4” deep. It is one of the longer deep water docks with attached floating dock and swim ladders. The three-level home takes full and creative advantage of space. The main level features an open living and entertaining area with water views everywhere you look and a full kitchen and dining area. The design flair is exemplified by the fireplace which is a folk art masterpiece. The main living area transitions seamlessly onto the 400 sq ft mahogany deck that is partially shaded with an awning. Here is where you can soak in the incomparable waterviews with a cup of coffee before anyone else wakes up, or with all your friends enjoying cocktails at sunset. In total there is 1000 sq ft of decking. There are two bedrooms on the ground level, both with decks and large water views. The master bedroom has a bathroom ensuite and the guest bedroom has a full bath adjoining it. On the third level there is a cozy bunk room with a half bath. The nearby bunkhouse is as charming as can be. It sleeps two people comfortably and is perfect for overflow guests or kids who want the adventure of sleeping apart from mom and dad. The current owners have created a magical Chappaquiddick setting for the next owners to enjoy.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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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43 Calebs Pond Road Edgartown MA

Price$1,650,000

Est. Mortgage: $/month

MLS Number 34532

  • Residential
  • Square Feet 1536
  • Bedrooms 3
  • Bathroom 2
  • Acreage 3

YEAR ROUND HOME IN A NATURAL, WATERFRONT SETTING -Designed by renowned, Vineyard-based, Danish architect Niels Gabel-Jorgensen, this open and airy Cape style home sits nestled along the shores of Caleb's Pond. The conservation-minded buyer will appreciate the Sheriff's Meadow Conservation that surrounds this home which is located on a point of land stretching to the edge of the pond. With the ease of access to the shoreline and easy access for canoe, kayak or paddle boards, ply the waters of the pond or out into the Edgartown Harbor and into Katama Bay. All the offerings of Chappy with ease of access to Edgartown for shopping and dining. Enjoy this beautiful setting from inside looking out over the water through a wall of glass or out on the new, large deck. An open and airy Kitchen, Living and dining area with easy access to the expansive deck allows for fabulous options in entertaining. Two large guest rooms with a shared bath complete the first floor. The Master bedroom spans the entire second floor of this home with a bath en-suite. Did we mention the private tennis court that graces this 3 acre property?

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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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44 Calebs Pond Road Edgartown MA

Price$5,650,000

Est. Mortgage: $/month

MLS Number 34550

  • Residential
  • Square Feet 5310
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

HIGH ON A BLUFF- DEEPWATER DOCK- Designed by renowned Vineyard architect Niels Gabel-Jorgensen, the welcoming presence of this home can be felt immediately. Perched high on a bluff with a commanding view of the celebrated Edgartown harbor and replete with a deepwater dock permitted to accept 9 vessels. At the age of 35, this home remains grand and relevant in the current market. Vaulted ceilings throughout the living areas and wall of glass connect to the expansive harbor views and vistas beyond. You will have front row seats for the most glorious sunsets on the Island! Call the launch to meet you at your dock and whisk you into town for dinner or shopping. Located just 1 Mile from the Chappy Ferry, it is also an easy bike ride. Offered individually or as a compound with an adjacent property, guest house and tennis court. See listing #34532

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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

Price$1,399,000

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: 4.06% last updated on May 23, 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

Price$2,690,000

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: 4.06% last updated on May 23, 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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55 North Neck Road Edgartown MA

Price$5,950,000

Est. Mortgage: $/month

MLS Number 33826

  • Residential
  • Square Feet 4896
  • Bedrooms 6
  • Bathroom 5
  • Acreage 3.15

This private three-acre property on prestigious North Neck Road offers a charming, winding driveway, sprawling landscaped lawn, deep-water dock, and spectacular views of the Edgartown harbor, lighthouse and waterfront. This classically-designed home offers a spacious kitchen that opens to a large deck, patio and grilling areas - perfect for entertaining, a formal dining and living room, a fabulous screened porch, den, and four bedrooms including a luxurious master suite. The detached three-car garage and two-bedroom carriage suite complete this perfect setting. This is a truly rare and special offering that must be seen to be appreciated.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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

Price$1,950,000

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 grossing over $45,000 in 2018. Currently rented for 7 weeks in 2019.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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

Price$1,495,000

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: 4.06% last updated on May 23, 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

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: 4.06% last updated on May 23, 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

Price$14,900,000

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: 4.06% last updated on May 23, 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

Price$14,900,000

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: 4.06% last updated on May 23, 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

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: 4.06% last updated on May 23, 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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