Chappy Luxury Homes

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

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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

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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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321 Chappaquiddick Road, Edgartown, MA

Price$1,175,000

Est. Mortgage: $/month

MLS Number 34328

  • Residential
  • Square Feet 2286
  • Bedrooms 3
  • Bathroom 3
  • Acreage 1

Expansive and recently renovated, this three bedroom three bath cape, is the perfect place to call home. Easy living, both inside and out, with open concept kitchen and dining area and sprawling back deck complete with outdoor shower and hot tub. A large barn, the most recent addition to the property, adds charm and function, ideal for storage of all things boating, beaching and fishing! Surrounded by conservation land and less than a mile to the calm waters of Katama Bay, the property is conveniently located to all Chappy has to offer!

Listed by Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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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107 Washque Avenue, Edgartown, MA

Price$3,250,000

Est. Mortgage: $/month

MLS Number 33791

  • Residential
  • Square Feet 3688
  • Bedrooms 5
  • Bathroom 3
  • Half Bath 1

Waterfront property on Chappaquiddick with extensive private beach and water views that stretch as far as the eye can see. Spread out over 4 acres, this property is ideal for the buyer who wants a beach vacation for their family and guests. Sweeping water views are available from most interior living space, and the large decks each offer their own different perspectives. The 5-bedroom “modern rustic” home is immaculately maintained - the pickled wood beams pay tribute to the driftwood found on the surrounding beaches. And speaking of beaches, the property has 400 feet of sandy private beach on Katama Bay, and abuts rarely-used conservation land with an even longer stretch of sandy barrier beach. A quick paddle across the calm, shallow water takes you to an ocean beach with big surf and some of the best fishing on the eastern seaboard. The waters in front of the house are filled with shellfish that are yours for the raking. Need more elbow room? The town has approved plans for the construction of a garage and screened porch. Photographs cannot capture the full scope of this property and it has to be experienced first hand to be fully appreciated. Watch this 1-minute video at this URL: https://vimeo.com/277174251

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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$2,000,000

Est. Mortgage: $/month

MLS Number 33726

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

Walking distance to Chappy Ferry to Edgartown Village. Sitting atop Manaca Hill, this Chappy compound enjoys sweeping water views over Edgartown Harbor on out to Cape Pogue. 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,. The home has an established rental history grossing over $45,000 in 2017.

Listed by Point B Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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$1,565,000

Est. Mortgage: $/month

MLS Number 33773

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

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 oversized lot and a current septic system which can accommodate six bedrooms make expansion possibilities endless. Delightful and immaculate, you'll truly be Happy on Chappy!

Listed by Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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 & 28 Litchfield Road, Edgartown, MA

Price$3,875,000

Est. Mortgage: $/month

MLS Number 33721

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

Perched on the edge of a bluff overlooking pristine Caleb's Pond, “Clamalott”, as it's affectionately known, is a wonderful family retreat offering much privacy and natural beauty. This 4-bedroom / 3-bath home offers panoramic, 180 degree water views, North to South, with spectacular Western sunsets over the Caleb's Pond and refreshing southwest breezes. Migratory seashore and land bird watching is plentiful. The property totals 6.3-acres, which are comprised of two separate, fully buildable lots (3.3 and 3.0 acres respectively). The additional lot offers the flexibility of creating the ultimate family compound or could be developed separately to maximize one's investment on this 6+ acre parcel that extends from Caleb's Pond to Litchfield Road. The property also includes a private mooring and use of the Caleb's Shore Association Beach nearby, facing Edgartown's Outer Harbor. Just a short walk or bike ride to the Chappy Ferry, providing parking and quick, convenient access to downtown Edgartown.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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: 4.45% last updated on Jan 17, 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: 4.45% last updated on Jan 17, 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

Magnificent Chappy estate overlooking Katama Bay and surrounded by conservation land. Designed by Patrick Ahearn, this custom residence is perched high on a hill on 5.95 acres with over 180 degrees of unobstructed water views. 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. Offering over 10,000 square feet of luxurious living space, this home features 8 bedrooms and 11 baths. 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: 4.45% last updated on Jan 17, 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 33189

  • Residential
  • Square Feet 9441
  • Bedrooms 8
  • Bathroom 8
  • Half Bath 2

You cannot find a more complete package! This home has covered all the bases for comfort and elegance. Each of the rooms is designed to capture the strong views from the land looking over Edgartown Harbor and the Atlantic Ocean. The house is designed to allow guest and family to be together on the multiple porches or sharing meals as well as relaxing or watching a movie together. The home has several wings for everyone to spread out and have privacy and quiet time as well. Each bedroom has a bathroom and each wing has a private laundry. The views are really outstanding from all points of the house. Patrick Ahearn was able to capture the natural beauty of this property and what it overlooks by designing a home that embraced the land completely with the home design. If you like privacy and easy access to secluded sandy beaches, you should see this home. Conservation land abuts the property securing what is so special about the natural aesthetic of Chappaquiddick open meadows, water views and sandy long beaches.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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: 4.45% last updated on Jan 17, 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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