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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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

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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$15,900,000

Est. Mortgage: $/month

MLS Number 33684

  • Residential
  • Square Feet 11677
  • Bedrooms 8
  • Bathroom 8
  • Acreage 5.95

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

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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6 Armstrong Lane, Edgartown, MA

Price$3,975,000

Est. Mortgage: $/month

MLS Number 33345

  • Residential
  • Square Feet 1519
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.56

Enjoy unobstructed views from this dynamic waterfront property, complete with deep water dock and private sandy shore on the protected waters of Edgartown Inner Harbor. This uniquely versatile offering, comprised of two cottages, is ideal for casual summer living or future expansion, within close proximity to the Chappy ferry and all Village amenities. Top Mast Head, as it is affectionately known, has been held in the same family for generations, and must be experienced firsthand for a full appreciation of it's worth.

Listed by Sandpiper Realty

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 Caleb Pond Road, Edgartown, MA

Price$1,895,000

Est. Mortgage: $/month

MLS Number 33481

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

Caleb's Pond - Contemporary in design, yet casual in style, this three bedroom home is the perfect Chappaquiddick escape. Enjoy shell fishing and fishing in the tranquil waters or a simple kayak paddle around the bend to explore the comings and goings on Edgartown Harbor. Complete with private tennis court and located within close proximity to both ferry and beach, this property can't be missed!

Listed by Sandpiper Realty

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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20 Jason Drive, Edgartown, MA

Price$869,000

Est. Mortgage: $/month

MLS Number 33395

  • Residential
  • Square Feet 1832
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1

SIMPLY CHARMING ON CHAPPY. Privately sited at the end of a lightly traveled road, this simply charming saltbox is surrounded by beautiful perennial gardens and a park-like setting for ideal year-round or seasonal Chappy living. Meticulous craftsmanship and quality can be found throughout the home, which was custom-built by its current owner, who is a well-known island builder. The bright and sunny interior features a formal Living Room with wood-burning fireplace and French doors that open onto a screened porch, perfectly integrating indoor and outdoor living. The open-designed Dining Room and Kitchen also opens onto the screened porch, creating a perfect flow for dining and entertaining indoors or out -- and the outdoor space spills out further onto a wraparound mahogany deck and a stone patio surrounded by beautiful landscaping and gardens. There are a total of three bedrooms, including a first-floor bedroom and a second-floor master bedroom with fireplace and office alcove. This property is move-in perfect and features many extras like gleaming hardwood floors, central a/c, a one-plus garage and more. All the best of Chappy living is just outside the door . . . from sandy beaches and nature trails, to coveted fishing spots and island farms. This charming home is an ideal setting for gathering friends and family and creating treasured Chappy memories for years to come.

Listed by Point B Realty LLC

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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$15,900,000

Est. Mortgage: $/month

MLS Number 33391

  • Residential
  • Square Feet 10099
  • Bedrooms 8
  • Bathroom 9
  • Acreage 5.95

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

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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$15,900,000

Est. Mortgage: $/month

MLS Number 33189

  • Residential
  • Square Feet 9441
  • Bedrooms 8
  • Bathroom 8
  • Acreage 5.95

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

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

Price$2,195,000

Est. Mortgage: $/month

MLS Number 33287

  • Residential
  • Square Feet 2692
  • Bedrooms 4
  • Bathroom 2
  • Acreage 4.5

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

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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14 Washque Avenue, Edgartown, MA

Price$525,000

Est. Mortgage: $/month

MLS Number 33163

  • Residential
  • Square Feet 704
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.34

“Eastview”, at 14 Washque Ave. on the island of Chappaquiddick sits at the high point of a gently sloping lot overlooking Pocha Pond, East Beach, Nantucket Sound and beyond. Solidly built by Ross Gannon of the famed Gannon and Benjamin boat builders, and with a creative use of space, this home offers a private, quiet and tranquil getaway in a natural setting. With two bedrooms and bath on the lower level, the upper level is a cozy open layout with a wood burning stove. Upper and lower decks offer additional indoor/outdoor living space. The property sits adjacent to many acres of conservation land and has direct access to miles of walking trails. Those who know Chappaquiddick covet the departure from in-town living. Just a few miles from the Chappy Ferry, one can access all that Edgartown has to offer.

Listed by Point B Realty LLC

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 Caleb Pond Road, Edgartown, MA

Price$5,895,000

Est. Mortgage: $/month

MLS Number 32881

  • Residential
  • Square Feet 5310
  • Bedrooms 4
  • Bathroom 4
  • Acreage 3

Edgartown Harbor- A remarkable location offering sandy shoreline and a deep water dock. The expansive four bedroom home, superbly designed to afford views from nearly every room, exudes elegance. Privately situated, yet within close proximity to the Village, even closer by water, this truly is the best of both worlds.

Listed by Sandpiper Realty

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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23 North Neck Road, Edgartown, MA

Price$2,950,000

Est. Mortgage: $/month

MLS Number 27357

  • Residential
  • Square Feet 4776
  • Bedrooms 5
  • Bathroom 4
  • Acreage 5.7

Waterfront perfection on Chappaquiddick's coveted north shore. Set high on a bluff with stunning views of Edgartown, the outer harbor, Nantucket sound and Cape Pogue, this beautiful property features 300' of private sandy beach and 5.7 acres. The contemporary style five bedroom home is bright and airy, with floor to ceiling windows framing the outstanding water views. The central living room features a massive stone fireplace and soaring ceilings, and is ideal for entertaining with easy access to the home's expansive decking. The thoughtful layout includes an exceptionally large master suite with private bath, and two additional bedroom wings - one with three bedrooms, two bathrooms and a play room and the other a large bedroom suite with private bath, sitting area, and view of the Sound. Offered for sale for the first time in over 40 years, this property is truly a outstanding offering in one of Martha's Vineyard's most sought after locations.

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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15 Maqua Way, Edgartown, MA

Price$2,999,000

Est. Mortgage: $/month

MLS Number 29277

  • Residential
  • Square Feet 2920
  • Bedrooms 7
  • Bathroom 3
  • Acreage 5.23

Enjoy private beachfront and stunning water views from this antique home with 7 bedrooms spread over 3000 square feet. The home is in immaculate condition and lives like a house more modern than its 300-year-old pedigree would suggest, with lots of privacy as well as expansive common space. This is the perfect home for a large extended family or those who like to entertain lots of guests. Above all, though, this is the ultimate Chappy vacation escape, perfectly located for you to enjoy the natural playground of sun, sand, and sea in your backyard, with extensive opportunities for fishing, clamming, swimming, boating, and watersports of all kinds. Note: Seller will discount property by $400,000 if buyer wishes to build a new home on the lot and agrees to let seller salvage the house. View a drone video of the property by pasting this URL into your browser: https://vimeo.com/174675397

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 North Neck Road, Edgartown, MA

Price$5,500,000

Est. Mortgage: $/month

MLS Number 26519

  • Residential
  • Square Feet 2500
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.85

This very special North Neck Road beachfront property offers nearly 6-acres of land. The four-bedroom / four-bath house is situated to take advantage of the expansive and spectacular views of the Edgartown Light House and the harbor front. The lot is surrounded by mature vegetation to the sides and rear while the interior offers rolling pastures, sloping to water's edge. A walking trail accesses over 200 feet of beach, a small beach house and a private pier. There are permit ready plans approved for a spectacular 8,500 Sq. Ft. main residence and carriage house. Please inquire to learn more on this very special opportunity.

Listed by Landvest MV

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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