Chappy

Chappaquiddick, or Chappy,  is a small island just a 3-minute ferry ride across the Edgartown harbor. Often times Chappy is connected by a barrier beach to Edgartown. There are around 100 year-round residents in Chappy and many more seasonal homeowners. There are more than 800 acres of public beach and conservation land in Chappaquiddick, allowing for many walking trails, and beaches to explore. There is no commercial zoning in Chappaquiddick. 

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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
  • Half Baths 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

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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
  • Half Baths 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

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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
  • Half Baths 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

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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

{$office->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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
  • Half Baths 1

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

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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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37 & 39 Jeremiah Road, Edgartown, MA

Price$4,750,000

Est. Mortgage: $/month

MLS Number 33855

  • Land
  • Village Chappy
  • Acreage 15.48

Now is the time to build a multigenerational estate on Martha's Vineyard! Start with one house as a base and add on as you go. Another family member house could be added later with a pool, garages, a barn, tennis court, guest house, boat house and more, let's call this Plan A. If circumstances change, as they sometimes do, keep the Main House and sell off the adjacent lot, this will likely increase in value as all land has on MV, call this Pan B. Plan C might be to build a 6 bedroom house with a pool on one lot and rent it out for an estimated $25,000 per week for a few years. Keep the other lot or build a Spec house there. Lots of options and opportunities with this rare offering. You will not find this opportunity again for 15+ acres of waterfront property. Easy to show, call now for an appointment. Allow 30-40 minutes for a showing. This property has potential spectacular views from the first and second levels of a house or deck. Final view channels and clearing will be done once lots are purchased per Conservation Committee request. Must be seen to be appreciated.

Listed by Sandpiper Realty

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Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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
  • Village Chappy
  • Square Feet 2486
  • Bedrooms 5
  • Bathroom 2

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

{$office->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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
  • Village Chappy
  • Square Feet 1519
  • Bedrooms 4
  • Bathroom 3

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

{$office->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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
  • Village Chappy
  • Square Feet 2146
  • Bedrooms 4
  • Bathroom 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

{$office->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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
  • Village Chappy
  • Square Feet 3688
  • Bedrooms 5
  • Bathroom 3

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

{$office->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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

26 Caleb Pond Road, Edgartown, MA

Price$3,200,000

Est. Mortgage: $/month

MLS Number 33737

  • Residential
  • Village Chappy
  • Square Feet 1194
  • Bedrooms 3
  • Bathroom 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

{$office->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 2018
* 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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