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Chappaquiddick Luxury Real Estate

Contact Sandpiper Realty to learn more about one of the Chappaquiddick luxury real estate listings below.  Register with our site to stay up to date on your favorite listings.  You might also like to browse Aquinnah luxury homes or Chappaquiddick luxury homes.

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43 & 44 Caleb Pond Road Marthas Vineyard MA

Edgartown MA 43 & 44 Caleb Pond Road, Chappy

Price: $8,550,000

Est. Mortgage: $/month

MLS Number 26507

  • Residential
  • Village Edgartown
  • Square Feet 5310
  • Bathroom 4
  • Bedrooms 4

An unsurpassed compound with two exquisite sites. The first is a stunning location with more than 300' of sandy frontage on Edgartown Harbor. The deep water dock is 4' wide dock, affording more than 8' depth with two T's and several tie-offs; a harbor mooring is also available. The house was superbly designed to afford views from nearly every room, and constructed with the finest quality materials of the time making it most competitive with today's new construction. The landscaping is simple, focusing on the views overlooking the Harbor, which are incredible. The adjacent site offers frontage on and views of Calebs Pond with quiet water for kayaking and small boating. The guest house is located on this parcel and offers more casual, relaxed living than the main house, as well as a tennis court. All is privately situated at the end of the road yet within close proximity to the village.

Listed by Sandpiper Realty, Inc.

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

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1 North Neck Road Marthas Vineyard MA

Edgartown MA 1 North Neck Road, Chappy

Price: $7,900,000

Est. Mortgage: $/month

MLS Number 26672

  • Residential
  • Village Edgartown
  • Square Feet 3500
  • Bathroom 5
  • Bedrooms 6

Splendid isolation. This landmark 5.2 acre property on the tip of John Oliver Point is akin to living on your own private island with a long stretch of white-sand beach. The stunning architect-designed post & beam house enjoys 360-degree water views so you can enjoy sunrise and sunset from the same seat. These are among the biggest and best water views from any home on Martha's Vineyard. You can see the twinkling lights of the mainland and ships far out at sea, lighthouses from Cape Cod, Nantucket, Oak Bluffs, Cape Poge, and Edgartown. Watch sailboats racing off Edgartown and yachts making their way from the Cape to Nantucket. Light and space are the defining characteristics, with soaring ceilings and large custom windows that take full advantage of the massive water views. A dramatic freestanding stone fireplace is the centerpiece of the great room, running upward through the exposed ceiling. The large master bedroom and bath enjoys a commanding setting, and each of the guest bedrooms has its own ensuite bathroom as well as its own sweeping waterviews. This house is also built for year-round living, and some say the setting here is even more dramatic in the off-season. The house has been featured in "Boston Common" magazine and also "Vineyard Home & Garden." The pristine 2-bedroom guest house cottage - romantic and quaint - lets you step back in time, and it also has huge waterviews from the house and deck. Privacy is assured but it is a mere 5 minute drive to the Chappy ferry - or you can take your Whaler over to Edgartown for dinner. The mooring has a 7-ft draft at low tide and the outhaul just off the sandy beach provides quick and convenient access. The fishing and clamming on this site are among the best on the Eastern seaboard. There are several watercraft that come included with the purchase price and the house is available fully furnished with oriental rugs and beautiful Swedish antiques. This is the setting for families to enjoy unforgettable vacations or year-round living in their own piece of paradise.

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

72 Chappaquiddick Avenue Marthas Vineyard MA

Edgartown MA 72 Chappaquiddick Avenue, Chappy

Price: $6,500,000

Est. Mortgage: $/month

MLS Number 27614

  • Residential
  • Village Edgartown
  • Square Feet 7595
  • Bathroom 11
  • Bedrooms 15

An unprecedented Family Estate offering on Sampson's Hill, the highest point on Chappaquiddick. Three adjacent lots including three homes, two heated pools, for hot tubs,tennis, volleyball, basketball and established gardens. Introducing "The Captain's House"- At home by the sea. Winding the way to the highest point on Martha's Vineyard one expects the commanding views offered by this home. Set along a quiet country road within minutes of downtown Edgartown, The Captain's house leaves very little to want. Above the treetops, the sweeping views to Nantucket Sound spread outward from the spacious and open living area. Gather around the large kitchen island and savor local fare picked from the nearby Slip Away Farm. Soak in the sunrise or toast the end to a perfect day on the expansive, east-facing deck. The Har-tru tennis court in Australian blue, basketball court, a sand volleyball court, heated pool, 8- person hot tub (the same as in the White House), enormous, lower level screened porch, an air hockey table and ping pong table round out the offering. The plentiful sleeping areas each with access to the screened porch offer room to rest, breathe and relax for all. Surrounded by conservation land, all trails lead to adventure and the pristine beaches lining Chappy's shore. Gather your family and friends and while away the hours of the day on your expansive 7.5 acre estate, head to a pristine Chappy beach or bike into town for culinary delights or premier Island shopping. The day is yours. Your home awaits. **Seller has current permit, cleared lot and available plans for 2 bedroom Guest house *** Solid rental history. Ask for details. See additional homes below.

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

44 Caleb Pond Road Marthas Vineyard MA

Edgartown MA 44 Caleb Pond Road, Chappy

Price: $6,500,000

Est. Mortgage: $/month

MLS Number 24979

  • Residential
  • Village Edgartown
  • Square Feet 5310
  • Bathroom 4
  • Bedrooms 4

A stunning location with more than 300' of sandy frontage on Edgartown Harbor. The deep water dock is 4' wide dock, affording more than 8' depth with two T's and several tie-offs; a harbor mooring is also available. The house was superbly designed to afford views from nearly every room, and constructed with the finest quality materials of the time making it most competitive with today's new construction. The landscaping is simple, focusing on the views overlooking the Harbor, which are incredible. All privately situated at the end of the road yet within close proximity to the village.

Listed by Sandpiper Realty, Inc.

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

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

10 Armstrong Lane Marthas Vineyard MA

Edgartown MA 10 Armstrong Lane, Chappy

Price: $6,350,000

Est. Mortgage: $/month

MLS Number 26371

  • Residential
  • Village Edgartown
  • Square Feet 3249
  • Bathroom 4
  • Bedrooms 5

The property's bluff top location offers panoramic views of Edgartown, Edgartown Harbor and Katama Bay. You can sit on the wraparound deck to watch boats cruising the harbor as well as enjoy absolutely spectacular sunsets. The SW orientation of the house delivers a constant cooling breeze. The main residence includes 4-bedrooms / 4-baths, a large kitchen/family/living room, a separate dining room, a TV room/den and two covered porches. The deep lot has ample room for a pool and other recreational uses and there is a detached two-car garage with one-bedroom / one-bath above. Steps lead down the bluff from the main house to a harbor side lower deck and boathouse, a deep-water dock and sandy shoreline. It's an easy 1/2-mile walk to the Chappy Ferry or a 5-minute stroll to the Chappy Beach Club or your own private beach on the outer harbor. This property offers all of the convenience of Edgartown without the congestion and should be a must see for anyone wanting an Edgartown Harbor waterfront location and dock!

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

24 Caleb Pond Road Marthas Vineyard MA

Edgartown MA 24 Caleb Pond Road, Chappy

Price: $3,900,000

Est. Mortgage: $/month

MLS Number 27520

  • Residential
  • Village Edgartown
  • Square Feet 1600
  • Bathroom 3
  • Bedrooms 2

SOMETHING SPECIAL HARBORFRONT, WATERFRONT, BOAT HOUSE, DEEP WATER DOCK, PRIVATE BEACH ACCESS and an Attractive asking price. Overlooking the beautiful blue waters of Edgartown Harbor this unique property is truly a special offering. This Chappy residence is a custom designed post and beam home with an embracing blend of rich wood and comfortable spaces. Wood floors, vaulted ceilings and windows just beckon the sensational views inside to every room. First floor central air, a full basement, garage and generator on this picturesque landscaped setting. Currently 2 bedrooms but has ability to be 4 bedrooms. A beautiful yard for entertaining or just relaxing and front views of Caleb Pond. 8/10ths of a mile from the Chappy Ferry - A must see to appreciate:

Listed by Sandpiper Realty, Inc.

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

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

6 and 10 Mead Lane Marthas Vineyard MA

Edgartown MA 6 and 10 Mead Lane, Chappy

Price: $3,450,000

Est. Mortgage: $/month

MLS Number 26450

  • Residential
  • Village Edgartown
  • Square Feet 1960
  • Bathroom 2
  • Bedrooms 3

Open the front door and immediately your eye is carried through the house and out to the magnificent open views of meadow, marsh and glistening waters of the Bay...the site is quite simply breathtaking. Green Pastures is a private, residential area offering 18 acres of open community owned property, exceptional privacy afforded by large individual home sites and shared access to, and use of, Bay side waterfront and dock. The property includes nearly 11 acres of land with two individual house sites, ideal for a family compound. This is a superb offering with many sought after amenities.

Listed by Sandpiper Realty, Inc.

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

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

24 Manaca Hill Road Marthas Vineyard MA

Edgartown MA 24 Manaca Hill Road, Chappy

Price: $3,100,000

Est. Mortgage: $/month

MLS Number 27350

  • Residential
  • Village Edgartown
  • Square Feet 1776
  • Bathroom 3
  • Bedrooms 5

Outer Harbor water views encompassing North Water Street, Edgartown lighthouse and Cape Cod are nothing short of spectacular. Deeded rights to a nearby, private beach are included. This bright and airy 5 bedroom, 3 bath Chappaquiddick property sits high on Manaca Hill and is just a short walk to the Chappy ferry. The main house features an open living plan oriented toward the water, 4 bedrooms, 2 full baths and a family/TV room. Spacious decks and a flagstone patio take full advantage of the beauty and privacy of this unique island setting. A charming guest/honeymoon cottage with a spacious bedroom and bath sits at the rear of the property.

Listed by Sandpiper Realty, Inc.

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

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

8 Caleb Pond Road Marthas Vineyard MA

Edgartown MA 8 Caleb Pond Road, Chappy

Price: $2,875,000

Est. Mortgage: $/month

MLS Number 26906

  • Residential
  • Village Edgartown
  • Square Feet 2385
  • Bathroom 1
  • Bedrooms 6

This 3 acres of land sits high atop Manaca Hill facing north with unobstructed views from North Water Street through the Edgartown Lighthouse to North Neck and Cape Pogue cliffs. The original 6-bedroom house was built in 1910 in its prominent position with a wrap around porch and 2nd floor screened sleeping porch. The unique combination of 2 parcels offers a long and sweeping drive access and the property includes 50% ownership of a beach parcel, which lies across the road. A must see for anyone looking to create a beautiful Chappaquiddick home with spectacular views, all a short walk to the ferry.

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

6 Mead Lane Marthas Vineyard MA

Edgartown MA 6 Mead Lane, Chappy

Price: $1,995,000

Est. Mortgage: $/month

MLS Number 25896

  • Residential
  • Village Edgartown
  • Square Feet 1960
  • Bathroom 2
  • Bedrooms 3

Open the front door and the magnificent open view of meadow, marsh and glistening waters of the Bay welcome you...the site is quite simply breathtaking. Green Pastures is a private, residential area offering 18 acres of open community owned property, exceptional privacy afforded by large individual home sites and shared access to and use of Bay side waterfront and dock. This is a superb offering with many sought after amenities. Additional acreage and privacy is available by combining the adjacent 5 acre site for a total of nearly 11; the combined price would be $3.45.

Listed by Sandpiper Realty, Inc.

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

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

5,15,16 West Cape Poge Avenue Marthas Vineyard MA

Edgartown MA 5,15,16 West Cape Poge Avenue, Chappy

Price: $885,000

Est. Mortgage: $/month

MLS Number 26242

  • Residential
  • Village Edgartown
  • Square Feet 2200
  • Bathroom 3
  • Bedrooms 5

Chappaquiddick ideal location. This contemporary home is just 1.5 miles from the ferry, a half mile to a private beach, overlooks Brine's Pond, close to Slip Away Farm stand and a short walk to the Chappy Community Center and tennis/basketball court. The house is set on over two private acres abutting 40 acres of conservation land and miles of bike trails. The three-story home offers an open living/dinning/kitchen/deck area on the second floor for scenic views. There are 5 bedrooms and 3 baths. The master bedroom and bath occupies the entire third floor, with views of Nantucket Sound from the third floor deck. The sales price includes a share to a private Chappy beach, valued at $60,000 (subject to first right of refusal by beach association). Come and enjoy the wonders of Chappy in this special retreat.

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

5 Pipn Road Marthas Vineyard MA

Edgartown MA 5 Pipn Road, Chappy

Price: $695,000

Est. Mortgage: $/month

MLS Number 26867

  • Residential
  • Village Edgartown
  • Square Feet 1752
  • Bathroom 2
  • Bedrooms 3

A traditional Cape house offering non-traditional and fun spaces... totally renovated with new additions that now provide super living inside and out, including marvelous screened "party porch" with fireplace, hot tub deck and patio, perfect yard for lawn games! All close to beach making it an ideal summer home...

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

29,30 Bay View Avenue/Wasque Avenue Marthas Vineyard MA

Edgartown MA 29,30 Bay View Avenue/Wasque Avenue, Chappy

Price: $665,000

Est. Mortgage: $/month

MLS Number 22531

  • Residential
  • Village Edgartown
  • Square Feet 1530
  • Bathroom 2
  • Bedrooms 3

Location, Location, Location...If you live for Fishing, Beach and Peace and Quiet...Welcome to one of the best kept secrets on Martha's Vineyard. Chappaquiddick ! This very comfortable house feels like "HOME" the minute you step in the door, according to the many return renters. Walking distance to both Katama Bay for kayaking or swimming with young children and Wasque (South) Beach for all the surf, sand, sun and fishing you could ask for. This house has very comfortable furnishings without a lot of upkeep. Neat ,Clean, and Simple the way it should be so you can spend your vacation enjoying all the beauty the Vineyard has to offer. Some of the renovations include, All New Shingles, Newly painted interior and exterior (trim), New sliding glass door, New Well, New dishwasher, counter tops newly painted cabinets with brand new carpet throughout. The basement has been repainted, brand new outdoor shower and exterior shingles complete all the work The attic is an empty slate just waiting for dormers on both sides to reveal the original water views towards South Beach for an amazing family or studio room!....Don't count out Chappy until you've seen it . The secret behind "Chappy" that people don't know is that you don't have to spend hours driving around Edgartown looking for parking .. just park at the point and walk on the little 3 car ferry to get you right into town for movies, restaurants, library, shopping and a vibrant night life. Or hop on the bus and go to Oak Bluffs for the Flying Horses or a different night out on the town. Once you've lived here you'll never want to go anywhere else. It's a piece of HEAVEN just waiting for the right person(s) to appreciate it! Lot size includes lot 29 and 30.

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

307 Chappaquiddick Road Marthas Vineyard MA

Edgartown MA 307 Chappaquiddick Road, Chappy

Price: $499,000

Est. Mortgage: $/month

MLS Number 24465

  • Residential
  • Village Edgartown
  • Square Feet 1140
  • Bathroom 1
  • Bedrooms 3

What Chappy is all about; A vintage 1930 farm house still intact, a detached guest suite with wood burning fireplace added in 2000, two additional buildings that can be used as workshops, studios or storage on a well cleared .92 acre parcel of land. The aged wood in the main house enhances the rustic interior. Located on the Chappaquiddick Road in the middle of the Island, it epitomizes Chappy living. Being sold turnkey with furnishings.

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

17 Bay View Avenue Marthas Vineyard MA

Edgartown MA 17 Bay View Avenue, Chappy

Price: $485,000

Est. Mortgage: $/month

MLS Number 25991

  • Residential
  • Village Edgartown
  • Square Feet 1156
  • Bathroom 1
  • Bedrooms 1

Wasque - A sweet summer cottage with a contemporary flair, just minutes from Katama Bay and South Beach…pine floors, fireplace and screened porch…fully furnished and ready for summer to begin!

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.80% last updated on 2014-12-18

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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