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Chappaquiddick Luxury Real Estate

Scroll down to find current luxury real estate for sale in Martha's Vineyard's Chappaquiddick village. 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.

15 East Meadow Avenue, Edgartown, MA

MLS Number 27324

  • Residential
  • Village Edgartown
  • Square Feet 1518
  • Bathroom 2
  • Bedrooms 3

Newly renovated contemporary home with many new upgrades !The property is enhanced with two separate outdoor sitting areas and large garden shed. Abutting conservation, this property lives large! Also included in purchase is 1 Lake Avenue, which affords flexibility and privacy with any potential expansion possibilities.

Listed by Sandpiper Realty, Inc.

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

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

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

6 Berry Avenue, Edgartown, MA

Edgartown MA6 Berry Avenue, Chappy

Price$550,000

Est. Mortgage: $/month

MLS Number 27553

  • Residential
  • Village Edgartown
  • Square Feet 2083
  • Bathroom 2
  • Bedrooms 4

Affectionately referred to as the "Pole House" this custom home is the perfect Chappaquiddick retreat. Quietly tucked away and abutting Pimpney Mouse Farm, the unique layout, offers all the space and amenities one would expect in their Vineyard home. The open living spaces, which spill onto on an exterior deck, is the perfect spot for gathering with family and friends! Rounded out with four generous bedrooms this house must be seen to be appreciated!

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: 3.87% last updated on 2015-06-04

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

17 Narragansett Avenue, Edgartown, MA

MLS Number 28893

  • Residential
  • Village Edgartown
  • Square Feet 3662
  • Bathroom 5
  • Bedrooms 6

Chappaquiddick Compound - House and guest house located within close proximity to the ferry, abutting conservation and offering distant outer harbor views! The reverse style four bedroom main house lives large complete with multiple interior and exterior living areas and open floor plan. The privacy and separation offered by the two bedroom guest cottage provides the perfect space for friends and family or even a separate rental opportunity. A must see!

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: 3.87% last updated on 2015-06-04

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

35B North Neck Road, Edgartown, MA

MLS Number 28940

  • Residential
  • Village Edgartown
  • Square Feet 3585
  • Bathroom 3
  • Bedrooms 5

This grand "summer camp" is like no other property on Chappaquiddick - Martha's Vineyard. It combines a stunning waterfront location with sweeping views of Edgartown Harbor, Nantucket Sound over to The Cape and Cape Pogue. The original 3 bedroom, rustic barn-style vintage home was built in 1915 and features a grand, water-facing wraparound porch, and a dramatic two-and-a half story Living Room with beach stone fireplace. Approximately 3.1 acres of grounds lead down to the water's edge, with over 300 ft of frontage and a private sandy beach. Completing this offering is an existing 2 bedroom cottage, deep water dock, mooring and breathtaking sunsets all abutting the 9-hole, Royal and Ancient Chappaquiddick Links. Continue the 100+ year tradition of this quintessential camp or choose to create your own dream allowing a 7 bedroom compound.

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: 3.87% last updated on 2015-06-04

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

9 Sampson Avenue, Edgartown, MA

MLS Number 28861

  • Residential
  • Village Edgartown
  • Square Feet 2055
  • Bathroom 2
  • Bedrooms 3

This well maintained year round home is located in a quiet central location on Chappy. Current owner renovated and updated the property with two additions including a new dining area with breakfast bar, hardwood floors ceiling fan and windows that brings in the natural light. On the opposite side of the house, a second addition is the family room with an efficient pellet stove, hardwood floors, ceiling fan and laundry access. Slider leads to expansive deck area with covered barbeque grill and screened in gazebo for outdoor dining. Second floor offers Master bedroom with walk-in closet and ceiling fan. Two additional bedrooms and a shared full bath. Quality carpeting throughout second floor including the stairway. The full dry basement is well kept and maintained. A nicely landscaped yard with plenty of space for outdoor activities and games. A standout feature is the brand new two car garage with ample storage above. Don't miss this great investment.

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: 3.87% last updated on 2015-06-04

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

44 Caleb Pond Road, Edgartown, MA

Edgartown MA44 Caleb Pond Road, Chappy

Price$6,500,000

Est. Mortgage: $/month

MLS Number 28626

  • 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: 3.87% last updated on 2015-06-04

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

15 Maqua Way, Edgartown, MA

Edgartown MA15 Maqua Way, Chappy

Price$3,950,000

Est. Mortgage: $/month

MLS Number 28623

  • Residential
  • Village Edgartown
  • Square Feet 2920
  • Bathroom 3
  • Bedrooms 6

Outstanding and truly unrivaled setting....on a gentle rise above Katama Bay with vistas across a gracious meadow, out to the ever changing scenery of a salt pond and across to the sparkling open waters of the Bay and even beyond to the Atlantic Ocean....this is truly an unparalleled site with 100' of private beach front....and it is graced by a 1700's farmhouse with a 1920's wing and a 1970's wing...all of which has been renovated over the years and meticulously maintained by three generations of the current owners. The (5+) acre lot allows for nearly unlimited expansion as well as guest house, garage, whatever a new owner needs/desires. View easement and no build zones protect the magnificent view!

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: 3.87% last updated on 2015-06-04

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

6 Mead Lane, Edgartown, MA

Edgartown MA6 Mead Lane, Chappy

Price$1,895,000

Est. Mortgage: $/month

MLS Number 28601

  • 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. If you are seeking additional privacy or perhaps further expansion possibilities, the adjacent five acres, offering the same stunning views, is also available for purchase. Don't miss the opportunity to own this truly 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: 3.87% last updated on 2015-06-04

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

10 Calebs Pond Lane, Edgartown, MA

MLS Number 23788

  • Residential
  • Village Edgartown
  • Square Feet 2500
  • Bathroom 3
  • Bedrooms 5

This wonderful family home with glorious water views from the top floor has lots of space for family and guests. This quintessential beach house has been the fun focal point of a large family and is in an ideal location to take advantage of the private beach association and pond access. The water views, large decks and porch create a great atmosphere for people to spread out and with the easy walk to the beach and ponds, it is a destination home that will bring adventure and joy for years to come. Heavily renovated in 2005, the improvements were geared towards making this home very low maintenance. Additionally, this house is unusually outfitted with an elevator to provide assistance and comfort for people of all ages. Priced well below it's assessment, this home is an excellent value for the discerning buyer.

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: 3.87% last updated on 2015-06-04

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

20 Litchfield Road, Edgartown, MA

Edgartown MA20 Litchfield Road, Chappy

Price$2,490,000

Est. Mortgage: $/month

MLS Number 27567

  • Residential
  • Village Edgartown
  • Square Feet 1635
  • Bathroom 2
  • Bedrooms 3

Simply Stunning. This perfectly appointed Chappaquiddick compound, perched on the shores of Caleb's Pond, is a true rarity. A 3 bedroom main house, capturing views from almost every room and a substantial 3 bedroom guest house is the perfect complement to this idyllic escape. Enjoy shellfishing and fishing in the tranquil waters or a simple kayak paddle around the bend to explore the comings and goings on Edgartown Harbor. The property, which has a strong rental history, is ready to go for the 2015 season! Located within close proximity to both ferry and beach this property can't be missed!

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: 3.87% last updated on 2015-06-04

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

4 Calebs Common Circle, Edgartown, MA

MLS Number 27819

  • Residential
  • Village Edgartown
  • Square Feet 2967
  • Bathroom 4
  • Bedrooms 6

A unique Chappy Compound - Two beautifully maintained buildings in a great location. Wonderful 3 bedroom main house, screened porch, on a pleasantly landscaped parcel of land along with a 1,260 sf 3 bedroom 2 bathroom guest house a private distance from the main house. A guest house of this size could never be built again. The compound provides excellent space for extended family or great rental income while you use one the buildings or choose to rent both. Located a short distance from the Chappy ferry. An exceptional property in an exceptional location.

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: 3.87% last updated on 2015-06-04

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

24 Manaca Hill Road, Edgartown, MA

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: 3.87% last updated on 2015-06-04

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

8 Caleb Pond Road, Edgartown, MA

Edgartown MA8 Caleb Pond Road, Chappy

Price$3,250,000

Est. Mortgage: $/month

MLS Number 26906

  • Residential
  • Village Edgartown
  • Square Feet 2385
  • Bathroom 2
  • Bedrooms 6

Prominently situated atop Manaca Hill, lies this 6-bedroom home on 3 acres of land with spectacular unobstructed views of the entrance to Edgartown Harbor. The 180-degree panoramic views stretch from North Water Street and sweep through Edgartown Lighthouse and across to the Cape Pogue cliffs. The original home built in 1910 is in good condition and a new 6-bedroom septic system was installed. A long private driveway winds through beautiful fields and the property includes ownership of a beach parcel within 100 yards of the front door and a mooring. A must see for anyone considering a very special Chappaquiddick offering.

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: 3.87% last updated on 2015-06-04

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

1 North Neck Road, Edgartown, MA

Edgartown MA1 North Neck Road, Chappy

Price$8,500,000

Est. Mortgage: $/month

MLS Number 26672

  • Residential
  • Village Edgartown
  • Square Feet 3500
  • Bathroom 10
  • Bedrooms 12

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: 3.87% last updated on 2015-06-04

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

17 Bay View Avenue, Edgartown, MA

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: 3.87% last updated on 2015-06-04

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

77 North Neck Road, Edgartown, MA

Edgartown MA77 North Neck Road, Chappy

Price$4,850,000

Est. Mortgage: $/month

MLS Number 26519

  • Residential
  • Village Edgartown
  • Square Feet 3748
  • Bathroom 4
  • Bedrooms 4

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 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: 3.87% last updated on 2015-06-04

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, Edgartown, MA

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: 3.87% last updated on 2015-06-04

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, Edgartown, MA

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. Current assessment without renovations.

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: 3.87% last updated on 2015-06-04

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