Chappaquiddick, MA homes for sale & real estate

7 homes

Sort:

Recommended

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
You truly can have it all—just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village, yet set along one of the most spectacular stretches of beach, with a 190’ private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartown Lighthouse. A gentle slope leads to the sandy shore, where days unfold along the pristine waters of the harbor. Inside, casual elegance defines the home, with a seamless blend of gracious formal spaces and inviting areas for relaxed gatherings. An enclosed porch opens onto a spacious deck overlooking the harbor, creating the perfect setting to take in picture-worthy sunsets, the beloved

$12,250,000

7 beds4 baths4,855 sq ft

139 Chappaquiddick Rd, Edgartown, MA 02539

Clay tennis court • Private dock • Sweeping views

FLOOR PLAN

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
Set amongst beautifully landscaped grounds and vibrant gardens, this inviting Chappaquiddick retreat offers a wonderful sense of privacy and tranquility. Stunning hydrangeas frame the property, also complemented by mature trees, colorful blooms, and established gardens, creating a beautiful setting throughout the seasons. Multiple outdoor spaces invite relaxing and entertaining, with a heated saltwater pool, completed in 2025, serving as the centerpiece. Inside, warm and inviting living spaces are filled with natural light, while shiplap details and a relaxed coastal aesthetic give the home a classic island feel. Vaulted ceilings and thoughtful attention to detail enhance the home’s c

$4,725,000

3 beds4 baths2,969 sq ft

149 Litchfield Rd, Edgartown, MA 02539

Landscaped grounds • Detached studio • Vibrant gardens

FLOOR PLAN

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
CHAPPAQUIDDICK – Opportunity awaits on this conforming 3-acre parcel, featuring a year-round home with a 5-bedroom septic system, offering exceptional potential for future expansion, including a guest house. Privately tucked away off the main road, yet conveniently located just minutes from the Chappaquiddick Community Center, the Ferry, Wasque Beach, and Quammox Preserve with its public access to Katama Bay, this property is perfectly positioned to enjoy the best of Chappy. Abutting conservation land, with the Cross Chappy Trail and Pocha Pond Reservation just outside your door, it offers direct access to some of the island's most treasured natural landscapes. The home's efficient fl

$1,500,000

3 beds2 baths1,717 sq ft

8 Pip'n Cir, Edgartown, MA 02539

Direct access • 3 acre parcel • Guest house

VIDEO TOUR

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
Life on Chappaquiddick has a rhythm all its own — and this exceptional compound is designed to savor every moment of it. Set on three park-like acres of meadows and woodland, two freshly painted log cabin-style homes offer a private world apart. The three-bedroom main house is open and generous, with living spaces that flow seamlessly from inside to out. The two-bedroom guest house is its own considered retreat, complete with covered porch, back deck, and outdoor shower. An oversized garage with loft provides additional space to gather and unwind. A circular drive and pea stone pathways connect the buildings across beautifully layered grounds. Adirondack chairs ring a custom firepit f

$2,195,000

5 beds3.5 baths2,628 sq ft

7 Pip'n Cir, Edgartown, MA 02539

Covered porch • Circular drive • Back deck

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shel

$2,399,000

4 beds2.5 baths1,910 sq ft

76 Washque Ave, Edgartown, MA 02539

Scenic trails • Wasque preserve • Abundant wildlife

Property at 23 Calebs Common Ln, Edgartown, MA 02539

$550,000

Land1.02 acres (lot)

23 Calebs Common Ln, Edgartown, MA 02539

Property at 0 Pocha Rd Ext, Edgartown, MA 02539

$3,495,000

Land11.39 acres (lot)

0 Pocha Rd Ext, Edgartown, MA 02539

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 62 at 131 N. Water Street is a beautifully appointed 865± sq. ft. , second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cook-top stove, microwave, and refrigerator/freezer. An outdoor shower adds to everyday convenience. Owners enjoy concierge servic

$2,425,000

2 beds2 baths895 sq ft

131 North Water St -rowley Cottage #62, Edgartown, MA 02539

Fitness center • Concierge services • Outdoor shower

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 22 at 131 N. Water Street is a beautifully appointed 960± sq. ft. , second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. An in-unit washer/dryer, outdoor shower, and elevator access add everyday convenience. Owners

$2,595,000

2 beds2 baths960 sq ft

131 North Water St-collins Cottage #22, Edgartown, MA 02539

Concierge services • Outdoor shower • Turnkey residence

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 94 at 131 N. Water Street is a beautifully appointed 730± sq. ft. , second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool

$1,975,000

2 beds2 baths730 sq ft

131 North Water St-huxford Cottage #94, Edgartown, MA 02539

Fitness center • Concierge services • Turnkey residence

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 96 at 131 N. Water Street is a beautifully appointed 1061± sq. ft. , second and third-floor condominium featuring 3 beds and 3 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cooktop, microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated

$2,875,000

3 beds3 baths1,061 sq ft

131 North Water St-huxford Cottage #96, Edgartown, MA 02539

Fitness center • Concierge services • Turnkey residence

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
Set on an exceptional . 65 -acre parcel, this rare offering combines privacy, space, and an unbeatable location just moments from town and the water. The expansive lot offers a unique opportunity to expand and create a custom estate tailored to your vision. Surrounded by mature landscaping and generous outdoor space, the property offers a peaceful retreat while remaining conveniently close to shops, dining, beaches, and waterfront activities. Whether you're seeking a year-round residence, a seasonal escape, or an investment with long-term upside, this property presents endless possibilities in one of the area's most desirable settings.

$3,495,000

2 beds1.5 baths1,388 sq ft

48 Plantingfield Way, Edgartown, MA 02539

Ample outdoor space • 0.65 acre lot • 4 parking spots

FLOOR PLAN

ABOUT THIS HOME
Chappaquiddick, MA Homes for Sale
Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an unforgettable first impression. Inside, the home features a bright and airy open-concept layout that seamlessly blends the living, dining, and kitchen areas, all enhanced by the dramatic “big sky, big water” setting. Spanning three levels, the residence offers 4 bedrooms, 3 full bath

$6,995,000

4 beds3 baths2,624 sq ft

103 Edgartown Bay Rd, Edgartown, MA 02539

Expansive front lawn • Private sandy beach • Wooden boardwalk

Property at 56 North Summer St, Edgartown, MA 02539, 10 beds, 12.5 baths

$21,500,000

10 beds12.5 baths7,598 sq ft

56 North Summer St, Edgartown, MA 02539

Property at 9 Marthas Way, Edgartown, MA 02539, 4 beds, 3.5 baths

$4,600,000

4 beds3.5 baths3,715 sq ft

9 Marthas Way, Edgartown, MA 02539

Property at 24 Katama Bay View Rd, Edgartown, MA 02539, 4 beds, 5 baths

$7,850,000

4 beds5 baths5,884 sq ft

24 Katama Bay View Rd, Edgartown, MA 02539

Property at 114 North Water St, Edgartown, MA 02539, 8 beds, 7.5 baths

$16,900,000

8 beds7.5 baths6,041 sq ft

114 North Water St, Edgartown, MA 02539

Average home prices near Chappaquiddick, MA

Cities

Neighborhoods

Martha's Vineyard homes for sale
$2,399,000
Edgartown Village Historic District homes for sale
$2,875,000

Chappaquiddick, MA real estate trends

$1.6M

Sale price

$815

Sale $/sq ft

Under list price

1.5%

Days on market

Down payment

—

Total homes sold

See more Chappaquiddick, MA market insights

More to explore in Chappaquiddick, MA

How to buy a house in Chappaquiddick, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Massachusetts

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.