Chappaquiddick, MA homes for sale & real estate

Chappaquiddick, MA Homes for Sale

Welcome to 68 Winter Street, a highly sought-after community of six, one bedroom condos located in Edgartown Village. Enjoy seasonal or year-round living at this sophisticated, garden level pied-a-terre. Elegant and well-appointed throughout, this stylish condo features open living with a nicely equipped kitchen, soaring ceilings, crown modeling, over-sized windows, and wood floors. Spacious bedroom has sliders out to a private back porch. The gracious bathroom has a tiled, glass-enclosed shower, stackable laundry, and storage. These units come with a deeded parking space, a highly sought after amenity in the downtown area. A front porch adorned with flower boxes and rockers welcomes you to

Chappaquiddick, MA Homes for Sale

This beautifully renovated Katama retreat blends refined design, luxury amenities, and flexible living. The main house offers three bedrooms, including a peaceful primary suite with private deck, a second en suite, and a cozy bunkroom. The octagonal living room, skylit dining room with gas fireplace, and chef’s kitchen with quartz counters and high-end appliances are perfect for entertaining. Upstairs, a state-of-the-art theater features a 4K projector, 110" screen, and surround sound—also ideal as a family room or game space. A home office nook and powder room complete the level. The detached guest retreat includes a bedroom, sitting area, en suite bath, and its own projec

Chappaquiddick, MA Homes for Sale

Mattakesett units continue to be in high demand and #B2 is the only unit currently on the market! Take advantage of all the Winnetu Resort amenities and a robust rental program which covers your fees and provides great revenue! This unit offers abundant views of the farm fields out front, open common space next to and behind, and is a short walk or bike to South Beach! There are 3 bedrooms, 2.5 baths and the bonus of a finished loft. With over 1,400 sq ft of living space this is one of the larger units. The outdoor rear deck offers additional space for dining or relaxing after a day at the beach. These units are seasonal, closed down in mid-November and re-opened starting in mid-April. This

Chappaquiddick, MA Homes for Sale

Move-In Ready – CONSTRUCTION COMPLETE - This stunning 8-bedroom, 7.5-bath generational home, completed in 2025, is fully furnished and move-in ready. The property features a 6-bedroom, 5.5-bath main residence, a 1-bedroom, 1-bath guest house with its own kitchen, and a 2-car carriage house with 1-bedroom living quarters. Designed for relaxation and entertainment, the private backyard oasis includes a 16' x 32' saltwater pool, spa, and cabana. Offered fully furnished with Ethan Allen selections, this property ensures effortless enjoyment. Window treatments for the main house are included but not pictured. Days on market reflect the construction period, and certificates of occupancy hav

Chappaquiddick, MA Homes for Sale

Coveted Down Harbor! This 3-bedroom 2-bath home sits in the Down Harbor association in a prime Katama location. This charming home is an entertainer's delight with a spacious yard, a large deck, an outdoor kitchen, pool, and recently built pool house with 2 outdoor showers, 1/2 bath and a storage shed. This home features vaulted ceilings, exposed beams, and a bright kitchen with a breakfast bar open to the dining area. The living room is bathed in natural light with 2 oversized sliding doors to the deck overlooking the pool and outdoor kitchen. A bonus loft offers additional living space. The current homeowners have gone through the approval process for an attached garage with room above, f

Chappaquiddick, MA Homes for Sale

This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown's finest restaurants and shops, this stunning property has been completely renovated by SternMcCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon entering, you'll be greeted by a sophisticated interior with open-plan living spaces designed for easy entertaining. The mainlevel features sleek modern furnishings, flowing from the kitchen and dining area through French doors to a beautifully landscapedoutdoor patio, ideal for al fresco dining and relaxati