Imagine a Day in the Life at 26 Caleb's Pond Road. Wake up to the gentle breeze, the sounds of birds, and the sea lapping against the shore line in this waterfront retreat. Then enjoy a cup of coffee on the front deck facing east for the sunrise. There's so much to do - or enjoy doing nothing at all. At one end of the property is some of the best clamming in all of MV. At the other end is your deepwater dock with floating dock for boating, fishing, kayaking, paddle boarding, and more. Want to head into Edgartown for dinner, shopping, or just to enjoy the village buzz? It's a short boat ride over to the town landing, and the Chappy ferry is just a mile away. In the evening, relax on your upper deck overlooking Edgartown Harbor, Katama, and South beach. Enjoy dinner or cocktails with friends as you watch technicolor sunsets. This 3-level home takes full and creative advantage of space sleeping a total of 10 and the nearby bunk house is as charming as can be. The bunkhouse sleeps 2 people comfortably and is perfect for overflow guests or for kids who want sleepover adventures. The casual beach decor is exemplified by the shell fireplace. This is a magical destination home with a front row seat to one of the most scenic waterscapes on the Eastern seaboard.

View Property Details >

Designed with entertaining and island living in mind, this completely renovated four-bedroom home is located right near South Beach and the Katama bike path. This property features a large pool, bluestone patios, expansive decks, and extensive landscaping. The detail-orientated renovation maximizes each space and offers modern coastal finishes throughout. The main floor features an open floor plan with a chef’s dream kitchen, dining room, living room with gas fireplace, half bath, and large sunroom. Heading upstairs to the third floor, one will find an office overlooking lush landscaping. The third floor features a luxurious bathroom, a balcony, and a large bedroom. Enjoy peaks of South Beach and beautiful sunsets from the balcony over Herring Creek Farm. The lower level features three oversized bedrooms with lots of natural light and views of the impeccable grounds. There is a full bathroom, laundry, and extra storage space on this floor. Custom quality craftsmanship and unique one-of-a-kind details can be found throughout the home. Between the superior indoor and outdoor living spaces, impressive rental history ($208K in 2020), and the prime location, this is an awesome investment property and / or family retreat. Offered fully furnished!

View Property Details >

This special Katama property offers a 3-bedroom, 2,341 sq. ft. main residence, a detached 2-car garage with 660 sq ft of finished living space above, and a swimming pool. These improvements are on a 5.2-acre corner lot at the entrance to Turkeyland Cove and off Slough Cove Road. The house has a spacious and open floor plan with cathedral ceilings, lots of natural light and views across the lawn to a heated 20'x40' swimming pool, all surrounded by mature trees for privacy. You can hear the ocean waves of South Beach in the distance, launch a kayak nearby to explore Edgartown Great Pond, all while being only 3 miles to the center of town. This property is located in an emerging neighborhood and would also lend itself toward creating a substantial family compound. *Guest Houses are not permitted in this zone.

View Property Details >

PRE-CONSTRUCTION OPPORTUNITY - GOING, GOING, GONE - ONLY ONE LOT REMAINS AVAILABLE!! Welcome to Edgartown's newest luxury community, Meshacket Woods, nestled in a lovely woodland setting. EXCELLENT LOCATION - short distance (approximately 1.5 miles) to Edgartown Village and offering easy access to South Beach. Build your brand new dream home designed by premier island architect Chuck Sullivan. Floor plans are included in the price and may be modified by the buyer. ROOM FOR A POOL at an additional cost! Connection to town sewer allows EXPANSION POSSIBILITIES of up to six (6) bedrooms under current Edgartown zoning regulations. Your Vineyard oasis awaits you!

View Property Details >

PRE-CONSTRUCTION: MODERN CHIC FARMHOUSE IN SOUTHRIDGE. Construction plans are now underway for this stylish, modern chic farmhouse -- to built by Shawn Chapps -- in Edgartown's newest luxury enclave, SOUTHRIDGE. Located equidistant to Edgartown Village and South Beach with easy access to the bicycle path and Morning Glory Farm, this is a perfect location to launch your island lifestyle. The open-designed floor plan is anchored around the dramatic Great Room with 12-foot ceilings, a handsome gas fireplace with custom built-ins and and large sliding glass doors that open onto a spacious covered porch and landscaped backyard. The perfectly designed cook's kitchen will feature Viking® stainless appliances, gorgeous stone countertops and a center island/breakfast bar with counter seating. There is a spacious butler's pantry with lots of cabinet storage and a second dishwasher -- plus sliding barn doors to close off any meal prep mess while you entertain in style! Top-notch architectural details and styling abound . . . including gorgeous hardwood floors, shiplap paneling, crown molding, designer-selected tile and more! There are a total of four bedrooms, including a first-floor Owner's Suite featuring vaulted ceilings, an ultra-spacious walk-in closet with built-ins plus a luxurious private bath with double vanity, soaking tub and glass walk-in shower. This stunning home features TWO spacious covered porches with over 600 square feet of combined outdoor living space. The backyard features a bluestone terrace and there is also room to add a pool. This home will include many extras such as two laundry rooms, a second-floor Family/Bonus Room and much more! ***Note: Floor plans and renderings attached. Final designs will be modified slightly. Tours of finished homes by the builder may be arranged by special appointment.

View Property Details >

South Beach Water Views - Located in the heart of Katama, this classic beach house is just what you are looking for in these work-from-home times. Rare to find Five-bedroom, 3 bath home with combined 3 levels of living space. The first floor welcomes you to an open living room and laundry area with 2 bedrooms and shared bath. Sliders lead out to a covered side porch. The second floor is a sun drenched living/kitchen area with lofted ceilings and 2 additional bedrooms with shared bath. There is a wall of windows with access to a large wrap around deck with beautiful South facing water-views. The 3rd floor occupies the master bedroom and bathroom with painting like setting over 186 acres of conservation land out to stunning Atlantic Ocean views. Many recent upgrades and excellent rental history. Hear and smell the ocean air and feel the Katama breezes. Minutes to Right Fork Diner, bike bath and South Beach.

View Property Details >

This traditionally styled home is located 3 properties from The Boulevard and has second and third floor water views. The spacious home is over 4,400 sq ft of creatively-designed living areas with decks on the 2nd floor, a large master suite on the 3rd floor, and additional bedrooms on the ground floor. In addition, a full basement, attached garage and separate 2-story office with full bath and separate entrance, complete the property. Landscaped grounds and plenty of room for a pool, will help a buyer create a special family compound in an improving neighborhood, close to the center of Town.

View Property Details >

PRE-CONSTRUCTION: ELEVATED STYLE IN SOUTHRIDGE. Construction plans are now underway for this stylish, coastal chic farmhouse -- to built by Shawn Chapps -- in Edgartown's newest luxury enclave, SOUTHRIDGE. Located equidistant to Edgartown Village and South Beach with easy access to the bicycle path and Morning Glory Farm, this is a perfect location to launch your island lifestyle. The open-designed floor plan is anchored around the Great Room with 9-foot ceilings, a handsome gas fireplace and a dramatic sunlit dining /breakfast alcove, wrapped in two stories of glass with beautiful views to the backyard living area. The kitchen is a cook's dream with high-end Viking® appliances, stone countertops and a center island with counter seating. Top-notch architectural details and styling abound . . . including gorgeous hardwood floors, rough hewn wood-beamed ceilings, shiplap paneling, crown molding and more! There are a total of four bedrooms, each with en suite bath, including a first-floor Owner's Suite featuring sliding glass doors out to outdoor deck, walk-in closet plus a private bath with double vanity and glass walk-in shower. This property will feature a beautiful landscaped yard with mahogany deck and plenty of room to add a pool. The attached "party barn" with wood-burning fireplace is the ultimate bonus, offering a perfect area for indoor-outdoor living and entertaining during the summer months. Detailed plans and specifications available upon request. ***Note: Photos shown depict interior and exteriors of other homes built by same builder. Tours of finished homes by the builder may be arranged by special appointment.

View Property Details >

LUXURIOUS COTTAGE-STYLE LIVING – WITH ROOM FOR A POOL! Opportunity abounds with this charming cottage-style home in the heart of Edgartown Village. The welcoming porch and French door entry open to a dramatic two-story foyer and open-designed Living/Dining/Kitchen area with gleaming hardwood floors, tasteful accents and a nicely appointed kitchen with classic white cabinets, stone countertops and stainless appliances. French doors open from the Dining area out to a gracious brick terrace and private fenced backyard, ideal for outdoor living and dining. There are a total of FOUR BEDROOMS, each with full bath, including a first-floor Owner’s Suite with full en suite bath and French doors that open out to the large mahogany porch and deck. The partially finished Lower Level includes an additional 540-sf of finished space including the 4th bedroom/bonus room with legal egress, a full bath and a separate laundry/utility room. This wonderful in-town cottage LIVES LARGE with over 2,000-s.f. of living space perfectly designed for indoor-outdoor living. There is established rental history with strong recurring demand – plus potential to boost rental income to $125,000+/year with the addition of a SWIMMING POOL (there is a pool permit already in-hand). MOST OF AUGUST (August 7th and on) is currently available for a buyer to enjoy this summer OR to rent for additional 2021 income. Furnishings and contents are available separately for a turnkey purchase opportunity. This charming home is a perfect in-town residence or investment property - make it yours!

View Property Details >

LIKE NEW Five years young expanded Cape located a short walk into town, convenient to all Village amenities: restaurants, shops, groceries, churches, and harbor. The home features quality construction, a bright open floor plan with cathedral ceilings, hardwood floors, central air, four bedrooms, including a first floor Master suite, a second floor Master suite, and two additional second floor guest bedrooms, three and a half baths, a gourmet kitchen with center island, stainless appliances, and granite counters, living room with gas fireplace, full basement, outside deck and shower, and a nicely landscaped , private yard.

View Property Details >

ROOM FOR A POOL! MOVE-IN-READY CUSTOM CAPE WITH FARMER'S PORCH AND ATTACHED GARAGE. Grandfathered FIVE BEDROOM per Edgartown Wastewater Dept. Three blocks from Edgartown Village. This well-maintained and thoughtfully renovated home is waiting for its next family. With an additional 1100sqft of finished Lower Level space, this home has a great setup for remote learning and/or work-from-home options. A light-filled Lower Level bedroom has walkout access to the private fenced backyard. There are a total of FOUR existing Bedrooms, each with a full bath. This in-town home lives large with over 2,600sqft of living space perfectly designed for indoor-outdoor living. The Chef’s Kitchen has stainless appliances, white cabinets, white quartz counters and a prep island with seating for five (5). The space is flooded with natural light from the French doors leading to the deck which allows for easy indoor/outdoor cooking and entertaining. The formal Dining Room has two sets of interior French doors for private dining options, while the Family Room has a wood burning fireplace to set the mood. At every turn, there is more storage space! The attached Garage has its own Minisplit so it can be heated or cooled as needed and offers additional storage. The expansive Farmer's Porch beckons you to sit and enjoy the peace and quiet of the neighborhood. This sweet home is perfect for year-round or summer living and would also make a wonderful vacation rental property. UPDATES INCLUDE: Two (2) New Tankless Water Heaters; New Minisplit HVAC units throughout; Newer Roof; Remodeled Primary Bedroom, Kitchen & Lower Level; Relocated & Enlarged Outdoor Shower; Remodeled Rear Deck with Quick Disconnect for BBQ Grill & New Electric Awning; New Cedar Shingles & Exterior Trim; Drip Irrigation for hanging plants on the Farmers Porch.

View Property Details >

This conforming lot is located in the exclusive Field Club Association, in the heart of Katama. This neighborhood, of master planned homes, continues to improve in desirability with the recent construction of several significant compounds as well as notable sales. The property is ready to build on, with electric, town water and town sewer in place. An owner can design a main residence, garage, pool and pool house, all as a matter of right subject to the local zoning. The property also includes a coveted Boathouse membership with all usages of the downtown Boathouse facility, use of its boats and the Field Club, with its clubhouse, swimming pools, spa, fitness center, tennis and kids camp. All of these benefits located halfway between downtown and beach, make this a very special opportunity.

View Property Details >