luxury houses with pool for sale Vineyard Haven, United States

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest of its kind on Martha’s Vineyard. Originally built in 1835 and masterfully renovated by renowned architect Patrick Ahearn, the estate seamlessly blends historic character with refined modern luxury. Just moments from Edgartown Harbor and the island’s premier dining and shopping, the property spans two lots and offers an extraordinary compound featuring 10 bedrooms and 14 baths. Designed for both elegant entertaining and comfortable everyday living, the main residence showcases refined architectural details and modern technology. Beautiful oak floors run throughout the home, complemented by sophisticated hardware, premium appliances, and walls tastefully finished with nickel board. A gracious living room with fireplace opens to a patio with retractable screens, creating effortless indoor-outdoor flow. The chef’s kitchen is impeccably appointed with dual dishwashers, a plumbed miele coffee bar, refrigerator drawers, and a wine refrigerator. A custom brass and glass bar is equipped with an ice maker and refrigerated drawers and can easily be converted into a secondary kitchen. Two private bedrooms with en-suite tile baths anchor opposite wings of the main level, providing both privacy and balance. The main floor also includes an inviting secondary living room with a gas fireplace, an elegant dining room wrapped in seagrass wallpaper, a generous walk-in pantry, and a spacious mudroom thoughtfully designed for effortless island living. Upstairs a spectacular primary suite serves as a retreat, complete with private balcony and a bonus two full spa-inspired baths. Three additional en-suite guest rooms and a spacious laundry room complete the second floor. The third level features a charming nautical-themed bunk room with four built-in beds and full bath. The finished lower level includes two bedrooms with en-suite baths, a media room, wine cellar, and additional laundry. Beyond the main house is a beautifully finished two-car garage with brick floors and wood-paneled walls. The carriage house above the garage offers a private guest suite with a balcony overlooking the pool. The outdoor setting is unparalleled for in-town living. Lush hydrangeas surround a resort-style pool and spa, complemented by a built-in grill, firepit, and an exceptional cabana with kitchenette, half bath, laundry, heating and air conditioning. This Edgartown estate offers privacy, scale, and sophistication rarely found within steps of Main Street. An iconic Martha’s Vineyard property reimagined for modern coastal living.

Located in the highly sought-after Nora’s Meadow community in Edgartown, this exceptional coastal property offers the rare combination of privacy, acreage, and close proximity to downtown Edgartown, South Beach, and the Katama bike path. Set on 1.8 beautifully landscaped acres, this custom home was built in 2014 and features over 4,000 square feet of thoughtfully designed living space across three levels. A welcoming mudroom, ideal for beach living, opens into a bright and expansive main living area featuring a spacious dining room, gourmet kitchen, and comfortable living room with oversized French doors leading to the pool patio. The first floor primary suite offers a luxurious spa-inspired bath and private French doors opening to a serene outdoor sitting area surrounded by lush landscaping. Four additional guest bedrooms are all generously sized, providing ample accommodations for family and friends. The finished lower level includes a media room, pool table area, and abundant storage space. Designed for effortless indoor-outdoor living, the backyard is a true Vineyard retreat featuring an oversized pool, outdoor kitchen, expansive stone patio, and a pool cabana complete with a full bath. A two-car garage includes unfinished space above with the unique potential to create a guest house, an exclusive feature permitted only for this property within the Nora’s Meadow association. A charming barn-style shed provides additional storage for kayaks, bikes, and boating equipment. This rare offering combines luxury, privacy, and exceptional outdoor living in one of Edgartown’s most desirable neighborhoods, creating the ultimate Martha’s Vineyard retreat for generations to enjoy.

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 Stern McCafferty 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 main level features sleek modern furnishings, flowing from the kitchen and dining area through French doors to a beautifully landscaped outdoor patio, ideal for al fresco dining and relaxation. Beyond the patio, a lush lawn and manicured gardens surround an impressive 42' x 18' swimming pool, creating a true outdoor oasis. The second level houses four spacious bedrooms, including a luxurious primary suite with an office, ensuite bath, and a private deck overlooking the pool. The third floor offers a large sleeping area with six twin beds, a full bath, a game area, and French doors leading to a sun-drenched deck. This home combines historic character with the finest modern conveniences. Located on North Water Street, this light-filled property is an exceptional opportunity to own a one-of-a-kind retreat in one of Edgartown’s most desirable locations.

Welcome to Seacoast Shores -- Cape Cod's beachside community on the shores of East Falmouth! This completely remodeled 3-bedroom, 2-bath gem has been transformed inside and out, offering the perfect blend of modern comfort and coastal charm. From the moment you arrive, the classic farmer's porch sets the tone -- the ideal spot to sip your morning coffee and soak in the Cape Cod breeze. Step inside to discover a thoughtfully redesigned interior featuring quality finishes throughout, all-new kitchen and baths, and a bright, welcoming flow that feels like a true retreat. Central A/C keeps things cool all summer long. Outside, the full exterior renovation gives this home tremendous curb appeal. Best of all, you're just steps from Bayside Beach -- the association's private 255-foot beach nestled between Eel Pond and the mouth of the Seapit River, with panoramic views of Washburn Island. Whether you're looking for a year-round residence or the ultimate Cape Cod getaway, this is the one. Pack your beach wagon and come home.

This Cape Cod Darling offers deeded ownership and membership rights to The Seacoast Shores Clubhouse, offering a pool, tennis, dining, bar and many more community activities. The home is also located less than 1/2 mile to the sandy Association Beach. Just bring your toothbrush and bathing suit and enjoy summer life in one of the most desirable ocean side penninsulas in Falmouth. No bridges and a public landing nearby make for a perfect boating experience and there are also numerous paths to the water throughout the neighborhood from where you can launch your kayak for an enjoyable paddle exploring the inlets or enjoying a picnic on Washburn Island. Features include easy care vinyl siding, updated windows, refinished wood floors, new range, interior paint throughout, deck and great potential basement expansion. If you enjoy central air conditoning, the ductwork is ready for you. You will be near all that makes Cape Cod so special This sweet home will not last! All information is deemed as accurate but should be confirmed by buyers and their representitives.

Experience luxury living with the timeless charm in this stunning townhouse-style condominium located in the prestigious Sea Quarters community of New Seabury. Overlooking the beautiful Dunes Golf Course, this bright and airy end unit offers exceptional privacy, comfort, and an inviting open floor plan designed for both entertaining and everyday living. The main level features a spacious living and dining area filled with natural light , stylish lighting fixtures, and a cozy gas fireplace--perfect for relaxing year-round. The updated kitchen is equipped with newer appliances and a breakfast bar perfect for casual dining. The primary ensuite offers convenience and luxury including a lovely updated bath, handsome wainscoting and newly installed California Closets. A half bath and laundry area with newer Miele washer/dryer complete the main level. Enjoy the newly updated deck accessible from the LR or Primary. Meander upstairs to enjoy a private bedroom and full bath, along with an office /study for added flexibility. The lower level provides a spacious family room, additional sleeping area, full updated bath and ample storage. For added enjoyment on site - 2 association pools!

This charming Seaside cottage-style townhome is ideally positioned in an elevated setting overlooking Maushop Village, with ocean views and offering refreshing ocean breezes and a relaxed coastal lifestyle. Enjoy just steps to your private, deeded beach, with the vibrant Popponesset Marketplace nearby for dining, shopping, and entertainment. The home features picturesque ocean views including the second-floor bedroom, complete with a cathedral ceiling, ceiling fan, and private en-suite bath. The first floor offers a comfortable guest bedroom, full bath, and an open-concept layout with a kitchen bar that flows seamlessly into the living and dining areas, along with a convenient laundry closet. Additional highlights include a walk-in closet for ample storage, an outdoor storage shed, and two spacious, fenced brick patios in both the front with ocean views and spacious back--perfect for relaxing or entertaining. Residents enjoy access to joining The private Club at New Seabury with amenities, including two 18-hole golf courses, a private beach and cabana club, pool, tennis and pickleball courts, a full athletic center, with a bubble for off season tennis & pickleball.

A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the property represents an irreplaceable opportunity, as a waterfront estate of this scale and caliber could no longer be replicated today. The main residence features six luxurious ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired bathrooms. Two state-of-the-art kitchens appointed with top-tier appliances provide exceptional spaces for entertaining, while the dramatic main living area showcases soaring cathedral ceilings and panoramic pond views. A screened porch and expansive waterfront deck create effortless transitions between interior and exterior living spaces. Upstairs, a striking glass-lined hallway with a dramatic glass floor overlooks the water, leading to guest suites with private baths and access to a second-floor deck. Exceptional amenities include a private theater with massage seating, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping waterviews. Set just beyond the main house is the pool house. The pool house is a private wellness retreat featuring a heated indoor pool, spa, sauna, cold plunge, steam room, wet bar, and spacious enclosed porch surrounded by retractable glass doors. The second floor includes a full guest suite with a bedroom, living room, laundry, and dual balconies overlooking Menemsha pond. The estate also includes an impressive 1,927 sq. ft. barn-style entertainment pavilion designed to complement the property’s contemporary aesthetic while offering exceptional recreational amenities. The upper level features a professionally designed fitness center with floor-to-ceiling windows overlooking the grounds and pond, alongside a sprawling recreation lounge with space for indoor basketball, billiards, ping pong, and additional sporting activities. Below, the structure houses an expansive six-car garage, ideal for luxury vehicle storage, boating equipment, and recreational gear. Completing this incomparable estate are a private tennis court and charming boathouse by the dock for paddleboards and waterfront equipment. An unparalleled modern retreat in one of Martha’s Vineyard’s most exclusive waterfront settings.

The Aldrich House returns to Red Brook Harbor. Built in 1890 as a seaside retreat for Boston travelers arriving by train, the Cataumet landmark was fully restored in 2022 with all-new systems, whole-house generator, and an 18-bedroom Title V septic, the kind of permit Cape towns no longer issue. Across three stories, more than 7,000 SF of refined interior: an open great room with floor-to-ceiling stone fireplace, a chef's kitchen, original hardwood restored throughout, and wraparound porches that hold the harbor view. 10 en-suite bedrooms, each with private sitting room, kitchenette, independent climate control, and a balcony for Buzzards Bay sunsets. Outside, 1.84 manicured acres with in-ground pool, gazebo, and firepit. Family compound, private retreat, or boutique hospitality; the choice is yours. Minutes from sandy beaches, Red Brook walking trails, the National Seashore, and the Islands ferries; and only 80 minutes from Boston. Private showings by request only. Google Maps. County Road to Shore Road to Red Brook Harbor / Scraggy Neck Road to Red Brook Harbor