luxury houses with pool for sale Osterville, United States

D esirable Deer Crossing Community - This beautiful townhouse could be your perfect year round residence or seasonal Cape Cod retreat! Tastefully updated, the condominium features an open floor plan w/ kitchen/ dining area/ fireplaced living room and slider opening to a composite deck & private yard. The kitchen has lovely cabinetry & granite counters. A 1/2 bath & hardwood floors complete the first floor. The second level offers 2 generous bedrooms w/ newer carpeting and a shared full bath. In addition there's a 555 sq.' finished room in the basement. Deer Crossing Amenities include a spacious Clubhouse, pool, tennis & pickleball courts and plenty of nicely landscaped green space. It is conveniently located to Mashpee Commons & South Cape Village shops & restaurants. Pets allowed: 1 dog 50#-breed restricted; 2 cats. Rentals ok w/ minimum 1 year lease. A refundable deposit of 2 months condo fee due to HOA at closing. Buyers & Buyers' Agents to verify all information contained herein.

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.

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!

A truly custom home offering expansive first floor living on a private lot of nearly an acre of land, complete with a stunning in ground pool with waterfall feature. This young home showcases gleaming hardwood floors throughout and exceptional attention to detail. The spectacular kitchen features luxury appliances, high end cabinetry with illuminated upper cabinets, stone countertops, and a beautiful walk in pantry, creating the perfect space for both everyday living and entertaining. The primary suite is a private oasis filled with natural light and complemented by a cozy fireplace, a spa inspired bathroom with double sinks, two water closets, a walk in rain shower, and a soaking tub. A custom walk in closet has been thoughtfully designed to organize your wardrobe. A spacious second bedroom offers a generous closet and convenient access to the well appointed hall bathroom. The home also features a wonderful laundry room designed for both functionality and ease. The backyard is a private retreat with a stunning in ground pool ideal for relaxing or entertaining. Additional highlights include a thoughtfully designed front closet that creates the perfect pet space, an impressive three car garage for your car collection and a four bedroom septic design. Bonus space above the garage and an expansive basement ready to be finished offer endless possibilities for additional living space. Owned solar panels, a generator, and an electric vehicle charging station add energy efficiency, convenience, and long term savings. If you've been searching for a truly custom home with a pool and a coveted East Sandwich address, this may be the perfect match.

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

A truly remarkable Bass River estate, set on an extraordinary 5.11 acres of private waterfront. This stunning property is the epitome of Cape Cod elegance, where timeless character meets thoughtful modern luxury. Lovingly restored to honor its original charm, the home has been impeccably updated throughout while preserving the architectural details that make it so special. At the heart of the residence is a grand, state of the art kitchen, designed for both everyday living and elegant entertaining. Spanning over five acres, the grounds create a rare private riverfront oasis, complete with a private dock offering direct access to the Bass River leading to the ocean. Outdoor living is elevated with a resort-style pool and gazebo, the perfect setting to unwind and take in unforgettable sunset views. For the equestrian enthusiasts there is a stable. With five generously sized bedrooms, this exceptional home offers space and comfort for family and guests alike. A property of this scale, setting, and craftsmanship is rarely available truly one of a kind and not to be missed.

Built in 2016 by Squash Meadow Builders, this exceptional five-bedroom Colonial is ideally situated just moments from the sandy shores of Tashmoo Beach on Vineyard Sound. Thoughtfully designed across four levels of living, the home seamlessly blends timeless architecture with modern comfort. The main level offers an inviting open floor plan with a spacious living room with gas fireplace anchored by a gourmet kitchen with custom built-ins and charming bench seating. The kitchen blends effortlessly into a light-filled sunroom, creating the perfect setting for relaxed coastal living. A generous first floor primary suite provides privacy and convenience. The second level features bedroom suite with a private bath and three well-appointed guest bedrooms share a full bath with recently updated modern tile and vanity. The finished third level offers an expansive bunk room, ideal for extended family or guests. The finished lower level is designed for entertainment and wellness, featuring a media room, home gym, and ample storage. Indoor and outdoor living connect beautifully where the new sunroom opens to a pergola-covered stone patio overlooking a saltwater pool framed by a classic stone wall. The backyard is a private oasis, complete with an outdoor stone fireplace and lush landscaping accented by blue hydrangeas, perennials, and native sea grass. Additional highlights include a one-car garage and solar panels for energy efficiency. A turnkey Martha’s Vineyard retreat offering comfort, style, and effortless summer living near one of the island’s most beloved beaches.

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.

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.

Your Turnkey Cape Cod Oasis and Income Generator has Arrived. Why wait for a ''dream home'' to be built when you can walk into one today? Set on a private acre, this isn't just a house--it's a high-end lifestyle package. Whether you're looking for a serene primary residence or a powerhouse investment, this 4 bedroom, 4.5 bath, new construction masterpiece comes fully furnished and ready to perform from Day One. Double the Luxury: This layout features two massive primary ensuites, each boasting spacious walk-in closets--perfect for multi-generational living or high-end rental appeal. Elevate your culinary game with a professional-grade Thermador range and oven, the centerpiece of a sun-drenched, open-concept heart of the home. Skip the furniture lead times; every inch of this home has been styled for comfort and coastal elegance. A shimmering pool is included, transforming your oversized lot into a private summer resort. With a rental permit in place, you can tap into the Cape's lucrative short-term rental market immediately. Tucked away in a tranquil, peaceful setting, you are just minutes from easy access to the walking trails of Thompsons Field and Cape Cod Rail Trail.

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts.

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.