luxury houses with pool for sale Winchester, United States

Sophisticated elegance on approximately an acre of land in highly desirable neighborhood. A warmth upon entering through the grand foyer reveals an abundance of natural light and 76 impressive oversized windows. Beautiful architectural elements are revealed as the floor plan flows through an open concept chef's kitchen • butler's pantry • 5 entertaining rooms • 2 private home offices • media room • 6 en suite bedrooms • main level bedroom suite • fitness center • game room • sports bar with lounge • wine cellar and tasting room • 2 large stone patios • outdoor kitchen and fireplace • tranquil views of large flat private rear yard • 3 car heated garage. Nearby entrance to 150 acres of historic conservation land including trails, ponds, meadows, and antique stone walls. Just blocks to historic Lexington center and both elementary and middle schools. Easy commuter location to routes 3, 2 and I-95.

When the best unit in the community finally hits the market. This six-bedroom, three-level villa was originally built for the developer, meaning elevated finishes, fortified structure, and superior craftsmanship. This villa features its own private pool, deck & backyard with not 2 but 3 parking spaces. A standalone feel with gated prestige in a prime, upscale location. This is a rare offering that cannot be missed.

Landmark Lexington property with an exceptional location on the Lexington Green, offering a rare opportunity for a complete restoration. This storybook New England home is being offered for the first time in generations and features a large front porch overlooking the town center. Enter through the original glass vestibule to spaces filled with natural light from floor-to-ceiling windows. Period architectural details include two fireplaces, formal and casual living areas, an eat-in kitchen, and a lower-level game room. The private rear yard, set behind a two-story barn, offers views of the Old Belfry and a rare, quiet outdoor retreat in Lexington Center. The barn presents excellent potential for a guest house, studio, office, or wellness space. Both the home and barn require complete restoration. The property is adjacent to 1900 Massachusetts Avenue, also for sale with the same listing agent.

Victorian style colonial on desirable street close to Bentley University with inground pool perfect for summer entertaining! This 5 bedroom home offers something for everyone. The first floor welcomes you into a living room with fireplace, dining room, eat in kitchen with exposed beams and atrium ceiling. There is access to the yard and patio. There are also 2 bedrooms and two full baths on this floor. The upper level has a flexible floor plan with 3 bedrooms plus a den with plenty of windows and natural light along with another full bath. The lower level has a family room with a wet bar for entertaining and an office and half bath. There is a huge detached 2 car garage with living area above that has both heat and air conditioning and a full bath so a great space for guests! There is a workshop below the garage so perfect for a contractor or gym! You will love the flexibility of this home and the convenience of the location. Roof approx. 4 years young roof w/ solar panels.

This spacious home offers over 3,100 square feet of living space with 12 rooms, five bedrooms, and two and a half bathrooms. Set on a private, fully fenced lot, the outdoor amenities include an in-ground gunite pool, spacious deck, and three-season enclosed porch—perfect for relaxing and entertaining. Inside, the main level features a formal living room with a bay window, a kitchen, and a dining room with direct access to the backyard. The bright and airy family room boasts cathedral ceilings and skylights, while a private office, laundry area, half bath and garage access add everyday convenience.The second floor offers a generous den or sitting area, a primary suite with a walk-in closet and private bath, four additional bedrooms, and a full bathroom. A partially finished basement provides space for fitness, recreation, or hobby space. Conveniently located near major highways, schools, shopping, and dining, this home offers an exceptional combination of space, comfort, and versatility.

New construction in desirable town of Melrose! This home features 9-ft ceilings & an open floor plan designed for today’s buyers. The chef’s kitchen offers white cabinetry, quartz countertops, an horseshoe island, stainless steel appliances w/industrial hood, flowing into a bright family room w/grey floor to ceiling ct fireplace access to a covered composite deck—perfect for entertaining w/Boston skyline views. The dining room w/custom moldings & wet bar connects seamlessly to the kitchen, while a first-floor living room is ideal as a playroom or office. Upstairs includes 4 bedrooms, 3Full Baths & Laundry room. Luxurious primary suite w/double quartz vanities, tiled shower, & two walk-in closets. A 5th bedroom, full bath, office, & bonus space on the upper level ideal nanny or guest suite. Lower level features exercise room, mudroom, & 3-car garage. Minutes to downtown Melrose; Starbucks, Whole Foods, Fine Dining, Shopping, Golf, Public Transportation the Commuter Rail & All Major Rtes

New construction in desirable town of Melrose! This home features 9-ft ceilings and an open floor plan designed for today’s buyers. The chef’s kitchen offers white cabinetry, quartz countertops, an oversized island, stainless steel appliances w/hood, flowing into a bright family room w/grey ct floor to ceiling fireplace & access to a covered composite deck—perfect for entertaining with Boston skyline views. The dining room w/custom moldings & wet bar connects seamlessly to the kitchen, while a first-floor living room is ideal as a playroom or office. Upstairs includes 4 bedrooms, 3 Baths & Laundry. Luxurious primary suite w/double quartz vanities, tiled shower, & two walk-in closets. A 5th bedroom, full bath, office, & bonus space on the upper level ideal nanny or guest suite. Lower level features exercise room, full bath, mudroom, 3-car garage. Minutes to downtown Melrose; Starbucks, Whole Foods, Fine Dining, Shopping, Golf, Public Transportation the Commuter Rail & All Major Routes.

Step into elevated living with this exquisitely designed fully furnished 5-bedroom, 5.5-bathroom townhouse, offering approximately 5,000 sq. ft. of refined living space. Thoughtfully crafted with an open-concept layout, elegant lighting, and premium finishes, every detail of this home exudes sophistication. Designed for both comfort and entertaining, the home features a private gym, home theater, helper's quarters and double garage. The expansive primary suite boasts two walk-in closets, while a stunning blend of wood, porcelain, and travertine flooring adds warmth and timeless elegance throughout. Residents also enjoy access to a communal swimming pool, jacuzzi, and 24-hour security, offering an exceptional lifestyle in an exclusive setting. Luxury, space, and impeccable design, all in one extraordinary home. Contact us today to schedule your private viewing.

Welcome home to this exquisitely crafted and luxuriously appointed NEW CONSTRUCTION townhome that delivers all of the comforts and living space of a single family home. Situated in an established neighborhood bordering Lexington in sought-after Bedford, 60 Neillian Street is Pearl Platinum Certified for its Green construction! The 3,238 SQFT residence offers 4 bedrooms, 3.5 baths, a coveted 1st floor primary suite, and a fully finished lower level that can be used as a 2nd full suite/media room/etc! The chef-inspired eat-in kitchen showcases beautiful custom cabinetry, flowing seamlessly into an open concept great room with wide-plank wood floors, soaring vaulted ceilings, a fireplace & oversized windows that flood the space with natural light. The 2nd floor has 3 spacious bedrooms, a spa-like full bathroom and a convenient laundry room, while the 3rd floor provides additional flexible space. Timeless details and master craftsmanship are found throughout this unique home. Head outside to a large, private fenced yard with hardscape patio that is perfect for entertaining, gardening, or simply relaxing! Forward thinking by design, 60 Neillian St is built for efficiency, sustainability & long-term value, featuring Solar-ready infrastructure & an EV charger. Conveniently located near Bedford’s vibrant town center, the scenic Minuteman Bikeway & I-95. BUYERS RECEIVE 12YR HVAC WARRANTY & complementary bi-annual HVAC servicing!

Welcome to 97 Hartwell Rd, an immaculate and versatile single-family home in the heart of Bedford with exceptional curb appeal (we love the front porch!). This unique property offers 5-6 BDs and 4.5 BAs, including a 1st-floor suite and attached accessory apartment, ideal for extended family, guests, or rental income. The main home features an updated kitchen at the center with adjacent family and dining rooms, plus a cozy living room with fireplace. The 1st-floor suite includes an updated bath and office area. Upstairs are 3 BDs, including one en-suite. The accessory apartment has its own entrance, mudroom, 1st-floor office/BD, and open upper level with kitchen, BD, and updated BA. Enjoy a flat, fully fenced backyard with custom party pavilion and huge garage for vehicles, storage, or workshop space. Pristine condition, stunning curb appeal, and a prime location near the Bikeway, The Edge, town forest, and town center make this a rare and versatile Bedford offering.

Welcome to 97 Hartwell Rd, an immaculate and versatile single-family home in the heart of Bedford with exceptional curb appeal (we love the front porch!). This unique property offers 5-6 BDs and 4.5 BAs, including a 1st-floor suite and attached accessory apartment, ideal for extended family, guests, or rental income. The main home features an updated kitchen at the center with adjacent family and dining rooms, plus a cozy living room with fireplace. The 1st-floor suite includes an updated bath and office area. Upstairs are 3 BDs, including one en-suite. The accessory apartment has its own entrance, mudroom, 1st-floor office/BD, and open upper level with kitchen, BD, and updated BA. Enjoy a flat, fully fenced backyard with custom party pavilion and huge garage for vehicles, storage, or workshop space. Pristine condition, stunning curb appeal, and a prime location near the Bikeway, The Edge, town forest, and town center make this a rare and versatile Bedford offering.

Situated on 38 acres (18 and 20 acre parcels) with more land available, this very comfortable, 4 bedroom country house can be found at the end of a very long, tree-lined drive to perfect privacy. It features tremendous charm such as 10 foot ceilings on the first floor, many archways between rooms, abundant light throughout, and 2 large, screened porches. There is a parlor with fireplace, large dining room, family room with fireplace, a deluxe, fully equipped kitchen and a bright breakfast café that opens to a screened porch, and a half bath. Primary suites – pick one: first floor with huge walk-in closet, private bath plus walk-in bay window; upstairs is a very large bedroom with a quiet, private nook for a desk, walk-in closet and full bath. Also upstairs, the other bedroom has a private bath, walk-in and best of all – a large, screened porch with views of the 50 foot pool and gardens … what a way to say goodnight to a moonlit countryside or greet your morning. On the lower level one finds a spacious recreation room with French doors to the patio and pool and a bedroom with walk-in and bath. There is plumbing roughed-in for a kitchen. Double garage with large storage attic. The stable has 2 wash racks, 2 grooming stalls, tack room, laundry and the extra wide center aisle. There are five board fenced paddocks, a lunging ring and an outdoor arena 300' by 180' with stone dust footing.

Sited privately in Lincoln Center on 6.25A park like grounds yet a mere 15 miles form Boston, this rare architectural gem seamlessly blends history, modernism and sustainability. Originally built in the 1860 as a Victorian manor, the home was reimagined in 1950 introducing the Bauhaus principles of clean lines, functional design and indoor-outdoor harmony. Today, after a meticulous LEED-certified restoration, the residence stands as both a preserved landmark and a showcase of modern luxury. Expansive glass walls, dramatic overhangs, and a sculptural spiral staircase define interiors that flow with light and openness. A kitchen with recycled glass and quartz countertops, professional-grade appliances and radiant-heated stone floors anchors the home. Five spacious bedrooms, spa-inspired baths and flexible living spaces include a library, office, music room, recreation room and wine cellar, offering comfort and versatility.

Elegance, sophistication & incredible architectural craftsmanship highlight this exquisite home, walkable to both Newton Centre & Newtonville. This contemporary colonial offers over 6900 sqft of luxurious living with 6 bedrooms & 6 full baths. The sunsplashed main level offers a formal dining, living room, office/bedroom with a 2 sided fireplace & full bath. The spacious chef's kitchen features Wolf & Subzero appliances, 2 dishwashers & 2 sinks, an island that seats 5 as well as a separate breakfast & sitting area. The inviting oversized family room with vaulted ceilings & fireplace lead out to a patio & private yard featuring an in ground pool & spa perfect for hours of entertaining. The 2nd level offers an gorgeous primary suite with a spa like bathroom & 2 walk in closets. Three additional generously sized en suite bedrooms & laundry complete this level. The finished lower level includes a spacious great room, wet bar, 2 mudrooms, bedroom, bathroom & elevator. A true masterpiece!

Positioned one of Skyline's most desirable streets with stunning jetliner views. This captivating 2-story home, built in 2020 and finished with an extensive amount of builder upgrades. A perfect blend of modern amenities and detailed craftsmanship. Featuring 3,546 square feet of living space, 5 bedrooms and 5 bathrooms .The two story entry opens with a direct view of the stunning backyard oasis. The modern chef’s kitchen features an oversized island with breakfast bar, stainless steel appliances, double ovens, and a walk-in pantry. The kitchen overlooks the dedicated dining room, and opens seamlessly to a spacious family room. A large multi-slide door connects the living space to the covered patio, creating effortless indoor-outdoor flow. A downstairs guest wing with it’s own private entrance offers versatility and perfect for multigenerational living or separate home office. A bonus room behind French doors—ideal as a home study or den.Upstairs, a bright loft anchors the secondary living space and two generously sized bedrooms with a shared bath along with an additional junior suite filled with natural light. The oversized primary retreat is a standout, complete with an expansive private balcony, spa-inspired bath with freestanding tub, walk-in shower, dual sinks, and a massive walk-in closet.Outside, the fully upgraded entertainers backyard offers an in-ground pool with custom lighting, built-in BBQ, and sweeping city-light views. Other features include fully paid-off solar panels, exterior lighting, and select areas prewired for sound, offering potential for integrated audio.Skyline residents enjoy access to two beautiful clubhouses with resort-style pools, a state of the art gym, spa, fire pits, and more. Close to award winning and highly coveted private and public schools, many shops and restaurants, and hiking trails with easy freeway access.

Positioned one of Skyline's most desirable streets with stunning jetliner views. This captivating 2-story home, built in 2020 and finished with an extensive amount of builder upgrades. A perfect blend of modern amenities and detailed craftsmanship. Featuring 3,546 square feet of living space, 5 bedrooms and 5 bathrooms . The two story entry opens with a direct view of the stunning backyard oasis. The modern chefs kitchen features an oversized island with breakfast bar, stainless steel appliances, double ovens, and a walk-in pantry. The kitchen overlooks the dedicated dining room, and opens seamlessly to a spacious family room. A large multi-slide door connects the living space to the covered patio, creating effortless indoor-outdoor flow. A downstairs guest wing with its own private entrance offers versatility and perfect for multigenerational living or separate home office. A bonus room behind French doorsideal as a home study or den. Upstairs, a bright loft anchors the secondary living space and two generously sized bedrooms with a shared bath along with an additional junior suite filled with natural light. The oversized primary retreat is a standout, complete with an expansive private balcony, spa-inspired bath with freestanding tub, walk-in shower, dual sinks, and a massive walk-in closet. Outside, the fully upgraded entertainers backyard offers an in-ground pool with custom lighting, built-in BBQ, and sweeping city-light views. Other features include fully paid-off solar panels, exterior lighting, and select areas prewired for sound, offering potential for integrated a

Positioned one of Skyline's most desirable streets with stunning jetliner views. This captivating 2-story home, built in 2020 and finished with an extensive amount of builder upgrades. A perfect blend of modern amenities and detailed craftsmanship. Featuring 3,546 square feet of living space, 5 bedrooms and 5 bathrooms . The two story entry opens with a direct view of the stunning backyard oasis. The modern chef s kitchen features an oversized island with breakfast bar, stainless steel appliances, double ovens, and a walk-in pantry. The kitchen overlooks the dedicated dining room, and opens seamlessly to a spacious family room. A large multi-slide door connects the living space to the covered patio, creating effortless indoor-outdoor flow. A downstairs guest wing with it s own private entrance offers versatility and perfect for multigenerational living or separate home office. A bonus room behind French doors ideal as a home study or den. Upstairs, a bright loft anchors the secondary living space and two generously sized bedrooms with a shared bath along with an additional junior suite filled with natural light. The oversized primary retreat is a standout, complete with an expansive private balcony, spa-inspired bath with freestanding tub, walk-in shower, dual sinks, and a massive walk-in closet. Outside, the fully upgraded entertainers backyard offers an in-ground pool with custom lighting, built-in BBQ, and sweeping city-light views. Other features include fully paid-off solar panels, exterior lighting, and select areas prewired for sound, offering potential for integrated audio. Skyline residents enjoy access to two beautiful clubhouses with resort-style pools, a state of the art gym, spa, fire pits, and more. Close to award winning and highly coveted private and public schools, many shops and restaurants, and hiking trails with easy freeway access.

When you hear something is a builders own home you should pay attention! The best of the best is found here, in this builder's custom home. SO many features, where to begin? *6 plus bedrooms, 7.5 baths *Huge kitchen w/ high end appliances *1st floor bed/bath *Gorgeous custom millwork *Stunning primary suite w/ fireplace, 2 custom walk-in closets, luxurious bath w/ steam shower *2 home offices, one above garage w/ sep entrance and 1/2 bath- easily converted to in-law. *Most incredible entertaining space in town- sports room w/tap, glassed in cigar room w/ ventilation, home theater, wine room/wet bar and more. *Porte cochere creates a courtyard and connects to home gym w/ full bath *Incredible outdoor living too- in-ground heated pool, expansive patio, hot tub, built-in firepit, extensive hardscape and mature landscaping, *Top location- dead end street of incredible homes, walking distance to upper school campus and historic downtown Bedford. Private showings to qualified buyers only.

Proudly standing behind a classic New England stone wall on a lush, private lot, 7 Davis Rd offers a perfect blend of timeless charm + modern sophistication. The heart of the home is a gorgeous kitchen that flows seamlessly into an incredibly open floor plan, designed for effortless entertaining and everyday living. Large windows invite an abundance of natural light, highlighting the thoughtful craftsmanship throughout.Retreat to the stunning primary suite, a true sanctuary featuring a spa-like bath for ultimate relaxation. Finished third floor provides exceptional versatility, boasting a guest suite and a spacious bonus area perfect for a home office or media room.The location is truly unbeatable—enjoy being just a stone’s throw from the center of town, offering easy access to local shops, dining, and seconds from both middle and high schools (grades 6-12) and fields. Experience the best of Bedford living in this meticulously maintained residence where every detail has been considered

Handsomely poised overlooking the Brookline Reservoir and nestled back from the street, this distinguished period home offers four finished levels and serene water views on nearly a half-acre with bluestone patio and pool. The gracious entry opens into a grand foyer flanked by sun-drenched rooms. Bay windows in the living room, dining room, family room, and primary suite frame reservoir and garden views. Four fireplaces, high ceilings, crown molding, and custom woodwork throughout. Well-equipped kitchen for serious cooks with breakfast area and counter seating. Private first-floor study. Enchanting screened porch access the dining and living rooms for al fresco dining. Second floor: three bedrooms, two baths, and a primary suite with large dressing room, ensuite bath, and private deck. Third floor: two additional bedrooms and full bath. Lower level: exercise room, sauna, wine cellar and lav. Two-car garage. Minutes from Chestnut Hill shopping, Longwood Medical Area, and universities.

Nestled on a private 0.92-acre lot in the prestigious Chestnut Hill neighborhood, this exceptional custom-designed Mid-Century Modern ranch, inspired by the timeless architecture of Frank Lloyd Wright, offers a rare blend of sophistication, privacy, and seamless indoor-outdoor living. Thoughtfully designed with gracious proportions and walls of glass, the home is filled with natural light and overlooks beautifully landscaped grounds. A spectacular four-season breakfast room with four skylights complements the chef's kitchen featuring top-of-the-line appliances, three ovens, two dishwashers, and custom cabinetry. The luxurious primary suite serves as a private sanctuary with dual showers and vanities, smart toilets, separate dressing areas, a soaking tub, and an attached office/library. The versatile lower level offers excellent potential for an in-law suite. Sliding glass doors line the rear of the home, opening to a serene outdoor retreat with an elegant patio and heated pool. Superb

A rare opportunity to reimagine and create a $20+M compound in Brookline, set on two private acres in the coveted estate area. Conceived by an award-winning architect, the proposed design masterfully blends timeless elegance and exceptional craftsmanship with the features most desired for modern living soaring ceilings, abundant natural light, clean architectural lines, and a thoughtfully designed floor plan ideal for both grand entertaining and everyday comfort. The proposed plans showcase an expansive open-concept kitchen and family room with a dramatic cathedral ceiling, elegant formal living and dining rooms, spacious library, a screened porch, a gracious 1st floor bedroom, and an exceptional 2nd floor primary suite. Additional customization options include an elevator servicing all levels, a golf simulator, and a swimming pool. Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay

This spectacular residence, set on 4.5 acres in the prestigious Brookline Estate area, has been renovated and is surrounded by private, scenic landscapes. The interior, distinguished by its grandeur and elegance, is adorned with intricate period details, beautiful woodwork, and bright spacious rooms. The grand 13 rooms include a double living room with picturesque views of the gorgeous, expansive grounds. There are 6 bedrooms, one of which is the luxurious primary suite. The meticulously designed grounds feature several unique amenities, including a stunning terrace patio expanding the length of the home, an in-ground swimming pool with fountain and whirlpool artfully integrated with a stone cliff, fully equipped cabana, koi pond, private tennis court, putting green, and magnificent hardscaping. The property also has a three-bedroom cottage and a two-bedroom unit above the free-standing garage. Near fine shops, restaurants, and Downtown Boston.

This California Contemporary defines sophisticated living at its finest. Majestically nestled on 2 private, stunning acres in the coveted Weston Country Club neighborhood.The terraced grounds are accented with stone patios, a salt water pool and cabana. Soaring ceilings and an abundance of sunlight flood the multiple levels of thoughtfully designed living spaces. A dramatic family room has sweeping views of the magnificent rolling grounds while overlooking the open floor plan of the main entertainment level The bright and spacious kitchen with a prep pantry and breakfast room lead to the outside patios. The primary suite is adorned with a beautiful wood beamed ceiling and brick fireplace. Dual spa-like bathrooms are complemented by dual walk in closets. 3 en-suite bedrooms are situated in their own private enclaves. The lower level features a fabulous playroom, traditional media room and a brick wine cellar. Stone walls, a receiving court and 4 car garage complete this special home