1,352 houses for sale in Wellesley Hills

Completely gut-renovated from top to bottom, this stunning 5-bedroom, 3-bath home offers modern design and exceptional craftsmanship throughout. Renovated by a premier builder using top-quality materials, the home features a bright open-concept layout ideal for both everyday living and entertaining. The spacious kitchen flows seamlessly into the dining and living areas, creating an inviting central gathering space. A first-floor en-suite bedroom provides flexibility for guests, multigenerational living, or a private home office. Upstairs, additional bedrooms offer generous space and comfort. Located in a highly desirable neighborhood with convenient access to major routes, this home offers an easy commute to Boston while providing the comfort of a beautifully renovated residence ready for you to move right in

Not all new construction is created equal. The result of a visionary collaboration between acclaimed architecture firm Of Possible and renowned custom builder NS Builders, 45 White Oak Rd represents a rare opportunity to own a residence where design, craftsmanship, and performance were never compromised. Conceived as a showcase of what is possible when architecture and construction are executed at the highest level, this 7,200+ sq. ft. home balances architectural significance with the warmth and functionality required for everyday living. Expansive walls of glass create a seamless connection to the beautifully landscaped grounds, while custom German white oak millwork, curated natural stone finishes, and exceptional detailing reflect an uncompromising commitment to quality throughout. Designed for both grand entertaining and comfortable daily living, the home offers a level of craftsmanship, sophistication, and performance rarely found in today's market

Picture-perfect and beautifully renovated, this fabulous sun-filled home is ideally located in Wellesley's highly desirable Country Club neighborhood. From the moment you arrive, its exceptional curb appeal and timeless elegance make an unforgettable first impression. Inside, an abundance of natural light highlights the sophisticated design, beautiful finishes, and thoughtful attention to detail throughout.The gracious open-concept layout offers an effortless blend of formal and casual living, with elegant entertaining spaces flowing seamlessly into inviting family areas. The beautifully appointed kitchen is the heart of the home, designed for both everyday living and memorable gatherings. Two first floor custom built offices are ideal for work from home spaces. Spacious bedrooms provide comfort and privacy, while the luxurious primary suite offers a peaceful retreat. With six bedrooms and generous living spaces, the home is perfectly suited to modern family life and entertaining. A fa

Perched atop Wellesley's prestigious Cliff Estates, this beautifully renovated Victorian blends timeless architectural charm with modern comfort. Offering 4 bedrooms and 3.5 baths, the home has been thoughtfully updated while preserving its original character and period details. The sun-filled kitchen features a breakfast nook overlooking the landscaped backyard, while elegant living, dining, and music rooms provide ideal spaces for everyday living and entertaining. The second floor includes three spacious bedrooms, including a serene primary suite. The third level offers an additional bedroom, full bath, and a flexible bonus room perfect for a family room, home office, gym, or playroom. Enjoy a private patio, oversized detached two-car garage, and a picturesque setting in one of Wellesley's most sought-after area. A rare opportunity to own a home where historic elegance meets modern living

Situated in the coveted Cliff Estates, this meticulously reconstructed contemporary home offers a sophisticated, light-filled interior designed for effortless modern living.This 4 bedroom, 4 full bathroom house is perfect for any stage in life. The main level features an open-concept flow anchored by an expansive gourmet kitchen with oversized island, vaulted ceilings and high end stainless steel appliances including a 6 burner Wolf range, Sub zero refrigerator, Bosch dishwasher, 2nd Bosch oven and microwave, Sub zero wine fridge and additional beverage fridges as well as ample counter space and storage in the butlers pantry. This space seamlessly transitions into a spacious dining area and a living room framed by custom built-ins and access to the backyard and patio. The home office is tucked away in the back of the house with custom built ins and two work stations. The upper level comprises the primary suite, complete with a generously proportioned walk-in closet with island and a ma

Set on a quiet residential cul-de-sac, this thoughtfully renovated 3-bedroom, 3-bath home offers a host of upgrades designed for effortless everyday living. The kitchen flows naturally into the sun-drenched dining room, where windows on three sides and one of three wood-burning fireplaces add warmth and character to the space. Together they look out over an expansive backyard, where a paver patio and mature landscaping create a private outdoor retreat perfect for entertaining or simply unwinding after a long day. Downstairs, the finished lower level adds tremendous flexibility with a secondary living room, a private office, a full bathroom, ample storage, and direct access to the garage. Close to Wellesley's town center, middle school, and high school, this is a home that truly has it all

This exceptional new construction home is the perfect blend of transitional elegance and modern design. It is crafted with impeccable attention to detail. Warm, rich white oak accents, custom millwork, and designer finishes create an inviting atmosphere throughout. A show stopping chef's kitchen features sleek custom cabinetry, quartz countertops, a massive center island. The kitchen flows seamlessly into the fireplaced family room, where soaring windows fill the space with natural light. An elegant dining room is topped with a contemporary tray ceiling, adding architectural interest and sophistication. Each bathroom offers unique finishes including a striking quartzite sink in the powder room. The luxurious primary is complete with a spa-inspired bath featuring a soaking tub, steam shower, and rain head. An outstanding lower level with a gym area, playroom, and wet bar. Ideally situated in a highly convenient location with every amenity just moments away

An inviting front porch welcomes you to this traditional New England Colonial, steeped in local history and timeless charm. Step inside the lovely foyer and gracious center hall, where a thoughtful floor plan offers effortless living and entertaining. An abundance of windows fills the home with natural light. The custom-designed kitchen is a chef's delight, featuring two sinks, two ovens, and generous counter and cabinet space. It opens to the formal dining room with its walk-in bay and the cozy family room, complete with built-ins. Pocket doors lead to the elegant living room, where a gas fireplace and window seat create the perfect setting for relaxing or enjoying a quiet read. Upstairs, the primary bedroom features two closets, a charming bay window, and an en suite bath with a large shower, double vanity and laundry. Two additional generously sized bedrooms and a full bath complete the second floor. The tree-top third-floor retreat, surrounded by a bank of windows, offers a peacefu

Tucked away on a quiet private lane in the heart of Wellesley Hills, this beautifully updated farmhouse seamlessly blends timeless character with modern comfort. Offering exceptional privacy while just moments from the train, shops, restaurants, and everyday conveniences, this distinctive home delivers the best of walkable village living.A welcoming front porch sets the tone for the warm and inviting interiors, where high ceilings, abundant natural light, and thoughtful architectural details create an effortless flow throughout. The spacious kitchen opens to a sun-filled family room, forming the heart of the home and an ideal setting for both everyday living and entertaining. Elegant living and dining rooms feature fireplaces, crown moldings, and classic details that reflect the home's rich heritage.The serene primary suite serves as a private retreat, highlighted by a stylishly renovated bath. Three additional bedrooms and convenient second-floor laundry complete the upper level.Addin

Welcome to this inviting 4 bedroom, 2.5 bath home featuring a desirable open floor plan. The updated kitchen with high end appliances, showcases quartz countertops, a spacious island, and a seamless connection to the living areas, creating an ideal space for both daily living and entertaining. A generous dining room sits just off the kitchen and family room, offering an easy layout for gatherings with friends and family. Upstairs, you'll find three well-sized bedrooms and two full baths, including a serene primary suite with marble bath. The expansive backyard provides a private outdoor retreat with ample space for recreation, dining, and relaxation. The landscaped setting enhances the outdoor experience while maintaining a sense of privacy. Thoughtfully designed and move-in ready, this home blends comfort, versatility and indoor-outdoor living. Conveniently located near shops, restaurants, commuter rail, and major highways for an easy commute into Boston! Come see all this home has to

Welcome to 38 Upwey Road, offering generous living space, a flexible floor plan and an unbeatable Wellesley location. Built in 1993, this 4-bedroom, 3.5 bath home offers three finished levels, an oversized 2-car garage and a bright, open-concept floor plan. Newly refreshed, the kitchen features brand-new countertops and appliances, while recent roof and system updates offer added peace of mind. A dedicated home office provides the perfect work-from-home space. The walk-out lower level adds tremendous versatility with a spacious recreation area, full bath and wine storage room. Enjoy a private backyard while being just moments from Linden Square, Wellesley's commuter rail, schools and major commuting routes. A wonderful opportunity to enjoy space, convenience and a prime Wellesley location

MAJOR $100,000 PRICE IMPROVEMENT-SELLER MOTIVATED! Stunning new-construction-quality renovation offering exceptional value in Wellesley. This completely gut-renovated 5BR/4.5BA home features a sun-filled open floor plan, designer finishes, and a chef's kitchen with premium appliances. Enjoy a bright sunroom, spacious living and entertaining areas, and a fully finished lower level perfect for a family room, gym, or guest suite. A professionally installed perimeter French drain system provides added peace of mind with a dry basement. Relax or entertain on the expansive deck overlooking the fully fenced backyard. Conveniently located near shopping, dining, parks, and the Mass Pike. Move-in ready with luxury finishes, modern systems, and incredible value. With a dramatic $100,000 price reduction, this is one of the best opportunities in today's Wellesley market. Schedule your showing today-this exceptional home is priced to sell and won't last!

Tucked away on a quiet private lane in the heart of Wellesley Hills, this beautifully updated farmhouse seamlessly blends timeless character with modern comfort. Offering exceptional privacy while just moments from the train, shops, restaurants, and everyday conveniences, this distinctive home delivers the best of walkable village living.A welcoming front porch sets the tone for the warm and inviting interiors, where high ceilings, abundant natural light, and thoughtful architectural details create an effortless flow throughout. The spacious kitchen opens to a sun-filled family room, forming the heart of the home and an ideal setting for both everyday living and entertaining. Elegant living and dining rooms feature fireplaces, crown moldings, and classic details that reflect the home's rich heritage.The serene primary suite serves as a private retreat, highlighted by a stylishly renovated bath. Three additional bedrooms and convenient second-floor laundry complete the upper level.Addin

Presenting a wonderful opportunity in Wellesley Hills! Charming, well maintained three bedroom colonial sited on.34 acres within walking distance to shops and restaurants. A thoughtful design for a young family or empty nesters looking to downsize. The first level offers a spacious front to back living room with fireplace and custom builtins, formal dining room with custom cabinets, a sun filled kitchen opening to the family room, plus a large sunroom with access to the exterior. The second floor offers the primary with two walk in closets, two additional bedrooms and a small study/office area. The bonus room with skylights on the third level offers great space for an office or play room. Enjoy the private back yard which also includes a fenced in kennel/play area

Rarely does a new construction opportunity of this scale arise in Wellesley Hills. Spanning an impressive 6,000 square feet, this 5-bedroom, 5-bathroom residence offers a level of space and volume that is nearly impossible to find at this price point. The sun-drenched interior features exquisite millwork and a thoughtful, modern floor plan. The first floor is designed for effortless living, boasting a formal living and dining room, a dedicated office or guest bedroom with a full bath, and a stunning chef's kitchen equipped with Thermador appliances that flows into an inviting fireplaced family room that overlooks the very private grounds. Upstairs, you'll find four generous bedrooms with large finished closets, including a sumptuous primary suite featuring three closets and a spa-like bathroom. The lower level has a play room, mud room, and full bath. Outside, a beautiful, secluded patio offers a private oasis for alfresco dining. If you've been searching for a high-design new build th

This charming Bungalow with an inviting front porch complete with a swing, will steal your heart. A gracious foyer leads to a sun-filled open concept living room and kitchen for easy everyday living. The separate dining room is perfect for entertaining. The versatile first floor includes a full bath and laundry room and a bonus room offering flexibility as a home office, guest room, playroom and a mudroom. The 2nd floor has 3 generous bedrooms and a luxurious spa-like bath room featuring double sinks, a soaking tub, and a stall shower. Step outside to enjoy a terrific fenced in backyard and deck-ideal for pets and relaxing summer evenings with family and friends. Perfectly situated a short distance to the vibrant Linden Square shops and restaurants, public schools, and Commuter Train. Experience the best of both worlds, where urban convenience meets the peace, space and charm of the suburbs. It is the home you have been waiting for and one not to miss!

This charming Bungalow with an inviting front porch complete with a swing, will steal your heart. A gracious foyer leads to a sun-filled open concept living room and kitchen for easy everyday living. The separate dining room is perfect for entertaining. The versatile first floor includes a full bath and laundry room and a bonus room offering flexibility as a home office, guest room, playroom and a mudroom. The 2nd floor has 3 generous bedrooms and a luxurious spa-like bath room featuring double sinks, a soaking tub, and a stall shower. Step outside to enjoy a terrific fenced in backyard and deck-ideal for pets and relaxing summer evenings with family and friends. Perfectly situated a short distance to the vibrant Linden Square shops and restaurants, public schools, and Commuter Train. Experience the best of both worlds, where urban convenience meets the peace, space and charm of the suburbs. It is the home you have been waiting for and one not to miss!

This exceptional new construction home is the perfect blend of transitional elegance and modern design. It is crafted with impeccable attention to detail. Warm, rich white oak accents, custom millwork, and designer finishes create an inviting atmosphere throughout. A show stopping chef's kitchen features sleek custom cabinetry, quartz countertops, a massive center island. The kitchen flows seamlessly into the fireplaced family room, where soaring windows fill the space with natural light. An elegant dining room is topped with a contemporary tray ceiling, adding architectural interest and sophistication. Each bathroom offers unique finishes including a striking quartzite sink in the powder room. The luxurious primary is complete with a spa-inspired bath featuring a soaking tub, steam shower, and rain head. An outstanding lower level with a gym area, playroom, and wet bar. Ideally situated in a highly convenient location with every amenity just moments away

Welcome to 44 Whiting Road, an exceptional residence set within Wellesley's coveted Country Club neighborhood. Built in 2009 by renowned builder McLaughlin/DeBenedictis, this distinguished five bedroom, six full bath center entrance Colonial offers three thoughtfully designed levels of refined living. An inviting grand foyer sets the tone for the stunning open-concept floor plan, anchored by a custom designed gourmet kitchen appointed with high-end appliances, marble countertops, and a generous center island. The kitchen flows effortlessly into a sunlit breakfast room with expansive picture windows and a gracious family room, where a stone-front gas fireplace provides a warm focal point and frames views of the bluestone terrace and beautifully landscaped grounds. A handsome wood-paneled office, elegant formal living room, formal dining room and well-appointed butler's pantry further enhance the main level.The second floor features four en-suite bedrooms, including a luxurious primary s

Location, Location, Location! Lovingly maintained Victorian home on a beautifully landscaped, fenced, level yard. First floor offers bright and inviting living room, dining room with French doors that lead to a large private brick patio, expanded and updated eat-in kitchen, and a large updated half bathroom. Three bedrooms and an updated full bath are located on the second floor. Additionally, there is a flexible bonus room located on the third floor that can be used as an office/playroom or fourth bedroom. This home is ideally situated just minutes from Linden Square, local shops, restaurants, schools, commuter rail, and Wellesley town center, with easy access to major routes and highways. Open House Sunday 9/13 from 1pm - 3pm!

Charming English Cottage ideally situated to support easy walking access to Wellesley amenities: shopping, Commuter Rail, library, schools, sports fields, and the idyllic Brook Path. Meticulously maintained, this treasured home's entrance invites you into a fireplace-focused living room, a bright new kitchen, and a spacious family room which can provide a flexible floor plan to support aging in place. A full bathroom and laundry are on the first level, and three bedrooms and a shared full bath are on the 2nd floor. Home includes a full basement for play, work, exercise and storage. Its recently-finished space features bright windows, tall ceilings, and interior and exterior access. Parking for three vehicles. A yard with lovely mature plantings and a patio complete the offering. Enjoy the convenience and lifestyle of this sought-after neighborhood of Wellesley!

A truly unique opportunity to live in the coveted Cliff Estates neighborhood, this distinctive contemporary residence offers an extraordinary combination of architecture, privacy, and setting. Surrounded by rare, exceptional privacy, the home is designed to bring the outdoors in, with dramatic cathedral beamed ceilings, oversized windows, and a stunning wall of floor-to-ceiling glass in the family room overlooking the patio and private grounds. The open-concept floor plan creates a wonderful sense of volume and light, while gorgeous original millwork adds warmth and character throughout. The home offers three bedrooms, two full baths, a two-car garage, and flexible living spaces ready to be reimagined for today's lifestyle. While cosmetic updates are needed, several major systems have been recently replaced and the existing systems are in good working order, providing an excellent foundation for the next owner. For buyers seeking a special home in an exceptional neighborhood-or builder

MAJOR $100,000 PRICE IMPROVEMENT-SELLER MOTIVATED! Stunning new-construction-quality renovation offering exceptional value in Wellesley. This completely gut-renovated 5BR/4.5BA home features a sun-filled open floor plan, designer finishes, and a chef's kitchen with premium appliances. Enjoy a bright sunroom, spacious living and entertaining areas, and a fully finished lower level perfect for a family room, gym, or guest suite. A professionally installed perimeter French drain system provides added peace of mind with a dry basement. Relax or entertain on the expansive deck overlooking the fully fenced backyard. Conveniently located near shopping, dining, parks, and the Mass Pike. Move-in ready with luxury finishes, modern systems, and incredible value. With a dramatic $100,000 price reduction, this is one of the best opportunities in today's Wellesley market. Schedule your showing today-this exceptional home is priced to sell and won't last!

An inviting front porch welcomes you to this traditional New England Colonial, steeped in local history and timeless charm. Step inside the lovely foyer and gracious center hall, where a thoughtful floor plan offers effortless living and entertaining. An abundance of windows fills the home with natural light. The custom-designed kitchen is a chef's delight, featuring two sinks, two ovens, and generous counter and cabinet space. It opens to the formal dining room with its walk-in bay and the cozy family room, complete with built-ins. Pocket doors lead to the elegant living room, where a gas fireplace and window seat create the perfect setting for relaxing or enjoying a quiet read. Upstairs, the primary bedroom features two closets, a charming bay window, and an en suite bath with a large shower, double vanity and laundry. Two additional generously sized bedrooms and a full bath complete the second floor. The tree-top third-floor retreat, surrounded by a bank of windows, offers a peacefu

Welcome to Wellesley Farms! Situated in a highly sought-after neighborhood, this beautifully renovated, energy-efficient home is set back from the street and enhanced with new windows and system upgrades.The sun-filled kitchen with cathedral ceilings flows into the family and dining rooms, perfect for both everyday living and entertaining. A stunning great room features custom built-ins and a wood-burning fireplace. Additionally, the floor plan offers the flexibility for a private guest bedroom or home office. A luxurious primary suite on the second floor, complete with a dual-head shower, freestanding soaking tub, and walk-in closet.The finished lower level offers a custom mudroom as you enter from the 2 car garage, and endless possibilities for a game room or home gym with a full bath.Close to Warren Park, Reidy Field, Sprague Elementary and restaurants/shops makes this Wellesley location so special. Seller can accommodate a quick closing

Great Location! Special Wellesley setting bordering conservation land and Fuller Brook! Light-filled 3BR/2.5BA Dutch Colonial offering privacy, character, and exceptional convenience to Wellesley Center, commuter rail, WHS, libraries, shops, parks and Brook Path. Spacious living room with fireplace, dining room opening to deck, and well-appointed kitchen with breakfast bar, pantry storage, Cafe induction range and stainless appliances. Recent improvements include, Hardie Plank siding, triple-pane ENERGY STAR windows (2023), new dishwasher (2025), refinished hardwood floors (2026), freshly painted deck (2026), and fresh interior paint. MantelMount TV system adds a polished entertainment solution. Upstairs features primary bedroom with double closets, two additional bedrooms and full bath with radiant floor heat. Walk-out lower level offers flexible family/bonus space with second fireplace/Jotul pellet stove, full bath, laundry and storage. Level wooded lot with native landscaping, raise

Great Location! Special Wellesley setting bordering conservation land and Fuller Brook! Light-filled 3BR/2.5BA Dutch Colonial offering privacy, character, and exceptional convenience to Wellesley Center, commuter rail, WHS, libraries, shops, parks and Brook Path. Spacious living room with fireplace, dining room opening to deck, and well-appointed kitchen with breakfast bar, pantry storage, Cafe induction range and stainless appliances. Recent improvements include, Hardie Plank siding, triple-pane ENERGY STAR windows (2023), new dishwasher (2025), refinished hardwood floors (2026), freshly painted deck (2026), and fresh interior paint. MantelMount TV system adds a polished entertainment solution. Upstairs features primary bedroom with double closets, two additional bedrooms and full bath with radiant floor heat. Walk-out lower level offers flexible family/bonus space with second fireplace/Jotul pellet stove, full bath, laundry and storage. Level wooded lot with native landscaping, raise

Presenting a wonderful opportunity in Wellesley Hills! Charming, well maintained three bedroom colonial sited on.34 acres within walking distance to shops and restaurants. A thoughtful design for a young family or empty nesters looking to downsize. The first level offers a spacious front to back living room with fireplace and custom builtins, formal dining room with custom cabinets, a sun filled kitchen opening to the family room, plus a large sunroom with access to the exterior. The second floor offers the primary with two walk in closets, two additional bedrooms and a small study/office area. The bonus room with skylights on the third level offers great space for an office or play room. Enjoy the private back yard which also includes a fenced in kennel/play area

Perched atop Wellesley's prestigious Cliff Estates, this beautifully renovated Victorian blends timeless architectural charm with modern comfort. Offering 4 bedrooms and 3.5 baths, the home has been thoughtfully updated while preserving its original character and period details. The sun-filled kitchen features a breakfast nook overlooking the landscaped backyard, while elegant living, dining, and music rooms provide ideal spaces for everyday living and entertaining. The second floor includes three spacious bedrooms, including a serene primary suite. The third level offers an additional bedroom, full bath, and a flexible bonus room perfect for a family room, home office, gym, or playroom. Enjoy a private patio, oversized detached two-car garage, and a picturesque setting in one of Wellesley's most sought-after area. A rare opportunity to own a home where historic elegance meets modern living

Charming English Cottage ideally situated to support easy walking access to Wellesley amenities: shopping, Commuter Rail, library, schools, sports fields, and the idyllic Brook Path. Meticulously maintained, this treasured home's entrance invites you into a fireplace-focused living room, a bright new kitchen, and a spacious family room which can provide a flexible floor plan to support aging in place. A full bathroom and laundry are on the first level, and three bedrooms and a shared full bath are on the 2nd floor. Home includes a full basement for play, work, exercise and storage. Its recently-finished space features bright windows, tall ceilings, and interior and exterior access. Parking for three vehicles. A yard with lovely mature plantings and a patio complete the offering. Enjoy the convenience and lifestyle of this sought-after neighborhood of Wellesley!