1,235 houses for sale in Overbrook, Wellesley town Norfolk County Massachusetts

Offers, if any, to be reviewed Monday at 6pm Don't miss your chance to own this unique income-generating 2-family home in the heart of downtown Natick, just steps from the Common, commuter rail and shops! This property is loaded with potential for investors, owner-occupants, or contractors ready to bring their vision and sweat equity. With its unbeatable location and versatile layout, you can rent both units for solid income or live in one and rent the other. Located in a Historic District, the home offers charm and character, but any renovations will require board review. Buyers and their agents should perform their own due diligence. Tons of potential in a sought-after neighborhood. Live/rent or invest, flexible use. This is truly a one-of-a-kind property ready for your finishing touches! Great investment opportunity! This well-maintained two-family property is currently fully rented, offering immediate rental income. Each unit is occupied by reliable tenants, making this an ideal tu

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!

Located in one of Wayland's most sought-after neighborhoods, Daymon Farms, this completely renovated residence blends timeless design with exceptional craftsmanship. Every detail has been thoughtfully curated, from the designer lighting and custom millwork to the premium finishes and fixtures, creating a home that is both sophisticated and inviting. The sun-filled open floor plan offers seamless flow between the kitchen, dining, and living spaces, making it ideal for everyday living and effortless entertaining. Set on a beautifully landscaped lot with an expansive backyard, the property offers endless opportunities for outdoor enjoyment. The existing in-ground pool presents exciting potential to create a private backyard oasis. Ideally situated just moments from top-rated Wayland schools, shopping, parks, playgrounds, and commuting routes, this turnkey home offers an exceptional combination of luxury, comfort, and an unbeatable location

Nestled in the heart of historic South Natick Village, this inviting 5-bedroom, 3-full-bath Colonial blends classic New England charm with the space and flexibility today's lifestyle demands. The main level features an updated eat-in kitchen with pantry and peninsula seating, along with a formal dining room accented by a classic chair rail and additional storage. A comfortable family room and welcoming living room with fireplace and sun-filled bay window provide plenty of space to gather and relax, while a versatile first-floor bedroom is ideal for guests, a home office, or additional living space. Upstairs are four generously sized bedrooms and two full baths, including a spacious primary suite with a private bath and two closets. The heated walk-out basement features large windows overlooking the backyard, offering terrific potential for future finished living space. Outside, enjoy an expansive, level yard with a storage shed and paved sport court. All of this in an exceptional South

Perfectly positioned on the coveted Wellesley line, this extraordinary custom residence offers the rare opportunity to enjoy the prestige and convenience of a premier location with the exceptional value of a South Natick address. Designed with uncompromising quality, this home showcases four finished levels of luxurious living, where timeless craftsmanship, custom millwork, designer finishes, and thoughtfully curated spaces create an unforgettable first impression. The stunning chef's kitchen anchors the home and flows effortlessly into elegant living and entertaining spaces, while the finished third floor and expansive finished lower level offer endless possibilities. Outside, beautifully landscaped grounds provide a private backdrop for relaxing and entertaining. Just minutes from Wellesley Square, Natick Center, commuter rail service, Elm Bank Reservation, the Charles River, the Cochituate Rail Trail, shopping at Natick Mall, exceptional dining, and major commuter routes!

Wonderful opportunity to own a charming, classic 1920's Colonial in the heart of Walnut Hill! This meticulously cared for home sits on just over a half acre of land and is filled with timeless character, high ceilings, tons of natural light and blends original period details with thoughtful updates. The large (updated) windows and gleaming hardwood floors create a bright and welcoming atmosphere throughout the home. A spacious foyer welcomes you to a classic floor plan, flanked by the living and dining rooms. The front-to-back living room has a wood burning fireplace and access to the lovely screened in porch while the spacious dining room boasts a charming built-in hutch. An updated kitchen overlooking the expansive backyard provides lots of storage with room for an island or small eat-in area, and a half bath completes the first floor. Upstairs you will find all four bedrooms and the generously sized full bath. And don't forget the unfinished walk-up attic that is primed for a future

Move right in to this beautifully appointed 4-bedroom home offering exceptional space, custom finishes, and designer details throughout. The sun-filled open floor plan features a white kitchen with Carrara marble countertops that flows effortlessly into the inviting family room with a gas fireplace. A private deck off the family room is perfect for grilling and outdoor entertaining, while abundant south-facing windows fill the home with natural light. A first-floor office provides an ideal work-from-home space. The spacious primary suite offers walk-in closet and a spa-inspired bath. Two addt'l bedrooms share a full bath. The walkout lower level boasts 12-foot ceilings, a large recreation room, and flexible bonus space for a 4th bedroom w/ a full bath or fitness room. A 2-car garage, professional landscaping, and a level backyard complete this exceptional property. Conveniently located near Boston, commuter rail, shops, restaurants, the Schofield School playground and tennis courts!

This updated 3/4-bedroom, 2 bath home is located in a wonderful area close to Volante farms, Wellesley square, Needham center and wonderful walking trails. Open floor plan is very inviting as you walk into the fireplaced living room or sit at the large island and chat with family or friends. Have breakfast or dinner out in the sunroom surrounded by trees and nature. The middle level office gives plenty of privacy to get work done. There is a large family room on the lower level for hanging out and play games or watching T.V. Just off of that is space for a playroom or gym. Large laundry room is great and has shelving for all your laundry supplies. This is an ice-cream truck, block party type of neighborhood yet has wonderful privacy in back with a huge new stone patio and firepit. This is a must see

Tasteful, timeless and exceptionally spacious, this beautifully crafted Colonial by award-winning Natick builder Trask Homes offers 4,700 sq ft of finished living space across three levels. Set at the end of a cul-de-sac with a wooded backdrop, the home showcases quality craftsmanship throughout, including a dramatic two-story foyer, hardwood floors, extensive crown molding, wainscoting and detailed millwork. The main level offers generous living and dining spaces, a private office with custom built-ins, and a spacious kitchen featuring Wellborn cherry cabinetry, granite countertops and a large center island that opens to an inviting family room with gas fireplace. Upstairs, the expansive primary suite features dual walk-in closets and a private bath with double vanity, soaking tub and separate walk-in shower, along with three additional bedrooms. The 1,292 sq ft finished walkout lower level with 3/4 bath provides exceptional flexibility, with generous recreation space plus a bonus roo

South Natick custom-built ranch in one of this area's most coveted neighborhoods, offering approximately 3,500+ sq. ft. of living space. The spacious family room with fireplace opens through glass sliders to an entertainment-sized private blue stone patio overlooking the serene, wooded backyard. The inviting kitchen with eat at island and generous counter space has direct access to the patio and back yard as well. Bright living and dining rooms feature walls of windows, while four generously sized bedrooms include a tranquil primary suite with abundant windows and peaceful views. Hardwood floors extend throughout the main level. A spacious lower-level playroom (2016) provides additional flexible living space. Central A/C (2022), first-floor laundry, 2 car attached garage and a full basement add comfort and convenience. A full house generator (2020), high efficiency furnace (2013) and hot water heater (2019) adds peace of mind. A lovely neighborhood setting close to major routes complet

South Natick custom-built ranch in one of this area's most coveted neighborhoods, offering approximately 3,500+ sq. ft. of living space. The spacious family room with fireplace opens through glass sliders to an entertainment-sized private blue stone patio overlooking the serene, wooded backyard. The inviting kitchen with eat at island and generous counter space has direct access to the patio and back yard as well. Bright living and dining rooms feature walls of windows, while four generously sized bedrooms include a tranquil primary suite with abundant windows and peaceful views. Hardwood floors extend throughout the main level. A spacious lower-level playroom (2016) provides additional flexible living space. Central A/C (2022), first-floor laundry, 2 car attached garage and a full basement add comfort and convenience. A full house generator (2020), high efficiency furnace (2013) and hot water heater (2019) adds peace of mind. A lovely neighborhood setting close to major routes complet

Beautifully reimagined and thoughtfully renovated, this contemporary split-level home offers the perfect blend of modern style, flexible living, and everyday comfort in one of the area's most sought-after neighborhoods. Sun-filled living spaces showcase clean architectural lines, custom built-ins, and a stunning gas fireplace that serves as a striking focal point. The beautifully updated interior flows seamlessly to an expansive deck overlooking the private yard-ideal for entertaining or relaxing outdoors. With versatile in-law or multi-generational living potential, this home offers exceptional flexibility to fit a variety of lifestyles, all while delivering the turnkey convenience and elevated design today's buyers are searching for

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

South Natick custom-built ranch in one of this area's most coveted neighborhoods, offering approximately 3,500+ sq. ft. of living space. The spacious family room with fireplace opens through glass sliders to an entertainment-sized private blue stone patio overlooking the serene, wooded backyard. The inviting kitchen with eat at island and generous counter space has direct access to the patio and back yard as well. Bright living and dining rooms feature walls of windows, while four generously sized bedrooms include a tranquil primary suite with abundant windows and peaceful views. Hardwood floors extend throughout the main level. A spacious lower-level playroom (2016) provides additional flexible living space. Central A/C (2022), first-floor laundry, 2 car attached garage and a full basement add comfort and convenience. A full house generator (2020), high efficiency furnace (2013) and hot water heater (2019) adds peace of mind. A lovely neighborhood setting close to major routes complet

Located in one of Wellesley's most sought-after neighborhoods, this handsome 1924 Colonial offers the timeless character of its era paired with an exceptional floor plan and outdoor spaces that are truly special. From the moment you arrive, the original architectural details and craftsmanship are evident, giving the home a warmth and sense of character that is increasingly difficult to find. The first floor is thoughtfully designed for both everyday living and entertaining, with generously proportioned rooms and a seamless connection to the outdoors. A recently expanded deck, accessible from both the family room and living room, creates an ideal setting for summer dinners, morning coffee, or gathering with friends. Beyond it, the expansive backyard is an uncommon feature for this neighborhood-beautifully private, unusually spacious, and offering wonderful possibilities for outdoor living, recreation, and play. The second floor offers four bedrooms, including a generously sized primary

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

Nestled in one of the area's most coveted neighborhoods with a seamless commute to Boston, this exceptional residence offers the perfect balance of luxury, privacy, and convenience. Thoughtfully gut-renovated with the finest materials and craftsmanship, the home showcases an open-concept floor plan designed for both elegant entertaining and everyday living. Expansive windows flood the interiors with natural light, creating bright, inviting spaces even on the gloomiest days. At the heart of the home is a stunning designer kitchen complemented by a fully equipped catering butler's pantry. A spacious three-car garage and custom mudroom provide exceptional functionality for modern living. Flexible living spaces include two private offices, while generously sized bedrooms each enjoy their own dedicated bathrooms. The finished walkout lower level is bathed in natural light and offers abundant additional and flexible living space. Professionally landscaped grounds provide remarkable privacy

Much admired 7 bedroom, 7000+sf estate home on an acre of manicured lawns on famed Cliff Road. Built and re designed by two of New England's most acclaimed architects, this home boasts the grandeur of stately proportions and sumptuous millwork with a newly renovated and superbly equipped chef's Kitchen and butler's pantry with adjacent family room. A banquet sized dining room and gracious living room both with fireplaces and french doors lead to the private grounds with stone walls, built in grill and multiple sitting areas. Handsome mahogany study with fireplace, ensuite bedroom with newly renovated bath plus a separate sun room complete the 1st floor. Up a curved staircase befitting the most prestigious of homes you will find 6 bedrooms and 4 full baths including the primary suite with, luxurious bath and laundry. Lower level with recreation room and state of the art wine cellar, 3 car heated garage, heated driveway and whole house generator. A once in a lifetime opportunity!

This thoughtfully designed Cape-style home offers first floor living with a master bedroom and full bath, large custom designed kitchen with an eat-in area and adjoining pantry. There is a lovely dining room with built-in cabinets that is connected to a fireplaced living room with a stunning bay window. A first floor den has extensive built-in cabinetry and a half bath. Each season can be enjoyed from the screened in porch overlooking a large and professionally maintained yard with mature plantings and total privacy. The lower level is spacious with a finished family room, full bath, and walkout to the backyard. On the 2nd floor are three bedrooms, an office area, a full bath, and large walk-in closet, plus a walk-in attic for extra storage area. Ideally located across from the Wellesley Country Club, town gardens, Centennial Park, and Longfellow Pond, this property has easy access to commuting routes

Fabulous opportunity! Set on a corner lot in a desirable location, this home offers flexibility and potential for a variety of buyers. Designed with the ease of first-floor living, the home features a spacious living room and dining room, a first-floor primary bedroom with an en suite full bath, a second full bath, and first-floor laundry. Two additional bedrooms on the second level provide space for family, guests, or a home office. Savvy buyers will recognize the opportunity to make cosmetic improvements, personalize the space, and build equity, while contractors and builders may see potential for a more extensive renovation, expansion, or redevelopment. Conveniently located near the High School, downtown Natick, the commuter rail, Route 9, and the Mass Pike, with easy access to shopping, dining, and major commuting routes. Whether you're looking to move right in and update over time or envision something entirely new, this property offers exceptional potential in a sought-after loca

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

Looking for newer construction ready for summer occupancy' Don't miss this stunning 4 year old Farmhouse Colonial you would swear is brand new! Conveniently located close to Natick Center, this quality built home features an open floorplan with 6 first floor rooms, center island chef's kitchen with Thermador appliances, first floor office, second floor office, 2 en-suite bedrooms and 2 bedrooms with jack and jill bath. The primary suite upstairs delivers a spa bath with heated floors and soaking tub and a center island dressing room. The finished lower level has high ceilings and adds a game room, full bath, and rubber-floored gym. High-end finishes with crown moldings, wainscoting, custom built-ins, and hardwood floors throughout. Beautiful lot with fenced yard and huge yard area ideal for a sports court or gardening. Ideal location close to the high school, great shopping and all major routes. Nothing has been compromised. Nothing needs to be done. Just move right in!

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

This updated 3/4-bedroom, 2 bath home is located in a wonderful area close to Volante farms, Wellesley square, Needham center and wonderful walking trails. Open floor plan is very inviting as you walk into the fireplaced living room or sit at the large island and chat with family or friends. Have breakfast or dinner out in the sunroom surrounded by trees and nature. The middle level office gives plenty of privacy to get work done. There is a large family room on the lower level for hanging out and play games or watching T.V. Just off of that is space for a playroom or gym. Large laundry room is great and has shelving for all your laundry supplies. This is an ice-cream truck, block party type of neighborhood yet has wonderful privacy in back with a huge new stone patio and firepit. This is a must see

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

Lovingly cared for by the same owner since it was built in 1958, this expanded Ranch has been a well-loved home for nearly seven decades. Offering 3 bedrooms and 2 full baths, the home has a comfortable, flexible layout with plenty of space to gather, relax, and make your own.The main level includes a formal dining room, eat-in kitchen with propane cooktop, and a warm and inviting family room with exposed beams and beautiful wood details. Wainscoting adds to the home's traditional character, while the sunroom overlooking the backyard is a lovely spot to enjoy your morning coffee, read a book, or unwind at the end of the day. Two good sized bedrooms close out the main level.Set privately above the two-car garage, the primary suite includes a bedroom, full bath, and sitting area, creating a comfortable space away from the main living areas.The finished lower level offers even more room to enjoy, with a fireplace, bar area, sink, laundry, 1/4 bath, and a separate room that could easily se

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

Rare opportunity to get into the Town of Wellesley. Situated on an oversized 26000 sqft lot on a cul-de-sac with potential for expansion.This well-maintained 4 Bedrooms, 2 1/2 bath home is in move-in condition. The main level has gleaming hardwood floors throughout, a master bedroom with an updated en-suite bath, and two good-sized bedrooms with shared updated full bath. New kitchen with SS appliances and granite counter tops and access to rear deck overlooking level backyard. Living room with fireplace and formal dining area complete the main floor. The fully finished ground level is sunny and bright, with a separate entrance and mud-room area and a bedroom with an updated half-bath, fireplace, and built-in shelving/storage. The large open floor plan provides great flexibility of use for an office, gaming lounge, work-out and entertainment room. Easy access to commuter rail, 95, Rt. 9, schools, parks, shopping and restaurants and Babson and Wellesley and Mass Bay colleges

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!