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

Attention Investors: Here is a rare opportunity to buy a turnkey side by side two family home built in 2019. Unit one has 3 bedrooms, 1.5 bathrooms and kitchen, living room and dining area, laundry and patio. The second unit has 2 bedrooms, 1 bathroom, kitchen, living and dining area, laundry and patio. The property is currently owned by the Town of Natick Affordable Housing Trust Fund. All offers must conform with the terms of the associated Request for Proposal (RFP) and will remain sealed until 9:00am on October 15. The RFP package can be obtained from Susie Gear/Coldwell Banker Realty. The current lease rates are below market given current use as transitional housing program

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

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

Bates Elementary is on this street. Start there, then walk the half acre. Level, fenced and private, reworked in 2020 under a landscape architect's plan with a new fieldstone wall, walkways on both sides, irrigation, underground water management and a driveway rebuilt to hold nine cars. The house is a 1940 colonial that was expanded and re-skinned the same year by Duckham Architecture and Interiors. New siding, windows and gutters on every side. An extra-large farmer's porch across the front. A new side entry where the bulkhead used to be. And a four-season room with a cathedral ceiling and glass on three sides, opening to a landing deck and bluestone patio. Inside, a twenty five foot eat-in kitchen with a Wolf range, double wall ovens, Sub-Zero wine refrigeration, custom cabinetry and a built-in banquette that seats eight. The living room has a fireplace and a wall of built-ins. The family room has a brick fireplace and a bay window. Upstairs, the primary suite occupies its own wing,

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

One of Wellelsey's signature properties! Rarely available 18 room estate w/ 4 floors of living situated in the heart of Peirce Estates. Stunning foyer w/ curved staircase. Sunken living room w/ coffered ceilings and stone fireplace. Oversized dining room w/ bay window plus large butler's pantry. Kitchen w/ stainless appliances, center island and breakfast nook. One of a kind family room filled w/ built-in bookcases, coffered ceiling, fireplace and wet bar perfect for entertaining and everyday living. Wood panel den/office. Main bedroom w/ 2 walk-in closets and fireplace. 3 additional beds and 2 baths. Large sitting room/bonus room w/ fireplace completes 2nd floor. Third floor w/ 2 more beds and bath plus another large bonus room with built-in bunk beds. Lower level w/ playroom, game room and bar room. Over 7700 sq ft with almost one acre of privacy abutting the reservoir. Fieldstone patio. 400 amp service. 3 car garage and steel beam construction. Your chance to own one of Wellesley's

A rare opportunity to own a truly versatile property in sought-after South Natick, featuring two residential dwellings plus a detached garage/barn. Offering exceptional flexibility for homeowners, extended family, guests, or rental potential, this unique property combines character, functionality, and thoughtful updates. The main residence offers 4 bedrooms and 3 bathrooms, including a newly added upstairs full bathroom (2020), along with a remodeled kitchen (2025), new furnace (2025), new siding (2021), and a partially finished basement with fireplace providing bonus living or recreational space. The home is also partially powered by an owned 36-panel solar array, offering an additional energy-efficient feature. A charming separate cottage provides 2 additional bedrooms and living space, making it ideal for guests, extended family, a home office, or potential rental income. Mini-split heating and cooling was added in 2023 to supplement the existing oil heat. Set in a desirable locatio

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

This early 1800s farmhouse in Newton Lower Falls offers character and potential on a flat, deep 1/4 acre lot in a single-family zone. Currently configured as a side-by-side two-family, the property features classic wood clapboard siding, a fieldstone foundation, high ceilings, a front farmer's porch, and options to maintain rental income, expand, or convert back to a single-family home. The larger right-side unit includes a kitchen, dining room, living room, full bath, and private side porch on the first floor, with three bedrooms and an office upstairs. The second unit offers a main-level kitchen, dining room, living room, full bath, and a second-floor bedroom. Deeded driveway easement rights lead to rear parking and an expansive backyard. Located blocks from village shops, dining, the Charles River, and Lower Falls Community Center, with fast access to the Riverside Green Line, I-95, and the Mass Pike

Natick's newest neighborhood is expanding, and construction is underway in phase III of Wyndemere South Natick- Brought to life by the area's preeminent developer this new home and neighborhood epitomizes refined living in a coveted enclave of estate-like homes- graced with classic New England charm and timeless allure. Step inside to discover 5 bedrooms, 5.5 baths, and 6,400+ square feet of meticulously designed living space. From the expansive kitchen, to the efficient scullery, every detail reflects a commitment to excellence. Outside, mature trees and illuminated stone walls line the street, creating a tranquil retreat. Entertain alfresco on the patio, complete with a built-in gas firepit amidst privacy landscaping and mature trees. Beyond its impeccable design, this home offers unparalleled convenience. Minutes from both downtown Wellesley and Natick, yet a world away in its serene setting. Wyndemere is anything but ordinary

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!

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

Exceptional newer construction in the heart of South Natick lives like a single family home. A welcoming front porch introduces this stunning home, which showcases superior craftsmanship, sophisticated finishes and thoughtful design across three beautifully finished levels. The exceptional chef's kitchen features high-end appliances, an expansive island and abundant workspace, flowing seamlessly into fresh, sun-filled living and entertaining spaces. A private first-floor office, fabulous walk-in pantry and beautifully designed laundry room enhance everyday living. All four bedrooms are thoughtfully located together on the second floor, along w/ an inviting loft area ideal for reading, gaming, or relaxing. Gorgeous primary suite w/ spa-like bath. The expansive finished lower level offers outstanding flexibility for guests, fitness, recreation or media. Enjoy a walkable lifestyle near Riverbend School, Memorial Elementary, South Natick village, Elm Bank Reservation, trails and the Charle

Price Improvement! Welcome home to this beautifully remodeled property offering the perfect blend of comfort, convenience, and location. Ideally situated with easy access to the Mass Pike, Route 9, and the Commuter Rail, this home is a train traveler's dream. The Natick Center Commuter Rail station is approximately 1.5 miles away, providing service to Boston's Back Bay in under an hour-without the hassle or expense of city parking. Remodeled in 2009, the home offers approximately 1,600 square feet of finished living space, including a partially finished lower level with a half bath that provides flexible space for a family room, home office, guest area, or potential in-law-style setup (buyer to perform due diligence). The main level features a desirable first-floor primary bedroom, second bedroom, full bath, and convenient first-floor laundry for easy one-level living. Gleaming hardwood floors, Central Air, and Porcelain Tile complement the inviting interior, while the kitchen showcase

Move-in ready 5BR, 3.5BA renovated residence in South Natick near the Dover/Wellesley line with Charles River views. Lives like a true single-family with a bright, open layout, brand-new kitchen, updated baths, new roof, windows, systems, and solar to lower energy costs. Flexible space for a home office, guest suite, or multi-generational living. The game-changer? A 1st-floor professional space with an active long-term lease and tenant-paid utilities-built-in income that offsets your carrying costs. Operating strictly during weekday business hours, the tenant leaves your evenings and weekends quiet and private. Set on 0.52 acres with 9+ parking, steps from Broadmoor Wildlife Sanctuary, waterfalls, and village parks. Minutes to Wellesley College, Natick shopping, Wellesley boutiques, local bistros, library, and Hunnewell Estate with fast access to Rts 135, 495, and Mass Pike. A rare opportunity to own more home in a prime MetroWest location. Home AND income-done right. Schedule your tou

Located on one of Wellesley's most coveted roads in Cliff Estates, 100 Albion is a beautifully appointed pillared white Colonial set on.77 acres of professionally landscaped grounds. Blending timeless architecture with modern living, the main level offers a gracious fireplaced living room with a large picture window, an elegant dining room, a private office, and an expansive kitchen centered around a large island. These spaces flow seamlessly into a spacious fireplaced family room with custom cabinetry and out to a brand-new deck ideal for indoor/outdoor entertaining. The first floor also includes a well-placed laundry room with a full bath. Upstairs are five bedrooms, including a serene primary suite with a walk-in closet, along with four additional bedrooms and two full baths. The finished walk-out lower level features a full bath and bar, providing versatile living space. Exceptional curb appeal, a circular driveway, and beautifully landscaped grounds complete this impressive home

Incredible opportunity to own a rare, conforming one-acre lot in the heart of Cliff Estates! This 4-bedroom, 4-bath home offers exceptional potential and is ready for its next chapter. Bring your vision and reimagine the possibilities in this highly desirable location. Easy to show!

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!

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

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

Exquisite renovation of this distinctive property blends historic architectural character with sophisticated luxury living. Set on picturesque grounds with beautiful views of gardens, patios, the historic barn, golf course, and skyline vistas. Gracious, light-filled interiors feature hardwood floors, fireplaces, architectural detail, and beautiful views throughout. The sunny kitchen opens to a family room with gas fireplace, wet bar, and french doors to patio while the adjoining breakfast room/sunroom opens to a deck with sunrise views. A spacious great room with beamed ceilings and fireplace provides exceptional entertaining space. A first-floor office with separate entrance and full bath offers potential for an in-law/nanny suite. A wood paneled library with built-ins and a well-appointed dining room round out the first floor. Upstairs are five bedrooms, a sitting room/nursery, and four renovated baths. The third floor features a game room. The expansive lower level includes a recrea

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

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

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

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

RARE FIND IN NATICK - 1.48 ACRES ABUTTING CONSERVATION! Step inside and discover a home that feels worlds away while keeping you close to everything Natick has to offer. This updated 3-bedroom, 1.5-bath ranch offers a surprisingly spacious and versatile layout with 2,124 sq. ft. of finished living space and a private natural setting that's increasingly hard to find. Sunlight fills the main level, where refinished hardwood floors, fresh paint and updated baths create a warm, move-in-ready feel. But the true showstopper may be out back - a covered composite deck overlooking a peaceful wooded landscape and conservation land, creating your own private retreat for morning coffee, summer dinners or simply unwinding at the end of the day. Downstairs, the finished walkout lower level adds approximately 600 sq. ft. of flexible living space - ideal for a family room, home office, gym, playroom or guest space - with direct access to the patio and backyard. Public water, public sewer, 200+ amp ele

Do not miss this beautifully expanded 4-bedroom Cape set far back from the quiet street, complete with an entertainer's dream backyard, in the super desirable Dug Pond neighborhood. The heart of the home is the updated eat-in chef's kitchen with attached two-story family room, complete with wood-burning fireplace and doors to the back patio. Also on this level is a second family room with vaulted ceilings, tons of light, and the full bathroom on the main level connected to the family room. Completing this level are a formal dining room and a bonus room that could be an office, playroom, formal living room, etc. The convenient side door entryway leads to the attached two-car heated garage (with EV charger.) Upstairs, stemming from the wide hallway that overlooks the downstairs, are 4 bedrooms including a large ensuite primary bedroom with heated floors and a huge walk-in closet, plus three additional bedrooms, another full bathroom, and laundry room. The basement has both finished and u

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

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