1,526 properties for sale in Overbrook, Wellesley town Norfolk County Massachusetts

Incredible new construction opportunity in one of Wellesley's most sought-after neighborhoods, ideally located within walking distance to the newly built John D. Hardy Elementary School and nearby Perrin Park. This exceptional home offers a fabulous floor plan featuring soaring ceilings, exquisite millwork, abundant natural light, and designer fixtures and finishes throughout. The first floor showcases a grand foyer, open-concept chef's kitchen with breakfast area, fire-placed family room, formal dining room, and a versatile first-floor study or bedroom. The second level includes four beautifully appointed bedrooms, highlighted by a spacious primary suite, one en-suite bedroom, and a shared double vanity bathroom. The finished lower level provides flexible space for a gym, additional bedroom, and family room. A two-car garage with high ceilings, mudroom, stunning stone patio, and level backyard complete this remarkable property

Tucked away on an idyllic side street in a charming Wellesley Farms neighborhood, this beautifully maintained Colonial offers classic character, stylish updates, sun-filled spaces, and an exceptional location. Inside, thoughtful updates blend seamlessly with the home's timeless appeal, including a beautifully updated kitchen with custom cabinetry and brass hardware that flows effortlessly into a sky-light lit eat-in area and oversized family room with built-ins. A formal dining room and living room offer flexibility for both everyday living and entertaining. Upstairs, you have four generous bedrooms, including a spacious primary suite with sparkling en-suite bath, along with a newly renovated family bath. The lower level provides versatile space for a playroom, home office, or gym, and your outside space is lush with a beautiful patio, grassy yard, and deck. Ideally located for the best of Wellesley living, with easy access to the Farms commuter rail, Lower Falls, walking trails, and m

Set within Wellesley's distinguished Cliff Estates, this contemporary residence, completed in 2025, blends scale, refined design, and modern luxury across three finished levels. A grand foyer with floating stair and walls of windows introduces light-filled interiors with generous ceiling heights. Formal living and dining rooms, supported by a Butler's station, elevate entertaining. The kitchen anchors daily life with an oversized island, premium appliances, and a separate pantry with patio access. A family room, private office, and first-floor en-suite complete the main level. Upstairs, the primary retreat offers a spa-inspired bath and custom walk-in closet, set apart from a lounge and three en-suite bedrooms. The walkout lower level extends the living space with recreation, media, gym, and an en-suite guest room. Two bluestone patios and a landscaped yard bordered by a mature tree line create a private outdoor setting near shops, dining, trails, and Wellesley Country Club

Don't miss this truly special 5 bed/2.5 bath, fully renovated home sitting on a 1.5 acre lot in peaceful South Natick! The first floor boasts a front-to-back living room w/center fireplace and wood-beamed cathedral ceiling. Adjacent dining room leads to the stunning, sun-filled kitchen w/massive center island, high end appliances, wet bar, eat-in area and exterior access to the deck and yard. Family room w/fireplace opens to an oversized screened porch overlooking the beautifully done pool area, cabana and massive backyard that offers a scenic setting for entertaining and relaxation. Lovely half bath and office/5th bed complete the 1st floor. Upstairs you will find 3 spacious bedrooms w/hardwood floors that share a newly updated full bath, while the dreamy primary suite offers beamed high ceilings, deck to enjoy your morning coffee w/a view, laundry area and incredible spa-like bath w/wet room. Enjoy a finished walk-out basement, newer septic tank, tons of storage and 2-car garage. Jus

Full gut renovation and addition to this 4 bedroom home in the Poet's corner neighborhood. Fabulous open floor plan with 11' ceilings and filled with windows and sunshine. High end kitchen opens to dining room and spacious family room with built-ins. Huge walk-in food and appliance pantry. Living room with gas fireplace perfect for entertaining. First floor private office. Cozy dining nook plus sitting area over looks the bluestone patio. Oversized mudroom with built-in cubbies. Main suite with spa-like bath and walk-in closet. 3 additional rooms all similar in size with 2 more full baths. Lower level ideal for playroom or exercise plus huge storage room. This is a location close to Warren Park, Wellesley Lower Falls, Boston, train and major routes. Garage with Tesla charger. Aqueduct walking trails in the back just adds another dimension to this incredible home in one of Wellesley's favorite neighborhoods! Move right in!

Welcome home! The front path to this lovely home leads to a Farmer's Porch with skylights, offering great curb appeal and a warm entry. Inside, this turnkey 3-bedroom Colonial features extensive updates and is ready for immediate occupancy. The first floor offers a surround-sound wired living room with a fireplace that flows seamlessly into a bright office surrounded by windows. Both the office and the well-designed cook's kitchen overlook an expansive, level backyard with weather-resistant decking-perfect for summer barbecues and outdoor entertainment. The second floor offers a spacious primary bedroom with dual closets, two additional bedrooms, and a stylish art deco black-and-white tiled four-piece bathroom. The finished lower level includes a versatile bonus living space for a workout space or playroom and a separate family room. Many upgrades include a recently updated heating system, a large water heater, and energy-efficient solar roof panels on a newer roof. Conveniently locate

Why rent when you can own' Rarely does a home like this come along, a detached condominium that is its own standalone cottage tucked away in a tree-lined pocket of Lower Falls. Thoughtfully renovated over the last few years, this 2bedroom home is filled with natural light and blends timeless character with modern updates, featuring an inviting living room, an eat-in kitchen with quartz countertops, stainless steel appliances and gas cooking, beautifully preserved original hardwood floors, and two levels of living space. The primary bedroom offers additional built-in closet storage, while the partially finished walk-out lower level features brand new washer and dryer, abundant storage, and flexible bonus space that's been completely updated and redone. Freshly painted with central air, two off-street parking spaces in driveway, and move-in ready from day one. Outside is where this home truly shines. Your own private backyard retreat features a newly built stone patio, lush lawn, mature

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

Don't miss this truly special 5 bed/2.5 bath, fully renovated home sitting on a 1.5 acre lot in peaceful South Natick! The first floor boasts a front-to-back living room w/center fireplace and wood-beamed cathedral ceiling. Adjacent dining room leads to the stunning, sun-filled kitchen w/massive center island, high end appliances, wet bar, eat-in area and exterior access to the deck and yard. Family room w/fireplace opens to an oversized screened porch overlooking the beautifully done pool area, cabana and massive backyard that offers a scenic setting for entertaining and relaxation. Lovely half bath and office/5th bed complete the 1st floor. Upstairs you will find 3 spacious bedrooms w/hardwood floors that share a newly updated full bath, while the dreamy primary suite offers beamed high ceilings, deck to enjoy your morning coffee w/a view, laundry area and incredible spa-like bath w/wet room. Enjoy a finished walk-out basement, newer septic tank, tons of storage and 2-car garage. Jus

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

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

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!

Incredible new construction opportunity in one of Wellesley's most sought-after neighborhoods, ideally located within walking distance to the newly built John D. Hardy Elementary School and nearby Perrin Park. This exceptional home offers a fabulous floor plan featuring soaring ceilings, exquisite millwork, abundant natural light, and designer fixtures and finishes throughout. The first floor showcases a grand foyer, open-concept chef's kitchen with breakfast area, fire-placed family room, formal dining room, and a versatile first-floor study or bedroom. The second level includes four beautifully appointed bedrooms, highlighted by a spacious primary suite, one en-suite bedroom, and a shared double vanity bathroom. The finished lower level provides flexible space for a gym, additional bedroom, and family room. A two-car garage with high ceilings, mudroom, stunning stone patio, and level backyard complete this remarkable property

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!

Beautifully conceived and architecturally inspired contemporary NY barn-style home with endless upgrade options that range from golf simulator to sauna/ pool/ cabana/ heated driveway list goes on. In one of Weston's most exclusive neighborhoods. Boasting 7500 +/- sf, 6-7 bedrooms and 7 full baths and 2 half baths this home was meticulously designed with an open floor plan, soaring walls of windows, 9.5-inch flooring, 2 story foyer with glass railings, and lower-level wellness/rec wing. The kitchen is elegantly appointed with custom cabinetry, full butler panty and integrated high-end appliances. The private adult suite provides a quiet sanctuary bathed in natural light, separate dressing room and a spa-like bathroom. A thoughtful arrangement of indoor and outdoor spaces creates a symbiotic relationship between interior and exterior, offering unlimited opportunities for both formal and casual entertaining in a neighborhood setting

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

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!

A rare opportunity to own in the desirable Natick Pond Condominiums! Enter into this charming condo, located in a stately Victorian farmhouse set on 1.45 acres of beautiful, tranquil, park-like grounds. Rich in character, this lovely home features large windows, high ceilings, a marble fireplace, gleaming woodwork, and hardwood floors. Enjoy your own private front porch, perfect for morning coffee or unwinding at the end of the day. The unit also includes two deeded parking spaces, additional basement storage, and a new washer and dryer for added convenience. Opportunity to add in dishwasher or in-unit laundry! Ideally located near Natick Center, the West Natick commuter rail, shopping, and wonderful local restaurants, with easy access to Route 9 and major highways. Filled with charm and character, this special condo is not to be missed!

Pristine and spacious, this beautifully maintained three-bedroom townhome offers an exceptional combination of comfort, versatility, and location, just minutes from downtown Natick, major routes, and public transportation. The main level features beautiful hardwood flooring and a bright, open-concept living and dining area that flows seamlessly into a warm, inviting kitchen featuring rich wood cabinetry, granite countertops, and a convenient breakfast bar. A slider opens to the back deck, overlooking an expansive, tree-lined yard, an inviting setting for outdoor dining and relaxation. The finished walk-out lower level adds valuable living space, with a dedicated office area and comfortable living area ideal for working from home, recreation, or guests. Direct access to a private patio and the backyard further enhances the flexibility of this level. Upstairs, hardwood flooring continues throughout the three bright bedrooms, which offer generous closets and abundant natural light. The co

Builders, contractors, investors. Pre-existing non-conforming use as a 2-family dwelling. This 2 family home is located on a 11,752 sq ft level lot close to Ben Hem Elementary and Wilson Middle Schools along with Cochituate Center. It is in disrepair and is your next project! Do you renovate what is there, do you start over, or do you add a second unit' Convenient to major routes and great shopping and entertainment

From the moment you arrive, you'll fall in love with this much-admired white brick Colonial, beautifully sited on a charming corner in Wellesley's coveted Cliff Estates. Set back from the road and surrounded by beautifully landscaped grounds, this exceptional home offers the perfect blend of elegance, comfort, and space for today's lifestyle. Inside, gracious rooms unfold with everything exactly where you want it-and more than you expect. The inviting fireplaced living room opens to a light-filled sunroom, ideal as a home office or quiet retreat, with French doors leading to the stone patio. The state-of-the-art kitchen features generous stone countertops, new ovens and Sub-Zero refrigeration, a charming dining area with banquette seating, and an exceptional walk-in pantry. A gracious dining room with a window seat and custom built-ins is perfect for entertaining.The oversized family room, with its dramatic barrel ceiling, abundant windows, and doors opening to the yard, is sure to bec

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!

Pristine and spacious, this beautifully maintained three-bedroom townhome offers an exceptional combination of comfort, versatility, and location, just minutes from downtown Natick, major routes, and public transportation. The main level features beautiful hardwood flooring and a bright, open-concept living and dining area that flows seamlessly into a warm, inviting kitchen featuring rich wood cabinetry, granite countertops, and a convenient breakfast bar. A slider opens to the back deck, overlooking an expansive, tree-lined yard, an inviting setting for outdoor dining and relaxation. The finished walk-out lower level adds valuable living space, with a dedicated office area and comfortable living area ideal for working from home, recreation, or guests. Direct access to a private patio and the backyard further enhances the flexibility of this level. Upstairs, hardwood flooring continues throughout the three bright bedrooms, which offer generous closets and abundant natural light. The co

New home in Cliff Estates with the ideal floor plan and one of Wellesley's favorite designers creating the perfect interior! Gracious foyer with large kitchen family room off of the back of the home. Oversized kitchen island with fireplace in family room. First floor private study. Living room with another fireplace and dining room both with custom millwork. Mudroom with cubbies and closet. Second floor with excellent main suite with sitting area, large walk -in closet and spa-like bath. 3 additional bedrooms with walk-in closets and 2 full baths. Third floor great space with bedroom and full bath plus a bonus room/office. Lower level with 6th bedroom and 5th full bath. Great playroom with beverage bar and lots of storage! Large flat yard with plenty of room for backyard parties along with a fun bridge in back of property. A must see!

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

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

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

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

Full gut renovation and addition to this 4 bedroom home in the Poet's corner neighborhood. Fabulous open floor plan with 11' ceilings and filled with windows and sunshine. High end kitchen opens to dining room and spacious family room with built-ins. Huge walk-in food and appliance pantry. Living room with gas fireplace perfect for entertaining. First floor private office. Cozy dining nook plus sitting area over looks the bluestone patio. Oversized mudroom with built-in cubbies. Main suite with spa-like bath and walk-in closet. 3 additional rooms all similar in size with 2 more full baths. Lower level ideal for playroom or exercise plus huge storage room. This is a location close to Warren Park, Wellesley Lower Falls, Boston, train and major routes. Garage with Tesla charger. Aqueduct walking trails in the back just adds another dimension to this incredible home in one of Wellesley's favorite neighborhoods! Move right in!

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