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

Exceptional Location and Stylish Updates! Beautifully refreshed 2-bedroom, 2-full-bath home just moments from Dug Pond and downtown. This desirable corner-lot property features a renovated kitchen with new cabinetry, granite countertops, and brand-new stainless steel appliances, plus new hardwood floors, windows, fresh paint, and an updated full bath. The finished lower level offers flexible living space, a bonus room, second fireplace, brand-new full bath, new cedar closet and walk-out access to the garage. Additional updates include new plumbing, four new mini-splits AC units, a new garage door opener, new retractable screens on the carport doors, and fresh landscaping. Enjoy the rare convenience of an underground garage and carport, with easy access to public transportation, shopping, parks, and major highways. Move-in ready and ideally located-don't miss this exceptional opportunity!

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

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

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

NEW BUILD! Nestled on a quiet cul-de-sac, 5 Haven Lane is a stunning home just minutes from major routes and top-rated schools. The open-concept main level features a half bath, chef's kitchen with wet bar and wine fridge, flowing into the dining area with deck access for seamless indoor-outdoor living. The living room impresses with custom built-ins and Venetian plaster finishes, while a dramatic foyer chandelier sets the tone from the moment you arrive. A glass-door home office completes the first floor.Upstairs offers four bedrooms and 3 bathrooms, including one private en-suite. The finished lower level is an entertainer's dream - full bath, wet bar, and built-in keg system included. A 2-car garage and generous lot round out this exceptional home

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!

Set in the heart of South Natick sits this incredible offering in a much desired neighborhood. Set back in an estate like setting this lovely home boasts a newly renovated kitchen that sparkles with quartz counters, new appliances and an impressive center island. The kitchen is adjacent to the fireplaced family room with a soaring ceiling- the perfect spot to relax and entertain. Formal living and dining rooms are also ideal for hosting and the private office with a wall of built-ins/shelves makes working from home a pleasure! Upstairs are four spacious bedrooms with generous closets and three full baths. A lower level offers even more living area with a playroom and gym area. Enjoy your spring, summer and fall days in the three season porch. In winter leave your coats behind in the redesigned mudroom. The fenced yard is a complete dream with a newly created landscape including a stunning heated pool, expansive patio and grassy play area with woods and trails as your backdrop

$10,000 SELLERS' CREDIT offered to Buyers for Interest Rate Buydown or Closing Costs with a signed PandS by 9/9/26. Tucked at the end of a quiet cul-de-sac in Natick, this spacious, sun-filled executive Colonial offers 4+ bedrooms, 3.5 baths, and 3,400+ sq ft of well-designed living space on an easy-to-maintain lot. The chef's kitchen features custom Wellborn cherry cabinetry, granite countertops, upgraded appliances, and an island with a built-in wine rack, opening to a spacious family room with a welcoming gas fireplace. A dedicated mudroom adds everyday convenience and organization. The primary suite upstairs includes dual walk-in closets, soaking tub, and separate shower. The finished walkout lower level adds ~1,300 sq ft of light-filled space, including a flexible bonus room ideal for 5th bedroom, playroom, office, or gym. The fenced backyard reveals mature landscaping with a brand-new composite deck. Fully owned solar panels provide energy efficiency. Conveniently located off Rou

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

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!

Unrivaled luxury, unbelievable value and uncommon efficiency live here. So can you! This rare single-family home in South Natick has everything you want and more! Situated on almost an acre with over 5,500 sf living area, 4 levels of living, w/ 5 bedrooms and 4 1/2 bathrooms. Originally custom built in 2020 w/ luxury finishes and features like imported tiles and granite, custom cabinets and quartz counter, a gas fireplace and more; now boasting over $375,000 in stunning owner upgrades and improvements, creating real value that would be costly to reproduce today. Ideal for discerning buyers seeking comfort, high-end finishes, abundant space, wellness features and smart updates for smart expense management and cost control. Notable features include: A five-star tiled chef's kitchen w/ new smart refrigerator, wine fridge, center gas cooking range, double-wall oven, premium venting and a spacious walk-in pantry; a massive primary bedroom w/ coved ceiling - retreat to an expansive suite w/

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!

Set in the heart of South Natick sits this incredible offering in a much desired neighborhood. Set back in an estate like setting this lovely home boasts a newly renovated kitchen that sparkles with quartz counters, new appliances and an impressive center island. The kitchen is adjacent to the fireplaced family room with a soaring ceiling- the perfect spot to relax and entertain. Formal living and dining rooms are also ideal for hosting and the private office with a wall of built-ins/shelves makes working from home a pleasure! Upstairs are four spacious bedrooms with generous closets and three full baths. A lower level offers even more living area with a playroom and gym area. Enjoy your spring, summer and fall days in the three season porch. In winter leave your coats behind in the redesigned mudroom. The fenced yard is a complete dream with a newly created landscape including a stunning heated pool, expansive patio and grassy play area with woods and trails as your backdrop

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

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!

Beautiful New Construction in desirable Wellesley Hills near Warren Park. The inviting front porch sets the tone of the home's warmth and craftsmanship. It's 5,800 sq.ft. of living over 4 levels. No detail has been overlooked, from the layout, custom built-ins, coffered ceiling and shiplap accents. The Chef's kitchen has Thermador appliances, large center island and sunny eat-in area that abuts a spacious family room. Flexible first floor w/office or living room and a formal dining room. 5 bedrooms, including a Primary Suite w/walk-in closet and spa-like bath. The expansive lower level has a full bath offering plenty of space for a playroom and gym. The oversized mudroom w/custom built-ins, easy access to the stone patio will not disappoint. A 2 car garage w/overflow parking space, making coming and going a breeze. It's an ideal commuter location near the Hills Train and short distance to shops, restaurants, and Hills Library. Delivery date is mid-June!

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!