3,146 properties for sale in Winchester Highlands, Winchester town Middlesex County Massachusetts

' Your search ends today! Welcome to this well-maintained, generously sized two-family home located in one of the most desirable areas in town, just a couple of blocks to Target and Beebe School, surrounded by restaurants and shops, only 5 minutes to the highway and about a 15-minute walk to Center T station; this move-in ready property features gleaming hardwood floors throughout, double-pane insulated windows, spacious square rooms with high ceilings, plus a walk-up attic offering 3 additional bedrooms for extra living space or expansion, along with a rare large parking area that fits up to 6 cars without needing to move any-perfect for both owner-occupants and investors looking to generate steady rental income

Situated on a desirable corner lot in Medford, this clean, thoughtfully updated two-family home features careful maintenance and numerous recent improvements. Exterior upgrades include durable Hardie-Plank siding, owned solar panels, enhanced yard space, and a fenced backyard ideal for outdoor enjoyment. Inside, both units offer comfortable and functional living spaces with updated floor plans, ceilings, kitchen appliances including induction ranges, and modernized baths. The fully renovated third floor adds valuable flexibility with modern finishes and expanded living spaces. Unit 1 features a 2021 efficient heat pump air system, while Unit 2 offers a gas air heating system. Additional updates and improvements provide added convenience and peace of mind. Ideally located near the MBTA, Ball Square, Davis Square, local shops, restaurants, Tufts University, Trum Field and Tufts Field/Park. This property offers exceptional accessibility and versatility in a vibrant neighborhood

Tucked away on a quiet cul de sac in Brooks Estates, one of Medford's most sought after neighborhoods, this spacious tri level home offers a rare opportunity in an exceptional location. Featuring 3 bedrooms and 2.5 baths, including a private en suite, the home provides a flexible layout designed for comfortable everyday living.Inside, hardwood floors run throughout while multiple living spaces offer flexibility for entertaining, working from home, or spreading out across three levels. Large windows bring in abundant natural light and create an open, inviting feel.Major updates include a new heating system and hot water heater (2025) offering peace of mind for years to come. Ideally located near West Medford Center, the Winchester line, Mystic Lakes, Tufts University, Medford Square, parks, restaurants, commuter rail access, major routes, and St. Raphael School with convenient access into Boston. An opportunity that doesn't come around often in Brooks Estates

Rare opportunity in the heart of West Medford! This traditional Colonial, set on a large private lot, offers exceptional potential for developers, investors, or buyers with vision. Currently zoned GR, the property presents the strong possibility for 2 units with street frontage on both Sharon and Sherman Streets. Historic Commission approval for removal has already been obtained by the owners but is not transferrable. However, the new owner may reapply. Ideally located with easy access to Cambridge, Boston, and Tufts University, while also convenient to the MBTA Commuter Rail with direct access to North Station. Enjoy nearby shops, restaurants, and the vibrant West Medford neighborhood. Whether restoring the existing home or pursuing redevelopment, this is a unique opportunity in a prime location

Welcome to 44 Warren Ave in Woburn, a rare opportunity to own a four-family property just moments from downtown. The main unit offers 3 bedrooms, while the additional three units each feature 1 bedroom and 1 bathroom, creating strong investment potential. Offering approximately 5,700 total square feet including a finished basement with additional flexible space, this property provides versatility and long-term value. Situated on a 10,454 sq ft lot, the property features ample driveway parking and a convenient location near restaurants, shopping, major highways, and public transportation

Welcome home to this beautifully maintained condo offering the perfect blend of comfort and convenience. This inviting unit features a flexible four-room layout with one spacious bedroom, one full bath, and the ease of in-unit laundry.The charming kitchen is complete with stainless steel appliances and a cozy breakfast bar, creating a warm and inviting space to enjoy your morning coffee. The generously sized bedroom offers a large walk-in closet, while sliding doors lead out to a peaceful private balcony overlooking the in-ground pool. Filled with natural light and ample storage throughout- this home also features a new heating/central AC system plus washer and dryer-offering comfort and peace of mind. Well-maintained building with elevator, 1 deeded parking spot(#239) and plenty of guest parking. Ideally located near shops, restaurants, major highways, and a bus stop at the entrance of the complex, this condo makes everyday living effortless

Full of charm, beautiful woodwork, and thoughtful modern updates, this stunning 3-bedroom, 1.5-bath home in Medford's Lawrence Estates neighborhood offers the perfect blend of timeless character and modern comfort. Rich hardwood floors and classic architectural details create a warm and inviting atmosphere throughout the home. Designed for today's lifestyle, the home features a finished lower level offering flexible living space, along with a wonderful mudroom and bright office filled with natural sunlight. The updated full bathroom includes radiant heated floors, adding an extra touch of comfort and luxury. Thoughtful updates throughout enhance the home's charm while preserving its unique character. Outside, the lush backyard provides a private retreat perfect for relaxing or entertaining, complete with an in-ground sprinkler system. 31 Whittier Rd is a truly special home offering warmth, functionality, and timeless appeal in one of Medford's most admired neighborhoods

Exceptional opportunity to own this well maintained two family property in a convenient Medford location! Situated on a desirable corner lot, this property offers a total of 11 rooms, 3 bedrooms, and 2 full bathrooms, providing flexibility for owner occupants, investors, or multigenerational living. This home features spacious rooms, beautiful wood floors, sun porch, detached garage, and a large backyard. Separately metered utilities, newer heating system, and updated electrical service add to the property's appeal. Conveniently located near major highways, shopping, restaurants, parks, and public transportation. Ideal for owner-occupants or investors seeking income potential and long term value

Beautifully maintained and updated 2 family in Medford right next to Magoun Park! On a 3,920 sq ft lot in a quiet desirable area, this spacious multi-family offers exceptional flexibility for investors or owner-occupants alike. Unit 1 features hardwood flooring, bright living room and updated kitchen with granite countertops, stainless steel appliances and huge pantry, 2 large bedrooms plus 3rd bedroom or versatile bonus room and full bath. Unit 2 spans two levels and offers expansive layout with gleaming hardwood floors, generous living room, kitchen w/pantry, 2/3 bedrooms and 1 full bath plus 3 bonus rooms on finished 3rd floor-additional bedrooms/offices/flex space. Major updates include fresh paint throughout, a restored slate roof 2 years ago and furnace approx 7 years old. Enjoy fenced yard with ample space for outdoor entertaining, gardening or recreation. Conveniently located near shops, restaurants, public transportation and major routes. Don't miss the opportunity to own this

A truly unique opportunity at Wellington Woods: an upper level corner unit tucked away on the back side of the most private building in the complex, this feels like a personal oasis away from the noise without sacrificing convenience. Onsite amenities include a gym, swimming pool, dog park, playground, grills and firepits, tennis/basketball court, EV charging stations and more. From each of the windows and private balcony, your view won't be of parking lots or other units or common areas, but instead of trees and greenery. Natural light pours in thanks to south-facing exposure, and the generously proportioned bedrooms are situated on opposite sides of the living space - ideal for guests, roommates, or a home office setup. Your mechanical room is located outside the unit, adding to the peace and quiet. Comes with TWO GARAGE SPOTS and extra storage. Ideally located near Wegmans, the Orange Line train, highway access, and loads of great dining and shopping options. Pet friendly!

Welcome to 15 Monument Street, an amazing 2-family with incredible single family quality and finishes in the desirable West Medford neighborhood. Beautifully set on a tree lined street with a large flat yard. This home has been thoughtfully renovated with tasteful finishes, delivering a turn-key property whether you're looking for multi-generational living, owner-occupancy with rental income, or you're looking to turn the home into a marvelous single family. Currently, both apartments have 3 bedrooms, 2 baths, central air, in-unit laundry and a private deck; bright living spaces with hardwood floors and high ceilings, updated kitchens and baths, and large bedrooms. Outside, you'll find off-street parking and a lush grassy backyard. Ideally situated just minutes from West Medford station, Whole Foods market, Mystic River walking path, and major commuter routes into Boston, this property combines unbeatable convenience with lasting value

Welcome to Unit 509 at the Regency Condominium. This spacious corner unit has 1192 Sq.Ft of living space featuring an open concept living /dining room, an in unit laundry, a master bd/rm with an en suite bathroom, 2nd good size Bd/Rm plus a second full bathroom off hallway. Long balcony has a storage space with sliders off the L/R and both Bd/Rms. Professionally managed building features an inground pool with detached clubhouse, fitness room, small library, and a meeting room. Centrally located, this Condo is a short distance to Medford Sq. with shopping, dining, fantastic new public library, medical facility, Chevalier theater and more. Lovely Mystic River with walking, jogging, and kayaking a block away. Tufts U. less than a mile away. Buses to all points right outside complex including Wellington and Malden Orange line stations plus the Tufts Green Line. Minutes to Rte 93. OPEN HOUSE SAT 6/20 1:15-2:30

Perfect 2-Family Home - Ideal for Owner-Occupant or Investment !This well-maintained two-family home offers a rare combination of space, style, and flexibility-perfect for an owner-occupant looking to offset their mortgage or an investor seeking strong rental potential.The first-floor unit features a spacious two-bedroom layout with impressive 20-foot ceilings that create an airy, open atmosphere. Recessed lighting adds a modern touch throughout, while elegant crown molding enhances the overall character. The living areas feel bright and expansive, offering both comfort and style.The upper unit spans two levels, providing generous living space. It includes a spacious living room for relaxing or entertaining, a formal dining room perfect for family meals or dinner parties, three good-sized bedrooms, and a bonus office room-ideal for remote work, a nursery, or additional storage.6+ Car Parking -Fenced Back yard, Convinent location !SCHEDULE YOUR VISIT TODAY !

Beautifully renovated and sunlit 3 bed / 2 bath upper-level condo on a quiet street in desirable West Medford moments from the trails, water views, and green space of the Lower Mystic Lake. This thoughtfully converted home offers modern finishes throughout, including new oak HW floors, white cabinetry, quartz countertops, central HVAC and upgraded 200-amp elec. service. The well-designed layout is the ideal entertaining space for dinner parties and more plus an expansive full walk-up finished attic is perfect as a media room, home office, fitness space, or guest den. In-unit washer/dryer and bonus basement flex space adds everyday convenience. Rare offering w/ 1 garage space plus 1 additional outdoor spot and a private rear deck. Ideally located near the commuter rail station for easy access to Downtown Boston, with close proximity to Winchester and Arlington steps away. Turnkey opportunity offering the dream of lifestyle, luxury and convenience, all set in a highly sought after neighb

Experience townhouse-style living in Medford in this designed two-level residence. This completely new home offers an open-concept floor with a well equipped contemporary kitchen featuring sophisticate cabinetry, timeless countertops and stainless steel appliances. This stunning 5-bedroom, 3-bath features high end finishes. This home provides a thoughtful separation of space, enhancing privacy and functionality. You'll find a primary bedroom with a modern bath and a walk in closet, recessed lighting off street parking and in-unit washer/dryer hook up. Moments away from Rt93 and Malden T station. This home offers convenience and accessibility

Welcome to 9 James Terrace, a well-maintained home tucked away on a quiet residential street in one of Woburn's convenient neighborhoods. This move-in-ready property features numerous updates, including a newer roof and gutters, vinyl siding, paved driveway, Mass Save blown-in insulation, heating system improvements, pellet stove, oil tank, updated kitchen appliances, chimney repointing, and a fully fenced yard.Enjoy outdoor living with a composite deck and newly added backyard patio, perfect for entertaining or relaxing. Ideally located just minutes from Woburn Center, shopping, dining, schools, and major commuter routes including I-93 and I-95/Route 128, offering easy access to Boston and surrounding communities. A fantastic opportunity to own a home where the major improvements have already been completed

Welcome to 4 Spring Court in desirable Woburn, Massachusetts-a charming and well-maintained 4-bedroom, 2-bath home perfectly situated in a convenient and friendly neighborhood. This inviting property offers a flexible layout with generous living space, ideal for both everyday living and entertaining. The home features four comfortably sized bedrooms, two full bathrooms, a bright living room filled with natural light and a wood burning fire place. Tucked away on a quiet court, the property provides a sense of privacy while still being close to town. Enjoy easy access to nearby Shamrock Elementary School, Moose Park, and Green Street playground-perfect for outdoor activities. Just minutes from Woburn Common, you'll love the convenience of local shops and dining. Additional updates include a new 200 amp service in 2026 and a new roof and windows in 2021. Solid bones, classic layout, and incredible potential - bring your vision to make this home truly your own!

Thoughtfully redesigned from top to bottom, this spacious four-bedroom home offers exceptional flexibility across three finished levels. The main living floor is centered around an expansive open-concept great room, where the kitchen, dining area, and living space come together to create an ideal setting for both everyday living and entertaining. Two well-proportioned bedrooms and a full bath complete this level. Upstairs, the private primary retreat features custom storage solutions and a beautifully appointed en-suite bath, creating a true separation from the rest of the home. The finished lower level adds versatility with a large recreation room, wet bar, fourth bedroom, and an additional full bath - perfect for guests, extended family, or a dedicated workspace. Originally renovated in 2019, the home benefits from updated systems, modern finishes, and contemporary design throughout. Outside, enjoy a private yard and off-street parking

Set in the heart of Woburn, this charming Colonial has been recently updated, including new bathroom plumbing, blending modern updates with timeless character. The inviting living room showcases a bay window, chair rail, and plush carpeting, while an additional family room offers even more space to relax and entertain. The galley kitchen features abundant cabinet storage and a convenient pass-through to the living room, while the dining room includes a pantry and slider leading to a composite deck overlooking the peaceful private backyard framed by a beautiful stone wall. Upstairs, you'll find two spacious bedrooms and a home office, all with plush wall-to-wall carpet, along with a full bath. The finished walk-up attic provides incredible bonus living space complete with a mini split system, perfect for a primary suite, playroom, guest area, or media room. A wonderful opportunity to enjoy thoughtfully updated living with flexible space in a convenient location

Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500+/- sq ft of thoughtfully designed living space. Elegant archways and a dramatic two-story living room create an immediate sense of scale and character. The chef's kitchen features custom cabinetry, Thermador appliances, and an oversized island, flowing seamlessly into the main living and dining areas, while the oversized pantry completes the space. Three bedrooms-including the primary suite-feature en suite baths, with two offering spacious walk-in closets. The primary suite provides a spa-inspired bath and a generous walk-in closet. The expansive lower level, with impressive ceiling heights over 10 ft, offers flexible space for an au pair, media room, gym, or additional living area. Designed by Salt and Stone Co with a two-car garage. Prime location under 1 mile to Winchester Center, commuter rail, and Lincoln Elementary

Move right into this beautifully updated Colonial set on a level, fenced corner lot. Designed for modern living, this 4-bedroom, 3.5-bath home offers a spacious floor plan with a warm, nature-inspired aesthetic throughout. The inviting family room impresses with a dramatic beamed ceiling, while the primary suite features a cathedral ceiling, walk-in closet and spa-like bath with an oversized shower, soaking tub and double vanity. A second en-suite bedroom, two additional bedrooms and full bath complete the second floor. The partially finished lower level provides flexible bonus space. Outdoors, enjoy a private sports court and expansive fenced yard, ideal for recreation and entertaining. An attached 2-car garage, including one heated bay, adds convenience. Ideally located adjacent to Town Forest walking trails and just minutes from Wedgemere Station, downtown Winchester, schools, parks, and commuter routes. A rare opportunity to enjoy comfort, recreation and convenience in a sought-aft

Experience townhouse-style living in Medford in this designed two-level residence. This completely new home offers an open-concept floor with a well equipped contemporary kitchen featuring sophisticate cabinetry, timeless countertops and stainless steel appliances. This stunning 5-bedroom, 3-bath features high end finishes. This home provides a thoughtful separation of space, enhancing privacy and functionality. You'll find a primary bedroom with a modern bath and a walk in closet, recessed lighting off street parking and in-unit washer/dryer hook up. Moments away from Rt93 and Malden T station. This home offers convenience and accessibility

Presenting this rarely offered loft-style condo in Old Medford High School. This complex was added to the National Register of Historic Places in 1983 and subsequently converted to 111 residential units. There are 2 levels of bright open living, with a central view over looking the American flag. The main level features an airy kitchen and living area with a dramatic Palladian window. A modern half bath is located in the foyer along with a spiral staircase leading to the penthouse-style bedroom suite. BR suite has dual closets, skylit primary bath, and a vast walk in closet. Custom California Closets throughout maximize organization. Additional highlights include central heat and air conditioning, deeded garage parking, and private storage locker. Enjoy resort-style amenities including a heated indoor pool, sauna, and tennis court. Ideally located one block from Medford Square with easy access to highways, public transportation, and an express bus to Boston

Charming Cape-style home located in Woburn's highly sought-after Central Square neighborhood, tucked away on a quiet cul-de-sac and conveniently located close to local schools, highways and shopping. This spacious 8-room home offers 3 bedrooms and 2.5 bathrooms, all freshly painted and thoughtfully updated. The modern kitchen and renovated baths mean there's nothing to do but move in. The main level features a welcoming FP living room, bedroom, full bath, dining room, and kitchen. Upstairs, you'll find 2 additional bedrooms, and beautifully updated full bath,(2020) and a versatile office or lounge w/custom built shelving. The finished lower level adds even more living space, including a freshly painted family/playroom, an office/guest room, and a half bath with a laundry area-perfect for today's lifestyle needs. The house was resided in 2015 w/ window replacements. The exterior has been maintained with an above ground pool in the fenced in back yard waiting for summer family fun

Sophisticated Medford home offering refined style and modern updates. This 3 bedroom, 1.5 bath residence features 1,320 sq ft with an open-concept living and dining area, a sleek kitchen with quartz counters, peninsula, brand new stainless steel appliances and beautifully updated bathrooms. First floor office and laundry add flexibility and convenience. Thoughtful upgrades include fresh paint and a new heat pump for efficient heating and A/C. Upstairs, a spacious, light filled primary and two well proportioned bedrooms. Private outdoor space completes the package, all in a desirable location near shops, dining and transit. Don't miss out on the opportunity to own this stunning home that blends nostalgic features of the past with today's comfortable living!