1,998 houses for sale in Winchester Highlands, Winchester town Middlesex County Massachusetts

Rare opportunity to own a nicely maintained 2-family home in the heart of desirable West Medford! Stately situated on a corner lot and owned by the same family for over 30 years, this versatile property offers 7 bedrooms, 3 full baths, and endless potential for owner-occupants, investors, or multigenerational living. Unit 1 features two levels of living with access to a walk-up third floor offering future expansion possibilities, while Unit 2 provides the ease of one-level living. The lower level presents additional potential to create more usable space with a walk up attic to explore expanding. Outside, enjoy two spacious decks, a fenced yard, garage, shed, and ample off-street parking. Ideally located just minutes to the commuter rail, major routes, shops, restaurants, parks, and everything Boston has to offer. Home to be delivered vacant at closing - this one won't last!

Planted on an oversized lot, this charming colonial nestled on a cul-de-sac has been a family home for over 30 years. The large wooded lot and quiet street become a sanctuary for peaceful living as you relax on a private covered porch. The open concept first floor has a remodeled kitchen with stainless steel appliances, granite counters, dining area and a breakfast bar. This spills onto a full bath, formal dining area and finally to a sun-drenched family room. The second floor has 4 bedrooms with two full baths and a remodeled master bath supporting a jacuzzi tub and a standalone tile shower. The master bedroom is highlighted with a walk-in closet and a small deck off the back surveying the beautiful landscape yard with three patios

Welcome to this impeccably maintained split-entry, perfectly situated on a quiet dead-end cul-de-sac just 9 miles from downtown Boston. Offering the ideal blend of comfort, convenience, and versatility, this well-maintained home features 2 generously sized bedrooms and 2 full bathrooms with a flexible layout designed for today's lifestyle.The sun-filled main level offers inviting living spaces, while the fully finished lower level provides exceptional additional living area-perfect for a family room, home office, gym, media room, or guest space. Whether you're entertaining friends or enjoying a quiet evening at home, this property offers plenty of room to spread out.Enjoy the peace and privacy of cul-de-sac living while remaining just minutes from Boston, major highways, shopping, dining, and public transportation. This move-in-ready home is an outstanding opportunity for commuters, first-time buyers, downsizers, or anyone seeking generous living space in a convenient location. Don't m

Set on a tree-lined street in desirable West Medford, this classic two-family has been lovingly cared for and reflects pride of ownership throughout. Bay windows, hardwood floors, high ceilings, and abundant natural light highlight the home's timeless character and architecture. Fully vacant and separately metered, the property offers flexibility for both owner-occupants and investors. Unit one features an oversized 2-bedroom, 1-bath layout with a spacious living room and a dining room. Unit two is a 4-bedroom, 1.5-bath upper-level duplex with three distinct living spaces and a private porch. Additional highlights include a driveway with parking for two cars and a beautifully landscaped backyard offering plenty of room for outdoor enjoyment or potentially more parking. Located just one block from the West Medford commuter rail station, this property provides easy access to local shops, restaurants, parks, and major commuting routes

Welcome to 44 Jerome St, a charming 3 BR, 2 bath W. Medford single fam ready for its next chapter, featuring warmth, character and exciting possibility. Set on a generously-sized lot, it offers comfortable living now AND has future potential that stirs the imagination. Enjoy a classic layout w/ inviting living space, formal dining, cathedral ceilings, original HW floors, period detail, fully-applianced kitchen, laundry, basement storage, parking for 4 cars, and abundant outdoor space perfect for gardening, entertaining, relaxing. Whether you're looking to move in, renovate, expand, or explore an ADU or development opportunity, do it here at a convenient Medford location close to Mystic Lake/Shannon Beach, public parks and trails, shopping, dining, schools, The Green Line@Medford/Tufts, Lowell Line commuter rail, Rt 16, I-93, and Route 2. This is truly your chance to create something special in a desirable residential setting

A rare opportunity to own a meticulously restored c.1875 Italianate home where historic character and modern luxury come together beautifully. Known historically as the Howes-Brooks House, this distinctive residence has been thoughtfully renovated with exceptional attention to detail while preserving its architectural heritage. Original character-defining elements-including the double-leaf front doors, decorative eave brackets, window surrounds and classic Italianate proportions-have been carefully restored. Inside, approximately 10-foot soaring ceilings, beautifully finished hardwood floors and expansive living spaces create an impressive sense of scale. The home features a designer kitchen, sophisticated baths and thoughtfully selected finishes throughout. Modern upgrades include new plumbing, electrical and a HERS-rated energy-efficient design with all-electric high-efficiency heating and central air conditioning. Electric Hybrid tank. Set on a level 0.23-acre lot surrounded by matu

Incredible location approximately 1 mile from Oak Grove Station, I-93, the hiking trails at Middlesex Fells Reservation, and walking distance to Fells Pond! This well maintained two family home is ideal for an investor or for an owner occupant looking to occupy a one bedroom apartment. The 3 bedroom (second floor) unit is currently rented through Aug 2027 at $3,000 per month. The 1 bedroom (first floor) unit is rented via tenant at will for $1,950 per month and could be deliverd vacant. First floor unit contains a one bedroom apartment with a walk-in closet, a large mud room/bonus closet space, eat-in kitchen, in unit laundry, and private outdoor deck. Second unit contains 3 bedrooms on two floors, two bathrooms, in unit laundry, large open-concept living room that can also accomodate dining space, and two private outdoor balconies. The units are serviced by a parking lot in the back that can comfortably fit 3 cars, or 4 with a tandem spot. Main roof done in 2023. Please allow 24-48 ho

Expansive modern colonial offering flexibility for multigenerational living. Cozy, semi open concept main floor plan offers beautiful hardwood floors, oversized windows and gas fireplace. The sleek renovated kitchen with working island offers direct access to partially screened in deck with glass inserts, creating an ideal extended space for indoor/outdoor entertaining. The first floor also features a half bath, bonus flex space, and first floor primary complete with engineered hardwoods and dual-entry full bath with convenient laundry. The second floor offers a spacious primary suite with walk-in closet and full bath, three additional bedrooms, full main bath and oversized family room providing versatility and privacy for a large family. The lower level custom in-law suite offers a full kitchen, living/dining area, separate bedroom, full bath with shower stall, storage space and standard size windows with slider leading to a patio and backyard, perfect for family and guests!

Excellent opportunity to own real estate property right off I-95. Owner updated several of the units with great current paying tenants in place. 3 units have leases expiring next year with opportunity to raise rent. Unit 1 is way under market value, opportunity to get much $700+ a month from it. 3 units are first floor. Very versatile property with great margins. 4 units with 3 having seen some recent updates. rent roll is current, property sold as is where is

Discover the timeless character and incredible potential of this classic New England colonial, perfectly positioned on a desirable corner lot where one of the streets is a dead end. A long driveway unfolds toward a detached one-car garage with a spacious storage area, possible conversion to a 2 car garage. A large level yard in a two family zone sets this home apart. Hardwood flooring carries through the living and dining areas and lots of windows draw plenty of natural light throughout the home. The kitchen pairs warm cabinetry with expansive counters and a functional island offering a comfortable space for the cook in you. There is a perfect breakfast room area at the end of the kitchen or perhaps room for a 2nd bathroom and/or 1st flr laundry' Upstairs, three bedrooms showcase wood floors and ample closet space, sharing a newer bath complete with a tiled shower. A convenient walk-up attic provides wonderful extra space for storage or future ideas, while a full unfinished basement wi

The historic Tidd Mansion has been thoughtfully restored, blending timeless elegance with modern comfort. Every major system has been updated, including windows, roof, electrical, heating, and central air. A stunning new kitchen and beautifully appointed new baths bring this grand residence fully into the present while preserving its classic character.Step through the impressive entryway into gracious living and entertaining spaces, including a banquet-size dining room and a formal living room with soaring 10-foot ceilings and exquisite wood detailing.Upstairs, you'll find four spacious bedrooms, three new baths, and a flexible bonus area perfect for a family room, playroom, or studio. A first-floor study, sitting room, chef's kitchen, inviting porch, generous mudroom, and attached two-car garage complete this remarkable home-where historic charm meets modern luxury

Fully enclosed backyard' Yup! we've got that here! Welcome to 6 Carter Place, a hidden gem tucked on a dead-end street near Woburn Center. The backyard is ready for pets, play, gardening, cookouts and relaxing afternoons at home. Need flexibility' Built in 1858, renovated in 2008, this two-level layout with 3 bedrooms on the 2nd floor and a full bath on each floor. Ideal for first-floor living, a dedicated office or comfortable guest space. Generous gathering areas, a spacious kitchen and convenient second-floor laundry make everyday life easier, while the welcoming front porch, four paved off-street parking spaces and full unfinished basement add even more functionality. Downtown dining and shopping, public transportation, parks, schools and major commuter routes are all nearby. Flexible inside, fun outside and close to the conveniences that matter. 6 Carter Place gives you plenty to say yes to

Nestled in the heart of West Medford's prestigious Brook Estates, 32 Sagamore Avenue is a rare opportunity to own a stately circa-1910 Colonial in one of Greater Boston's most admired neighborhoods. Surrounded by grand period homes and picturesque tree-lined streets, this distinguished residence blends timeless architectural character with exceptional potential. Offering six bedrooms, three and a half bathrooms, and over 2,900 square feet of living space, the home features a versatile floor plan ideal for multigenerational living, growing households, or today's work-from-home lifestyle. Original architectural details, generously sized rooms, abundant natural light, and classic craftsmanship provide the perfect foundation to restore, renovate, or customize while preserving the home's historic charm. The beautifully landscaped grounds create inviting outdoor spaces for entertaining, gardening, or simply enjoying the peaceful setting. Located just moments from the Middlesex Fells Reservat

Space, comfort, and effortless entertaining come together in this expansive 5-bedroom home in desirable North Medford. This home provides the flexibility today's buyers need, whether working from home, hosting guests, or simply enjoying extra space with potential for an ADU in the basement. The highlight is the stunning two-level deck complete with an outdoor kitchen, creating the perfect setting for summer cookouts, game days, and gatherings with family and friends. Inside, you'll find generous living areas and two full bathrooms designed for comfortable everyday living. Ideally located just minutes from downtown Boston, this home offers easy access to I-93, Route 28, and public transportation for a seamless commute. Enjoy nearby Middlesex Fells Reservation with miles of trails and outdoor recreation, along with convenient access to Assembly Row, Tufts University, shopping, dining, and everything Medford has to offer. A rare combination of space, convenience, and location

Welcome to 76 Saunders Street! This beautifully updated 3-bedroom, 2-bath single-family home offers a great mix of comfort, privacy, and convenience in a fantastic Medford location. The main level features a bright, open layout with modern updates and plenty of space to make yourself at home. You'll also find a dedicated laundry room, making everyday life a little easier. Upstairs are three bedrooms, including a spacious primary bedroom with a large walk-in closet. There are two full bathrooms -one with a modern glass shower and the other with a convenient shower/tub combination. Step outside and you'll find a large private yard and spacious wrap-around deck-perfect for summer dinners, morning coffee, entertaining friends, or simply enjoying some fresh air. The property also includes tandem parking for two cars, along with plenty of street parking. For those who love the outdoors, the location is hard to beat. Middlesex Fells Reservation, Wright's Pond, and Carr Park are all nearby, gi

Steeped in Medford history and filled with remarkable character, the Bartlett House at 8 Leonard Circle is a distinctive Federal/Greek Revival residence dating to approximately 1820-1830. A legal two-family currently enjoyed as a spacious single-family home, this special property offers exceptional flexibility for a variety of lifestyles and living arrangements. From the inviting three-sided wraparound porch, step inside to discover generously proportioned rooms, stunning hardwood floors with intricate inlaid designs, stained-glass windows, antique lighting, a built-in hutch and four fireplaces. Period details and craftsmanship are found throughout, creating a warmth and character rarely seen in today's homes. The expansive first floor offers wonderful spaces for both everyday living and entertaining, including a gracious living room, dining room, kitchen and eat-in area, den/bedroom and full bath. The second floor provides additional bedrooms, an office, family room, baths, kitchen an

Welcome to 227 Fulton Street, a charming and well-maintained single-family home located in Medford's scenic Fulton Heights neighborhood. Offering 3 bedrooms, 1 full bathroom, approximately 1,620 square feet of living space, an attached garage, and additional off-street parking, this move-in-ready property blends timeless character with everyday comfort.The bright and inviting interior features spacious living and dining areas, a functional fireplace, a well-equipped kitchen, generously sized bedrooms, and abundant natural light throughout. From the second floor, sunroom, and private backyard, enjoy impressive neighborhood views extending toward Cambridge and beyond.Outdoor enthusiasts will appreciate being near Wright's Pond, Carr Park, and the Middlesex Fells Reservation, offering miles of trails for walking, hiking, biking, and exploring nature. The property also provides convenient access to Medford Square, Tufts University, Assembly Row, Station Landing, local restaurants, shopping

A welcoming and sun-filled home with 2 bedrooms and 2 bathrooms. Sited on nearly a 1/4 acre lot with a large fenced-in back-yard with a deck and patio that's perfect for outdoor gathering. Enter into the main floor living room with a bay window that has a south-easterly view letting in plenty of sunshine. The dining area leads to a like new kitchen with an egress to the side deck. Also on the main level are 2 bedrooms and 1 bathroom. One of the bedrooms has a slider right onto the large deck! The lower-level features a large family room, playroom/office, full bath and a laundry area. Some recent updates include kitchen with new appliances(2022), a new roof (2020), fence (2018), bathroom (2016) and finished basement (2016). Easy access to I-95 and Route 3.Offer is due at noon time on Tuesday (09/22/2026)

Set on a tree-lined street in desirable West Medford, this classic two-family has been lovingly cared for and reflects pride of ownership throughout. Bay windows, hardwood floors, high ceilings, and abundant natural light highlight the home's timeless character and architecture. Fully vacant and separately metered, the property offers flexibility for both owner-occupants and investors. Unit one features an oversized 2-bedroom, 1-bath layout with a spacious living room and a dining room. Unit two is a 4-bedroom, 1.5-bath upper-level duplex with three distinct living spaces and a private porch. Additional highlights include a driveway with parking for two cars and a beautifully landscaped backyard offering plenty of room for outdoor enjoyment or potentially more parking. Located just one block from the West Medford commuter rail station, this property provides easy access to local shops, restaurants, parks, and major commuting routes

PERFECT AND READY FOR AN ADU (additional unit IN THE BASEMENT!) Well-maintained single-family home in Medford featuring 4 bedrooms and 2 full bathrooms. Bright living room with large windows and hardwood floors throughout. Formal dining room perfect for entertaining. Updated kitchen with modern cabinetry, stone countertops, stainless steel appliances, and center island. Spacious bedrooms with ample natural light. Two renovated full bathrooms with contemporary finishes and glass shower. Finished basement provides additional flexible space for family room, office, gym, or playroom. Private backyard area with patio space and fire pit ideal for outdoor gatherings. Driveway and attached garage included. Conveniently located near major routes, shopping, restaurants, and parks. A great opportunity to own a spacious home in desirable Medford

3 bed, 2 1/2 bath with 16 solar panels providing ample electricity. Enter a bright sunroom with full-view sliding doors that continue to the in-ground pool and elevated sunning deck, or proceed into the vaulted entry with a view to the second level and decorative drop lights. From here you can step into a sunny living space with a pass-through window to the kitchen, or enter a modern tiled kitchen with newer stainless steel appliances. Sliding doors exit to the pool and new composite deck with hotel-cable railings. Stairs lead to a beautifully finished basement with marble counters, wet bar, and 1/2 bath with washer and dryer, and a new energy-efficient indirect water heater. Excellent off-street parking for 4-5 cars side by side w/o blocking. One block from top parks and pond w/tennis, soccer, baseball and fishing! On newly paved roads with new water mains and gas lines. Minutes to major routes: 93, 60, 28, 16. Less than 30 minutes to beach, airport, and downtown Boston

Fully enclosed backyard' Yup! we've got that here! Welcome to 6 Carter Place, a hidden gem tucked on a dead-end street near Woburn Center. The backyard is ready for pets, play, gardening, cookouts and relaxing afternoons at home. Need flexibility' Built in 1858, renovated in 2008, this two-level layout with 3 bedrooms on the 2nd floor and a full bath on each floor. Ideal for first-floor living, a dedicated office or comfortable guest space. Generous gathering areas, a spacious kitchen and convenient second-floor laundry make everyday life easier, while the welcoming front porch, four paved off-street parking spaces and full unfinished basement add even more functionality. Downtown dining and shopping, public transportation, parks, schools and major commuter routes are all nearby. Flexible inside, fun outside and close to the conveniences that matter. 6 Carter Place gives you plenty to say yes to

As close to new construction as you'll find, this exceptional Colonial was comprehensively renovated in 2016, with numerous additional improvements since. Sophisticated and comfortable, the home offers beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level features hardwood floors, elegant architectural details, and thoughtfully designed spaces. At the center of the home is a spacious eat-in kitchen with island, abundant prep space, and seamless access to the patio and private backyard. A formal dining room, oversized fireplaced living room, first-floor bedroom, mudroom, and half bath provide both functionality and flexibility. Upstairs are two impressive primary suites with cathedral ceilings, walk-in closets, and private baths, along with two additional bedrooms, full bath, and laundry room. The finished lower level includes a spacious family room with fireplace and ample storage. An attached 2-car ga

This Meticulously maintained Colonial Revival is an expansive single-family residence, spanning 4,620 square feet across a generous 22,651SF lot, offering an exceptional blend of space and sophisticated living. The residence features Bedrooms (6), Bathrooms (4), Entertaining areas (3), Laundry rooms (2), Kitchens (2), Fireplaces (2) and a Full bar, providing more than ample space for family and guests ensuring convenience and comfort for all occupants. The property includes a Two-Car Garage, Sheds (2) Driveways (2) and a Rooftop Deck. Located.6 miles from the 1-95/Route 128 the property offers combination of both convenience and privacy. This exceptional property invites you to experience refined living; schedule your private viewing today

The historic Tidd Mansion has been thoughtfully restored, blending timeless elegance with modern comfort. Every major system has been updated, including windows, roof, electrical, heating, and central air. A stunning new kitchen and beautifully appointed new baths bring this grand residence fully into the present while preserving its classic character.Step through the impressive entryway into gracious living and entertaining spaces, including a banquet-size dining room and a formal living room with soaring 10-foot ceilings and exquisite wood detailing.Upstairs, you'll find four spacious bedrooms, three new baths, and a flexible bonus area perfect for a family room, playroom, or studio. A first-floor study, sitting room, chef's kitchen, inviting porch, generous mudroom, and attached two-car garage complete this remarkable home-where historic charm meets modern luxury

When opportunity knocks, 250 Tremont answers with open doors! This is a fantastic chance for first-time buyers and savvy investors alike. Imagine moving in and having the additional unit help cover your expenses, or purchasing this property as an investment and watching your equity grow over time. Prime Location - The location couldn't be more ideal-just around the corner from the commuter rail and the vibrant Melrose Highlands, known for its eclectic shops and delightful restaurants. With easy access to Routes 1 and I-93, commuting and exploring the area is a breeze. Well-Maintained Property - The current owner has meticulously cared for this property, ensuring it remains in excellent condition. Both units feature two bedrooms, with the second-floor unit boasting an extra bonus room currently utilized as a spacious walk-in closet. Enjoy updated kitchens and bathrooms, separate utilities for each unit, convenient laundry facilities in the building, and ample off-street parking.Don't mi

RARE WATERFRONT OPPORTUNITY on Upper Mystic Lake with spectacular sunset views! Tucked away on Lakeview Terrace, this special 1910 home offers a combination rarely found in Winchester: waterfront living, privacy, beautiful southwest light and exceptional convenience. Gracious rooms, period details and quality craftsmanship give the home wonderful character, while its generous layout offers an exciting opportunity to update and create something truly special. The home features 5-6 bedrooms, a home office and expansive living spaces designed to take advantage of the lake views. The kitchen, renovated some years ago, was thoughtfully positioned so the view can be enjoyed while preparing meals. An unfinished lower level with high ceilings offers additional possibilities. Just steps from Wedgemere Commuter Rail Station, 1/2 mile to Shannon Beach and less than a mile to Winchester Center via the Tri-Community Bikeway. A remarkable setting, beautiful sunsets and an opportunity that may not co

Tucked away on a quiet dead-end street, 111 Mitchell Ave is a home that feels inviting from the moment you walk in. Offering 3 bedrooms, 2.5 baths and approximately 1,854 sq ft, the home blends character, comfort and thoughtful updates. The standout is the beautifully renovated sunroom, transformed in 2023 with vaulted ceilings, warm wood accents, oversized windows and its own mini-split-an easy favorite for morning coffee, relaxing or entertaining year-round. A renovated primary bath, four mini-splits installed in 2025, upgraded 200-amp electrical and a flexible finished lower level add even more value. Refreshed front steps and landscaping complete the package, all just minutes from Route 93, the Fellsway, Wright's Pond, shopping, dining and public transportation

Expansive modern colonial offering flexibility for multigenerational living. Cozy, semi open concept main floor plan offers beautiful hardwood floors, oversized windows and gas fireplace. The sleek renovated kitchen with working island offers direct access to partially screened in deck with glass inserts, creating an ideal extended space for indoor/outdoor entertaining. The first floor also features a half bath, bonus flex space, and first floor primary complete with engineered hardwoods and dual-entry full bath with convenient laundry. The second floor offers a spacious primary suite with walk-in closet and full bath, three additional bedrooms, full main bath and oversized family room providing versatility and privacy for a large family. The lower level custom in-law suite offers a full kitchen, living/dining area, separate bedroom, full bath with shower stall, storage space and standard size windows with slider leading to a patio and backyard, perfect for family and guests!

Introducing The Homes@Mary Kenney Way, an exclusive new cul-de-sac community in the highly sought-after West Medford area, just 10 minutes from Boston. This limited collection of 10 architecturally crafted single-family luxury homes is tailored for today's modern living. Each residence boasts 3 spacious bedrooms (EXPANDABLE TO 5), 3.5 baths, and an expansive, open-concept first floor designed for comfort and flexibility. Perfect for both work and entertaining, the layout includes multiple living areas, a wet bar, and formal dining spaces, all bathed in natural light from soaring ceilings. Crafted with impeccable attention to detail, the interiors feature wide plank white oak floors, custom cabinetry, elegant built-ins, and a thoughtfully appointed wet bar. With only 10 homes available, this is a rare opportunity to customize your dream home in a vibrant, new community. Reserve your space now, as demand is high for this soon-to-be jewel just minutes from the city