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

Welcome to this beautifully maintained residence nestled in the coveted Brooks Estate neighborhood. Step inside to a lovely spiral staircase and a welcoming foyer, opening to a formal living-room with a fireplace and rich period details, including wood-paneled walls, built-in bookcases and beveled glass windows. Just beyond the living-room, find a fabulous screened-in porch and French-glass doors leading to the spacious kitchen and dining room, which features abundant cabinets and premium appliances. Sliding glass doors open to a private, fenced backyard with mature plantings, a patio, and a newer deck with an awning. A half-bath completes the main level. The second floor offers four spacious bedrooms, a full bath, and a hallway with built-in linen cabinets and drawers. Need extra space for family or guests' The lower level offers an additional 884 sq. ft. of updated finished space, including a kitchenette and bathroom. Prime location: close to the Mystic Lakes, commuter rail, Whole Fo

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

This well-loved two-family home bordering the Lawrence Estates neighborhood of Medford has been well cared for by the same family for over 80 years. This home sits on a corner lot just 0.5 miles from vibrant downtown Medford Square, offering a quiet residential setting with fast access to local shops, parks and commuter routes. The house is located on 7500 sq. ft. of level land with a large yard/garden area, a two-car garage and additional parking for up to six cars in the driveway. The first-floor unit opens to a lovely foyer, living room, dining room, 2 bedrooms, 1 bath and an eat-in-kitchen. The second-floor unit consists of a large open living/dining area, 3 bedrooms, 1 bath and an eat-in-kitchen. The home has gleaming hardwood floors throughout, tile baths and front and rear enclosed porches. The large open basement contains all separate utilities for each unit. Blown in insulation, double pained windows and roof were all replaced within the past 15 years, all in good condition wi

Completely reimagined and gut-renovated in 2023, this exceptional home blends sophisticated design with modern luxury. The main level features an expansive open-concept living area centered around a spectacular chef's kitchen, custom arched built-ins, and a sleek gas fireplace. Upstairs, the luxurious primary suite offers dual closets and a spa-inspired bath with a soaking tub and oversized walk-in shower with dual shower heads. Two additional bedrooms, a full bath, and laundry complete the second floor. The ground level features a spacious flex room with a wet bar, while the top floor offers an additional bedroom, full bath, and bonus living area that opens to a private roof deck. Enjoy a private yard, two parking spaces, including a garage with EV hookup, and an unbeatable location near Tufts University, the Green Line, West Medford Commuter Rail, and I-93

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

Meticulously maintained Medford 2-family with lots of updates by the current owner that still offers an opportunity for upside improvements. Both units have had regular updates, including recently refinished hardwood floors, regular paint updates, and updated kitchens and baths. Both units are currently rented under leases, making it a great investment property with an opportunity for future owner-occupancy. The walk-up heated attic provides a great opportunity for expanding the 2nd-floor unit. Electric was updated to 200amp, boilers were done in the early 2000s, and water heaters were recently replaced. The roof was done in 2008. Full basement waterproofing just completed. Mini splits were added to unit 2 in 2020, and 1st floor windows have just been updated

Rare Two-Unit Offering in Prime Medford Location! This exceptional offering combines the expansive lower-level Unit 9 with the detached ADU, Unit 9A, creating a truly unique opportunity to own two residences together. Unit 9 features three bedrooms and two full bathrooms with thoughtfully designed living space, modern finishes, and an ideal layout for comfortable everyday living. The additional 9A ADU offers a private two-bedroom, two-bathroom residence, providing exceptional flexibility for extended family, guests, a home office setup, or additional rental income. Live in one and rent the other, accommodate family members while maintaining privacy, or take advantage of the strong rental demand in Medford. With contemporary construction, separate living spaces, and an incredibly convenient location close to public transportation, major highways, shopping, dining, and everything Medford has to offer, this is a rare opportunity for both homeowners and investors. A distinctive property of

OPEN HOUSE for WEDNESDAY, AUGUST 19TH HAS BEEN CANCELLED.* OFFERS ARE DUE BY WEDNESDAY, AUGUST 19TH BY 4:00PM. *Please submit your PDF offer to the email address noted below. * Welcome to this charming ranch style home that offers 2 bed, 1 bath situated on.43 acre lot in a great neighborhood. Walk through the front door to an open floor plan with kitchen, dining area and living room with fireplace featuring vaulted ceilings. Great living space with lots of closets, 1st floor laundry and hardwood floors throughout. Walk through the side entrance into a cozy sunroom filled with natural light. Basement is unfinished with lots storage space and bulkhead to backyard. House was completely renovated in 2014, completely gutted to the studs, all new electrical, plumbing, heating system and roof. Conveniently located with access to shopping, restaurants, schools, parks, and commuter rail. This home is a must see

Some homes are simply a place to live. Others become the backdrop to years of memories-and 10 Albion Street is ready for its next chapter. This classic Colonial offers an impressive amount of space with a layout that provides flexibility throughout. The second floor features three well-proportioned bedrooms plus a separate office, while the finished attic adds valuable additional living space and has been used as a fourth bedroom. With two full bathrooms and multiple levels of finished space, there's room to spread out, work from home, entertain, or simply enjoy having a little extra breathing room. Thoughtfully cared for over the years, recent improvements include a new roof and gutters in 2024, along with new decking and power vented hot water tank completed the same year. Set in an excellent Medford location with convenient access to neighborhood amenities, Ball Square Train stop, and everything the city has to offer. 10 Albion Street has been a place where memories were made for ye

Perfectly poised cape style home with beautiful curb appeal in central square. Offering one story living with incredible expansion potential, this flexible floorplan serves as an amazing condo alternative. A lovely farmers porch welcomes you before entering the living room with brand new carpet. A bedroom or sunny office space sits adjacent before leading into the eat in kitchen. A dining room with hardwood flooring offers views through a sliding door to the private backyard. The full bath has access from the hallway as well as into the primary bedroom with ample room for a king sized bed. The second level is accessible from stairs off of the living room and is unfinished but offers rough plumbing for future use. A massive basement also serves as future expansion potential and offers plenty of storage space. Enjoy the home's central location which is walking distance to new Wyman/Hurld elementary school, close to major highways, Woburn Village amenities and Woburn center

Historic character meets modern luxury with exquisite design details in this beautifully reimagined Victorian in Medford's desirable Hillside Historic District. Renovated for today's lifestyle while preserving the elements that make the home special, 20 Hillside features gracious entertaining rooms, soaring ceilings, original hardwood floors, graceful archways, antique door hardware, distinctive millwork and a finely preserved fireplace mantel.The stunning,new kitchen serves as the heart of the home, appointed with a Wolf induction range, Bosch appliances, quartz countertops, cabinetry extending to the 9' ceilings, a pantry, coffee bar and wine fridge. Just beyond, elegant living and dining areas provide an inviting backdrop for everything from casual gatherings to holiday entertaining.Upstairs, the expansive primary suite feels like a private retreat, complete with two closets and a spa-inspired bath featuring a soaking tub, walk-in shower and double vanity. A second bedroom and addit

This move-in ready 3b/2b home offers a smart, flexible layout with convenient access to Boston - ideal for those who want space, function, and connectivity. The open-concept kitchen and dining area is designed for everyday living, featuring tile backsplash, luxury plank flooring, refinished cabinetry, and updated appliances. Hardwood floors flow through the main living areas, freshly sanded, stained, and sealed to a clean, polished finish. Both full bathrooms have been thoughtfully updated - one showcasing fresh tiling, a new tub, and a sleek vanity. The converted garage delivers a true year-round office or rec room, complete with windows, a dedicated heat source, and updated flooring. Outside, a refreshed patio, updated deck, rebuilt front stairs with quality pressure-treated materials, updated siding, and refreshed exterior lighting create strong curb appeal and inviting outdoor living. A garage, generous backyard, and abundant natural light complete this well-appointed home

New construction in desirable town of Melrose! This home features 9-ft ceilings and an open floor plan designed for today's buyers. The chef's kitchen offers white cabinetry, quartz countertops, an horseshoe island, stainless steel appliances w/industrial hood, flowing into a bright family room w/grey floor to ceiling ct fireplace access to a covered composite deck-perfect for entertaining w/Boston skyline views. The dining room w/custom moldings and wet bar connects seamlessly to the kitchen, while a first-floor living room is ideal as a playroom or office. Upstairs includes 4 bedrooms, 3Full Baths and Laundry room. Luxurious primary suite w/double quartz vanities, tiled shower, and two walk-in closets. A 5th bedroom, full bath, office, and bonus space on the upper level ideal nanny or guest suite. Lower level features exercise room, mudroom, and 3-car garage. Minutes to downtown Melrose; Starbucks, Whole Foods, Fine Dining, Shopping, Golf, Public Transportation the Commuter Rail and

Exactly what the right buyer has been waiting for. Let's get the obvious out of the way first: This isn't your typical MLS listing. 84 Orchard Street has been condemned by the city due to broken plumbing pipes and flooding. It's being sold strictly as-is, where-is, and no interior access is permitted.Now for the fun part: Behind today's challenges is a classic two-family in Medford's sought-after Hillside neighborhood with a timeless layout, off-street parking, a nice little backyard, and potential to expand into the walk-up attic and lower level (buyer to perform all due diligence). Situated moments from Tufts University, the Green Line Extension, and the best restaurants and shopping Medford has to offer, the location is unbeatable. This isn't just a renovation project-it's a blank canvas in one of the most resilient markets in the Greater Boston area. Some buyers will scroll right past this listing. The right buyer will stop scrolling. Roll up your sleeves, assemble your team, let y

PRICE ADJUSTMENT! Impressive residence on Winchester line where timeless sophistication, exceptional land and an unrivaled setting create a truly rare find. Beautifully set on a 19K sq ft wooded lot directly across from the Middlesex Fells, this stately beauty boasts the feel of peaceful seclusion yet is only minutes to I-93 and the area's finest amenities: dining, shops, Wright's Pond and more. Rich in character and classic details, this home showcases hardwd floors on all 3 levels, distinctive woodwork, moldings, wainscotting, Fr doors, and custom built-ins. Gracious, well-appointed space: elegant front-to-back fireplaced LR opens to sun-filled den. DR leads to spacious kitchen w/oversized counters and charming custom eating area. Relax in the screened-in porch, on the private deck off the primary BR suite, or the patio and take in the serenity of your surroundings. Versatile living w/3 more BRs on 2nd level; BR and bath w/clawfoot tub on 3rd level, and room to expand. Create a lifes

Welcome to this charming 3-bedroom central-entrance Colonial in desirable Lawrence Estates, offering a wonderful combination of classic character, spacious living areas, and expansion potential. The front-to-back primary bedroom provides generous space and comfort, while the fireplace living room creates a warm and inviting setting. The spacious kitchen offers ample cabinetry and a dedicated dining area, complemented by a formal dining room with a built-in hutch. A first-floor office provides a convenient work-from-home space. The unfinished basement offers excellent storage and utility space, while the expandable walk-up attic presents exciting potential for future expansion. Additional features include 2.0 baths, ceramic tile, and a one-car garage. Outside, professionally landscaped grounds create a beautiful setting, with a gorgeous patio perfect for relaxing, entertaining, and enjoying the outdoors. The property offers a peaceful and private feel while remaining convenient to local

UNRIVALED ACCESS! PRIVATE VIEWINGS ONLY! Timeless New England charm meets prime Winchester living at 9 Priscilla Lane. Tucked along a quiet, tree-lined neighborhood on Winchester's East side, this inviting 4-bedroom home offers the perfect balance of suburban tranquility, outdoor adventure, and seamless connectivity.Inside, the sun-drenched home features rich hardwood floors, a gorgeous kitchen, wood burning fireplace, flexible living areas, and an intuitive layout designed for both daily relaxation and effortless entertaining. Step outside to an expansive, private backyard-a sunlit haven perfect for weekend barbecues, garden projects, or crisp New England evenings.Outdoor enthusiasts will love living moments away from the endless hiking, trail running, and scenic escapes of the Middlesex Fells Reservation. For commuters, rapid access to I-93 and Route 128/I-95, combined with nearby Commuter Rail stations, makes reaching Boston, Cambridge, or local tech hubs exceptionally fast and dire

Don't miss out on this opportunity! Highly desirable Medford loaction. This 4 Bedroom 2 1/2 bath colonial style home is located within close proximity to Boston, Tufts University, parks, restaurants and shopping with easy access to major highways and public transportation. When you enter the first floor, you're greeted with a large foyer and spacious living room that leads to the kitchen and beautiful outside deck. The first floor also has a full bath, bedroom and office. On the second floor there are 3 Bedrooms and a half bath. The roof is three years old with 30 year Architectural Shingles and there is a natural gas furnace that is also only 3yrs old. This house is priced to sell and won't last!

LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center and steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance and sweeping water views from every room! Located in one of Winchester's most sought-after neighborhoods, the home blends high ceilings, rich original details, and a flowing floor plan ideal for both everyday living and elegant entertaining. The 2 room primary suite features a sitting room w/ fireplace, spa-like bath, and BR w/ picture window and stunning lake views. 4 bedrooms on the second floor plus 2 on the 3rd offer space for all. Step outside to a welcoming deck, level lawn, and lakeside fire pit. perfect for hosting or unwinding. Enjoy direct access to the lake for paddle-boarding, kayaking, and fishing direct rom your back yard

New construction in desirable town of Melrose! This home features 9-ft ceilings and an open floor plan designed for today's buyers. The chef's kitchen offers white cabinetry, quartz countertops, an oversized island, stainless steel appliances w/hood, flowing into a bright family room w/grey ct floor to ceiling fireplace and access to a covered composite deck-perfect for entertaining with Boston skyline views. The dining room w/custom moldings and wet bar connects seamlessly to the kitchen, while a first-floor living room is ideal as a playroom or office. Upstairs includes 4 bedrooms, 3 Baths and Laundry. Luxurious primary suite w/double quartz vanities, tiled shower, and two walk-in closets. A 5th bedroom, full bath, office, and bonus space on the upper level ideal nanny or guest suite. Lower level features exercise room, full bath, mudroom, 3-car garage. Minutes to downtown Melrose; Starbucks, Whole Foods, Fine Dining, Shopping, Golf, Public Transportation the Commuter Rail and All Ma

A truly unique 3-family property located just 5 miles north of Boston. All units consist of 2 levels of living. Starting with the owner's unit. Enjoy the oversized primary suite, with hot tub fireplace and walk in closet. Not to be out done, the rest of the unit boasts great space throughout. From a finished basement to a sunroom/den area leading to a covered rear deck and private pool oasis, that includes a pool house with full kitchenette. You get the true feeling of living in a single family, but with the benefits of rental income. Unit 2 is updated and has a townhouse layout with living room and eat in kitchen on the main level and 2 bedrooms and full bathroom upstairs. Unit 2R is in overall good condition. The main level has the primary bedroom, bathroom and living room; small staircase leading down to kitchen and 2nd bedroom. Other features include central heat/ac in owner's unit. 2 storage sheds, 8 car parking and carport. Close to I-93 and within walking distance to Medford Sq

Fully renovated and move-in ready, this classic North Medford Colonial delivers modern style, flexible living and exceptional outdoor space on a rare 11,000+ sq. ft. lot. Offering approximately 1,445 sq. ft. across three finished levels, the home features two bedrooms, 1.5 updated baths, a dedicated home office and a versatile bonus room ideal for fitness, media, hobbies or guests. The chef-inspired kitchen is the heart of the home, showcasing custom cabinetry, quartz countertops, stainless steel appliances, gas cooking, a direct-vented hood and an oversized center island designed for gathering. Hardwood floors, contemporary lighting, a fresh neutral palette and two distinct living areas create a warm, polished setting for everyday life and entertaining. Upstairs, two well-proportioned bedrooms and a renovated full bath provide a comfortable retreat. The finished walkout lower level expands the possibilities with valuable work-from-home and recreation space. Major improvements include

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

Some homes are simply a place to live. Others become the backdrop to years of memories-and 10 Albion Street is ready for its next chapter. This classic Colonial offers an impressive amount of space with a layout that provides flexibility throughout. The second floor features three well-proportioned bedrooms plus a separate office, while the finished attic adds valuable additional living space and has been used as a fourth bedroom. With two full bathrooms and multiple levels of finished space, there's room to spread out, work from home, entertain, or simply enjoy having a little extra breathing room. Thoughtfully cared for over the years, recent improvements include a new roof and gutters in 2024, along with new decking and power vented hot water tank completed the same year. Set in an excellent Medford location with convenient access to neighborhood amenities, Ball Square Train stop, and everything the city has to offer. 10 Albion Street has been a place where memories were made for ye

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

Perfectly poised cape style home with beautiful curb appeal in central square. Offering one story living with incredible expansion potential, this flexible floorplan serves as an amazing condo alternative. A lovely farmers porch welcomes you before entering the living room with brand new carpet. A bedroom or sunny office space sits adjacent before leading into the eat in kitchen. A dining room with hardwood flooring offers views through a sliding door to the private backyard. The full bath has access from the hallway as well as into the primary bedroom with ample room for a king sized bed. The second level is accessible from stairs off of the living room and is unfinished but offers rough plumbing for future use. A massive basement also serves as future expansion potential and offers plenty of storage space. Enjoy the home's central location which is walking distance to new Wyman/Hurld elementary school, close to major highways, Woburn Village amenities and Woburn center

Charming Tufts-area bungalow. This sweet home offers comfortable one-level living w/ beautiful hardwood floors throughout most of the main level, an eat-in kitchen, formal dining room with built-in hutch, and an updated bathroom. Currently configured as a one-bedroom home, the flexible layout offers the possibility of creating a second bedroom. Updates include vinyl replacement windows throughout most of the home. The attic provides a great storage area. Enjoy a large lot with a fenced yard, storage shed, and a driveway offering 3+ parking spaces. Gas heat and cooking. 100-amp electrical service. The spacious lot may offer potential for future expansion, subject to approvals. This is a from an estate. Property is being sold as-is. First showings at open house on 8/22/2026

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)

Welcome to 76 Harrison Avenue. Discover the potential of this quaint New England Colonial set on an 8000+/- sq. ft level lot. This charming 2 bedroom home offers hardwood floors, high ceilings and 2 built in hutches. First floor is a formal living room opens to large kitchen with separate dining area. First floor laundry off the kitchen.Second floor has 2 good sized bedrooms with a full updated bath. Walk up to 3rd floor for expansion. Walking distance to Horn Pond, downtown Woburn and restaurants, Library Park and pickleball courts

Step into 50 Stearns Avenue and you'll immediately feel the warmth of a home that perfectly balances classic Medford character with the space you've been searching for. From the moment you arrive, the enclosed front porch offers a bright, welcoming spot to enjoy your morning coffee or settle in with a good book. Inside, the craftsmanship takes center stage. You'll find original hardwood floors that have been meticulously maintained, stretching across an inviting layout. The living space is anchored by a stunning, full-brick accent wall, adding a layer of texture and timeless style that's hard to find. The heart of the home is a fully equipped kitchen, ready for everything from quick weeknight meals to holiday hosting. The transitions between indoor and outdoor living are where this property truly shines. Off the back, a sun-drenched sunroom provides a peaceful retreat regardless of the season. If you love to entertain, the two full decks offer incredible versatility for al fresco dinin