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

Sat (5/23) 11:30-1:00 group showing. Welcome to this bright, well-maintained condo in a professionally managed building. This spacious upper-floor unit offers comfortable living a functional layout and beautiful views. The home features a generous living area, ample closet space, and a well appointed kitchen. What truly sets this property apart is the unparalleled facility package arguably the best amenity building in Medford and neighboring towns. Residents enjoy an indoor heated swimming pool, saunas, squash and racquetball courts, a fitness center, and a stylish clubroom with a public kitchen for entertaining. Residents also benefit from elevator access and pristine common areas. Perfectly located near Assembly Row, Wellington Station, R93, and downtown Boston, this home offers the ultimate balance of relaxation, active living, and urban accessibility. Experience a premium lifestyle in a highly desirable location. Don't miss this standout opportunity

Beautiful 3-Bedroom Condo overlooks the Mystic River and a delightful park setting directly outside your door! Converted and Renovated in 2018 from top to bottom including new Electrical and Plumbing, new Natural Gas Heating and Central Air. Wonderful Open Concept throughout main living spaces with high ceilings and lots of bright sunshine! Fabulous Gourmet Kitchen featuring Breakfast Bar, stainless steel appliances, and polished Quartz countertops. Gorgeous hardwood floors. Tastefully done tiled bathroom. Welcoming front porch enjoys sunset views of the Mystic River, and the private back porch overlooks a well manicured yard with pretty gardens. Full storage in basement. Two off-street parking spaces. Walk to the Boston Commuter Rail. Tufts University, 10 minutes to Harvard Square, and easy access to all major routes. You won't want to miss this lovely home in a super special location!

Take the opportunity to experience this move in ready, 3-level, freshly updated 4bed/1.5 bath townhouse. Refinished hardwood, new SS appliances, and a renovated half bath are the highlights of the first level. The second level consists of 2 beds and the updated full bathroom. There are 2 more generously sized rooms to complete the 3rd level There are many options on how to use this move in ready space that this property has to offer. Enjoy the views of Horn pond from the private rear deck. With seamless access to I-95/I-93 and within miles of Boston, this makes an attractive prospect for many. Make this property yours by scheduling your showing today

Move-in ready corner unit in a super convenient location! This bright home features a spacious living/dining room with an oversized east-facing picture window, an updated kitchen, two generously sized bedrooms, and a full bath. Enjoy close proximity to the Middlesex Fells Reservation, Wright's Pond, Spot Pond, and other parks, with easy access to I-93, public transportation, and Medford Square. Heat and hot water are included in the condo fee. Additional amenities include laundry in the building, elevator access, assigned parking (spot #36) in a secure, camera-monitored lot, and on-street permit parking. Professionally managed, well-maintained brick building with beautiful outdoor common space. Cats allowed. Some photos are virtually staged. A wonderful place to call home! Open House Sunday 6/7 1-2 pm

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

Prepare to fall in love with this exceptional, turnkey Medford Square condo, where classic architectural charm meets a beautifully modernized interior. The inviting, open-concept layout showcases pristine hardwood floors that flow into a sleek, contemporary kitchen fully equipped with premium Quartz countertops and stainless steel appliances. A sun-drenched sunroom offers the perfect dedicated home office or reading nook, while the convenience of in-unit laundry accommodates daily routines. Boasting a 92 Walk Score(R), this vibrant location places you moments from the historic Chevalier Theatre, local cafes, and dining. Commuting is seamless with immediate access to I-93 and quick transit connections to the Medford/Tufts Green Line T. Rare exterior amenities include a shared backyard and two coveted parking spaces, including a detached garage spot providing excellent additional storage. The ideal place to call home, with city convenience right at your doorstep

Beautifully remodeled in 2013, this spacious 3-bedroom townhome in Woburn offers approximately 1,200 sq ft of comfortable living space with large rooms, hardwood flooring, and high ceilings throughout. The updated kitchen features a center island and plenty of workspace for everyday cooking and entertaining. Additional highlights include 1.5 baths, in-unit laundry, and two assigned off-street parking spaces with easy EV charging access. Enjoy access to a common-area backyard, plus a commuter-friendly location convenient to major highways, restaurants, and everyday amenities

Conveniently located in the impeccably maintained Place Lane community, this meticulously cared for 2bd 2bth end-unit offers low maintenance and resort style iving. The layout features two spacious bedrooms, including a desirable primary with en-suite bath and two full-size closets, central air, and an open-concept kitchen, dining, and living area ideal for both everyday living and entertaining. The spacious, sun-filled living room creates a warm and inviting atmosphere and features recessed lighting and LVP flooring. Stainless steel gas range and microwave, young hot water tank (2019), newer windows and in-unit washer/dryer add everyday convenience. Exceptional storage throughout includes hallway linen and entryway closets, along with utility room storage. Additional amenities include elevator, assigned parking, ample guest parking, tennis court, outdoor pool and inside bike storage.Ideally situated close to downtown Woburn, commuter rail and easy highway access

This isn't just another Cape-it's the one. Tucked into one of Melrose's most walkable neighborhoods, this home delivers the trifecta: classic New England character, practical modern living, and a true primary suite-all with standout curb appeal. Step inside and you're home! The sun-drenched kitchen is perfect for entertaining, featuring a Thermador cooktop w/pot-filler and microwave and wall oven. The first floor flows beautifully from the kitchen to the dining room and into an oversized fireplaced living room. Off kitchen, a cozy screened-in porch begs for outdoor movie nights! Upstairs offers 3 generously sized bedrooms, full bath, storage closets and spacious primary suite with a large walk-in shower and ample storage. Need more' Mini splits for AC and a finished basement ideal for a home office, playroom, or den, an attached garage, 2 fireplaces, and a backyard made for relaxing and BBQs. All this in the Horace Mann neighborhood, a short walk to everything that makes Melrose so liv

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 !

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

2 family split-entry style set on a large 9,583 sq ft lot! Ideal for investment, owner-occupants, multi-generational living or development potential. Each unit offers 2 beds, 1 bath, laundry hookups, separate utilities, generous parking with dedicated driveways and private yards. The recently renovated 1st floor unit highlights a kitchen with white cabinetry, granite countertops, cozy living room, and sleek bathroom with tub. The 2nd floor unit has just undergone a complete renovation and showcases a new kitchen, inviting living room, bathroom with tub, tile flooring, shelving, and dedicated laundry room with hookups. Separate utilities. Electric baseboard heat throughout both units. Newer roof in 2022, vinyl siding, and a large level lot. Convenient location perfect for commuters going into Boston. Close to shopping, dining, and major highways (I-93 and I-95). Whether seeking rental income, flexible living or future possibilities, this property delivers exceptional value

Discover the charm and potential of 265 Main Street in Melrose, a 3-bedroom, 2-bath home ready for its next chapter. This inviting property features high ceilings, a wonderful sense of space, and a flexible layout with great bones-ideal for bringing your vision to life. Inside, you'll find a bright and spacious family room filled with natural light from an abundance of windows, while the impressive ceiling height enhances the open feel. The living room offers a cozy gas fireplace, and charming built-in china cabinets add character and timeless appeal. A private home office provides the perfect space for remote work or a quiet retreat. The home also includes a one-car garage and a lovely backyard with room to relax, garden, or entertain. Set in a phenomenal location, you're just moments from downtown Melrose, Sylvan Street Park, and the Oak Grove train station, making commuting, dining, shopping, and everyday conveniences incredibly accessible. Don't miss this opportunity to make this h

Dramatic price improvement! Much bigger than it looks, this fully updated Cape features 4 bedrooms and 3 full baths spread across three fully-finished levels. Plenty of room to spread out in the giant living room with charming pellet stove and in the open floor plan kitchen/dining area. Upstairs are three bedrooms, including a very large primary. The lower level in-law suite has a separate walk-out entrance (requiring NO STAIRS from the driveway), which opens up so many possibilities: extended family living, teen suite, au pair quarters, or maybe the possibility of rental income from an ADU. Endless summertime fun awaits in the fully fenced yard, on the recently renovated deck, and on the charming brick patio. Many recent updates including BRAND NEW A/C system. Phenomenal location 1 mile to commuter rail, close to bus and Orange Line, less than 2 miles to the Fells, very close to all schools and the Early Childhood Center, and near numerous shops, restaurants and markets in downtown Me

Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living and dinning area with a family room. 2nd floor featuring (3) main bedroom with full baths suites. The stunning finished lower level includes a custom wine cellar and recreation area, and flexible rooms perfect for a home office, gym, media room, or guest accommodations. Ideally located just minutes from Winchester's highly rated schools, town center, parks, dining, and commuter routes. Move-in ready and thoughtfully redesigned for modern living-this is a rare opportunity in one of Winchester's most sought-after neighborhoods

Presenting a truly exceptional and one-of-a-kind renovation, thoughtfully designed with the latest in modern smart-home technology. It's offering easy access to major universities such as Harvard, Tufts, and MIT. The main house spans three levels and over 1900 sq. ft. of living space. It artfully balances preserved architectural details with high-end finishes, creating an atmosphere that is both warm and modern. The X-factor is a rare, detached, two-story matching building. Featuring three finished rooms, this versatile space is limited only by your imagination-think professional home studio, private guest wing, or the ultimate in-law suite. Enjoy your private deck, which leads to a four-car driveway with EV charging. You are close to the Somerville line and minutes from the Green Line extension and Route 93. SCHEDULE YOUR SHOWING TODAY!

Beautifully updated single-family cape in a prime Medford location! This 3-bedroom, 2 full bath home offers an open and inviting floor plan with hardwood floors throughout and stylish kitchen and bathroom upgrades. The spacious main level features a bright living area, oversized kitchen with island seating, and a first-floor bedroom perfect for guests, office, or flexible living. Upstairs, the primary suite includes a full bath with a double vanity and a walk-in closet, while the second bedroom offers a deep closet and a private balcony. The lower level is prepped for finishing with heat, a finished ceiling with recessed lighting, and partially finished walls. Enjoy a large backyard with endless potential, a detached garage, and ample off-street parking. Minutes to Assembly Row, Wellington Station, major highways, and an easy commute to Boston by car or public transportation. Open House on Sunday, 4/26 from 11:30 AM-1:00 PM

Place Lane Condominiums! Looking for a home for the large or extended family or a home office, this 2 - level, 9 room, 4-bedroom, 3 bath Condominium is perfect for all of your needs. 2800 sq ft and 2 floors of living space. ss appliances, hardwood floors, wall to wall carpet, Gas heat, Central Air, and Central Vac, Enjoy your patio and private entrance from your parking space. Conveniently located near downtown Woburn, Rt 95 and 128, shopping, Bus and Train. Call today for your private viewing. Bring Offers !

Open House - Sunday 12-1:45. Currently Rented for $5,875/mo!. READY FOR AN OWNER OCCUPANT! Perched at the top of one of Medford's most sought-after hills/neighborhoods, this stunning 5-bedroom, 5-bath single-family home offers four levels of fully renovated living space, including a brand-new third floor addition. Enjoy breathtaking views of the Boston skyline from this hilltop retreat, blending modern style with exceptional functionality. The home features spacious, sun-filled rooms, a sleek contemporary kitchen, and three bedrooms with en-suite bathrooms, perfect for today's lifestyle. Thoughtful updates and high-end finishes are showcased throughout, providing a turnkey living experience. With parking for 3-4 cars, this property offers both convenience and comfort in a prime location. Just minutes from local shops, dining, and transit, it's an incredible opportunity to own a move-in ready home in an amazing community. Don't miss it!

Rarely available! A true Penthouse w/exclusive wrap-around 40'x19' roof-top deck w/atrium and amazing tree-top views!This sunny Southwest corner unit w/1,644 sq ft. lives like a single family Ranch style home and features a HUGE Primary ensuite, smooth ceilings, a 2nd balcony, gorgeous custom Chef's kitchen w/Bosch stainless steel appliances, double wall ovens, induction stove top, Quartz counters and recessed lighting. Open and flexible floor plan, w/a 3rd bedroom which has a huge 2nd walk-in closet, custom built-ins and can be used as a 2nd Primary Suite or Family Room w/direct access to the atrium. Includes 2 GARAGE parking spaces, PLUS 1 outdoor space, located right outside the rear door. Easy walk to Orange Line Train, Mystic River Reservation and Marina, Station Landing and the ever expanding Assembly Row with all the bars, shops, restaurants and entertainment it offers. Via car or boat, minutes to the Encore Casino Resort. Minutes to Downtown Boston. Community offers Pool, sauna

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

ATTENTION INVESTORS FLIPPERS and CONTRACTORS! This 4-bedroom 2 bath (public record has it as 1 bath) Colonial home is ready for a rehab. First floor has 2 kitchens, bedroom, full bathroom, dining room, living room and laundry. Second floor has 3 bedrooms and a full bathroom. 3rd floor has 2 bonus rooms that could be used as bedrooms and an unfinished bathroom. With over 3,000sqft, 11 rooms and the potential for more bedrooms and baths, this is truly a diamond in the rough! Only minutes from the highway, fenced in yard, driveway, vinyl sided and roof is newer but small flat roof needs to be replaced. Home is heated by gas forced hot water radiators. This home is in need of more than just some elbow grease. Perfect project for someone looking to build major equity. Being sold AS IS - AS SEEN. Will not pass FHA or VA. Seller would prefer cash buyer or private lending

This quintessential antique 3 bedroom, 2 bath colonial home beautifully blends timeless character with thoughtful modern updates, creating a curated European-country aesthetic rich in warmth, history, and rustic elegance. Filled with Old World charm, the home showcases original wide pine floors, soaring ceilings, and classic period details throughout. The stunning 2023 skylit chef's kitchen with gas cooking complements the home's storied character, while the generous living room, large dining room, and adjacent family room or office offer flexibility for today's lifestyle. A practical mudroom adds everyday convenience. Step outside to an expansive backyard oasis with a private deck, flat grassy yard, patio, and custom fire pit area-perfect for outdoor entertaining and celebrations. Oversized one-car garage plus updates including 5 zones of A/C, electrical upgrades, 2012 windows, and more. Close to schools, shopping, bike path, and the hiking trails of the Middlesex Fells

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

Beautiful and bright 2-bedroom / 2-bathroom unit in a multi-generational community. This pristine unit features 2 full baths, including a walk-in shower in the primary suite, an open concept living/dining area, and a kitchen with stainless steel appliances. The shared common space includes a kitchen, dining and living room, meeting rooms, kids' space, exercise room, art room, and soundproof music room. A shared patio and yard for gathering or gardening, underground garage parking with an assigned parking space, and EV chargers add to the convenience of this home. Includes solar panels for energy efficiency. Only a 3-minute walk from Malden Center T-station (Orange Line), and a short walk to downtown restaurants, shops, schools, groceries, and parks. Quick access to the Fellsmere Pond, Bike Trail, and Middlesex Fells Recreation Area