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

Major Price IMPROVEMENT! $50,000+ for this Fresh, stylish, and move-in ready Medford Condo. 3-bedroom, 2-bath first-floor condo in Medford Hillside offers 1,035 sq ft on the main level plus a beautifully finished lower level with its own separate entrance. Renovated in 2017 and just refreshed with new paint and newly finished hardwood floors, the home combines modern updates with a smart, flexible layout that works for everyday living, hosting, or working from home. Upstairs features 2 bedrooms, 1 full bath, and an updated kitchen, while the lower level expands your options with a large family room, third bedroom, full bath with an oversized tiled shower, laundry, and generous storage, ideal for guests, media space, or a private home office. Off-street parking adds everyday convenience. Ideally located near Tufts University, the Medford/Tufts Green Line station, Boston Avenue shops, cafes, and restaurants, Tufts Park, the Mystic River Path, Teele and Davis Squares

Exceptional opportunity to own a well-maintained multi-family home in a desirable neighborhood of Medford! This versatile property offers strong owner-occupant or investment potential with two spacious units. Unit 1 features 2 Bedrooms, 1 full bath, kitchen, dinning and living room. Unit 2 offers 3 bedrooms, 1 full bath, kitchen and dinning room. A stand out feature of this unit is the vaulted ceilings in the living room, creating and open, airy feel filled room with natural light from the skylights. Private yard and plenty of parking. Washer and dryers available for both units. Conveniently located with easy access to major commuter routes, public transportation, shopping, dinning, parks, and all that vibrant Medford has to offer. Enjoy proximity to Boston, and schools/ colleges. Don't miss your chance to own a multi-family property in one of Greater Boston's sought-after communities

This magnificent home is perfectly situated on a dead-end street in Medford's prestigious Lawrence Estates. Spanning more than 3K sq ft, this stunning, updated colonial features 4 spacious bedrooms and 4.5 baths, including 2 stylish en-suite primaries for added privacy and luxury. Gleaming hardwood floors guide you through an open, thoughtful layout that feels both elegant and effortlessly livable. A striking 2-sided gas fireplace, the heart of the home, seamlessly connects the living room and family room while adding warmth and ambiance. The finished basement offers versatile flex space for playroom, office, or gym. Step outside to your private oasis: an expansive fenced yard with sparkling in-ground pool, refreshed deck, lush garden beds, and smart irrigation. Energy-efficient OWNED solar panels reduce costs; the attached garage adds everyday ease. A rare blend of generous living space, thoughtful updates, and unbeatable location just minutes to Medford Square, Route 93, and all Bost

Modern and updated with TWO parking spaces-1 garage and 1 outdoor-welcome to 100 High St.! This beautifully maintained home offers comfort, convenience, and an unbeatable location just minutes from Medford Square, restaurants, the Chevalier Theatre, Routes 93, 38, 16 and 60, CVS, the library, and public transportation. Behind the building, enjoy the Mystic Valley Reservation with a bike path, canoeing, outdoor concerts, and a seasonal farmers market. Inside, the spacious living room opens to a private balcony with seasonal river views. The primary suite features a walk-in closet and full bath with newer flooring, while the second bedroom offers double closets and is river facing. Additional highlights include in-unit laundry, extra storage, newer heating/cooling system, and an oversized end garage space with bonus storage for bikes, a motorcycle, and more! Stop by any one of our Open Houses this weekend. No Pets allowed in this building

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

Tucked away on a quiet cul-de-sac, this gorgeous new home offers an inspired floor plan that strikes the perfect balance between open gathering spaces and private retreats. The chef's kitchen is a true showpiece with high-end appliances, sleek quartz counters, and a large island that flows right into the dining area and fireplaced family room-made for entertaining and everyday living.Need a first-floor bedroom with an ensuite' You've got it. Dreaming of a primary suite with a walk-in closet that would make any Bravo's housewife jealous' It's here. And the bonus third floor' The ultimate flex space-think playroom, home office, exercise room, or creative hideaway.Moments from shopping, dining, and major commuter routes, this home delivers luxury, comfort, and convenience in one irresistible package. Welcome to the Wu-where style lives!

WELCOME to this Spacious 2nd and 3rd floor condo offering 2,293 square feet of well-appointed living space with 3 bedrooms and 1.5 baths. Features include high ceilings, central air, Nest thermostat, private laundry, and private front and rear porches, including a newly built front porch. Enjoy a beautifully maintained shared backyard patio, solar-assisted hot water, and all new top-quality Marvin windows. Additional highlights include excellent Mass Save insulation, extra storage, one garage parking space with new electric doors, plus two tandem outdoor spots. Nestled in the vibrant Hillside neighborhood near popular restaurants and local favorites like Danish Pastry House, with easy access to Tufts University, the new MBTA Green Line station, Davis Square (under 30 minutes on foot), and Whole Foods (under 15 minutes walking or 5 minutes driving).Offers will be reviewed on Tuesday 6/23 at 4 PM. Please allow 24 hrs for seller response. Seller has right to accept an offer at any time

This beautifully gut renovated, Woburn condo checks all the boxes! With over 1800 sq ft of living area over the 2nd + 3rd floors, including a 3rd floor master suite with master bath and bonus office, this unit has it all! The open-concept living and kitchen area showcases stainless steel appliances: gas stove, dishwasher, microwave, and fridge, each updated in 2019. New 2025 w/d in-unit, plus central AC/heating with a 2024 replacement condenser, and 2019 windows means most of the high ticket items are in like-new condition. 2 off-street parking spots, dedicated basement storage, small outdoor area and an enclosed porch round out the package. The basement features a 2024 French drain plus 2 sump pumps for added peace of mind. Small, two-unit association with an owner-occupied neighbor keeps things quiet and well-maintained. Ideal locations just 1.3 miles to Winchester Commuter Rail, 1 block to Horn Pond, and minutes to Rt-93, Rt-95, Rt-3, Middlesex Fells Reservation and downtown Woburn!

Welcome to 1 Newport Ave in Medford. This charming beautiful home features 4 bedrooms and 1.5 baths with a spacious and inviting layout throughout.The main level features a spacious sun-filled living room that flows seamlessly into the formal dining area,creating the perfect setting for everyday living and entertaining.The nicely sized kitchen offers ample cabinet space and convenient access to the large composite outdoor deck.The second level features 4 bedrooms, a full tiled bath.Additional bonus finished attic space provides flexibility for home gym or a kids' playroom.Nice size laundry room in the partial finished basement along with plenty of ample storage space in basement. Step outside and enjoy the large composite deck overlooking the beautifully landscaped yard complete with a mature apple tree,creating the perfect outdoor setting for relaxing or gatherings. Conveniently located near restaurants, shops,markets,parks,and major highway access

Original wide plank hardwood floors in the hallways and living room blend with new hardwood throughout the kitchen, bathrooms, and bedrooms, creating a home full of timeless character. A fully remodeled kitchen, new first-floor bath, fresh paint, and updated electrical make it completely move-in ready, while original details like the kitchen's sliding wooden window and classic living room bay windows preserve its charm.Upstairs offers three bedrooms and a full bath, plus a flexible bonus room perfect as an office, playroom, mudroom, or four-season retreat. Laundry hookups on the first floor and in the basement, along with abundant storage in the attic, basement, and full-sized garage. Outside, enjoy a covered back patio and a spacious yard wrapping three sides of the home for rare privacy. Walk to Shamrock Elementary, Woburn High, Green Street Splash Pad, and nearby green space, with quick access to I-93, I-95, and Boston

Presenting 58 Winchester Street, a single-family residence close to Tufts. Great rental potential.1910 construction encompassing 2541 square feet living space on 2 levels w/ huge walk up attic for additional needs.Property features 4 thoughtfully appointed bedrooms,providing ample private accommodations. two full bathrooms and one half bathroom, designed for both convenience and comfort.Renovated Kitchen and baths. Roof, windows 2016. Gas Heat. Hardwood floors, great natural light. Situated on a generous 4755 square foot lot, property offers a large private outdoor area, and off street parking for 2 vehicles. Large Basement for utilities, laundry and plenty of storage. Property being sold in as is condition. Close to restaurants, shopping, parks and more.Easy access to Rts 93,16 and Public transportation. Showings begin at Open House 6/12 11:30 - 1:00. Additional Open houses Saturday and Sunday 6/13 and 6/14 11:00 - 1:00.Offers due 6/15 by 1:00

In the heart of the sought-after Lawrence Estates, w/ tree-lined streets just 7 miles from Boston, this exceptional colonial is a rare find. Pride of ownership radiates from every corner of this meticulously maintained home, with craftsmanship beyond even what the eye can see. Manicured grounds, a picture-perfect lawn, and flowering trees set the tone. Inside, the main floor flows though the lovingly updated living spaces, formal dining room and renovated kitchen. The finished basement was built for good times, complete w/ a custom crafted bar. The 2nd floor offers 3 gracious bedrooms and a tiled full bath, w/ a walk-up attic prepped for extra storage or future expansion. A beautiful deck and patio extend the living area for effortless entertaining overlooking the fenced in yard. The converted garage holds a rare surprise -front half for storage, and the back reimagined as an office and gym w/ central heat and air. With a high level of care and unbeatable location, this home is special

Welcome to this spacious top-floor 1B1B condo at Monterosa in the heart of Stoneham! This move-in ready home offers 780 sq. ft. of living space, featuring an open living and dining area, a spacious bedroom that easily fits a king-size bed, a bath with walk-in shower and in-unit laundry. Sliders lead to a private balcony with peaceful views, plus additional balcony storage. Other highlights: Nest-controlled central heating/cooling, NO lead paint, one assigned parking, and plenty of guest parking. Located in a secured elevator building, residents enjoy a professionally managed association, outdoor swimming pool, clubhouse, landscaping, and snow removal. Commuters love the prime location near I-93 and I-95, with easy access to Boston Seaport, Cambridge, Woburn, and Burlington. Target, Stop and Shop, cafes, restaurants, and daily essentials are all within walking distance, while Middlesex Fells Reservation offers beautiful lakes and trails. Low-maintenance living with comfort and convenien

Perched above Fellsmere Pond in Malden's West End, this beautifully updated home offers charm, space, and an unbeatable location! Gorgeous hardwood floors welcome you as you enter the spacious foyer. The sun-splashed living room features a wood burning fireplace with brick surround. The stunning kitchen with quartz countertops, SS appliances and a vast peninsula flows seamlessly into the dining room as well as the oversized outdoor deck - making this house perfect for entertaining! Three generously sized bedrooms, renovated bathrooms, and a walk-in closet offer comfort and functionality. Enjoy multiple exceptional outdoor spaces, including a covered front porch with picturesque pond and park views, ideal for relaxing summer evenings. A one-car garage with abundant storage and bonus basement space complete the home. The close proximity to the Orange Line, highway access, shops and restaurants in Malden and Medford, Amerige Park, and the Middlesex Fells make this the best deal in Malden!

Introducing 32 Oak Street, located in Stoneham's coveted Robin Hood school district. This beautiful, move-in ready three-bedroom home measures over 1,500 square feet. The home welcomes you into an open-concept main level, featuring a newly renovated eat-in kitchen, with island drink fridge, seamlessly connected to a family room with working fireplace. Down the hall, you'll find two bedrooms, a full bathroom and conveniently located laundry. Privately situated upstairs, is the primary suite, complete with an attached bath and generous closet space. Set on a spacious open lot, the inviting deck and back yard are well suited for gatherings and outdoor enjoyment. Recent improvements include: roof, windows and tankless hot water. Conveniently offering access to I-93 and I-95

$200K+ price reduction. Now listed below Assessed Value! Bring your vision and make this property shine again. Location and lot can't be beat! GEM of an opportunity in West Medford close to all amenities, major routes, Commuter Rail and Playstead Park. A 2-unit multi-family home w/an expansive lot in highly sought after area. Offers a 2 car garage w/driveway; individual porches; patio and large fenced-in yard w/room for possible expansion/ADU or outdoor fun. Units offer large eat-in kitchens with w/d hookups. Unit 1 functions as 2 bed/1 bath, while Unit 2 spans 2 flrs w/4+ beds, 1 bath and office/closet space. LL plumbed w/capped gas connection, 3/4 bath and possibility of wet bar/kitchen w/plenty of storage too (perhaps add'l space for U1 or maybe something more with city approvals') Needs renovating, possible expansion/condo conversion or more - opportunities abound! Perfect for an investor, owner/occupant wanting sweat equity (restored to SFM or left as a multifamily). AS IS

Set in one of Winchester's most coveted neighborhoods, this distinguished Robert Coit-designed residence seamlessly blends timeless architecture with exceptional modern living. Rich in original detail and brimming with character, this 4-bedroom, 2.5-bath home is a true testament to enduring craftsmanship. Gracious living spaces are anchored by three fireplaces, creating warmth and elegance throughout. The expansive kitchen is a showpiece-generous in scale and thoughtfully designed for both everyday living and entertaining. A cypress-paneled den with a fireplace is located on the first floor. The top floor offers 1 room with sink and a large open gallery space, perfect for a home office. Outside, the property unfolds into spectacular, professionally curated gardens and lush landscaping, offering a private oasis that changes beautifully with the seasons. There is a full unfinished basement for additional space. Large welcoming front porch, close to the center and top-rated schools

Charming bungalow offering 3 bedrooms and 3 full bathrooms in a convenient location close to Boston. This well-maintained home features gas heat, central air conditioning, off-street parking with a private driveway, and a spacious backyard with beautiful views. The kitchen features granite countertops and a slider leading directly to the backyard, creating a great flow for indoor and outdoor living. The primary bedroom includes a private full bath with a Jacuzzi tub and separate shower. The finished walkout basement includes a 3/4 bath, providing excellent additional living space and flexibility. A rare opportunity to own a home that combines character, comfort, and accessibility

Completely renovated and absolutely stunning, this second-floor condo feels more like a penthouse than a traditional apartment. Featuring a designer kitchen, spa-like bathroom, two mini-split A/C systems, and beautiful finishes throughout. Ideally located near Tufts University, Medford Square, the Green Line, restaurants, shopping, and major commuter routes. Luxury, style, and convenience come together in one exceptional home. Make sure to check out the virtually stage pictures and imagine yourself living here!

Height, sunlight and soaring ceilings radiate throughout this stunning corner unit at the historic Hervey Schoolhouse, where each space beautifully unfolds into the next. Oversized windows span across the living and dining rooms, creating an open, airy vibe that feels like a luxurious treehouse retreat. Loads of kitchen cabinetry, a fantastic pantry and generous breakfast bar make cooking and entertaining feel effortless. Just down the hall is a full bath, spacious bedroom w/double closet, and a primary suite featuring custom closets, a newly refreshed en-suite bath, and fantastic walk-in storage closet. Two parking spots, private storage, in-unit laundry, and an exercise room add everyday convenience, while this self-managed association is known for being exceptionally well run. All of this in highly coveted West Medford, just a short stroll to the commuter rail to Boston, bus to the Green Line T + minutes to many multicultural restaurants and shops, the tennis courts and the Mystic R

Nestled in one of Medford's most desirable neighborhoods, 43 Doonan Street offers endless potential and an incredible opportunity to make this home your own. Lovingly maintained by its original owners, this home features 3 generously sized bedrooms, 1 full and 1 half bath, a first-floor bonus room, and an oversized family room ideal for entertaining. The pristine hardwood floors reflect years of exceptional care, while a new hot water tank adds value and peace of mind. Outside, enjoy a private patio and rare flat, level backyard, perfect for entertaining, gardening, or play. Conveniently located near parks, schools, shopping, dining, major highways, and public transportation, this solidly built home is ready for your personal touches. A wonderful opportunity to renovate, customize, and build equity in a highly sought-after Medford location. Some photos have been virtually enhanced for marketing purposes

Welcome to the freshly renovated 32 Manning St. Unit 2. Talk about charm! The exterior resembles an intricate gingerbread house! This recent condo conversion features up to 5 bedrooms with flexibility to convert one or more into an office or entertainment space. A full bathroom on each level and laundry on the second floor provides convenient living. New kitchen cabinets and stainless steel appliances with a large island flow nicely into the dining and living room space. New flooring and paint throughout the Unit. All new systems including Heat Pump for central a/c and heat; water heater and electrical upgrade. Common yard space and basement access. Unit 2 features the full use of the driveway and 5 off street parking spots. Set on a one way residential street, enjoy easy access to I-93, steps to Mystic River and the Medford Farmer's Market. Close to Medford Square and Tufts. Offers due Tuesday, 5/19 at Noon

You will love this luxurious and sprawling two Bedroom-two bath atop the highly desirable 100 Station Landing! Wonderfully renovated with high quality finishes and details throughout. This fine home features a chef's kitchen with granite counters, high end appliances, ample storage space, gleaming hardwood floors, high ceilings, many sunny windows with magnificent river and city views from every room and on your own private balcony! Other features include two wonderful spacious bedrooms, two full tile and marble baths, one with custom shower and soaking tub, and in unit washer/dryer and a garage parking space! 100 Station Landing is a beautiful concierge building featuring a modern fitness room and enormous common lounge/business room with magnificent views! Living by Assembly Row/Square you are a very short distance to the Wellington T stop and easy access to Downtown Boston. You can choose from dozens of fine restaurants, scores of stores and cafes, a movie theater, and much more!

Fantastic single-family home featuring 3 floors of finished living space designed to maximize every square inch. Main level offers a seamless open flow between the living room, dining room and kitchen. Highlighting a unique breakfast bar w/granite counters surrounding a rustic exposed brick chimney, complemented by a projector movie screen, pendant lighting, half-bath and direct exterior access. The 2nd floor hosts three bedrooms with built-in storage, an updated full bath with a tub/shower, and a dedicated small home office. Finished lower level, provides excellent flexibility w/pantry storage, a second full bath, and a versatile flex space perfect for guests, a playroom, or home gym. The functional laundry rm includes a retractable folding table and convenient outdoor access. Step outside to a generous, flat rear yard built for entertaining, featuring a deck and patio.This home perfectly blends character w/modern updates. Take advantage of the outstading location and all Medford offe

Stunning new 3BR residence with luxury finishes in sought-after Medford, just minutes from Tufts University and Boston. The open-concept layout seamlessly connects the living, dining, and gourmet kitchen, featuring quartz countertops, custom cabinetry, and stainless steel appliances. Hardwood floors and oversized windows fill the home with natural light. The private 3rd-floor primary suite offers a spacious sitting area, fireplace, and spa-inspired bath with its own fireplace-creating a true retreat. Two additional bedrooms are located on the 2nd level. 2.5 baths, in-unit laundry, private deck, front balcony, and 1 off-street parking. Exceptional turnkey living in a prime location