Winchester, MA Real Estate | Winchester, MA 4 Bedroom Homes for Sale

Welcome to 16-18 Russell Road, a classic two-family home tucked along a tranquil one-way street just a short walk from downtown Winchester. The bright upper level features 3 bedrooms and 1 bath, while the flexible lower level offers a 1-bedroom, 1-bath layout with the potential to expand to two bedrooms, providing added versatility for investors, multigenerational living, or owner-occupants looking to offset their mortgage with rental income. Hardwood floors run throughout much of the home, while ductless mini-split systems provide efficient heating and cooling, complemented by a gas forced-air system in the basement. Vinyl siding and an asphalt roof help keep exterior maintenance manageable, while ample off-street parking and a yard add everyday convenience. Located within the district for the newly built Lynch Elementary School, the home is also just a short walk to the commuter rail, a new neighborhood coffee shop, restaurants, and amenities of Winchester's vibrant town center.

16-18 Russell Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.

$2,650,000

4 Beds ⋅ 5 Baths ⋅ 73593868 MLS

Inspired by the timeless villas of Europe, this exceptional residence blends classic elegance with modern design. A dramatic curved staircase and soaring architectural details introduce inviting living spaces featuring handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that connect seamlessly to the outdoors. At the heart of the home, a chef’s kitchen showcases custom cabinetry, luxury appliances, and an adjoining mudroom. The outdoor setting offers a private retreat with a granite-columned loggia, heated saltwater pool, landscaped grounds with irrigation, and multiple areas for entertaining.The spa-inspired primary suite, ensuite guest bedrooms, and finished lower level with flexible bonus spaces provide comfort and versatility. Heated driveways and walkways add year-round convenience. Ideally located within walking distance of downtown, the new Lynch School, the new commuter rail station, and an array of shops and restaurants, this home offers a thoughtful balance of timeless style, modern amenities, and everyday comfort.

18 Middlesex St, Winchester

Listing courtesy of Listing Agent: Jennifer Taves from Listing Office: Coldwell Banker Realty - Boston.

$4,500

4 Beds ⋅ 3 Baths ⋅ 73590971 MLS

--IMMEDIATELY AVAILABLE --- A rare opportunity to rent a detached home in Winchester with the space, privacy and flexibility often missing from condo or townhome living. The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 4 bedrooms, 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides a third bedroom plus an additional flex space ideal for a home office, fitness room, playroom, hobby space or guests. Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Pets negotiable. First month's rent & security deposit due at lease signing. Lease term negotiable.

258 Cross Street, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.

$1,985,000

4 Beds ⋅ 4 Baths ⋅ 73589478 MLS

Set on over an acre of beautifully landscaped grounds abutting acres of woodland, this extensively renovated Contemporary Cape offers exceptional privacy and a peaceful connection to nature. A thoughtfully designed open floor plan features hardwood floors, a fireplaced living room, elegant dining room, and a beamed-ceiling family room adjoining the remodeled kitchen with stone counters, stainless appliances, and island. A private great room off the foyer, with windows on three walls and a slider to the spacious deck, offers a wonderful retreat. French doors open to the expansive deck overlooking the fenced backyard and wooded surroundings. Upstairs, four bedrooms include a primary suite with custom closets and private bath. The finished walkout lower level offers flexible space for a home office, gym, or guests, with separate entrance and full bath. Stone walls, mature landscaping, a long private driveway, and two-car garage complete this exceptional home.

30 Surrey Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.

$1,529,000

4 Beds ⋅ 4 Baths ⋅ 73584817 MLS

An exceptional opportunity in one of Winchester’s most desirable neighborhoods, directly across from the Winchester Country Club. Set on a beautiful .39-acre lot, this distinctive 4-bedroom, 3.5-bath Colonial offers approximately 2,709 sq. ft. of living space, a 2-cargarage, generous room proportions, and a flexible floor plan ready for its next chapter. Offering wonderful possibilities with its generous proportions, flexible floor plan, and impressive setting, the property presents an ideal canvas for buyers looking to renovate and personalize a home to their exact vision. Reimagine the existing spaces with sophisticated modern finishes, create a timeless renovation that complements the home’s character, or explore the possibilities for a more extensive transformation. The spacious lot also provides plenty of room to enhance the outdoor experience with thoughtfully designed landscaping, gardens, patios, entertaining areas, or other outdoor amenities. Beyond the property itself, the location stands out, with the Winchester Country Club just across the street and downtown Winchester conveniently nearby, offering restaurants, cafés, shops, services, and commuter rail access to Boston. Convenient access to Winchester public schools, major routes, and nearby public transportation makes commuting and exploring the Greater Boston area easy. Bring your architect, contractor, and creativity and transform this property into something truly special. With its substantial lot, desirable neighborhood setting, proximity to downtown, and access to everything Winchester has to offer, 25 Arlington Street presents a rare chance to create a home that reflects your own style in an exceptional location.

25 Arlington St, Winchester

Listing courtesy of Listing Agent: Domingo Medina from Listing Office: Coldwell Banker Realty - Lexington.

$1,750,000

4 Beds ⋅ 3 Baths ⋅ 73581571 MLS

NEW Photos! Welcome to One Overlook Way in Winchester. This home is located on a 1/3 acre corner lot on a short cul-de-sac off High Street- a premier location close to Ambrose Elementary School and the Winchester Country Club. Don't miss this spacious 4+ bedroom center-entrance Colonial. with a thoughtfully designed circular flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen with room to add an island or large table also opens naturally into the comfortable family room - with gas fireplace, custom built-ins, a new split AC and access to the back and side yard! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a split AC, private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a second home office, hangout zone or storage. The finished lower level adds another playroom, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished storage space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

1 Overlook Way, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,325,000

4 Beds ⋅ 2 Baths ⋅ 73579538 MLS

1st OPEN HOUSE! SUNDAY, OCTOBER 4th, 11:30am-1:00pm! 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 direct. Complete with proximity to top-rated Winchester public schools and vibrant downtown dining and shops, this property delivers the quintessential North Shore lifestyle in an unmatched location. MAKE 9 PRISCILLA LANE YOUR HOME TODAY!

9 Priscilla Ln, Winchester

Listing courtesy of Listing Agent: Robert Del Greco from Listing Office: Compass.

$1,250,000

4 Beds ⋅ 3 Baths ⋅ 73574928 MLS

Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

465 Washington Street Unit 465, Winchester

$1,250,000

4 Beds ⋅ 3 Baths ⋅ 73574929 MLS

Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street Unit 465, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$2,199,000

4 Beds ⋅ 4 Baths ⋅ 73572955 MLS

Welcome to 19 Hancock Street, a stunning transformation where timeless New England character meets sophisticated modern living. Completely reimagined through an extensive renovation, this exceptional Winchester residence preserves the charm and presence of a classic home while delivering the design, finishes and functionality expected for today’s lifestyle. The beautifully designed first floor features a bright, open layout with an effortless flow from room to room, creating an ideal setting for both elegant entertaining and comfortable everyday living. Thoughtful details throughout include a spacious pantry and dedicated mudroom, blending style with exceptional functionality. Upstairs, four bedrooms include a luxurious primary suite designed as a private retreat, complete with a beautifully appointed bath and oversized walk-in shower. Convenient second-floor laundry and well-designed secondary bedrooms make this level as practical as it is polished. The finished lower level offers another impressive dimension of living space, perfect for a media room, home gym, playroom, office or guest retreat. With 3.5 beautifully finished baths, a two-car garage, and a rear deck ideal for outdoor dining and entertaining, every level of the home has been thoughtfully considered. All of this is set in one of Winchester’s most convenient locations—just minutes from Winchester Center, the commuter rail, shops, dining and schools. Classic character, completely renewed. Modern luxury without sacrificing warmth. 19 Hancock Street is a rare opportunity to enjoy the best of Winchester living in a home that feels both established and entirely new.

19 Hancock Street, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

$1,599,000

4 Beds ⋅ 2 Baths ⋅ 73572661 MLS

Price Change!! **Open House this weekend or call for private showings** Great offering~ Extensively rebuilt and expanded, this impeccably maintained 4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room w/living area and dining area features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling, dining, and relaxing. The main level also includes formal living room w/ fplc, plus 2 spacious bedrooms & full bath. offering flexibility for various uses. Upstairs are two additional generously sized bedrooms with hardwood floors and ample closet space, along with a full hall bath featuring a skylight. Additional highlights include a finished lower level, laundry and storage areas, and direct access to a two-car garage. Beautifully landscaped grounds feature perennial gardens, flowering trees, natural stone walls, and exceptional privacy—nestled into one of Winchester’s most desired neighborhoods, all just 7 miles from Boston with convenient access to the town center, Fells trails, major routes and highways. Please see feature/ update list attached.

4 Churchill Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,049,000

4 Beds ⋅ 3 Baths ⋅ 73571480 MLS

Tucked on a quiet side street just north of Main Street, this circa-1853 antique pairs the character of a classic Winchester home with the space of a beautiful, sun-filled addition (completed in 2003): A lovely farmer's porch welcomes you and, once inside, hardwood and tile floors run through the main living spaces. Front rooms include a quaint sitting room and private office. A gas fireplace adds warmth in the family room off the kitchen, which has a slider out to a generous sized deck overlooking the serene back yard. Fresh paint throughout means there is nothing to do but move in. The same addition brought two bedrooms (primary with en suite bath), a walk-in closet, and updated kitchen cabinetry. Out back, a wood deck steps down to a spacious fenced yard with a built-in tree house, a garden area, storage shed, and in-ground sprinkler system. Central air conditioning, gas heat, town water and sewer, a one-year-old hot water tank, a partially finished, heated basement, a walk-up attic, and a four-car driveway. The location is the real headline: walk to the commuter rail, the bus, and Winchester Center's shops and restaurants, with the park, bikeway, and conservation trails minutes away. Newly renovated Lynch Elementary, McCall Middle and Winchester High School.

24 Richardson St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.

$1,899,000

4 Beds ⋅ 3 Baths ⋅ 73565817 MLS

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

85 High St, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$2,399,000

4 Beds ⋅ 5 Baths ⋅ 73555666 MLS

Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with custom built-ins and entertaining bar,formal dining with butler’s pantry, private office,and luxurious primary suite with vaulted ceilings, walk-in closets,and spa bath.Expanded outdoor living features a custom outdoor kitchen,fire pit,and multiple patios designed for exceptional entertaining.The finished lower level offers a bonus room, home gym, mudroom, and oversized 2-car garage.Professionally landscaped with exceptional privacy, yet just moments to the Vinson-Owen School,steps to the Swim & Tennis Club,and major commuter routes.A rare opportunity to own one of Winchester’s finest newer homes. See Video: https://player.vimeo.com/progressive_redirect/playback/1217669935/rendition/1080p/file.mp4%20%281080p%29.mp4?loc=external&log_user=0&signature=65fb6c1e2692e9ac8d5b781ceed13c02239d5128d88af87ce725ce6cd7907704

54 Squire Road, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.

$919,999

4 Beds ⋅ 2 Baths ⋅ 73561829 MLS

Discover a rare opportunity to own a versatile ranch in sought-after Winchester, offering flexible living with a two-bedroom main level and a full two-bedroom in-law suite below. The gracious first floor welcomes you with gleaming hardwood floors and a handsome fireplace anchoring the living room. A generously proportioned dining room, complete with a classic built-in china cabinet, opens effortlessly into a bright eat-in kitchen — an inviting space for both everyday living and entertaining. Two well-sized bedrooms with ample closet space and a full bath complete the main level, kept comfortable year-round by central air-conditioning.The lower level offers exceptional flexibility with its own private in-law suite, featuring a warm, fireplaced living room, two bedrooms with plush wall-to-wall carpeting, and a full bath — ideal for extended family, guests, or additional living space.Outside, enjoy a level, easy-to-maintain backyard, convenient off-street parking, and a one-car garage. Ideally located just minutes from Skillings Field and McDonald Field, this home offers wonderful access to local recreation, with Lynch Elementary only 0.8 miles away and the scenic Horn Pond Recreation Area close at hand. Enjoy the convenience of nearby Winchester Hospital, easy access to Route 3, and commuter rail service for a smooth trip into Boston. A home that blends comfort, versatility, and an unbeatable location — a must-see that won't last long. Showings begin 8/22 @ Open House 1:30-3PM

96 Loring Ave, Winchester

Listing courtesy of Listing Agent: Jeremy Smith from Listing Office: StartPoint Realty.

$3,700

4 Beds ⋅ 2 Baths ⋅ 73559841 MLS

Spacious 4-bedroom, 2-bath apartment available for immediate occupancy in a two-family home just minutes from Winchester Center. Please note: This is NOT a single-family home. This unique unit occupies the entire first floor and finished lower level. The main level features hardwood floors throughout, a living room, dining room, two spacious bedrooms, a full bath, and an eat-in kitchen with a new refrigerator and dishwasher. The finished lower level offers a large family room, two additional bedrooms, a second full bath, laundry, and ample storage. Private driveway with parking for up to 3 cars, patio, and shared backyard. Conveniently located near Winchester Center, shopping, restaurants, commuter rail, and major routes.

10-12 Webster St Unit 1, Winchester

Listing courtesy of Listing Agent: Ryan Kelly from Listing Office: Real Broker MA, LLC.

$1,999,000

4 Beds ⋅ 4 Baths ⋅ 73556476 MLS ⋅ ['The Ledges'] BLDG.

Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home offers an elegant first-floor primary suite w/ dual walk-in closets and a stunning spa-inspired bath. Meticulously reimagined from top to bottom, every element of this extraordinary renovation was thoughtfully curated using the finest imported designer finishes and bespoke craftsmanship, creating an unparalleled level of luxury. The dramatic open-concept main level is highlighted by soaring vaulted ceilings, a fireplaced living room w/ a custom-designed mantel, & walls of glass that open to a private deck overlooking breathtaking western sunsets & tranquil natural surroundings. The designer kitchen is a true showpiece, featuring premium finishes, a sun-filled breakfast area, & seamless flow into the elegant dining room, ideal for both intimate gatherings & entertaining.The second floor offers 3 rooms including a spacious bedroom, beautifully renovated full bath, loft ideal for a home office, & an additional sitting room/TV room or guest space. The walk-out lower level it’s another suite in itself offering a spacious family room, second kitchenette, dining area, game room, additional bedroom with double closets, a luxurious spa bath, oversized laundry room, and abundant storage. Step outside to a private patio surrounded by peaceful, picturesque grounds, creating the perfect retreat for relaxing or entertaining. Ideally located w/ easy access to Winchester Center, Whole Foods, major highways, restaurants, and shops, this exceptional home offers luxury living just 7 miles from downtown Boston.

7 Wainwright Road Unit 113, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

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