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$974,900
4 Beds ⋅ 3 Baths ⋅ 73575764 MLS ⋅ NEW Status
Looking for a quiet retreat, with a SIDE STREET DRIVEWAY, built in privacy but still connected to the urban hustle and bustle of Boston metro? A rare Winchester opportunity, has arrived, priced comfortably under $1M. 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2.5 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Owners JUST put in an unused half bathroom on the first floor PERFECT for entertaining and preserving the privacy of your 2nd floor bathrooms. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Minutes from the iconic, and picturesque downtown Winchester where you'll find quaint coffee shops, local boutiques, and even a Commuter rail stop! Quick entry to Boston, Burlington, and the surrounding metro Boston area via nearby I95, Rt2, Rt3. Like spending your free time outdoors? You are mere minutes from the Medford Fells, one of Greater Boston's greenest and most resident friendly (humans and dogs alike) stretches of nature. Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS). Some of the previously prepared conceptual expansion plans are in the photos, the rest are available for review upon request.

258 Cross St, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.
$1,599,000
5 Beds ⋅ 3 Baths ⋅ 73575069 MLS ⋅ NEW Status
Set on a generous lot in one of Winchester’s most highly sought-after locations, this stately brick colonial presents a rare opportunity to create your dream home. Offering 2,944 square feet of living space, with high ceilings & oak hardwood flooring. This classic residence has been lovingly enjoyed & maintained by one family and proudly showcases timeless architectural character, generously proportioned rooms, and an abundance of natural light. The inviting front to back living room features a fireplace and serves as a wonderful gathering space, along with formal dining room, eat in kitchen, 1/2 bath plus a sunroom/den and a home office! The upper floors offer 5 spacious bedrooms & provide exceptional flexibility for family, guests, office space, or future customization. Enjoy the rear deck and the vast lot with lush grass, gorgeous perennial gardens and flowering trees offering plenty of space for outdoor entertaining, gardening or expansion. With this home's beautiful brick exterior, classic charm, substantial lot, and premier location, it offers an exceptional opportunity to renovate, reimagine, and create your dream home!

143 Arlington Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 73574928 MLS ⋅ NEW Status
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.
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 73574929 MLS ⋅ NEW Status
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.
$975,000
4 Beds ⋅ 3 Baths ⋅ 73573734 MLS ⋅ NEW Status
Enjoy being just a few blocks from Winchester Center in this spacious condo with unique separate guest suite or home office. This single family alternative features 3 bedrooms on the main level and a fourth tucked away in the back of the second floor along with a 3rd bath and kitchenette. Come in the back door from the 1-car garage, or 3 parkings spaces in the driveway, straight into the large, remodeled kitchen with dining area. Appreciate the large windows in the living room. Charming details complement modern improvements. The primary suite is large enough to have an office setup within the space. Primary and hall bath have been updated. Looking for outdoor space? Whether you love the Middlesex Fells, want to have friends over for al fresco dining or do a little gardening, this is the home for you. Condo expenses are split between the 2 units. Town Center, schools, commuter rail, restaurants, shopping and the farmers market are all just a few blocks away. Boston and Cambridge are less than 9 miles away from this spot conveniently located to 93 and 95.

199 Washington Street Unit 199, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,099,000
4 Beds ⋅ 3 Baths ⋅ 73571480 MLS ⋅ ACTIVE Status
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.
$1,050,000
5 Beds ⋅ 3 Baths ⋅ 73571418 MLS ⋅ ACTIVE Status
Situated on a large,10k+ level corner lot with frontage on both Cross Street and Verplast Avenue! The upper level features a fireplaced living room w picture window, updated kitchen, three bedrooms, 1.5 baths, and a large sunroom overlooking the expansive backyard. The first level offers additional flexible living space with a kitchenette, living area, two bedrooms, laundry, and a full bath, providing great potential for an in-law setup, guest space, home offices, or extended living. The generous lot and existing footprint create an ideal opportunity to modernize the home, expand the living space, or explore future possibilities. Put your personal touch on this home and build some great equity! This property is full of potential and ready for its next chapter!

257 Cross Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,999,000
4 Beds ⋅ 3 Baths ⋅ 73565817 MLS ⋅ ACTIVE Status
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.
$1,329,000
3 Beds ⋅ 3 Baths ⋅ 73562273 MLS ⋅ ACTIVE Status
110 Thornberry Road. Strong west side location near Vinson-Owen Elementary School and the Winchester Swim & Tennis Club. An exceptional opportunity to establish roots in Winchester. 2021 Natural Gas Brute FT Floor Standing Boiler. Replacement windows. Central cooling. 200 amp electric. Updated Kitchen w Double oven. Prefinished hardwood floors. Therma-Tru French doors flow from the dining room to a window-lined bonus room off the dining room provides flexible year-round living space. In-ground swimming pool.

110 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Mark Kiklis from Listing Office: Kiklis Real Estate, LLC.
$1,549,000
3 Beds ⋅ 3 Baths ⋅ 73556633 MLS ⋅ ACTIVE Status
Completely remodeled with exceptional custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted breakfast nook. The open floor plan flows into the dining room, complete with a custom built-in wine bar, ensuring easy entertaining. The second floor provides two very large bedrooms with great closet space and a tastefully remodeled hall bath. The beautifully finished lower level offers incredible flexibility with a cozy family room, kitchenette, laundry and 1/2 bath, with potential for a 4th BR, making it ideal for entertaining, guests, or extended living space. Step outside to an extraordinary backyard that feels like a resort! Enjoy the professionally landscaped grounds, lush gardens, and an expansive patio creating the ultimate outdoor oasis-featuring a built-in grill, pizza oven, bar seating, a hot tub, greenhouse, and shed. The retractable awnings make for comfortable shaded entertaining. It is truly a backyard that you will use all year round! Ideally located just outside Winchester center, enabling you to enjoy all the benefits of being close to town! This turn-key home is a must see, don't miss this one of a kind, move in ready home with so many recent upgrades!

50 Holland Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$650,000
3 Beds ⋅ 3 Baths ⋅ 73549877 MLS ⋅ ACTIVE Status ⋅ ['Winchester Green'] BLDG.
Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for everyday living and entertaining. The second floor includes a full bath, a bedroom, and a versatile bonus room ideal for a home office, playroom, or guest space. The private third-floor primary suite features skylights, a custom-designed bath with a built-in makeup vanity, and generous storage. The finished lower level offers a family room, half bath, oversized closets, and an in-unit laundry area with additional storage. Enjoy easy access to the 2,600-acre Middlesex Fells Reservation, offering miles of scenic walking, running, and biking trails.

247 Washington St Unit 11, Winchester

Listing courtesy of Listing Agent: Heejeong Joo from Listing Office: Coldwell Banker Realty - Lexington.
$2,400,000
5 Beds ⋅ 3 Baths ⋅ 73544924 MLS ⋅ ACTIVE Status
Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for year-round comfort, the home features central AC, central humidification, and an air exchanger. Outside, enjoy beautifully landscaped gardens, a spacious deck overlooking the private yard, lush irrigated grounds with an invisible dog fence, and a hot tub for unwinding after a long day. A wood-burning fireplace adds warmth and character to the living space. Located just minutes from top-rated schools, Winchester Center, and convenient commuter access to Boston, this is a rare opportunity to enjoy privacy, nature, and timeless New England living in an exceptional location.

9 Plymouth Rd, Winchester

Listing courtesy of Listing Agent: Steph Crawford Group from Listing Office: Real Broker MA, LLC.
$1,350,000
4 Beds ⋅ 3 Baths ⋅ 73541775 MLS ⋅ ACTIVE Status
Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The home offers exceptional curb appeal and privacy with mature evergreens, specialty trees, and an elevated setting. Inside, a central staircase creates a focal point while naturally defining the open concept living and dining rooms, perfect for everyday living and entertaining. The living room is full of natural light, with a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The spacious, thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast bar island, and laundry. A convenient side entry provides direct access to the first of two driveways, the deck, and the large, private backyard beyond. The deck overlooks a fully fenced backyard that offers the perfect setting for relaxation, recreation, and entertaining. The flexible floor plan is designed to fit a variety of needs with a versatile main level bedroom, a sunny and cheerful space with hardwood floors and direct access to the first of three full bathrooms. The bathroom, also accessible from the hall, offers a dual sink vanity and tiled tub with a shower. A convenient laundry area adds the finishing touch to the main level. Designed with comfort and functionality in mind, the second level features a private primary suite, two additional bedrooms, a family room, and a full family bathroom, all connected by a wide central hallway. The primary bedroom offers a large walk-in closet and an updated bathroom featuring a dual sink vanity and a beautifully tiled shower. The family bedrooms are full of natural light with hardwood floors and ample closets, sharing the family bathroom with a tub and shower. One of the bedrooms also works well as an office if needed. Double French doors open to the inviting family room, where cozy carpeting and a large window overlooking the backyard create the perfect space to relax. Set on a large corner lot with two driveways and a detached two-car garage accessed from quiet Englewood Road, this special property offers a prime location just moments from the Middlesex Fells Reservation, the town center, the commuter rail and Muraco ES. Nothing left to do but move right in.

423 Washington St, Winchester

Listing courtesy of Listing Agent: Danielle Fleming from Listing Office: MA Properties.
$1,075,000
3 Beds ⋅ 3 Baths ⋅ 73519082 MLS ⋅ ACTIVE Status
Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

53 Lake Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,110,000
5 Beds ⋅ 3 Baths ⋅ 73515601 MLS ⋅ ACTIVE Status
Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home. The first-floor unit includes two bedrooms and one full bath, making it ideal for rental income, extended family, or multi-generational living. Each unit has its own garage space, something tenants and owners always appreciate, plus a long driveway with plenty of additional parking. The layout offers separation, functionality, and strong future potential. Location matters, and this property comes with access to the highly desirable Winchester Public Schools, adding even more long-term value. Investment properties in Winchester do not come along often, especially ones with this much upside.

63-65 Harvard Street, Winchester

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

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