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$1,125,000
5 Beds ⋅ 3 Baths ⋅ 73555597 MLS ⋅ NEW Status
Thoughtfully updated 1870 home with a versatile footprint offering many options for multi-generational living, a grand home office setup, dedicated au pair quarters, or separately rented as an Accessory Dwelling Unit (ADU). Elegant renovations have preserved the home's original historic character while seamlessly incorporating today's modern luxuries. A charming farmer's porch welcomes you into the main living area, featuring 8 rooms, 4 bedrooms, and 1.5 baths. The beautifully renovated 2024 eat-in kitchen showcases timeless cabinetry, quartz countertops, a functional butcher block island, custom blue-and-white tile backsplash, an exterior-vented gas range, and direct access to a new 2024 TimberTech deck. Interior highlights include an inviting living room with a striking embossed tin ceiling, a flexible first-floor bedroom or office featuring floor-to-ceiling windows, and gorgeous wide-plank flooring. The walk-out lower-level family room adds excellent bonus space with direct access to the backyard, while three additional bedrooms sit on the second floor. The full bath was tastefully renovated in 2020 with vintage-inspired washstand sinks, and the unfinished basement provides laundry space and storage. The separate, fully integrated living area is ideal for extended family, guests, an au pair, or rental income. This bright secondary suite offers a sunlit living room with its own deck access, an eat-in kitchen, full bath, and a spacious second-floor bedroom. Original pine floors on main level and carpet in bedroom. Modern mini-split heating and A/C units provide year-round climate control throughout both distinct living areas. The main home also features gas baseboard and radiator heat, while the suite is independently served by radiator heat. Outside, a patio and three off-street parking spaces complete this exceptional property. The location is an absolute commuter's dream, situated just a short stroll to vibrant Winchester Center, boutique shops, local cafés, and acclaimed restaurants. Commuters will love being near two MBTA Commuter Rail stations, offering a quick two-stop ride straight into Boston's North Station. Best of all, this property sits within the highly sought-after Lynch Elementary School district, placing you directly inside Winchester's top-rated, award-winning public school system. This rare property truly offers the perfect combination of timeless historic charm, high-end modern updates, and outstanding lifestyle versatility.

8 Oak Street, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
$1,125,000
5 Beds ⋅ 3 Baths ⋅ 73555245 MLS ⋅ NEW Status
Elegantly updated, two-family home offers flexibility for multi-generational living, rental income, or as a spacious single-family. Thoughtful renovations preserve the home's original character while adding modern comforts. A charming farmer's porch leads to an inviting patio. The larger side, 8 Oak, features 8 rooms, 4 beds, 1.5 baths, a 2024 eat-in kitchen with timeless cabinetry, quartz countertops, butcher block island, blue-and-white tile backsplash, exterior-vented gas range, and direct access to a 2024 TimberTech deck. Highlights include an inviting living room with embossed tin ceiling, a first-floor bedroom or office with floor-to-ceiling windows, wide-plank floors, a lower level family room that has a full walk-out to back yard, and 3 second-floor bedrooms. The full bath was beautifully renovated in 2020 with vintage-inspired washstand sinks. The unfinished basement includes laundry and ample storage. The apartment, 10 Oak, is a bright 3 rooms, 1 bed, 1 bath featuring original pine floors, a living room with access to deck, an eat-in kitchen, and a second-floor bedroom suite. Both sides feature mini-split heat and A/C. 8 Oak also offers gas baseboard and radiator heat and 10 Oak also has radiator heat. Three off-street parking spaces. Enjoy an unbeatable location just a short walk to Winchester Center, two MBTA Commuter Rail stations (only two stops to North Station), restaurants, cafés, and shops. Located in the sought-after Lynch Elementary School district and Winchester's top-rated school system. This special property blends timeless charm, modern updates, and exceptional versatility.

8-10 Oak St, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
$1,099,000
5 Beds ⋅ 3 Baths ⋅ 73553083 MLS ⋅ ACTIVE Status
Exceptional two-family opportunity with incredible potential to renovate/expand! Situated on a large, level corner lot with frontage on both Cross Street and Verplast Avenue, this property offers endless possibilities for investors, builders, or owner-occupants. The first-floor unit features a fireplaced living room, an updated kitchen, three bedrooms, 1.5 baths and sunroom overlooking the expansive backyard. The second unit offers a spacious and flexible layout with a living room, kitchen, 2 bedrooms, laundry room and full bath. The generous lot, separate entrances, and existing footprint create an ideal opportunity to modernize the current two-family, expand the living space, or explore redevelopment possibilities. Whether you're looking for a strong income property or your next renovation project, this property is full of potential and ready for its next chapter!

257 Cross St, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,064,000
4 Beds ⋅ 2 Baths ⋅ 73547513 MLS ⋅ ACTIVE Status
Welcome to this meticulously renovated four-bedroom Colonial, ideally situated on a quiet dead-end street just steps from downtown Winchester, the commuter rail, and the newly built Lynch Elementary School. The sun-filled first floor features gorgeous floors, a charming living room, a dining room that opens to a spacious deck, a stunning updated kitchen with new countertops and appliances, as well as a mudroom and a full bath. The fenced backyard is perfect for entertaining. Upstairs, four bedrooms each offer generous closet space. The lower level--with new half bath, new carpet, laundry and storage--is ideal for a media space or playroom. Newer roof, tankless water heater, and a new 200-amp electrical panel provide peace of mind. Close proximity to Horn Pond Reservation, trails, and parks, and easy access to Boston via rail and bus. A rare chance to own a fully updated home in a truly special neighborhood.

46 Clark St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$1,099,000
3 Beds ⋅ 2 Baths ⋅ 73530959 MLS ⋅ ACTIVE Status
Charming colonial with lots of character! Step into a welcoming foyer that leads into an open concept kitchen and dining room area. Kitchen is fully equipped along with gas cooking and breakfast bar,front to back living room with a cozy fireplace surrounded by built-ins and slider out to a big sunny deck and crown moldings, french doors from living room lead out to a 4 season sun room perfect for den, home office or playroom area. First floor half bath. Upstairs features 3 well proportioned bedrooms and a full bath, hardwood floors throughout, partially finished basement with bonus room, 2 car garage and ample driveway parking, sunny back yard. Freshly painted exterior,Showings delayed until Tenant moves out. Please schedule starting July 2nd.

150 Cambridge Street, Winchester

Listing courtesy of Listing Agent: Diane Plunkett from Listing Office: Plunkett Properties.
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 73537786 MLS ⋅ ACTIVE Status
Lovingly maintained by the same family for more than 50 years, 38 Robinhood is filled with warmth and ready for its next chapter. This versatile home offers a flexible layout with a fireplaced family room, playroom, bedroom, or home office on the entry level, along with a half bath, laundry area, and direct access to the two-car garage. Upstairs, the sun-drenched living room flows into the open dining area with direct access to the oversized screened porch—perfect for relaxing or entertaining. The eat-in kitchen provides access to the patio and backyard, ideal for summer cookouts. The top floor also features three bedrooms with hardwood floors, a full bath, and a half bath. Conveniently located with easy access to all that Winchester has to offer, this cherished home is not to be missed.

38 Robinhood Rd, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,199,000
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.
$1,150,000
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.
$1,099,000
3 Beds ⋅ 4 Baths ⋅ 73513572 MLS ⋅ ACTIVE Status ⋅ ['The Washington Street Condominium'] BLDG.
Experience the best of Winchester with a home that pairs exceptional value with an unbeatable location. Just moments from Winchester Center, enjoy a low-maintenance lifestyle within walking distance of downtown, the commuter rail, and all three school levels. This townhouse-style condo lives like a single-family home, offering space, flow, and flexibility across four finished levels. The open main level seamlessly connects the kitchen, dining, and living areas, highlighted by coffered ceilings, wainscoting, and a beautifully renovated kitchen with stainless steel appliances and modern finishes. Upstairs, the front-to-back primary suite features custom closets and a spa-inspired bath with a soaking tub and glass shower. The finished lower level provides the perfect flex space for a home office, media room, fitness area, or playroom. Complete with two deeded parking spaces, this is effortless living in one of Winchester's most desirable locations.

129 Washington St Unit 129, Winchester

Listing courtesy of Listing Agent: The Mary Scimemi Team from Listing Office: Leading Edge Real Estate.
$1,150,000
73507899 MLS ⋅ ACTIVE Status
A must see Professional Office Condo with Flexible Layout, plenty of Parking and Move-In Ready. Bright, versatile, and move-in ready, this well-appointed office suite is located in the desirable Russell Hill Office Building. The flexible layout features a spacious reception and waiting area, five private offices/exam rooms, a large conference room, staff workspace, kitchenette with dining area, abundant storage, and two restrooms, including a private full in-suite bath. Four offices include sinks, offering flexibility for medical, wellness, legal, accounting, insurance, real estate, financial, consulting, educational, nonprofit, and other professional uses. Furniture is included. The professionally managed, elevator-served building offers on-site parking and handicap-accessible entry. Conveniently located near Winchester Center, Winchester Hospital, Route 38, I-93, and I-95/128. Zoned for medical and professional office use by right. Renovated in 2009,and one recent room renovation.

955 Main St Unit 305, Winchester

Listing courtesy of Listing Agent: Zuby Singh from Listing Office: Coldwell Banker Realty - Lexington.

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