Refine Search
Map
Sort by
$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.
$1,150,000
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.
$1,899,000
6 Beds ⋅ 5 Baths ⋅ 73507145 MLS ⋅ ACTIVE Status
Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add' bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac in the Lynch School district

16 Glenwood Ave, Winchester

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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.