Welcome to 39 Winslow Rd in Cheshire-a beautifully updated Cape set in one of the town's most desirable locations. This 3-bedroom, 2 full bath home blends charm, functionality, and modern updates in all the right ways. Step inside to a spacious foyer that doubles as a cozy sitting area, complete with a built-in coffee bar-perfect for starting or ending your day. The fully renovated kitchen features stainless steel appliances, ample cabinetry, and generous counter space, flowing seamlessly into a formal dining room with refinished hardwood floors. Across the way, the sun-filled living room showcases a stunning bay window that floods the space with natural light. The main level also offers a versatile bedroom and a beautifully remodeled full bath-ideal for guests or a private home office. Upstairs, you'll find two additional bedrooms along with a large family room anchored by a wood stove, creating the perfect setting for cozy winter nights. An additional office space in the rear adds even more flexibility. Outside, enjoy a professionally landscaped front yard bursting with seasonal color, while the backyard offers a peaceful natural setting overlooking a stream. Additional highlights include a partially finished basement, updated roof, vinyl siding, thermopane windows, and ceiling fans in every bedroom. Truly move-in ready-just unpack and enjoy.
Est. $2,703 per month, based on comparable rentals
Sale and tax history for 39 Winslow Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24168914
Jun 25, 2026
Sold
$450,000
$256/sq ft
May 12, 2026
Pending
—
May 7, 2026
Listed
$449,900
$256/sq ft
May 6, 2026
Coming Soon
$449,900
$256/sq ft
Smart MLS #170499663
Jun 28, 2022
Listing Removed
—
Jun 14, 2022
Listed
$389,900
$222/sq ft
Smart MLS #170397871
Jun 25, 2021
Sold
$330,000
$188/sq ft
May 11, 2021
Contingent
—
May 8, 2021
Listed
$299,900
$171/sq ft
Adorable 3 bedroom, 2 full bath cape in Cheshire. This home has been lovingly cared for and is ready for it's new owner. The large foyer/sitting room welcomes you into this home. The kitchen has been completely updated and offers loads of cabinets, tile flooring and newer stainless appliances. Formal dining room with refinished wood floors. The living room has hardwood underneath the carpet and has a beautiful bay window with streaming sunshine. A bedroom and full bath complete the first floor. Upstairs offers two additional bedrooms and a large family room with wood stove for cozy fires in the winter. There is also an office leading to un upper deck. Enjoy the summer on the deck overlooking the yard with wonderful stream. The front yard is full of blooming flowers. This home offers many updates including: Kitchen, Roof, Vinyl siding, Thermopane windows, and Furnace. Just move right in!