39 Winslow Rd Cheshire, CT 06410
Estimated payment $2,952/month
Highlights
- Cape Cod Architecture
- Deck
- Sitting Room
- Darcey School Rated A-
- Partially Wooded Lot
- Workshop
About This Home
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.
Listing Agent
Luxe Realty LLC Brokerage Phone: (860) 839-8331 License #REB.0794369 Listed on: 05/06/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $6,322
Year Built
- Built in 1956
Lot Details
- 25,265 Sq Ft Lot
- Partially Wooded Lot
- Property is zoned R-20
Home Design
- Cape Cod Architecture
- Concrete Foundation
- Block Foundation
- Frame Construction
- Fiberglass Roof
- Wood Siding
- Vinyl Siding
Interior Spaces
- 1,758 Sq Ft Home
- Thermal Windows
- Entrance Foyer
- Sitting Room
- Workshop
- Partially Finished Basement
- Basement Fills Entire Space Under The House
Kitchen
- Oven or Range
- Dishwasher
Bedrooms and Bathrooms
- 3 Bedrooms
- 2 Full Bathrooms
Laundry
- Laundry Room
- Laundry on lower level
Parking
- 2 Car Garage
- Parking Deck
Outdoor Features
- Balcony
- Deck
Location
- Property is near golf course
Schools
- Doolittle Elementary School
- Dodd Middle School
- Cheshire High School
Utilities
- Window Unit Cooling System
- Hot Water Heating System
- Heating System Uses Oil
- Private Company Owned Well
- Hot Water Circulator
Listing and Financial Details
- Assessor Parcel Number 1079181
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $6,322 | $212,590 | $51,030 | $161,560 |
| 2024 | $5,838 | $212,590 | $51,030 | $161,560 |
| 2023 | $5,442 | $155,100 | $51,060 | $104,040 |
| 2022 | $5,323 | $155,100 | $51,060 | $104,040 |
| 2021 | $5,230 | $155,100 | $51,060 | $104,040 |
| 2020 | $5,152 | $155,100 | $51,060 | $104,040 |
| 2019 | $5,152 | $155,100 | $51,060 | $104,040 |
| 2018 | $5,022 | $153,950 | $51,410 | $102,540 |
| 2017 | $4,917 | $153,950 | $51,410 | $102,540 |
| 2016 | $4,725 | $153,950 | $51,410 | $102,540 |
| 2015 | $4,725 | $153,950 | $51,410 | $102,540 |
| 2014 | $4,657 | $153,950 | $51,410 | $102,540 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 05/13/2026 05/13/26 | Pending | -- | -- | -- | |
| 05/07/2026 05/07/26 | For Sale | $449,900 | +36.3% | $256 / Sq Ft | |
| 06/25/2021 06/25/21 | Sold | $330,000 | +10.0% | $188 / Sq Ft | View Prior Sale |
| 05/08/2021 05/08/21 | For Sale | $299,900 | -- | $171 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $330,000 | None Available | |
| Warranty Deed | $330,000 | None Available |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $264,000 | Purchase Money Mortgage | |
| Closed | $264,000 | Purchase Money Mortgage |
Source: SmartMLS
MLS Number: 24168914
APN: CHES-000024-000054
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