Winchester Rd, Winsted, CT Property Records

Winchester Town property records for 58 addresses on Winchester Rd, Winsted, CT · Last verified July 2026

Winchester Rd Highlights

Properties 58
Median Sale Price $515,000
Deeds and Mortgages on File 49
Median Price per Sqft $190
Owner Occupied 71%
Median Annual Tax Bill $5,007
Median Year Built 1957
Median Ownership Tenure 17 years

Properties on Winchester Rd

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

111 Winchester Rd

4 bd · 1.5 ba · 2,096 sqft · built 1906 · 0.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$130,000Oct 1995 $7,6182025 1 Name on Record AssessorUpdated Jul 2026

114 Winchester Rd

2 bd · 2 ba · 1,581 sqft · built 1819 · 7.83 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,0972025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

124 Winchester Rd

36.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$545,000Aug 2009 1 Name on Record AssessorUpdated Jul 2026

154 Winchester Rd

273 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record AssessorUpdated Jul 2026

304 Winchester Rd

3 bd · 1 ba · 1,702 sqft · built 1860 · 3.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,4642025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

306 Winchester Rd

2 bd · 1.5 ba · 1,080 sqft · built 1830 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$117,500Jul 2001 $3,3752025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

307 Winchester Rd

3 bd · 2 ba · 1,064 sqft · built 1959 · 2.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$135,000Jan 2021 $6,6812025 —Nov 2018 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

311 Winchester Rd

3 bd · 2.5 ba · 1,930 sqft · built 2006 · 0.85 acres

Last Sale Tax Bill Prior Sale Owner Records
$277,500Jun 2007 $6,1362025 Amount on Record May 2006 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

313 Winchester Rd

3 bd · 1 ba · 1,546 sqft · built 1954 · 0.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$123,250Oct 1996 $4,7112025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

314 Winchester Rd

3 bd · 1 ba · 1,374 sqft · built 1920 · 1.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$209,900Aug 2007 $4,4762025 Amount on Record — 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

317 Winchester Rd

3 bd · 2 ba · 1,975 sqft · built 1981 · 4.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,6042025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

318 Winchester Rd

3 bd · 2 ba · 1,782 sqft · built 1950 · 4.51 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,3002025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

320 Winchester Rd

2 bd · 2.5 ba · 1,475 sqft · built 1959 · 2.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,0072025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

322 Winchester Rd

2.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,3882025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

323 Winchester Rd

3 bd · 1 ba · 1,819 sqft · built 1930 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$97,500Jul 2008 $4,4722025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

328 Winchester Rd

5 bd · 4.5 ba · 3,443 sqft · built 2005 · 3.78 acres

Last Sale Tax Bill Prior Sale Owner Records
$16,7462025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

329 Winchester Rd

3 bd · 2 ba · 1,410 sqft · built 1900 · 0.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$65,000Sep 1995 $5,0112025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

331 Winchester Rd

3 bd · 3 ba · 1,714 sqft · built 1966 · 0.519 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,3422025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

333 Winchester Rd

3 bd · 2 ba · 1,869 sqft · built 1953 · 0.51 acres

Last Sale Tax Bill Prior Sale Owner Records
$160,000Jun 2017 $4,1802025 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

335 Winchester Rd

4 bd · 2 ba · 2,749 sqft · built 1950 · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$192,500Jun 2002 $7,6732025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

336 Winchester Rd

5.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$17,5172025 2 Names on Record AssessorUpdated Jul 2026

338 Winchester Rd

4 ba · 12,960 sqft · built 1998 · 244 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record AssessorUpdated Jul 2026

339 Winchester Rd

3 bd · 2 ba · 2,354 sqft · built 1980 · 1.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,9152025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

343 Winchester Rd

2 bd · 1 ba · 960 sqft · built 1956 · 0.589 acres

Last Sale Tax Bill Prior Sale Owner Records
$84,000Apr 1997 $4,2432025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

359 Winchester Rd

3 bd · 3.5 ba · 2,943 sqft · built 2000 · 7.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$653,500Aug 2021 $10,3732025 Amount on Record Jan 2004 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

361 Winchester Rd

3 bd · 1.5 ba · 1,500 sqft · built 1953 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$329,900May 2024 $4,7602025 Amount on Record Nov 2020 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

363 Winchester Rd

2 bd · 3.5 ba · 1,424 sqft · built 1998 · 2.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,7192025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

367 Winchester Rd

3 bd · 2 ba · 1,991 sqft · built 1999 · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,1012025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

369 Winchester Rd

1.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,000Dec 2017 $6042025 Amount on Record Aug 2001 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

371 Winchester Rd

3 bd · 2 ba · 988 sqft · built 1957 · 0.93 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Aug 2013 $4,1292025 Amount on Record Aug 2001 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

373 Winchester Rd

3 bd · 2.5 ba · 2,278 sqft · built 1976 · 1.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$282,000Dec 2015 $7,4842025 Amount on Record Sep 2008 1 Name on Record AssessorUpdated Jul 2026

379 Winchester Rd

2.95 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record AssessorUpdated Jul 2026

383 Winchester Rd

3 bd · 2 ba · 1,726 sqft · built 1956 · 7 acres

Last Sale Tax Bill Prior Sale Owner Records
$845,000Aug 2009 $4,2982025 1 Name on Record AssessorUpdated Jul 2026

390 Winchester Rd

100 acres

Last Sale Tax Bill Prior Sale Owner Records
$845,000Aug 2009 $24,4252025 Amount on Record Aug 1999 1 Name on Record AssessorUpdated Jul 2026
Last Sale Tax Bill Prior Sale Owner Records
$1,5542025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

399 Winchester Rd

2 bd · 1 ba · 1,016 sqft · built 1938 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$175,000Nov 2007 $4,9562025 Amount on Record Oct 2006 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

403 Winchester Rd

3 bd · 1 ba · 1,248 sqft · built 1958 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000Mar 2019 $3,9652025 Amount on Record Aug 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

405 Winchester Rd

3 bd · 1 ba · 1,821 sqft · built 1976 · 8.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,3742025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

407 Winchester Rd

2 bd · 1 ba · 1,267 sqft · built 1976 · 4.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$155,000Jan 2021 $3,8762025 —Sep 2019 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

409 Winchester Rd

1.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,2442025 1 Name on Record AssessorUpdated Jul 2026

411 Winchester Rd

3 bd · 2 ba · 1,568 sqft · built 1975 · 3.91 acres

Last Sale Tax Bill Prior Sale Owner Records
$153,000Sep 1999 $4,2002025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

412 Winchester Rd

1 bd · 1 ba · 1,040 sqft · built 1970 · 0.91 acres

Last Sale Tax Bill Prior Sale Owner Records
$450,000Jul 2006 $10,6982024 2 Names on Record AssessorUpdated Jul 2026

413 Winchester Rd

4 bd · 3 ba · 2,776 sqft · built 1976 · 3.68 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,5652025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

415 Winchester Rd

2 bd · 1 ba · 1,182 sqft · built 1977 · 3.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,7842025 1 Name on Record Assessor + 3 DocumentsUpdated Jul 2026

417 Winchester Rd

3 bd · 4.5 ba · 5,134 sqft · built 1986 · 3.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$649,900Apr 2024 $12,8212025 Amount on Record Nov 2022 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

419 Winchester Rd

3 bd · 2.5 ba · 1,709 sqft · built 1986 · 3.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$213,500May 2019 $4,8172025 Amount on Record Oct 2001 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

421 Winchester Rd

2 bd · 2 ba · 1,504 sqft · built 1933 · 0.719 acres

Last Sale Tax Bill Prior Sale Owner Records
$89,000Jul 1997 $4,2212025 Amount on Record Jul 1987 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

423 Winchester Rd

4 bd · 2 ba · 1,995 sqft · built 1955 · 1.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,3132025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

425 Winchester Rd

4 bd · 1.5 ba · 1,767 sqft · built 1949 · 1.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,5692025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

430 Winchester Rd

121 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,3842025 2 Names on Record AssessorUpdated Jul 2026

436 Winchester Rd

3 bd · 2.5 ba · 2,881 sqft · built 1988 · 52.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$549,000Aug 2020 $8,3862025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

438 Winchester Rd

6 bd · 2 ba · 5,629 sqft · built 1874 · 47.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$17,8972025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

439 Winchester Rd

2 bd · 1 ba · 1,141 sqft · built 1938 · 10.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$131,000Oct 1997 $5,1932025 1 Name on Record Assessor + 2 DocumentsUpdated Jul 2026

443 Winchester Rd

3 bd · 1 ba · 1,104 sqft · built 1973 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$129,500Jul 1998 $4,0312025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

463 Winchester Rd

15.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$515,000Jul 2024 $3,1472025 Amount on Record Jul 1998 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

465 Winchester Rd

3 bd · 1.5 ba · 1,268 sqft · built 1957 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,5132025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

467 Winchester Rd

3 bd · 1.5 ba · 1,664 sqft · built 1900 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000Jul 2021 $5,8282025 Amount on Record Aug 2001 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

473 Winchester Rd

2 bd · 1 ba · 1,128 sqft · built 1950 · 0.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$51,000Jul 2015 $3,5962025 Amount on Record May 2000 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

Wildfire Risk on Winchester Rd

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank above 17% of the US · above 46% of Connecticut
Wildfire LikelihoodLess than 1 in 10,000 per year
ExposureDirect
17 of 24 cells directly exposed · 23 adjoin burnable vegetation

Property Records in Nearby Streets