27 WINSTON DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(5)
Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.
District: Regional School District 12
Neighborhood · ZIP 06794These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.
Index scale: 100 = US average (tick). Lower is better.
Owner Tools
Data by ATTOM. Valuations are automated estimates, not appraisals. Photos from Google Street View and may not depict the current property state.
How this home compares
27 Winston Dr measured against every home in its neighborhood, its ZIP code and its county, using county assessor records refreshed nightly. A home can stand out in one of those areas and look ordinary in another, because each one holds a different mix of homes.
- Worth more than 89% of homes in Northwest Hills County
- Costs less per square foot than 89% of homes in Washington Depot 06794
- Bigger than 89% of homes in Northwest Hills County
- Has a bigger lot than 73% of homes in Northwest Hills County
What homes are worth in Washington Depot 06794
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 56% of homes in Washington Depot 06794.
How it measures up in Washington Depot 06794
The dot is this home. The mark in the middle is the typical home in Washington Depot 06794.
Pricier than 56% of homes nearby
Pricier than 11% of homes nearby
Bigger than 72% of homes nearby
Bigger than 42% of homes nearby
Newer than 59% of homes nearby
| Measure | This home | Washington Depot 06794 | Northwest Hills County |
|---|---|---|---|
| Estimated valuepricier than | $941,514 | 56% of homes | 89% of homes |
| Price per ft²pricier than | $308 | 11% of homes | 69% of homes |
| Living areabigger than | 3,058 ft² | 72% of homes | 89% of homes |
| Lot sizebigger than | 3.06 ac | 42% of homes | 73% of homes |
| Year builtnewer than | 1977 | 59% of homes | 60% of homes |
About 27 Winston Dr
How much is 27 Winston Dr, Washington Depot, CT worth?
The TopHap Estimate for 27 Winston Dr, Washington Depot, CT is $941,514 as of Sep 24, 2026. The likely range is $790,016 to $1,093,012. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 27 Winston Dr, Washington Depot, CT last sell?
27 Winston Dr, Washington Depot, CT last sold on Sep 26, 2018 for $373,000, according to the county's recorded deed.
How big is 27 Winston Dr, Washington Depot, CT?
27 Winston Dr, Washington Depot, CT has 4 bedrooms, 2.5 bathrooms, 3,058 square feet of living space and a 3.06-acre lot.
When was 27 Winston Dr, Washington Depot, CT built?
27 Winston Dr, Washington Depot, CT was built in 1977, making it 49 years old. It is a colonial home. The building has 2 stories.
What schools serve 27 Winston Dr, Washington Depot, CT?
27 Winston Dr, Washington Depot, CT is assigned to Washington Primary School (elementary), rated B-; Shepaug Valley School (middle), rated A-. All sit in Regional School District 12. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 27 Winston Dr, Washington Depot, CT compare to other homes in Washington Depot 06794?
Among the 559 homes in Washington Depot 06794, it is worth more than 56% of them ($941,514 against a typical $869,339), its price per square foot is higher than 11% of them ($308 against a typical $443), it is bigger than 72% of them (3,058 ft² against a typical 2,186 ft²), its lot is bigger than 42% of them (3.06 ac against a typical 3.73 ac) and it is newer than 59% of them (1977 against a typical 1971). Measured against all of Northwest Hills County, it is worth more than 89% of homes there. These shares are recounted nightly from the full county assessor record for each area, not from active listings.
What are the property taxes on 27 Winston Dr, Washington Depot, CT?
The 2026 property tax bill for 27 Winston Dr, Washington Depot, CT was $5,165. The county assessed it at $476,070.
More homes on Winston Dr
- 26 Winston Dr$666K3 bd · 2 ba · 2,065 ft² · Sold $638K · Jul 2025
- 48 Winston Dr$1.1M3 bd · 3.5 ba · 1,756 ft² · Sold $572K · Oct 2021
- 38 Winston Dr$1.3M3 bd · 2.5 ba · 3,753 ft² · Sold $719K · Nov 2020
- 31 Winston Dr$1.1M5 bd · 4 ba · 2,931 ft² · Sold $1.1M · Oct 2020
- 23 Winston Dr$1.1M3 bd · 3.5 ba · 2,600 ft² · Sold $984K · Sep 2020
- 18 Winston Dr$1M4 bd · 2.5 ba · 2,646 ft² · Sold $545K · Jan 2020
- 37 Winston Dr$1.1M5 bd · 2.5 ba · 2,870 ft² · Sold $460K · Apr 2017
- 43 Winston Dr3 bd · 2.5 ba · 1,904 ft² · Sold $580K · Mar 2008
- 12 Winston Dr3 bd · 3 ba · 2,309 ft² · Sold $68K · Mar 2004
- 19 Winston Dr$896K4 bd · 2.5 ba · 2,474 ft² · Sold $319K · Apr 2001
- 42 Winston Dr$859K4 bd · 3.5 ba · 2,068 ft² · Sold Jan 1900
Closest homes
- 23 Winston Dr$1.1M228 ft · 3 bd · 3.5 ba · 2,600 ft² · Sold $984K · Sep 2020
- 31 Winston Dr$1.1M252 ft · 5 bd · 4 ba · 2,931 ft² · Sold $1.1M · Oct 2020
- 26 Winston Dr$666K526 ft · 3 bd · 2 ba · 2,065 ft² · Sold $638K · Jul 2025
- 19 Winston Dr$896K468 ft · 4 bd · 2.5 ba · 2,474 ft² · Sold $319K · Apr 2001
- 18 Winston Dr$1M0.1 mi · 4 bd · 2.5 ba · 2,646 ft² · Sold $545K · Jan 2020
- 37 Winston Dr$1.1M0.1 mi · 5 bd · 2.5 ba · 2,870 ft² · Sold $460K · Apr 2017
- 38 Winston Dr$1.3M0.2 mi · 3 bd · 2.5 ba · 3,753 ft² · Sold $719K · Nov 2020
- 13 Steeples Rd$1.9M0.2 mi · 3 bd · 2.5 ba · 3,405 ft² · Sold $1.7M · Jun 2023
More homes in Washington Depot 06794
- 124 W Morris Rd$825K2 bd · 1 ba · 800 ft² · Sold $820K · Sep 2026
- 41 River Rd$527K3 bd · 2 ba · 1,279 ft² · Sold $525K · Sep 2026
- 19 Juniper Meadow Rd$599K2 bd · 3 ba · 1,444 ft² · Sold $595K · Aug 2026
- 64 Calhoun St$940K2 bd · 2 ba · 2,163 ft² · Sold $6.4M · Aug 2026
- 62 Calhoun St$6.4M4 bd · 7.5 ba · 7,357 ft² · Sold $6.4M · Aug 2026
- 37 Church Hill Rd$451K2 bd · 2.5 ba · 792 ft² · Sold $450K · Aug 2026
- 76 Blackville Rd$832K3 bd · 2.5 ba · 1,824 ft² · Sold $825K · Jun 2026
- 36 Sunset Ln$794K4 bd · 2.5 ba · 2,745 ft² · Sold $767K · Jun 2026
- 109 Church Hill Rd$936K3 bd · 2.5 ba · 1,239 ft² · Sold $922K · Apr 2026
- 337 Romford Rd$1.3M2 bd · 2.5 ba · 2,186 ft² · Sold $1.3M · Feb 2026
- 54 Scofield Hill Rd4 bd · 3.5 ba · 3,023 ft² · Sold $1.1M · Feb 2026
- 114 Bee Brook Rd4 bd · 2 ba · 2,085 ft² · Sold $505K · Nov 2025
Assigned schools
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