2 CALDWELL 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: New Milford School District
Neighborhood · ZIP 06776These 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
2 Caldwell 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 less than 78% of homes in Western Connecticut County
- Costs more per square foot than 94% of homes in New Milford 06776
- Smaller than 87% of homes in Western Connecticut County
- Has a smaller lot than 88% of homes in New Milford 06776
- Older than 72% of homes in New Milford 06776
What homes are worth in New Milford 06776
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 New Milford 06776.
How it measures up in New Milford 06776
The dot is this home. The mark in the middle is the typical home in New Milford 06776.
Pricier than 56% of homes nearby
Pricier than 94% of homes nearby
Bigger than 24% of homes nearby
Bigger than 12% of homes nearby
Newer than 28% of homes nearby
| Measure | This home | New Milford 06776 | Western Connecticut County |
|---|---|---|---|
| Estimated valuepricier than | $504,869 | 56% of homes | 22% of homes |
| Price per ft²pricier than | $457 | 94% of homes | 59% of homes |
| Living areabigger than | 1,104 ft² | 24% of homes | 13% of homes |
| Lot sizebigger than | 0.31 ac | 12% of homes | 31% of homes |
| Year builtnewer than | 1965 | 28% of homes | 48% of homes |
About 2 Caldwell Dr
How much is 2 Caldwell Dr, New Milford, CT worth?
The TopHap Estimate for 2 Caldwell Dr, New Milford, CT is $504,869 as of Aug 30, 2026. The likely range is $458,116 to $551,622. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 2 Caldwell Dr, New Milford, CT last sell?
2 Caldwell Dr, New Milford, CT last sold on Dec 29, 2025 for $485,000, according to the county's recorded deed. TopHap holds 4 recorded sales for this parcel.
How big is 2 Caldwell Dr, New Milford, CT?
2 Caldwell Dr, New Milford, CT has 3 bedrooms, 1.5 bathrooms, 1,104 square feet of living space and a 0.31-acre lot.
When was 2 Caldwell Dr, New Milford, CT built?
2 Caldwell Dr, New Milford, CT was built in 1965, making it 61 years old. It is a raised ranch home. The building has 1 story.
What schools serve 2 Caldwell Dr, New Milford, CT?
2 Caldwell Dr, New Milford, CT is assigned to Hill and Plain Elementary School (elementary); New Milford High School (high), rated B-; Schaghticoke Middle School (middle), rated C+. All sit in New Milford School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 2 Caldwell Dr, New Milford, CT compare to other homes in New Milford 06776?
Among the 10,061 homes in New Milford 06776, it is worth more than 56% of them ($504,869 against a typical $482,064), its price per square foot is higher than 94% of them ($457 against a typical $284), it is bigger than 24% of them (1,104 ft² against a typical 1,563 ft²), its lot is bigger than 12% of them (0.31 ac against a typical 0.93 ac) and it is newer than 28% of them (1965 against a typical 1977). Measured against all of Western Connecticut County, it is worth more than 22% 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 2 Caldwell Dr, New Milford, CT?
The 2025 property tax bill for 2 Caldwell Dr, New Milford, CT was $7,780. The county assessed it at $168,560.
More homes on Caldwell Dr
- 24 Caldwell Dr$523K3 bd · 2 ba · 1,087 ft² · Sold $515K · May 2026
- 31 Caldwell Dr$526K3 bd · 2.5 ba · 1,104 ft² · Sold $506K · Dec 2025
- 1 Caldwell Dr$372K3 bd · 2 ba · 1,060 ft² · Sold $350K · Aug 2025
- 40 Caldwell Dr$445K3 bd · 1 ba · 989 ft² · Sold $300K · Jan 2023
- 17 Caldwell Dr$445K3 bd · 1.5 ba · 1,060 ft² · Sold $350K · Nov 2022
- 22 Caldwell Dr$540K3 bd · 1 ba · 1,128 ft² · Sold $325K · Sep 2022
- 46 Caldwell Dr$544K3 bd · 2.5 ba · 1,050 ft² · Sold $370K · Jun 2022
- 36 Caldwell Dr$497K3 bd · 2 ba · 1,060 ft² · Sold $340K · May 2022
- 25 Caldwell Dr$639K3 bd · 3 ba · 1,030 ft² · Sold $240K · Dec 2018
- 38 Caldwell Dr$592K4 bd · 2.5 ba · 1,104 ft² · Sold $299K · Jul 2018
- 28 Caldwell Dr$461K4 bd · 1.5 ba · 1,104 ft² · Sold $177K · Sep 2016
- 30 Caldwell Dr$534K3 bd · 2.5 ba · 1,104 ft² · Sold $22K · Oct 2015
Closest homes
- 4 Caldwell Dr$446K90 ft · 3 bd · 1.5 ba · 1,060 ft² · Sold Jan 1900
- 58 Sunny Valley Rd$374K132 ft · 3 bd · 1.5 ba · 1,176 ft² · Sold Jan 1900
- 11 Howe Rd$417K158 ft · 3 bd · 2 ba · 1,060 ft² · Sold $195K · Apr 2016
- 1 Caldwell Dr$372K206 ft · 3 bd · 2 ba · 1,060 ft² · Sold $350K · Aug 2025
- 3 Shepherds Path215 ft · 5 bd · 2 ba · 2,847 ft² · Sold $305K · Nov 2004
- 6 Caldwell Dr$491K180 ft · 3 bd · 1 ba · 1,008 ft² · Sold Jan 1900
- 10 Howe Rd$484K198 ft · 3 bd · 1.5 ba · 1,660 ft² · Sold $295K · Aug 2023
- 3 Caldwell Dr$495K220 ft · 3 bd · 1 ba · 1,056 ft² · Sold $147K · Jul 1998
More homes in New Milford 06776
- 15 Glen Ridge Ct$217K1 bd · 1 ba · 682 ft² · Sold $229K · Aug 2026
- 14 Carlson Ridge Ct$533K2 bd · 2 ba · 1,931 ft² · Sold $530K · Aug 2026
- 15 White Swan Dr$493K3 bd · 1.5 ba · 1,232 ft² · Sold $380K · Aug 2026
- 120 Sullivan Farm$550K2 bd · 3 ba · 1,785 ft² · Sold $550K · Aug 2026
- 32 Ferris Estates Rd$1.6M3 bd · 4 ba · 2,460 ft² · Sold $1.4M · Aug 2026
- 36 Maple Dr$439K3 bd · 1 ba · 1,069 ft² · Sold $439K · Aug 2026
- 85 Aspetuck Vlg$269K2 bd · 1.5 ba · 1,152 ft² · Sold $275K · Aug 2026
- 35 Hillendale Dr$415K3 bd · 1 ba · 1,144 ft² · Sold $415K · Aug 2026
- 17 Bridle Rd$504K4 bd · 2.5 ba · 1,948 ft² · Sold $405K · Aug 2026
- 214 Pumpkin Hill Rd$400K3 bd · 2 ba · 1,842 ft² · Sold $400K · Aug 2026
- 14 Westview Rd$500K3 bd · 3 ba · 1,436 ft² · Sold $500K · Aug 2026
- 3 Halletts Rd$551K3 bd · 2 ba · 1,379 ft² · Sold $551K · Aug 2026
Assigned schools
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