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Single Family ResidenceResidential
$559,031$308 / ft²
TopHap EstimateOur estimate of what this home would sell for today, based on nearby sales, the home's size and features, and local price trends. It is a starting point, not an appraisal.· confidence 89How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Oct 21, 2026

27 UPLAND RD

MIDDLEBURY, CT 06762
4
Beds
3.5
Baths
1,817 ft²
Living AreaTotal finished area of the structures, from county records. Some counties include shared space like hallways or a building gym, so it may not match a listing.
0.31 ac
Lot SizeThe size of the land the home sits on, from county records.
1976
Year BuiltThe year the home was originally built, according to county records.
1
StoriesHow many floors the home has above ground.
10
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.
2
ParkingThe number of parking spaces on the property, including the garage.

Valuation

$559K
$496K low$622K high

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$8,267 (2025)
Assessed ValueThe value the county assigns to this home to calculate property tax. It is often lower than what the home would sell for.$254,200 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$56,100
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$198,100
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$254,200
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$363,143

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
StyleThe architectural style of the home, such as ranch or colonial.Raised Ranch
CountyNAUGATUCK VALLEY
Effective Year BuiltAn adjusted build year that accounts for condition and major remodels. A big renovation can make a home count as newer than it is.1985
Lot (acres)The size of the land the home sits on, from county records.0.31
RoofThe main material covering the roof, such as asphalt shingle or tile.Asphalt
HeatingThe type of heating system in the home.Hot Water
CoolingThe type of cooling or air conditioning in the home.Yes
FireplaceWhether the home has a fireplace, and what kind.Yes
GarageWhether the property has a garage, and details like whether it is attached to the home.Garage, Basement
PoolWhether the property has a pool, and what kind, such as in-ground.No

Transaction History(2)

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.

M
Memorial Middle SchoolB
Middle · Grades 6–8 · 0.7 mi
E
Middlebury Elementary SchoolB-
Elementary · Grades PK–5 · 1.3 mi
H
Pomperaug Regional High SchoolA-
High · Grades 9–12 · 4.2 mi

District: Regional School District 15

Neighborhood · ZIP 06762These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.

CrimeLocal crime compared with the rest of the country, where 100 is average. It reflects things like population density, income, and how crime gets reported.110
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.104
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.69

Index scale: 100 = US average (tick). Lower is better.

Homes occupiedThe share of homes here that someone lives in. The rest sit empty, including vacation and for-sale homes.95%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.30%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.5.8%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.0%
PopulationHow many people live in this area.7,893
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.429 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$134,216
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$150,984
Average tempThe average temperature here across a full year.49°F
Annual precipHow much rain and melted snow falls here in a typical year.52 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.58%

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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 Upland Rd 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 79% of homes in Naugatuck Valley County
  • Costs more per square foot than 76% of homes in Naugatuck Valley County
  • Bigger than 65% of homes in Naugatuck Valley County
  • Has a smaller lot than 93% of homes in Middlebury 06762

What homes are worth in Middlebury 06762

Each bar is how many homes fall in that price range. The marker is this home.

This home
$273K$1.3M

This home is worth more than 49% of homes in Middlebury 06762.

How it measures up in Middlebury 06762

The dot is this home. The mark in the middle is the typical home in Middlebury 06762.

Estimated value$559,031
CheaperTypical $563,068Pricier

Pricier than 49% of homes nearby

Price per ft²$308
CheaperTypical $274Pricier

Pricier than 72% of homes nearby

Living area1,817 ft²
SmallerTypical 2,074 ft²Bigger

Bigger than 39% of homes nearby

Lot size0.31 ac
SmallerTypical 1 acBigger

Bigger than 7% of homes nearby

Year built1976
OlderTypical 1972Newer

Newer than 54% of homes nearby

How 27 Upland Rd ranks against every home in each area.
MeasureThis homeMiddlebury 06762Naugatuck Valley County
Estimated valuepricier than$559,03149% of homes79% of homes
Price per ft²pricier than$30872% of homes76% of homes
Living areabigger than1,817 ft²39% of homes65% of homes
Lot sizebigger than0.31 ac7% of homes42% of homes
Year builtnewer than197654% of homes61% of homes

About 27 Upland Rd

How much is 27 Upland Rd, Middlebury, CT worth?

The TopHap Estimate for 27 Upland Rd, Middlebury, CT is $559,031 as of Oct 21, 2026. The likely range is $496,311 to $621,751. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 27 Upland Rd, Middlebury, CT last sell?

27 Upland Rd, Middlebury, CT last sold on Jan 1, 1900, according to the county's recorded deed.

How big is 27 Upland Rd, Middlebury, CT?

27 Upland Rd, Middlebury, CT has 4 bedrooms, 3.5 bathrooms, 1,817 square feet of living space and a 0.31-acre lot.

When was 27 Upland Rd, Middlebury, CT built?

27 Upland Rd, Middlebury, CT was built in 1976, making it 50 years old. It is a raised ranch home. The building has 1 story.

What schools serve 27 Upland Rd, Middlebury, CT?

27 Upland Rd, Middlebury, CT is assigned to Memorial Middle School (middle), rated B; Middlebury Elementary School (elementary), rated B-; Pomperaug Regional High School (high), rated A-. All sit in Regional School District 15. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 27 Upland Rd, Middlebury, CT compare to other homes in Middlebury 06762?

Among the 3,076 homes in Middlebury 06762, it is worth more than 49% of them ($559,031 against a typical $563,068), its price per square foot is higher than 72% of them ($308 against a typical $274), it is bigger than 39% of them (1,817 ft² against a typical 2,074 ft²), its lot is bigger than 7% of them (0.31 ac against a typical 1 ac) and it is newer than 54% of them (1976 against a typical 1972). Measured against all of Naugatuck Valley County, it is worth more than 79% 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 Upland Rd, Middlebury, CT?

The 2025 property tax bill for 27 Upland Rd, Middlebury, CT was $8,267. The county assessed it at $254,200.

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