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166 Thoreau Drive

Shelton, Connecticut 06484

ACTIVE - NEW$699,900
Beds
5
Baths
3 | 2
SqFt
3,884
Acres
1.36
Year Built
1985
Matt Caiola

Matt Caiola

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About This Home

Lovingly maintained by its original owner, this exceptional home offers over 3,800 sq. ft. and a spacious two-level in-law suite that feels like a home of its own. With a private driveway, entrance and one-car garage, the suite is ideal for multigenerational living, extended family or long-term guests. It features an eat-in kitchen with cherry cabinetry and a skylight, open living and dining areas, a laundry room with half bath, and a bedroom with a walk-in closet and private full bath. The lower level adds a family room with sliders to a private deck, an office area and storage. A mudroom and laundry area connect the suite to the main home, where an eat-in kitchen offers granite counters, a peninsula and two pantry closets. The living and dining room has hardwood floors, and the spacious family room features a vaulted ceiling and wood-burning fireplace. Upstairs are four bedrooms, including a primary suite with a walk-in closet and full bath, plus a full hall bath. A main-level half bath and full basement with access to the two-car garage complete the main home. Set on 1.36 acres bordering open space and the Paugussett hiking trails, the property features a two-tiered deck overlooking the private, wooded backyard.

Key Facts

City/Town
Shelton
Neighborhood
White Hills
Property / Style
Single Family · Colonial
Year Built
1985
Days on Market
0 days
Beds
5
Baths
3 full · 2 half
Living Area
3,884 sq ft
Lot Size
1.36 acres
Garage / Parking
3 garage
Property Taxes
$9,732 / Annually

Market Snapshot

The Shelton Market

Single Family · trailing 12 months

Median Days on Market

46

58 active listings

Median $ / Sq Ft

$269

58 active listings

Sale-to-List Ratio

100.0%

282 sales

How this home compares

List Price

$699,900

vs $644,950 median

8.5% above median

Price / Sq Ft

$180

vs $269 median

33.1% below median

Days on Market

0 days

vs 46 days median

46 days fresher than median

Based on 58 active and 282 closed sales (trailing 12 mo) of single family in Shelton. Source: SmartMLS · As of November 5, 2026.

Location

166 Thoreau Drive, Shelton, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,860

per month

  • Principal & Interest$3,816
  • Property Taxes$811
  • Insurance$233
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Shelton
Neighborhood
White Hills
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1985
New Construction
No/Resale
Living Area
3,884 sq ft

Schools

Elementary
Elizabeth Shelton
Middle
Perry Hill
High
Shelton

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
None
Fireplaces
1
Laundry
Main Level
Laundry Location
main level on both sides
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullHeatedGarage AccessInterior AccessPartially FinishedLiveable SpaceFull With Walk-Out
In-Law Apartment
YesSeparate Entry

Exterior & Lot

Lot Size
1.36 acres
Zoning
R-1
Garage / Parking
3 garage spacesUnder House Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
Wood
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
PorchDeck
Lot Description
Lightly WoodedOn Cul-De-Sac

Listing & Financials

Property Taxes
$9,732 / Annually
Days on Market
0
MLS #
24218570
MLS Status
Active

Similar Properties

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Listed By

Jodi Dawley

(203) 521-2233

Real Estate Two

(203) 926-1122

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 11/5/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 11/5/2026 at 7:35 PM UTC.