20 Chimney Hill Road
Middletown, Connecticut 06457
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 4,271
- Acres
- 0.98
- Year Built
- 1962
- Neighborhood
- Highland
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Nestled in the sought-after Chimney Hill neighborhood, this spacious Colonial offers over 4,200 square feet of thoughtfully designed living space on a beautifully landscaped lot. The home features 4 bedrooms, 2.5 bathrooms, a bright, open floor plan, generous living and dining areas, and a spacious kitchen perfect for everyday living and entertaining. The family room provides a warm gathering space, while the primary suite offers a private retreat with ample closet space and an en-suite bath. Additional highlights include a two-car attached garage, a large backyard ideal for outdoor entertaining, and a prime location just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, and major commuter routes. This is a rare opportunity to own a beautiful home in one of Middletown's most desirable neighborhoods.
Key Facts
- City/Town
- Middletown
- Neighborhood
- Highland
- Property / Style
- Single Family · Colonial
- Year Built
- 1962
- Days on Market
- 1 day
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 4,271 sq ft
- Lot Size
- 0.98 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $15,634 / Annually
Market Snapshot
The Middletown Market
Single Family · trailing 12 months
Active Listings
39
49 under contract
Median List Price
$425,000
39 active listings
Median Closed Price
$405,000
323 sales
Median Days on Market
16
39 active listings
Median $ / Sq Ft
$254
39 active listings
Sale-to-List Ratio
102.2%
323 sales
How this home compares
List Price
$799,000
vs $425,000 median
88.0% above median
Price / Sq Ft
$187
vs $254 median
26.4% below median
Days on Market
1 day
vs 16 days median
15 days fresher than median
Based on 39 active and 323 closed sales (trailing 12 mo) of single family in Middletown. Source: SmartMLS · As of August 8, 2026.
Location
20 Chimney Hill Road, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 6, 2026per month
- Principal & Interest$4,120
- Property Taxes$1,303
- Insurance$266
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middletown
- Neighborhood
- Highland
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1962
- New Construction
- No/Resale
- Living Area
- 4,271 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 1
- Appliances
- Gas Cooktop
- Basement
- None
Exterior & Lot
- Lot Size
- 0.98 acres
- Zoning
- R-15
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Color
- Gray
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- On Cul-De-Sac
Listing & Financials
- Property Taxes
- $15,634 / Annually
- Days on Market
- 1
- MLS #
- 24197740
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/8/2026. 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 8/8/2026 at 9:21 AM UTC.