76 Thimble Rock Road
Middletown, Connecticut 06457
Reduced from $675,000
- Beds
- 4
- Baths
- 2 | 2
- SqFt
- 2,671
- Acres
- 2.62
- Year Built
- 1990
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Tucked away on a quiet cul-de-sac in Middletown's South End near the Durham line, 76 Thimble Rock Road offers approximately 2,600 square feet of well-maintained living space. This 4-bedroom, 2 full, 2 half bath Colonial has been carefully cared for over the years by a single owner and is ready for its next chapter. Inside, you'll find spacious rooms, abundant natural light, hardwood flooring, and solid wood doors throughout. The floor plan provides plenty of flexibility for everyday living, entertaining, working from home, or accommodating changing needs over time. The partially finished walkout lower level adds valuable bonus space and offers a variety of potential uses, including a recreation room, home office, gym, hobby area, or possible in-law setup. Direct access to the yard makes the space feel like a natural extension of the home. Conveniently located near Middletown's amenities while offering a quieter setting, this property provides space, functionality, and quality construction in a sought-after area of town. Estate sale subject to probate court approval.
Key Facts
- City/Town
- Middletown
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1990
- Days on Market
- 152 days
- Beds
- 4
- Baths
- 2 full · 2 half
- Living Area
- 2,671 sq ft
- Lot Size
- 2.62 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $13,774 / Annually
Market Snapshot
The Middletown Market
Single Family · trailing 12 months
Active Listings
41
48 under contract
Median List Price
$449,900
41 active listings
Median Closed Price
$405,000
325 sales
Median Days on Market
38
41 active listings
Median $ / Sq Ft
$254
41 active listings
Sale-to-List Ratio
102.7%
325 sales
How this home compares
List Price
$649,900
vs $449,900 median
44.5% above median
Price / Sq Ft
$243
vs $254 median
In line with median
Days on Market
152 days
vs 38 days median
114 days longer than median
Based on 41 active and 325 closed sales (trailing 12 mo) of single family in Middletown. Source: SmartMLS · As of November 11, 2026.
Location
76 Thimble Rock Road, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$3,522
- Property Taxes$1,148
- Insurance$217
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middletown
- Neighborhood
- N/A
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1990
- New Construction
- No/Resale
- Living Area
- 2,671 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Middletown
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Oven/RangeRefrigeratorDishwasher
- Basement
- FullPartially FinishedFull With Walk-Out
- In-Law Apartment
- PossibleLower Level
Exterior & Lot
- Lot Size
- 2.62 acres
- Zoning
- R-60
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- TreedSloping LotOn Cul-De-Sac
Listing & Financials
- Property Taxes
- $13,774 / Annually
- Days on Market
- 152
- MLS #
- 24183475
- MLS Status
- Under Contract - Continue to Show
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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 11/11/2026. 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 11/11/2026 at 6:25 PM UTC.