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76 Thimble Rock Road

Middletown, Connecticut 06457

ACTIVE$649,900

Reduced from $675,000

Beds
4
Baths
2 | 2
SqFt
2,671
Acres
2.62
Year Built
1990
Matt Caiola

Matt Caiola

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2-Car Garage2 FireplacesPrice Reduced

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
46 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
$13,204 / Annually

Market Snapshot

The Middletown Market

Single Family · trailing 12 months

Median Days on Market

46

28 active listings

Median $ / Sq Ft

$248

28 active listings

Sale-to-List Ratio

101.9%

316 sales

How this home compares

List Price

$649,900

vs $455,000 median

42.8% above median

Price / Sq Ft

$243

vs $248 median

In line with median

Days on Market

46 days

vs 46 days median

In line with median

Based on 28 active and 316 closed sales (trailing 12 mo) of single family in Middletown. Source: SmartMLS · As of July 28, 2026.

Location

76 Thimble Rock Road, Middletown, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,631

per month

  • Principal & Interest$3,314
  • Property Taxes$1,100
  • 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
$13,204 / Annually
Days on Market
46
MLS #
24183475
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Carl Guild

(860) 813-2275

Carl Guild & Associates

(860) 474-3500

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:10 AM UTC.