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44 Chamberlain Hill Road

Middletown, Connecticut 06457

ACTIVE$829,000

Reduced from $925,000

Beds
6
Baths
3 | 1
SqFt
5,599
Acres
8.50
Year Built
1980
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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1-Car Garage2 FireplacesVirtual TourPrice Reduced

About This Home

Experience over 5,500 square feet of beautifully updated living space in this fully remodeled 6+ bedroom, 3.5-bath residence, perfectly situated on a quiet and expansive 8+ acre lot. Every detail has been thoughtfully upgraded, creating a truly move-in-ready home offering exceptional flexibility and design versatility. The expansive kitchen is the heart of the home, featuring elegant quartz countertops, stainless steel appliances, a double oven, and generous prep and storage space-ideal for both everyday living and entertaining. Large windows and glass doors throughout flood the interior with natural light, enhancing the open-concept layout and spacious living areas. Designed with flexibility in mind, the floor plan offers multiple configuration options, including potential for a private secondary living area-perfect for multi-generational living, guests, or home-based business needs. Interior highlights include: * Large loft with adjoining office space * Two fireplaces * Hardwood flooring * High-end luxury vinyl plank flooring in key living areas The primary suite provides a peaceful retreat, complete with a spacious 7x10 walk-in closet and a beautifully designed bath featuring dual vanities and a custom tile shower. Step outside to enjoy the large deck just off the kitchen and dining area-an ideal setting for relaxing evenings or hosting gatherings.

Key Facts

City/Town
Middletown
Neighborhood
N/A
Property / Style
Single Family · Contemporary
Year Built
1980
Days on Market
162 days
Beds
6
Baths
3 full · 1 half
Living Area
5,599 sq ft
Lot Size
8.50 acres
Garage / Parking
1 garage · 6 total
Property Taxes
$15,016 / 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

$829,000

vs $455,000 median

82.2% above median

Price / Sq Ft

$148

vs $248 median

40.3% below median

Days on Market

162 days

vs 46 days median

116 days longer than 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

44 Chamberlain Hill Road, Middletown, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,754

per month

  • Principal & Interest$4,227
  • Property Taxes$1,251
  • Insurance$276
  • 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
Contemporary
Year Built
1980
New Construction
No/Resale
Living Area
5,599 sq ft
Below Grade
2,400 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot AirOther
Heat Fuel
Electric
Cooling
Ceiling FansCentral AirSplit System
Fireplaces
2
Laundry
Lower Level
Laundry Location
Attached to another Bedroom Suite
Appliances
Electric CooktopWall OvenRefrigeratorDishwasher
Basement
Full
In-Law Apartment
PossibleUpper Level
Interior Features
Auto Garage Door OpenerCable - Available

Exterior & Lot

Lot Size
8.50 acres
Zoning
R-60
Garage / Parking
1 garage space6 total parking spacesAttached GarageDrivewayUnpavedPrivateUnpaved
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Wood
Color
Blue
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckGuttersFrench Doors
Lot Description
Lightly WoodedLevel Lot

Listing & Financials

Property Taxes
$15,016 / Annually
Days on Market
162
MLS #
24148860
MLS Status
Active
Financing
FHA,VA,CHFA

Similar Properties

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

Listed By

Gary Peacock

(719) 314-9898

Berkshire Hathaway NE Prop.

(860) 739-6666

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 6:55 AM UTC.