44 Chamberlain Hill Road
Middletown, Connecticut 06457
Reduced from $925,000
- Beds
- 6
- Baths
- 3 | 1
- SqFt
- 5,599
- Acres
- 8.50
- Year Built
- 1980
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
28
63 under contract
Median List Price
$455,000
28 active listings
Median Closed Price
$400,000
316 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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 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.