29 Jackson Hill Road
Middlefield, Connecticut 06455
- Beds
- 4
- Baths
- 3 | 2
- SqFt
- 4,718
- Acres
- 1.16
- Year Built
- 2004
- Property Type
- Single Family

Matt Caiola
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About This Home
Exceptional custom built home tucked away at the end of a private enclave of only four custom homes. This thoughtfully designed residence offers over an acre of privacy, oversized living spaces, handcrafted millwork, solid six-panel doors, hardwood floors, and insulated interior walls. Designed for both everyday living and elegant entertaining, the open floor plan is spacious, bright and cheerful; including a large kitchen with abundant cabinetry and counter space and an expansive island that naturally becomes the heart of the home. Two wall ovens make preparing meals for large gatherings a breeze. The kitchen flows into a dining nook with bay windows and a fireplaced family room with double-french doors opening to a 60' x 16' deck overlooking the spacious yard which is framed with trees in summer and provides expansive horizon views in the winter. Once the leaves fall, you can see all the way to the Portland Bridge and beyond! Enjoy the breathtaking sunrises/moonrises from this east-facing deck. Desirable feature is the presence of 2 private primary suites. Huge first floor primary suite w/12' tray ceiling includes a cozy fireplace, 2 double French doors to huge deck TWO WALK-IN CLOSETS!, plus two additional linen closets in a hall leading to the oversized spa bathroom complete with jacuzzi tub, walk-in shower, two extra-long sink vanities with mirrored cabinets, and a separate doored toilet room. The first floor also includes formal & living rooms for all your lifestyle &
Key Facts
- City/Town
- Middlefield
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 2004
- Days on Market
- 6 days
- Beds
- 4
- Baths
- 3 full · 2 half
- Living Area
- 4,718 sq ft
- Lot Size
- 1.16 acres
- Garage / Parking
- 3 garage · 9 total
- Property Taxes
- $11,640 / Annually
Market Snapshot
The Middlefield Market
Single Family · trailing 12 months
Active Listings
5
6 under contract
Median List Price
$600,000
5 active listings
Median Closed Price
$423,000
34 sales
Median Days on Market
26
5 active listings
Median $ / Sq Ft
$285
5 active listings
Sale-to-List Ratio
101.4%
34 sales
How this home compares
List Price
$750,000
vs $600,000 median
25.0% above median
Price / Sq Ft
$159
vs $285 median
44.2% below median
Days on Market
6 days
vs 26 days median
20 days fresher than median
Based on 5 active and 34 closed sales (trailing 12 mo) of single family in Middlefield. Source: SmartMLS · As of July 29, 2026.
Location
29 Jackson Hill Road, Middlefield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,824
- Property Taxes$970
- Insurance$250
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middlefield
- Neighborhood
- N/A
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 2004
- New Construction
- No/Resale
- Living Area
- 4,718 sq ft
- Below Grade
- 1,320 sq ft
Schools
- Elementary
- John Lyman
- High
- Coginchaug Regional
Interior
- Heating
- Hydro Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Laundry Location
- Mud roomnear front & garage entrances
- Appliances
- Electric CooktopWall OvenMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullHeatedStorageInterior AccessConcrete FloorFull With Walk-Out
- In-Law Apartment
- No
Exterior & Lot
- Lot Size
- 1.16 acres
- Zoning
- MD
- Garage / Parking
- 3 garage spaces9 total parking spacesAttached GaragePavedOff Street ParkingDrivewayPrivatePavedAsphalt
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Hardie Board
- Color
- Beige
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGuttersLightingStone WallFrench DoorsUnderground Sprinkler
- Lot Description
- On Cul-De-SacProfessionally Landscaped
Listing & Financials
- Property Taxes
- $11,640 / Annually
- Days on Market
- 6
- MLS #
- 24193789
- MLS Status
- Coming Soon
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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 7/29/2026. 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 7/29/2026 at 10:10 AM UTC.