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29 Jackson Hill Road

Middlefield, Connecticut 06455

COMING SOON - NEW$750,000
Beds
4
Baths
3 | 2
SqFt
4,718
Acres
1.16
Year Built
2004
Matt Caiola

Matt Caiola

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3-Car Garage2 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,044

per 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

Similar Properties

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

Listed By

Sandra Blevins

(917) 519-3339

William Raveis Real Estate

(860) 344-1658

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.