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1446 Randolph Road

Middletown, Connecticut 06457

COMING SOON - NEW$549,900
Beds
3
Baths
3
SqFt
2,537
Acres
4.60
Year Built
1950
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

About This Home

Set well back from the road on 4.6 secluded acres, this beautifully maintained ranch combines generous one-level living with a bright, welcoming feel throughout. Large windows on all sides bring in abundant natural light and frame views of the expansive landscaping, lawn, and surrounding trees. The spacious remodeled kitchen anchors the home's everyday living, with beautifully crafted cabinetry, substantial granite countertops, a large custom center island, and generous workspace, complemented by expansive backyard views and seamless flow to the outdoor living space. The private bedroom wing includes a generous remodeled primary suite with hardwood floors, 3 spacious closets, and a modern private bath designed for the comfort, style, and functionality today's buyers expect. Just beyond the primary suite, a dedicated office with extensive built-ins offers flexible space for working from home, studying, meetings, or enjoying a hobby. The living and dining rooms flow together with warm hickory floors and custom millwork, while a thoughtfully designed mudroom/pantry just off the kitchen adds character and function with built-in cubbies and cabinetry. Outside, the broad, open lawn offers room to gather, play, garden, or enjoy the private setting. A Trex deck and paver patio extend the living space outdoors, creating an inviting place to relax or entertain. Meticulously cared for and truly move-in ready, this home feels spacious, comfortable, and private from the moment you arrive.

Key Facts

City/Town
Middletown
Neighborhood
N/A
Property / Style
Single Family · Ranch
Year Built
1950
Days on Market
0 days
Beds
3
Baths
3 full
Living Area
2,537 sq ft
Lot Size
4.60 acres
Garage / Parking
2 garage
Property Taxes
$11,366 / Annually

Market Snapshot

The Middletown Market

Single Family · trailing 12 months

Median Days on Market

24

38 active listings

Median $ / Sq Ft

$252

38 active listings

Sale-to-List Ratio

102.6%

324 sales

How this home compares

List Price

$549,900

vs $414,950 median

32.5% above median

Price / Sq Ft

$217

vs $252 median

13.9% below median

Days on Market

0 days

vs 24 days median

24 days fresher than median

Based on 38 active and 324 closed sales (trailing 12 mo) of single family in Middletown. Source: SmartMLS · As of September 15, 2026.

Location

1446 Randolph Road, Middletown, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,986

per month

  • Principal & Interest$2,856
  • Property Taxes$947
  • Insurance$183
  • 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
Ranch
Year Built
1950
New Construction
No/Resale
Living Area
2,537 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Laundry Location
Private Wing of Home
Appliances
Convection RangeMicrowaveRefrigeratorDishwasherDisposalCompactorWasherDryerWine Chiller
Basement
Crawl SpacePartialUnfinishedStorageHatchway AccessInterior AccessConcrete Floor
Interior Features
Auto Garage Door OpenerCable - Pre-wiredOpen Floor Plan
Accessibility
Bath Grab Bars

Exterior & Lot

Lot Size
4.60 acres
Zoning
R-15
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedPorchDeckGuttersPatio
Lot Description
SecludedLightly WoodedRolling

Listing & Financials

Property Taxes
$11,366 / Annually
Days on Market
0
MLS #
24204996
MLS Status
Coming Soon
Financing
FHA,VA,CHFA

Similar Properties

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

Listed By

Jay Smolenski

(203) 848-0859

Berkshire Hathaway NE Prop.

(203) 294-9114

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

The IDX display contains information sourced from SmartMLS, Inc. as of 9/15/2026. 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 9/15/2026 at 8:00 PM UTC.