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85 Oakcliff Road

Middletown, Connecticut 06457

ACTIVE - NEW$615,000
Beds
4
Baths
2 | 1
SqFt
1,908
Acres
1.11
Year Built
1969
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

About This Home

Welcome Home! 85 Oakcliff is a beautifully updated 4-bedroom, 2.5 bath home in a desirable Middletown neighborhood, privately set back from the road. Featuring an updated kitchen, new windows throughout, remodeled baths and a finished walk-out basement with a full bathroom this home offers space, flexibility and privacy. The finished lower level provides potential for an in-law apartment or separate living space, subject to town approval, making it ideal for extended family, guests, a home office or recreation. The expansive deck overlooks a beautiful yard for entertaining, a game of catch or running with your favorite four legged pal. Close to major highways, 20 minutes from Downtown Hartford, 35 minutes to New Haven, 45 minutes to CT Casinos, a little over an hour to the Rhode Island line and minutes from Wesleyan University, great shopping and restaurants in downtown Middletown! Major updates include: Brand New Septic- 2019 Kitchen remodeled - 2024 All windows replaced - 2024 Basement remodeled - 2023 Garage doors replaced - 2023 Full bathroom remodeled - 2022 AC air handler & condenser - 2021 Electrical upgrades & generator hookup - 2021 Well pump - 2021 Front door - 2021 Paver walkway & gutter/fascia improvements - 2020 Chimney repair & cap - approx. 2019 Boiler -2014 With a private setting, extensive updates, 4 bedrooms, 2.5 baths and a versatile walk-out lower level, this Middletown Colonial is ready to welcome its next owner!

Key Facts

City/Town
Middletown
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1969
Days on Market
0 days
Beds
4
Baths
2 full · 1 half
Living Area
1,908 sq ft
Lot Size
1.11 acres
Garage / Parking
2 garage
Property Taxes
$9,154 / Annually

Market Snapshot

The Middletown Market

Single Family · trailing 12 months

Median Days on Market

19

35 active listings

Median $ / Sq Ft

$239

35 active listings

Sale-to-List Ratio

101.9%

320 sales

How this home compares

List Price

$615,000

vs $425,000 median

44.7% above median

Price / Sq Ft

$322

vs $239 median

34.7% above median

Days on Market

0 days

vs 19 days median

19 days fresher than median

Based on 35 active and 320 closed sales (trailing 12 mo) of single family in Middletown. Source: SmartMLS · As of August 17, 2026.

Location

85 Oakcliff Road, Middletown, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,133

per month

  • Principal & Interest$3,165
  • Property Taxes$763
  • Insurance$205
  • 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
Colonial
Year Built
1969
New Construction
No/Resale
Living Area
1,908 sq ft

Schools

Elementary
Per Board of Ed
High
Middletown

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Appliances
Electric CooktopElectric RangeMicrowaveRefrigeratorDishwasherDisposalWasherDryer
Basement
FullFully FinishedFull With Walk-Out
In-Law Apartment
PossibleLower Level
Interior Features
Auto Garage Door OpenerCable - Available
Additional Rooms
Mud Room

Exterior & Lot

Lot Size
1.11 acres
Zoning
R-30
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedDeckGutters
Lot Description
Lightly Wooded

Listing & Financials

Property Taxes
$9,154 / Annually
Days on Market
0
MLS #
24198723
MLS Status
Active

Similar Properties

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

Listed By

Carissa Mastriano

(203) 996-7437

GRL & Realtors, LLC

(203) 781-0000

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

The IDX display contains information sourced from SmartMLS, Inc. as of 8/17/2026. 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 8/17/2026 at 5:25 PM UTC.