85 Oakcliff Road
Middletown, Connecticut 06457
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 1,908
- Acres
- 1.11
- Year Built
- 1969
- 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
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
Active Listings
35
57 under contract
Median List Price
$425,000
35 active listings
Median Closed Price
$405,000
320 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per 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.
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.