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27 Fairview Avenue

Middletown, Connecticut 06457

ACTIVE - NEW$244,900
Beds
4
Baths
1
SqFt
1,235
Acres
0.14
Year Built
1934
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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About This Home

Set on a quiet dead-end street near Wesleyan University and downtown Middletown, 27 Fairview Ave is a classic 1934 Colonial with character, convenience, and potential. This estate property features 1,235 sq ft, 4 bedrooms, 1 full bath, (with room for a 2nd bath on the upper level) and walk-in attic space. MAJOR RECENT IMPROVEMENTS INCLUDE: NEW ROOF IN 2024 (stripped & reroofed=1 layer), NEW 200 AMP ELECTRICAL SERVICE IN 2025, a NEW OIL BOILER AND OIL TANK in 2025 as well as a NEW CEILING IN both the LIVING ROOM and ONE BEDROOM, all of which creates a strong starting point for a remodel. The traditional layout offers defined living spaces, a manageable footprint, and room to bring fresh ideas to the kitchen, bath, finishes, and overall design. Its central Middletown location provides easy access to nearby campus, downtown shops, restaurants, parks, and commuter routes. Best suited for an investor or contractor. This property will not qualify for FHA or VA financing. Cash, renovation loan or conventional financing only. This home to be sold strictly AS-IS. Seller will not make any repairs. Sale is subject to Probate Court approval.

Key Facts

City/Town
Middletown
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1934
Days on Market
0 days
Beds
4
Baths
1 full
Living Area
1,235 sq ft
Lot Size
0.14 acres
Garage / Parking
2 total
Property Taxes
$6,010 / 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

$244,900

vs $414,950 median

41.0% below median

Price / Sq Ft

$198

vs $252 median

21.4% 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

27 Fairview Avenue, Middletown, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,855

per month

  • Principal & Interest$1,272
  • Property Taxes$501
  • Insurance$82
  • 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
1934
New Construction
No/Resale
Living Area
1,235 sq ft

Schools

Elementary
Per Board of Ed
High
Middletown

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
None
Laundry
Lower LevelMain Level
Appliances
Oven/RangeRefrigeratorDishwasherWasher
Basement
FullUnfinished

Exterior & Lot

Lot Size
0.14 acres
Zoning
M
Garage / Parking
2 total parking spacesDrivewayPaved
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Aluminum
Color
White
Roof
Asphalt Shingle
Foundation
BlockConcrete
Exterior Features
Porch-EnclosedPorch
Lot Description
Lightly Wooded

Listing & Financials

Property Taxes
$6,010 / Annually
Days on Market
0
MLS #
24205927
MLS Status
Active

Similar Properties

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Listed By

Diane Fahey

(203) 605-5098

Berkshire Hathaway NE Prop.

(860) 621-6821

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.