27 Fairview Avenue
Middletown, Connecticut 06457
- Beds
- 4
- Baths
- 1
- SqFt
- 1,235
- Acres
- 0.14
- Year Built
- 1934
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
38
49 under contract
Median List Price
$414,950
38 active listings
Median Closed Price
$405,500
324 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per 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
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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.