153 Eastern Drive
Middletown, Connecticut 06457
Reduced from $299,000
- Beds
- 3
- Baths
- 1 | 1
- SqFt
- 1,209
- Acres
- 0.28
- Year Built
- 1900
- Neighborhood
- Highland
- 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
Investors are you looking for a charming 2/3 bedroom, 1.5 bath Colonial that is located on a quiet street in a desirable neighborhood, offering convenient location just minutes from the shops, restaurants, Wesleyan University, hospitals, and major healthcare centers? This is an excellent choice for anyone seeking an easy commute and access to everyday amenities. Filled with warmth and character, this inviting home is ready for its next chapter. Whether you're a first-time homebuyer, looking to make it your forever home, or searching for a great investment opportunity, this property offers endless potential. Add your personal touch and some love to make this charming Colonial truly your own while creating lasting memories for years to come. City water and city sewer. Don't miss the opportunity to own a home in a convenient and quiet location. Schedule your showing today and discover all that 153 Eastern Drive has to offer!
Key Facts
- City/Town
- Middletown
- Neighborhood
- Highland
- Property / Style
- Single Family · Colonial
- Year Built
- 1900
- Days on Market
- 59 days
- Beds
- 3
- Baths
- 1 full · 1 half
- Living Area
- 1,209 sq ft
- Lot Size
- 0.28 acres
- Property Taxes
- $5,086 / Annually
Market Snapshot
The Middletown Market
Single Family · trailing 12 months
Active Listings
38
50 under contract
Median List Price
$422,450
38 active listings
Median Closed Price
$405,000
323 sales
Median Days on Market
25
38 active listings
Median $ / Sq Ft
$245
38 active listings
Sale-to-List Ratio
102.6%
323 sales
How this home compares
List Price
$269,000
vs $422,450 median
36.3% below median
Price / Sq Ft
$222
vs $245 median
9.4% below median
Days on Market
59 days
vs 25 days median
34 days longer than median
Based on 38 active and 323 closed sales (trailing 12 mo) of single family in Middletown. Source: SmartMLS · As of September 14, 2026.
Location
153 Eastern Drive, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$1,397
- Property Taxes$424
- Insurance$90
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middletown
- Neighborhood
- Highland
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1900
- New Construction
- No/Resale
- Living Area
- 1,209 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Laundry
- Main Level
- Laundry Location
- Main floor
- Appliances
- Oven/RangeRefrigerator
- Basement
- PartialUnfinishedWalk-outPartial With Walk-Out
Exterior & Lot
- Lot Size
- 0.28 acres
- Zoning
- MXI
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Color
- Yellow
- Roof
- Asphalt Shingle
- Foundation
- MasonryStone
- Exterior Features
- DeckGuttersCovered Deck
- Lot Description
- Interior LotLightly Wooded
Listing & Financials
- Property Taxes
- $5,086 / Annually
- Days on Market
- 59
- MLS #
- 24191998
- MLS Status
- Under Contract
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 9/14/2026. 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 9/14/2026 at 8:25 PM UTC.