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Back 44 Trailside Crossing
Off Market

44 Trailside Crossing

Middletown CT 06457

4
3
4
2356 sq. ft.
0.84 ac.
Single-Family
Last sold for $635,000
Juliet CavanaughJuliet Cavanaugh, last sold this property on 29 January 2026 after 51 days on market.

Overview

Tucked away on a quiet cul-de-sac, this beautifully maintained colonial offers serene privacy, sweeping sunrise and sunset views, and .84 acres of land that stretch all the way to Crystal Lake Road - with a fenced rear yard to keep anything you love safe. Inside nearly 2,500 sq ft, the home balances spacious comfort with a cozy, welcoming atmosphere. The main floor boasts gleaming hardwood floors throughout, an open-concept layout with a large family room anchored by a gas fireplace, and a chefs-ready eat-in kitchen featuring granite counters, center island, and stainless-steel appliances. A formal dining room and convenient half bath complete the main level. A dramatic 2-story foyer leads to a carpeted second floor with a generous primary suite - tray ceiling, walk-in closet with dressing area, and a full ceramic bath with a walk-in shower. Three additional bedrooms and a full bath finish the upper level. The basement receives ample natural light and presents a blank canvas, ready to become additional living space, a home office, gym, or media room. Efficient propane heating (with a 500-gallon in-ground tank) ensures cozy winters. Enjoy your morning coffee on the sun-drenched 3-season porch and plan lazy summer evenings in the expansive yard. This is a rare opportunity to own one of just 11 homes on Trailside Crossing. Schedule your private showing and make this special home yours.

Features

4 bedrooms
3 bathrooms
4 carspaces
2 garage spaces
2356 sq. ft. floor area
0.84 ac. lot size
Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Middletown over the last 12 months, the estimated median property value of 44 Trailside Crossing is $450k.

Median value
$450k
Estimated value range
$205k - $1.88m
Median days on market
9
Estimated value trend
11%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Middletown. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 44 Trailside Crossing

2026
Sold
$635,000
29 Jan 2026 by Juliet Cavanaugh, of Cavanaugh & Company LLC
2014
Sold
$399,900
07 Nov 2014 by Matthew Denorfia, of Realty 3 CT

Happy sellers in Middletown

94%
94% of sellers in Middletown reported that their sale price either exceeded or met their price expectations.

Middletown stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 3 reviews in Middletown over the last 12 months.

Local market activity for 4 bedroom single-family properties in Middletown

In the last 12 months, 71 four-bedroom single-family properties similar to 44 Trailside Crossing, have been sold.

This represents a 14% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Middletown

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Danny Hernandez

Danny Hernandez is an award winning recommended agent for Middletown.  They have 2 local sales and collected 2 local reviews across the last 12 months.

  •   5   (20 reviews)
  •  2 Reviews in Middletown
  •  2 Sales in Middletown
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Gregory Hanner

Sellers who recommend Gregory Hanner have praised them for being local expert, responsive, clear communication, supportive, detail-oriented, patient, and reliable

  •   5   (267 reviews)
  •  1 Review in Middletown
  •  2 Sales in Middletown
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Shari Jones

Shari Jones is a recommended agent for Middletown.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (32 reviews)
  •  1 Review in Middletown
  •  1 Sale in Middletown
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Che Hesse Frey

Che Hesse Frey is a recommended agent for Middletown.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (4 reviews)
  •  1 Review in Middletown
  •  1 Sale in Middletown
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