44 Trailside Crossing

Middletown, CT 06457

$605,000
Price
4
Beds
2,356 Sq. Ft.
$257 / Sq. Ft.
2,356
Sq. Ft.
$257
per Sq. Ft.
Under Contract
Under Contract
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Description

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...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.
  1. Listed by Juliet L Cavanaugh • Cavanaugh & Company LLC
    P: (860)-398-0058 C: (860)-398-0058 juliet@cavanaughandcompany.com

Property Details for 44 Trailside Crossing

Basement Description
Full, Unfinished, Full With Hatchway
Direct Waterfront
No
Garages Number
2
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Attached Garage, Driveway
Swimming Pool
No
LISTING UPDATED: 12/12/2025 02:56 PM

Property Details for 44 Trailside Crossing

StatusUnder Contract
MLS #24143271
Days on Market3
Taxes$10,712 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built2014
Lot Size0.84 AC / 36,590 SF
CountyMiddlesex County

Location

Listing Courtesy of Cavanaugh & Company LLC, Juliet L Cavanaugh
Add your commute

Building Information for 44 Trailside Crossing

Stories-Year Built2014Building Size-Lot Size0.84 AC / 36,590 SF

Payment Calculator

$3,841 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,949

Property Taxes

$893

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 44 Trailside Crossing

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Randolph Road to Ridge Road to Prout Hill. East on Prout Hill to Trail Crossing. 2nd house om left.
  • Elementary School: Farm Hill
  • Flood Zone: No
  • High School: Middletown
  • Latitude: 41.525467
  • Longitude: -72.640721
  • Neighborhood Amenities: Lake, Park
  • State: Connecticut
Parking
  • Parking Total Spaces: 4
HOA and Fees
  • Home Owner's Assocation: No
  • Tax District Amount: $1,795
  • Tax Year: July 2025-June 2026
  • Property Tax: $10,712
Interior and Exterior Features
Exterior Features
  • Exterior Features: Shed, Porch
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Dryer
  • Attic Description: Unfinished, Access Via Hatch
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Home Automation: Lock(s)
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired
  • Laundry Room Info: Main Level
  • Laundry Room Location: Side hall
  • Rooms Total: 7
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Gas Log Fireplace,Hardwood Floor
  • Room Length: 21.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 14.0
Room 2
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Hardwood Floor
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 14.0
Room 3
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Bedroom Suite,Dressing Room,Full Bath,Walk-In Closet,Wall/Wall Carpet
  • Room Length: 18.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 15.0
Room 4
  • Room Entry Order: 4
  • Room Features: 9 ft+ Ceilings,Wall/Wall Carpet
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 5
  • Listing Key: 45126AE990311348E0631A01100A0F46
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,Wall/Wall Carpet
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 6
  • Room Entry Order: 6
  • Room Features: 9 ft+ Ceilings,Wall/Wall Carpet
  • Room Length: 11.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Room 7
  • Room Entry Order: 7
  • Room Features: 9 ft+ Ceilings,Granite Counters,Dining Area,French Doors,Island,Hardwood Floor
  • Room Length: 22.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 14.0
Property
Property and Assessments
  • Color: Beige
  • Construction Description: Frame
  • Driveway Type: Paved
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Ground
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2014
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Sq Ft Est Heated Below Grade: 0
  • Living Area SQFT Per Public Records: 2356
Lot Information
  • Lot Description: Level Lot, On Cul-De-Sac, Open Lot
  • Parcel Number: 2584265
  • Sq Ft Est Heated Above Grade: 2356.0
  • Sq Ft Total: 2356.0
  • Zoning: R-30
Utilities
  • Energy Features: Generator Ready
  • Heat Fuel Type: Propane
  • Hot Water Description: Electric, 40 Gallon Tank
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 44 Trailside Crossing

DateEvent & SourcePriceAppreciation
Nov 7, 2014

Closed (Public Record)

Public Record #483217108

$399,900—
DateEvent & SourcePrice
11/07/2014

Closed (Public Record)

Public Record #483217108

$399,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 44 Trailside Crossing

Taxable ValueLand$74,160Additions$263,770Total$337,930
Tax Record2023$11,966 ($997 / month)
Home Facts
Beds4Baths2.5Total Finished SqFt2,356 SqFtAbove Grade Finished SqFt2,356 SqFtStories2Lot Size36,590 SqFtStyleSingle Family ResidenceYear Built2014ZoningR-30CountyMIDDLESEXAPNMTWN M:38 L:0274Fireplace TypeHas Fireplace

Schools near 44 Trailside Crossing

This home is within Middletown School District.
Rating
School
Type
Grades
Distance
Farm Hill School
Public - K to 5
Beman Middle School
Public - 6 to 8
Middletown High School
Public - 9 to 12
ICM-Farm Hill
Public - 1 to 2
Rating
School
Distance
Farm Hill School
PublicK to 5

Beman Middle School
Public6 to 8

Middletown High School
Public9 to 12

ICM-Farm Hill
Public1 to 2

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Cavanaugh & Company LLC, Juliet L Cavanaugh

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.