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$605,000

  • For Sale
  • Under Contract
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,356 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 44 Trailside Crossing

General

  • Price: $605,000
  • Taxes: $1,795 (July 2025-June 2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24143271
  • Updated: 12/12/2025
  • Added to Site: 39 day(s) ago

Interior

  • Number of Rooms: 7
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - 9 ft+ Ceilings, Bedroom Suite, Dressing Room, Full Bath, Walk-In Closet, Wall/Wall Carpet, 18 x 15, Upper
  • Bedroom 1: Bedroom - 9 ft+ Ceilings, Wall/Wall Carpet, 11 x 11, Upper
  • Bedroom 2: Bedroom - 9 ft+ Ceilings, Wall/Wall Carpet, 12 x 12, Upper
  • Bedroom 3: Bedroom - 9 ft+ Ceilings, Wall/Wall Carpet, 14 x 12, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Gas Log Fireplace, Hardwood Floor, 21 x 14, Main
  • Kitchen: Kitchen - 9 ft+ Ceilings, Granite Counters, Dining Area, French Doors, Island, Hardwood Floor, 22 x 14, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Hardwood Floor, 12 x 14, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Shed, Porch
  • Color: Beige

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 4
  • Parking: Attached Garage, Driveway

Location

  • County: Middlesex
  • Driving Directions: Randolph Road to Ridge Road to Prout Hill. East on Prout Hill to Trail Crossing. 2nd house om left.

School Information

  • Elementary School: Farm Hill
  • High School: Middletown

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Propane
  • Heating Fuel: Propane
  • Water Heater: Electric, 40 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Unfinished, Full With Hatchway
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,356
  • Above Ground: 2,356 Sq. Ft.
  • Year Built: 2014

Lot Features

  • Lot Size (Acres): 0.84
  • Driveway/Sidewalk: Paved
  • Zoning: R-30
  • Lot Description: Level Lot, On Cul-De-Sac, Open Lot

Green Features

  • Energy Features: Generator Ready

Financial Considerations

  • Assessment Amount: $337,930
  • Tax Amount: $1,795
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 2584265

Listed by Cavanaugh & Company LLC, Juliet Cavanaugh

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Listing agent

— 44 Trailside Crossing —

  • Juliet Cavanaugh

    Cavanaugh & Company LLC

Agent Contact: (860) 398-0058 Office Contact: (860) 346-8900

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 44 Trailside Crossing

School District:Middletown School District
NameGradesDistance
Farm Hill School
390 Ridge Road, Middletown, CT 06457
K-50.9 mi
Keigwin Middle School
99 Spruce Street, Middletown, CT 06457
6-4.2 mi
Beman Middle School
370 Hunting Hill Avenue, Middletown, CT 06457
6-81.1 mi
Middletown High School, Middletown, CT
200 La Rosa Lane, Middletown, CT 06457
9-124.1 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 44 Trailside Crossing Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/08/2025
Listed
$605,000
51.29%
MLS
11/07/2014
Sold
$399,900
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 44 Trailside Crossing

Year
Property Taxes
Change
Tax Assessment
Change
2024
$12,507
5%
$337,930
—
2023
$11,966
5%
$337,930
—
2023
$11,358
3%
$337,930
27%
2022
$10,981
16%
$266,180
—
2021
$9,503
-13%
$266,180
—
2020
$10,914
—
$266,180
—
2019
$10,967
4%
$266,180
—
2018
$10,589
3%
$266,180
—
2017
$10,311
3%
$266,570
1%
2016
$10,029
10%
$264,580
8%
2015
$9,085
-8%
$245,080
-8%
2014
$9,832
289%
$265,510
229%
2013
$2,528
—
$80,640
—
2011
$2,528
—
$80,640
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 44 Trailside Crossing

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Cavanaugh & Company LLC, Juliet Cavanaugh

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44 Trailside Crossing, Middletown, CT 06457 (MLS# 24143271) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 44 Trailside Crossing is currently listed for $605,000 and was received on December 08, 2025. Want to learn more about 44 Trailside Crossing? Do you have questions about finding other Single Family real estate for sale in Middletown? You can browse all Middletown real estate or contact a Coldwell Banker agent to request more information.

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