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.
Source: School Digger
Source: Public Records
Source: Sperling's Best Places
11/100
Walk Score ®
29/100
Bike Score ®
The average walkability score in the surrounding area is Walk Score: 16/100, Transit Score: 0/100, Bike Score: 16/100.
4 bds • 3 ba • 2,006 sqft
Lot 3 Coleman Road, Middletown, CT 06457
3 bds • 3 ba • 2,549 sqft
41 Day School Drive, Middlefield, CT 06455
4 bds • 3 ba • 2,570 sqft
36 Brookview Lane, Middletown, CT 06457
3 bds • 3 ba • 2,151 sqft
Lot 3 Sisk Street, Middletown, CT 06457
5 bds • 3 ba • 2,602 sqft
602-2 Higby Road, Middletown, CT 06457
3 bds • 3 ba • 2,214 sqft
601 Higby Road, Middletown, CT 06457
4 bds • 3 ba • 2,285 sqft
10 Talias Trail, Middletown, CT 06457
5 bds • 2 ba • 2,010 sqft
58 Middle Haddam Road, East Hampton, CT 06456
3 bds • 3 ba • 2,214 sqft
1 Freya Lane, East Hampton, CT 06424
3 bds • 3 ba • 2,151 sqft
7 Freya Lane, East Hampton, CT 06424
3 bds • 2 ba • 2,113 sqft
16 Walkley Hill Road, Haddam, CT 06438
4 bds • 3 ba • 2,200 sqft
13 Freya Lane, East Hampton, CT 06424
4 bds • 3 ba • 2,357 sqft
14 Freya Lane, East Hampton, CT 06424
4 bds • 3 ba • 2,691 sqft
16 Freya Lane, East Hampton, CT 06424
3 bds • 3 ba • 2,146 sqft
79 Brechlin Drive, Middletown, CT 06457
3 bds • 3 ba • 2,212 sqft
180 Bee Street, Meriden, CT 06450
3 bds • 3 ba • 2,212 sqft
170 Bee Street, Meriden, CT 06450
3 bds • 3 ba • 2,212 sqft
160 Bee Street, Meriden, CT 06450
4 bds • 3 ba • 2,200 sqft
9 Freya Lane, East Hampton, CT 06424
4 bds • 3 ba • 2,200 sqft
5 Freya Lane, East Hampton, CT 06424
4 bds • 3 ba • 2006 sqft
Lot 3 Coleman Road
3 bds • 3 ba • 1900 sqft
498 Pine Street
3 bds • 4 ba • 3576 sqft
208 Highmeadow Lane
3 bds • 3 ba • 2549 sqft
41 Day School Drive
3 bds • 3 ba • 1761 sqft
Lot 3 Nathan Hale Road
3 bds • 3 ba • 1761 sqft
Lot 1 Nathan Hale Road
3 bds • 3 ba • 1761 sqft
Lot 4 Nathan Hale Road
3 bds • 3 ba • 1761 sqft
Lot 2 Nathan Hale Road
4 bds • 3 ba • 2570 sqft
36 Brookview Lane
3 bds • 2 ba • 2853 sqft
36 Maiden Lane
3 bds • 3 ba • 2151 sqft
Lot 3 Sisk Street
4 bds • 4 ba • 2806 sqft
5 Race Track Hollow
5 bds • 3 ba • 2602 sqft
602-2 Higby Road
3 bds • 3 ba • 2214 sqft
601 Higby Road
2 bds • 2 ba • 1555 sqft
134 Webster Lane 2-15
2 bds • 2 ba • 1555 sqft
123 Webster Lane
2 bds • 2 ba • 1430 sqft
137 Webster Lane 2-42
2 bds • 2 ba • 1555 sqft
145 Webster Lane 2-41
2 bds • 3 ba • 1404 sqft
9 Pear Orchard Road 9
4 bds • 3 ba • 2285 sqft
10 Talias Trail
Source: Realty.com
44 Trailside Crossing, Middletown, CT 06457 is a Single Family 2,356 sq. ft. home listed for sale. Realty.com has 40 photos available of this 4 bed, 3 bath house, listed at $605,000. View sales and tax history, use our mortgage calculator and more on Realty.com
Realty.com has 40 photos of 44 Trailside Crossing.
Our records indicate that 44 Trailside Crossing was built in 2014.
The full address for this home is 44 Trailside Crossing, Middletown, CT 06457.
44 Trailside Crossing has been listed on Realty.com since Mon December 08, 2025
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
The average walkability score in the surrounding area is Walk Score: 16/100, Transit Score: 0/100, Bike Score: 16/100.
There are 3 schools assigned to this home. Check out the schools near 44 Trailside Crossing. Farm Hill School (Grades: PK - 5), Woodrow Wilson Middle School (Grades: 7 - 8), Middletown High School (Grades: 9 - 12)
Listing provided courtesy of:
Cavanaugh & Company Llc
(tel: 860-346-8900)
Listing agent:
Juliet Cavanaugh
(tel: 860-346-8900)
(#CAVANAJU)
This content last refreshed on 2025-12-19 00:38:39. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Export listing data of 44 Trailside Crossing, Middletown, CT 06457 : MLS# 24143271
