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65 Trailside DriveMonroe, CT 06468

For Sale

$1,174,900

Smart Buyer Rebate $11,749

Located on a desirable cul de sac in one of Monroe's most sought after neighborhoods, this exceptional Colonial is set on two beautifully usable acres and offers an impressive blend of scale, sophistication, and versatility. Thoughtfully designed for today's lifestyle, the residence features five spacious bedrooms and four full and one half baths, delivering both comfort and refined living in a premier setting. A full main level in law apartment provides private, self contained living ideal for multigenerational households, extended guests, or long term flexibility without compromise. The main level is enhanced by gleaming hardwood flooring throughout and offers a seamless flow between formal and informal spaces, creating an inviting environment for both everyday living and elegant entertaining. Upstairs, the primary suite serves as a true retreat. The brand new primary bath has been beautifully renovated with elevated finishes and a sophisticated, spa inspired design. Three additional bedrooms, including one with en suite bath, complete the upper level with style and functionality. The finished lower level is designed for entertainment, featuring a dedicated movie room and an impressive bar area perfect for hosting gatherings or enjoying relaxed evenings at home. A three car garage offers generous storage and convenience, while a large deck overlooks the expansive, level backyard, providing privacy and endless possibilities for outdoor living. Schedule your showing today!

Listed by Brian Christy

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William Raveis Real Estate

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(203) 455-1223

Last updated July 13, 2026

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Source: SmartMLS #24156537

Listing Facts

  • TypeSingle-family
  • NeighborhoodMonroe
  • Bedrooms5
  • Bathrooms5
  • Days on Prevu150
  • Taxes$19,584/year
  • Size5,304 sqft
  • Price per sqft$222

Location

Mortgage Calculator

Listing History

07/14/2026
Price Decreased
$1,174,900
03/04/2026
Listed by William Raveis Real Estate
$1,199,900

Property Details for 65 Trailside Drive

Exterior

Construction

  • New Construction: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2003
  • Year Built Details: Public Records
  • Architectural Style: Colonial
  • Construction Materials: Frame

Features

  • Waterfront Features: Not Applicable

Measurements

  • Lot Features: Level Lot, On Cul-De-Sac
  • Lot Size Acres: 2.00

Financial

Taxes

  • Parcel Number: 2380592
  • Tax Annual Amount: $19,584.00
  • Tax Year: 25

Interior

Features

  • Appliances: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer
  • Fireplaces Total: 1

Measurements

  • Living Area: 3,930

Rooms

  • Basement: Full, Fully Finished
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 5
  • Rooms Total: 15

Parking

Parking

  • Attached Garage: Attached Garage
  • Garage Spaces: 3

Schools

Elementary School

  • Elementary School: Per Board Of Ed

High School

  • High School: Masuk

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Hydro Air
  • Laundry Features: Main Level
  • Sewer: Septic
  • Water Source: Public Water Connected

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 5 bedrooms and 5 bathrooms in this single-family home at 65 Trailside Drive.

What schools are nearby to 65 Trailside Drive?

Nearby schools include the Per Board Of Ed Elementary School and Masuk High School.

Does this single-family home have parking?

Yes, there are 3 parking spaces available for 65 Trailside Drive.

What are the annual taxes for 65 Trailside Drive?

Annual taxes for this single-family home are estimated at $19,584.

How does 65 Trailside Drive compare to other single-family homes in Monroe?

This single-family home is listed 48% above the average price for single-family homes in Monroe and has been on the market for 97 more days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 5,304 sqft.

65 Trailside Drive is a 5-bedroom, 5-bath single-family home for sale in Monroe CT 06468. Listed on Prevu for 150 days at $1,174,900. This includes a recent price decrease of $25,000. This residence features 5,304 square feet of living space, located in Monroe. The median listing price for single-family homes in this area is $699,900. Nearby schools include Per Board Of Ed Elementary School and Masuk High School. View other single-family home listings in Fairfield County.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.