Active Under Contract
Price CutPrice Drop: $25K (10/27)
Single family home for sale at 65 Trailside Dr, Monroe, CT 06468 | MLS# 24156537 | Listing updated on 2026-10-27
Photo 1 of Single family home for sale at 65 Trailside Dr, Monroe, CT 06468 | MLS# 24156537 | Listing updated on 2026-10-27
Photo 2 of Single family home for sale at 65 Trailside Dr, Monroe, CT 06468 | MLS# 24156537 | Listing updated on 2026-10-27
Photo 3 of Single family home for sale at 65 Trailside Dr, Monroe, CT 06468 | MLS# 24156537 | Listing updated on 2026-10-27
Photo 4 of Single family home for sale at 65 Trailside Dr, Monroe, CT 06468 | MLS# 24156537 | Listing updated on 2026-10-27
35+
Beds Icon

Street View

$1,174,900

Monthly Est:$5,848

  • Beds Icon5 Beds
  • Beds Icon
    5 Baths
  • Beds Icon5,304sqft

65 Trailside Dr, Monroe, CT 06468

$5,848/moEst:

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  • Single Family Residence

  • Built in 2003

  • $-- HOA

  • 2 acres lot

  • $222/sq.ft

Description

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!

  • Houzeo last checked: 8 minutes ago
  • Listing updated: October 27, 2026 at 6:07 pm
  • Listing Provided by: Brian Christy | William Raveis Real Estate
  • Source: SMART MLS-CT | MLS#: 24156537 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Fairfield County

  • City

    Monroe

  • Neighborhood

    --

  • Year Built

    2003

  • HOA Fees

    -

  • Finished Area

    5,304 sqft

  • Lot Size

    2 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24156537

  • MLS Status

    Under Contract - Continue to Show

  • Days on Market

    240

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 5

Interior

  • Heating

    Oil

  • Appliances

    Oven/range, Refrigerator, Dishwasher, Washer, Dryer

  • Cooling

    Central Air

  • Sewer

    Septic

Construction

  • Year Built

    Year Built: 2003

  • Home type

    Single Family Residence

  • Architectural Style

    Colonial

  • Foundation Details

    Concrete

  • Roof

    Asphalt Shingle

Utilities & Energy

  • Laundry Features

    Main Level

  • Parking Features

    Attached Garage

  • Water Source

    Public Water Connected

  • Basement

    Full, Fully Finished

Other Features

  • Subdivision Name

    N/a

  • Lot Features

    Level Lot, On Cul De Sac

Price History

DateEventPrice

10/27/2026

Source: mls_logoSMART MLS-CT #24156537

Contingent (Active Under Contract)

$1,174,900

$222/sqft

07/13/2026

Source: mls_logoSMART MLS-CT #24156537

Price Decreased

$1,174,900 -2.08%

$222/sqft

03/04/2026

Source: mls_logoSMART MLS-CT #24156537

Listed for Sale

$1,199,900 +50.93%

$226/sqft

02/18/2009

Source: mls_logoSMART MLS-CT #98404675

Price Increased

$795,000 +6.00%

$150/sqft

01/12/2004

Source: #98160067

Sold

$750,000

$141/sqft

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Oct 31, 2026, 08:00AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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