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65 Trailside Drive

Monroe, Connecticut 06468

ACTIVE$1,174,900

Reduced from $1,199,900

Beds
5
Baths
4 | 1
SqFt
5,304
Acres
2.00
Year Built
2003
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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3-Car Garage1 FireplacePrice Reduced

About This Home

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!

Key Facts

City/Town
Monroe
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
2003
Days on Market
146 days
Beds
5
Baths
4 full · 1 half
Living Area
5,304 sq ft
Lot Size
2.00 acres
Garage / Parking
3 garage
Property Taxes
$19,584 / Annually

Market Snapshot

The Monroe Market

Single Family · trailing 12 months

Median Days on Market

41

44 active listings

Median $ / Sq Ft

$259

44 active listings

Sale-to-List Ratio

100.0%

180 sales

How this home compares

List Price

$1.17M

vs $757,000 median

55.2% above median

Price / Sq Ft

$222

vs $259 median

14.3% below median

Days on Market

146 days

vs 41 days median

105 days longer than median

Based on 44 active and 180 closed sales (trailing 12 mo) of single family in Monroe. Source: SmartMLS · As of July 28, 2026.

Location

65 Trailside Drive, Monroe, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,014

per month

  • Principal & Interest$5,990
  • Property Taxes$1,632
  • Insurance$392
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Monroe
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
2003
New Construction
No/Resale
Living Area
5,304 sq ft
Below Grade
1,374 sq ft

Schools

Elementary
Per Board of Ed
High
Masuk

Interior

Heating
Hydro Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Appliances
Oven/RangeRefrigeratorDishwasherWasherDryer
Basement
FullFully Finished
In-Law Apartment
YesFirst Floor

Exterior & Lot

Lot Size
2.00 acres
Zoning
RF2
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Level LotOn Cul-De-Sac

Listing & Financials

Property Taxes
$19,584 / Annually
Days on Market
146
MLS #
24156537
MLS Status
Active

Similar Properties

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Listed By

Brian Christy

(203) 455-1223

William Raveis Real Estate

(203) 255-6841

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/28/2026 at 6:10 AM UTC.