Date
Details
Price
Change
Source
3/04/2026
Listed
$1,199,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Join us at 65 Trailside Drive on:
- Open House: 1:00 PM - 3:00 PM
Sunday 3/8 1:00 PM - 3:00 PM
65 Trailside Drive,Monroe, CT 0646865 Trailside DriveMonroeCT06468
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Property 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!
Full Property Details
Full Property Details for 65 Trailside Dr
General
- Price: $1,199,900
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24156537
- Updated: 3/6/2026
- Added to Site: 2 day(s) ago
Interior
- Number of Rooms: 15
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 4
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 5
- Primary Suite: Full Bath, Walk-In Closet, Wall/Wall Carpet, 17 x 13.5, Upper
- Bedroom 1: Bedroom - Bedroom Suite, Full Bath, Main
- Bedroom 2: Bedroom - Full Bath, Wall/Wall Carpet, 12.5 x 10, Upper
- Bedroom 3: Bedroom - Wall/Wall Carpet, 12.75 x 11, Upper
- Bedroom 4: Bedroom - Wall/Wall Carpet, 14.25 x 11.75, Upper
Other Rooms
- Living Room: Living Room - Fireplace, Hardwood Floor, 19 x 22, Main
- Eat In Kitchen: Eat-In Kitchen - Granite Counters, Island, Hardwood Floor, 22 x 14, Main
- Dining Room: Dining Room - Hardwood Floor, 14.5 x 13, Main
- Office: Office - Hardwood Floor, 13.5 x 13, Main
- Game room: Yes
- Game Room: Rec/Play Room, 19 x 18, Lower
- Rec Room: 19 x 18, Lower
- Theater/Media: Media Room, 19 x 20, Lower
- Laundry: Main Level
- Other Room 1: Other, 16.5 x 14, Lower
- In-Law/Au Pair Suite: Yes
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Parking: Attached Garage
Location
- County: Fairfield
- Driving Directions: 65 Trailside
School Information
- Elementary School: Per Board of Ed
- High School: Masuk
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hydro Air, Oil
- Heating Fuel: Oil
- Water Heater: 65 Gallon Tank
Utilities
- Sewer: Septic
- Water: Public Water Connected
Structural Information
- Architectural Style: Colonial
- Construction Status: No/Resale
- Exterior Const.: Vinyl Siding
- Basement Desc.: Full, Fully Finished
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 5,304
- Above Ground: 3,930 Sq. Ft.
- Below Ground: 1,374 Sq. Ft.
- Year Built: 2003
Lot Features
- Lot Size (Acres): 2
- Zoning: RF2
- Lot Description: Level Lot, On Cul-De-Sac
Financial Considerations
- Assessment Amount: $683,100
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 2380592
Listed by William Raveis Real Estate, The Zerella Christy Team of William Raveis Real Estate, Brian Christy
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 65 Trailside Dr —
Brian Christy
William Raveis Real Estate
Agent Contact: (203) 455-1223 Office Contact: (203) 255-6841
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 65 Trailside Dr
School District:Monroe School District
| Name | Grades | Distance |
|---|---|---|
Fawn Hollow Elementary School 375 Fan Hill Road, Monroe, CT 06468 | K-5 | 2.7 mi |
Jockey Hollow School 365 Fan Hill Road, Monroe, CT 06468 | 6-8 | 2.9 mi |
Masuk High School 1014 Monroe Turnpike, Monroe, CT 06468 | 9-12 | 1.3 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 65 Trailside Dr
Tax History
Tax History for 65 Trailside Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$19,584
9%
$683,100
46%
2023
$17,941
2%
$468,800
—
2023
$17,603
2%
$468,800
—
2022
$17,280
1%
$468,800
—
2021
$17,046
2%
$468,800
—
2020
$16,633
-4%
$468,800
-3%
2019
$17,263
1%
$485,200
—
2018
$17,098
-1%
$485,200
—
2017
$17,351
2%
$485,200
—
2016
$16,982
2%
$485,200
—
2015
$16,667
2%
$485,200
-10%
2011
$16,353
—
$537,740
—
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
Estimate the Cost for 65 Trailside Dr
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- Single Family
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- Updated 4 days ago
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- 2,600Sq. Ft.
Listed by Brian Fitzgerald (203) 275-6414
- Apartment
- Active
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- Single Family
- Closed
- Updated 4 days ago
- 4Beds
- 5Total Baths
- 5,254Sq. Ft.
Listed by Carey & Guarrera Real Estate
Sold by Mary Keklik
Sold by Mary Keklik
65 Trailside Drive, Monroe, CT 06468 (MLS# 24156537) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 65 Trailside Drive is currently listed for $1,199,900 and was received on March 04, 2026. Want to learn more about 65 Trailside Drive? Do you have questions about finding other Single Family real estate for sale in Monroe? You can browse all Monroe real estate or contact a Coldwell Banker agent to request more information.