Searching ...

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!

  • Bedrooms
    5
  • Bathrooms
    4 full · 1 half
  • Year Built
    2003
  • Architectural Style
    Colonial
  • Construction Materials
    Frame, Vinyl Siding
  • Foundation
    Concrete Perimeter
  • Garage Spaces
    3.0
  • Parking Features
    Attached
  • Living Area
    5304.0
  • Interior Features
    In-Law Floorplan
  • Appliances
    Dryer, Dishwasher, Refrigerator, Washer, Range, Oven
  • Cooling
    Central Air
  • Heating
    Oil
  • Basement
    Finished, Full

  • Acres
    2.0
  • Lot Features
    Level, Cul-De-Sac
  • Water
    Public

  • County
    Fairfield
  • City
    Monroe
  • Zip Code
    06468
  • High School
    Masuk
  • Elementary School
    Per Board of Ed

Ask a Question

What's your home worth?

Calculate your current home value within seconds.

Frequently Asked Questions

How do I schedule a tour of 65 Trailside Dr?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 65 Trailside Dr.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 65 Trailside Dr?

Click Ask a Question to talk with our team. You already know it is a 5 bed, 4 bath, listed for $1,174,900. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Monroe, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 65 Trailside Dr?

With a 20% down payment and a 30-year fixed loan at an illustrative 6.75% rate, the ez Mortgage Calculator estimates the monthly payment for 65 Trailside Dr at around $8,071. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 65 Trailside Dr?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Fairfield County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 65 Trailside Dr?

In most cases, yes. Whether 65 Trailside Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Monroe's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 65 Trailside Dr?

We can handle that for you. Our preferred local agent specializes in residentials in Monroe and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $1,174,900 with 5,304 sqft of space—that comes out to approximately $222 per square foot.

How long has this property been on the market?

65 Trailside Dr was listed on March 04, 2026, which means it's been on the market for 248 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 2003, making it approximately 23 years old.

What is the lot size of this property?

65 Trailside Dr sits on a 2.0-acre lot, which is 87,120 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Per Board of Ed
  • High: Masuk

Want to see how these schools compare? Check out our Fairfield County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 65 Trailside Dr?

The most recent public record shows annual property taxes for 65 Trailside Dr were approximately $20,411. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 65 Trailside Dr still available for sale?

This home is under contract, but may still accept backup offers. Click ♥ to track updates or connect with our local expert to see if it's still worth pursuing.

Source: ez Home Search, MLS Data

Popular Home Searches in Monroe, CT


Search Nearby Cities


Search Nearby Counties


Search Nearby Postal Codes

Listing information provided exclusively 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. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, SmartMLS. All rights reserved.

Last Updated: November 07, 2026 at 03:54AM | Source: SmartMLS | MLS#: 24156537