25 Charter Oak Drive - Cheshire, CT

$749,900

Beds

3.00

Baths

2,440

SqFt

2.16

Acres

Pricing Insight: Originally listed for $749,900, the price has remained unchanged for approximately 45 days. This property has been on the market for approximately 45 days. MLS reports 41 Days on Market (DOM) before it went under contract.

25 Charter Oak Drive, Cheshire, CT is a 4-bed, 3-bath, 2,440 square foot home built in 1996 , featuring colonial architecture.

This home is within the Cheshire school district. Local, with nearby schools including Barnum Elementary.

MLS #: 24183898

Offered Price: $749,900

Residence Type: Single Family

Architectural Style: Colonial

Living Area: 2,440 Sq. Ft.

Lot Size: 2.16 Acres

Neighborhood: N/A

County: New Haven

Year Built: 1996

Design & Construction: Frame

Heating: Hot Air

Cooling: Ceiling Fans,Central Air,Split System

Garage Spaces: 2

Price per Sq Ft as listed: $307

Estimated Tax: $11,294

Days on Market: 41

$479,900

4 Beds · 4 Baths · 1,928 Sq Ft

1757 Musso View Avenue, Cheshire

$650,000

4 Beds · 3 Baths · 3,301 Sq Ft

29 Nathan Hale Court, Cheshire

Home Automation: Not specified

Energy Features: Ridge Vents

Solar Contract: Not specified

Heating Fuel: Oil

Fuel Type: Hot Air

Fuel Tank Location: In Basement

Cooling System: Ceiling Fans, Central Air, Split System

Hot Water System: Oil, Upright Tank

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $307 / Sq. Ft.

Tax assessed value: $379,750

Estimated Tax: $11,294

Architectural Style: Colonial

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1996

Living Area: 2,440 Sq. Ft.

Lot Size: 2.16 Acres

Fuel: Oil

Loading automated valuation...

AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

Request CMA Schedule Tour

Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in Cheshire
Statistical modeling algorithms

Local Market Context

Active Listings: 41

Average Price: $525,110

Average DOM: 41 days

Complimentary CMAs, no obligation

Tucked away in a quiet neighborhood, this 4-bedroom Colonial showcases exceptional pride of ownership inside and out. Set on beautifully manicured, park-like grounds, the backyard is a destination all its own, designed for entertaining, recreation, and relaxation. Enjoy a half-court basketball court that also accommodates pickleball, a putting green, a spacious patio, a covered pavilion with TV and surround sound, an above-ground pool, and plenty of room to gather and enjoy the outdoors. Inside, hardwood flooring flows throughout the home, while inviting living spaces and a spacious kitchen provide the perfect setting for both entertaining and unwinding. The flexible layout offers comfortable spaces for hosting guests, celebrating special occasions, or simply enjoying a quiet evening at home. Meticulously maintained and thoughtfully improved, this home reflects a level of care that is rarely found. With substantial recent investment and an extensive list of improvements available for review, this property offers a unique opportunity to enjoy a home that has been exceptionally cared for and designed to be enjoyed for years to come.

Continue reading ▾

Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain • 2.2 acres

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

41

Homes For Sale

$525,110

Average List Price

Mechanicals & Utilities: Hot Air • Oil • Ceiling Fans,Central Air,Split System • Private Well water • 1 fireplaces

Exterior Features

Exterior Construction: Vinyl Siding

Roof Type: Asphalt Shingle

Foundation: Concrete

Garage: Attached Garage (2 car)

Patio/Deck: Shed,Cabana,Gutters,Garden Area,Stone Wall,Underground Sprinkler,Patio

Pool: Vinyl,Above Ground Pool

Utilities: Water: Private Well

Outbuildings: Shed,Cabana,Gutters,Garden Area,Stone Wall,Underground Sprinkler,Patio

Only motif connects you to a certified
"Local Market Expert"

Steve Simos

Real Estate Advisor

Cheshire • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(203) 915-6183

george@appzentric.com

Good morning Steve, I'm interested in
25 Charter Oak Drive, Cheshire, Connecticut

By proceeding, you consent to receive calls and texts at the number you provided, and artificial voice, and email, from motif about your inquiry and similar properties. Your personal information will never be sold or given to a 3rd party.

motif, the motif logo, and other various trademarks, logos, designs, and slogans are the registered and unregistered trademarks of motif, LLC. dba Motif Luxe International Realty in the U.S. and/or other countries. Corporate Responsibility, Privacy & Legal Notices: motif is a licensed real estate broker, licensed to do business as Motif LLC. No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property conditions), such should be independently verified, and Motif expressly disclaims any liability in connection therewith. No financial or legal advice provided. Equal Housing Opportunity.

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. MLS

. Designed by Appzentric for motif

Good morning. Welcome to 25 Charter Oak Drive, Cheshire, CT