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Good morning. Welcome to 41 Chestnut Drive, Windsor, CT

$274,925
2
Beds
2.00
Baths
1,452
SqFt
0.55
Acres

Pricing Insight: Originally listed for $314,925, the price was last adjusted to $274,925 on January 27, 2026, a –$40,000 (12.7%) change, approximately 0 days ago. This property has been on the market for approximately 62 days. MLS reports 32 Days on Market (DOM) before it went under contract.

41 Chestnut Drive, Windsor, CT is a 2-bed, 2-bath, 1,452 square foot home built in 1955 , featuring cape cod architecture.

This home is within the Windsor school district. Local, with nearby schools including Per Board of Ed.

MLS #: 24142259

Offered Price: $274,925

Residence Type: Single Family

Architectural Style: Cape Cod

Living Area: 1,452 Sq. Ft.

Lot Size: 0.55 Acres

Neighborhood: N/A

County: Hartford

Year Built: 1955

Design & Construction: Brick

Heating: Hot Water

Cooling: Central Air

Garage Spaces: 2

Price per Sq Ft as listed: $189

Estimated Tax: $6,190

Days on Market: 32

$369,900
3 Beds · 2 Baths · 1,943 Sq Ft
26 Hickory Drive, Windsor

Home Automation: Not specified

Energy Features: Not specified

Solar Contract: Not specified

Heating Fuel: Oil

Fuel Type: Hot Water

Fuel Tank Location: In Basement

Cooling System: Central Air

Hot Water System: Electric, Domestic

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $189 / Sq. Ft.

Tax assessed value: $217,560

Estimated Tax: $6,190

Architectural Style: Cape Cod

Design & Construction: Brick

Residence Type: Single Family

Year Constructed: 1955

Living Area: 1,452 Sq. Ft.

Lot Size: 0.55 Acres

Fuel: Oil

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AUTOMATED VALUATION ESTIMATE

Powered by Realtors Property Resource® (RPR)

Note: Computer-generated estimate, not an appraisal.

Understanding This Valuation

The RPR AVM considers:

  • Recent sales of comparable properties
  • Property characteristics and location
  • Market trends in Windsor
  • Statistical modeling algorithms
Local Market Context
Active Listings: 31
Average Price: $341,664
Average DOM: 32 days

Complimentary CMAs, no obligation

Welcome to 41 Chestnut Drive, a charming and well-maintained Cape Cod style home nestled in a quiet Windsor neighborhood, perfect for those seeking comfort, convenience, and classic New England character. This bright and inviting residence has 2 spacious bedrooms with an extra room for either a den or an office, 2 full baths with one being totally renovated, with a flexible floor plan that blends functionality and warmth. A spacious kitchen with ample cabinetry flows easily into the dining area, making meal preparation and gatherings seamless. Hardwood floors add timeless appeal, while thoughtful updates ensure modern comfort. Upstairs bedrooms provide privacy and flexibility for family, guests, or a home office. The home sits on a generous, level 0.55-acre lot with a beautifully landscaped yard-ideal for outdoor activities, gardening, or relaxing on warm afternoons. A private driveway and garage offer plenty of parking and storage. Located just minutes from Windsor Center, schools, shopping, dining, and major highways, this property combines suburban tranquility with easy access to Hartford, Bradley International Airport, and all that the Connecticut River Valley has to offer. Whether you are a first-time owner, downsizing, or simply seeking a welcoming place , 41 Chestnut Drive is a wonderful opportunity to make your next move in Windsor.

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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 • 0.6 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.

31

Homes For Sale

$341,664

Average List Price

Mechanicals & Utilities: Hot Water • Oil • Central Air • Private Well water • 1 fireplaces

Exterior Features

Exterior Construction: Brick

Roof Type: Asphalt Shingle,Gable

Foundation: Concrete

Driveway: Private

Garage: Attached Garage,Paved,Driveway (2 car)

Parking: 4 Total

Utilities: Water: Private Well

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

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George Antonopoulos
Real Estate Advisor
Windsor • Connecticut Shoreline
Licensed Real Estate Agent – Connecticut
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 Verified Motif Advisor
Good morning George, I'm interested in
41 Chestnut Drive, Windsor, Connecticut
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George Antonopoulos
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Presented by motif • Source: MLS • Listed by: Jayson Kemp • Five Stars Realty • MLS# 24142259