38 Upland Road - Winchester, CT

$269,000

Beds

2.00

Baths

1,736

SqFt

0.34

Acres

Pricing Insight: Originally listed for $284,000, the price was last adjusted to $269,000 on February 11, 2026, a –$15,000 (5.3%) change, approximately 0 days ago. This property has been on the market for approximately 130 days. MLS reports 130 Days on Market (DOM) before it went under contract.

38 Upland Road, Winchester, CT is a 3-bed, 2-bath, 1,736 square foot home built in 1870 , featuring colonial architecture.

This home is within the Winchester school district. Local, with nearby schools including Harry P. Hinsdale.

MLS #: 24131432

Offered Price: $269,000

Residence Type: Single Family

Architectural Style: Colonial

Living Area: 1,736 Sq. Ft.

Lot Size: 0.34 Acres

Neighborhood: Winsted

County: Litchfield

Year Built: 1870

Design & Construction: Frame

Heating: Radiator

Cooling: None

Garage Spaces: 1

Price per Sq Ft as listed: $155

Estimated Tax: $3,974

Days on Market: 130

$269,999

3 Beds · 2 Baths · 1,652 Sq Ft

118 Meadow Street, Winchester

$230,000

2 Beds · 2 Baths · 1,172 Sq Ft

9 John Street, Winchester

$49,000

0 Beds · 0 Baths · 0 Sq Ft

99 Hubbard Street, Winchester

Home Automation: Not specified

Energy Features: Storm Doors

Solar Contract: Not specified

Heating Fuel: Oil

Fuel Type: Radiator

Fuel Tank Location: In Basement

Cooling System: None

Hot Water System: Electric, 40 Gallon Tank

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $155 / Sq. Ft.

Tax assessed value: $136,220

Estimated Tax: $3,974

Architectural Style: Colonial

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1870

Living Area: 1,736 Sq. Ft.

Lot Size: 0.34 Acres

Fuel: Oil

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AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

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Understanding This Valuation

The RPR AVM considers:

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

Local Market Context

Active Listings: 26

Average Price: $217,445

Average DOM: 130 days

Complimentary CMAs, no obligation

TO SETTLE ESTATE: Available for Immediate Occupancy is this Immaculate 3 to 4 Bedroom Colonial tucked away on a quiet street. Features Hardwood Floors throughout the house, 24' x 14' Family Room with Propane Gas Stove, Country Kitchen. Primary Bedroom with it's own office area. Oversized Full Bath. 3-Season 21' x 8' Enclosed Porch. 26' x 10' Concrete Patio. Detached One Car Garage. Attractive Park-Like Landscaped Grounds. Off Street Parking for 6 Vehicles. City Water and Sewer. All Kitchen Appliance as well as Washer & Dryer remain with the property. Close Proximity to Town Center for General Shopping, Medical, Variety of Food Venues. "MOVE-IN CONDITION".

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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 • 0.3 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.

26

Homes For Sale

$217,445

Average List Price

Mechanicals & Utilities: Radiator • Oil • None • Public Water Connected water

Exterior Features

Exterior Construction: Clapboard

Roof Type: Asphalt Shingle

Foundation: Stone

Garage: Detached Garage,Off Street Parking (1 car)

Parking: 6 Total

Patio/Deck: Porch-Enclosed,Porch,Gutters,Lighting

Utilities: Water: Public Water Connected

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

George Antonopoulos

Real Estate Advisor

Winchester • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(800) 555-0001

george@appzentric.com

Good evening George, I'm interested in
38 Upland Road, Winchester, Connecticut

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