39 Winslow Road - Cheshire, CT

$449,900

Beds

2.00

Baths

1,758

SqFt

0.58

Acres

Pricing Insight: Originally listed for $449,900, the price has remained unchanged for approximately 5 days. This property has been on the market for approximately 5 days.

39 Winslow Road, Cheshire, CT is a 3-bed, 2-bath, 1,758 square foot home built in 1956 , featuring cape cod architecture.

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

MLS #: 24168914

Offered Price: $449,900

Residence Type: Single Family

Architectural Style: Cape Cod

Living Area: 1,758 Sq. Ft.

Lot Size: 0.58 Acres

Neighborhood: N/A

County: New Haven

Year Built: 1956

Design & Construction: Frame

Heating: Hot Water

Cooling: Window Unit

Garage Spaces: 2

Price per Sq Ft as listed: $256

Estimated Tax: $6,322

Days on Market: 4

Home Automation: Not specified

Energy Features: Thermopane Windows

Solar Contract: Not specified

Heating Fuel: Oil

Fuel Type: Hot Water

Fuel Tank Location: Above Ground

Cooling System: Window Unit

Hot Water System: Domestic

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $256 / Sq. Ft.

Tax assessed value: $212,590

Estimated Tax: $6,322

Architectural Style: Cape Cod

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1956

Living Area: 1,758 Sq. Ft.

Lot Size: 0.58 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 Cheshire
Statistical modeling algorithms

Local Market Context

Active Listings: 41

Average Price: $488,685

Average DOM: 4 days

Complimentary CMAs, no obligation

Welcome to 39 Winslow Rd in Cheshire-a beautifully updated Cape set in one of the town's most desirable locations. This 3-bedroom, 2 full bath home blends charm, functionality, and modern updates in all the right ways. Step inside to a spacious foyer that doubles as a cozy sitting area, complete with a built-in coffee bar-perfect for starting or ending your day. The fully renovated kitchen features stainless steel appliances, ample cabinetry, and generous counter space, flowing seamlessly into a formal dining room with refinished hardwood floors. Across the way, the sun-filled living room showcases a stunning bay window that floods the space with natural light. The main level also offers a versatile bedroom and a beautifully remodeled full bath-ideal for guests or a private home office. Upstairs, you'll find two additional bedrooms along with a large family room anchored by a wood stove, creating the perfect setting for cozy winter nights. An additional office space in the rear adds even more flexibility. Outside, enjoy a professionally landscaped front yard bursting with seasonal color, while the backyard offers a peaceful natural setting overlooking a stream. Additional highlights include a partially finished basement, updated roof, vinyl siding, thermopane windows, and ceiling fans in every bedroom. Truly move-in ready-just unpack and enjoy.

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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.

41

Homes For Sale

$488,685

Average List Price

Mechanicals & Utilities: Hot Water • Oil • Window Unit • Private Well water

Exterior Features

Exterior Construction: Vinyl Siding,Wood

Roof Type: Fiberglass Shingle

Foundation: Block,Concrete

Garage: Attached Garage (2 car)

Patio/Deck: Balcony,Deck

Utilities: Water: Private Well

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"Local Market Expert"

George Antonopoulos

Real Estate Advisor

Cheshire • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(800) 555-0001

george@appzentric.com

Good morning George, I'm interested in
39 Winslow Road, Cheshire, Connecticut

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