365 Winthrop Road - Deep River, CT

$475,000

Beds

2.00

Baths

1,984

SqFt

1.20

Acres

Pricing Insight: Originally listed for $475,000, the price has remained unchanged for approximately 20 days. This property has been on the market for approximately 20 days. MLS reports 17 Days on Market (DOM) before it went under contract.

365 Winthrop Road, Deep River, CT is a 3-bed, 2-bath, 1,984 square foot home built in 1840 , featuring colonial architecture.

This home is within the Deep River school district. Local, with nearby schools including Deep River.

MLS #: 24189405

Offered Price: $475,000

Residence Type: Single Family

Architectural Style: Colonial

Living Area: 1,984 Sq. Ft.

Lot Size: 1.20 Acres

Neighborhood: Winthrop

County: Middlesex

Year Built: 1840

Design & Construction: Frame

Heating: Hot Air

Cooling: Central Air

Garage Spaces: 0

Price per Sq Ft as listed: $239

Estimated Tax: $6,705

Days on Market: 17

$849,900

4 Beds · 3 Baths · 2,782 Sq Ft

16 Glen Grove Road, Deep River

Home Automation: Not specified

Energy Features: Not specified

Solar Contract: Not specified

Heating Fuel: Oil

Fuel Type: Hot Air

Fuel Tank Location: In Basement

Cooling System: Central Air

Hot Water System: Electric, 50 Gallon Tank

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $239 / Sq. Ft.

Tax assessed value: $209,650

Estimated Tax: $6,705

Architectural Style: Colonial

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1840

Living Area: 1,984 Sq. Ft.

Lot Size: 1.20 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 Deep River
Statistical modeling algorithms

Local Market Context

Active Listings: 16

Average Price: $974,906

Average DOM: 17 days

Complimentary CMAs, no obligation

Welcome to 365 Winthrop Road in Deep River, where historic charm meets thoughtful updates. This beautifully maintained 3-bedroom, 2-bathroom home offers timeless character alongside the conveniences of modern living. The spacious main level features a large kitchen, formal dining room, inviting living room, cozy den, and a stunning great room with French doors leading to the backyard, perfect for entertaining or everyday living. Upstairs, you'll find a convenient laundry room, two bedrooms and a generous primary suite filled with natural light, featuring cathedral ceilings, exposed post-and-beam construction, ample closet space, and an en suite bathroom. Step outside to enjoy a picturesque setting with beautiful stonework, mature gardens, and a charming gazebo. A storage shed and a separate workshop with electricity and heating/cooling provide endless possibilities for hobbies, projects, or additional workspace. Recent improvements include hot water heater (December 2025) a new roof and well pump (April 2026). Don't miss this unique opportunity to own a home that seamlessly blends historic character and exceptional outdoor living in Deep River.

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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 • 1.2 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.

16

Homes For Sale

$974,906

Average List Price

Mechanicals & Utilities: Hot Air • Oil • Central Air • Private Well water • 2 fireplaces

Exterior Features

Exterior Construction: Clapboard,Wood

Roof Type: Asphalt Shingle

Foundation: Concrete,Stone

Patio/Deck: Shed,Gazebo,Garden Area,Lighting,Stone Wall,French Doors,Patio

Utilities: Water: Private Well

Outbuildings: Shed,Gazebo,Garden Area,Lighting,Stone Wall,French Doors,Patio

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George Antonopoulos

Real Estate Advisor

Deep River • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(203) 675-3399

george@appzentric.com

Good morning George, I'm interested in
365 Winthrop Road, Deep River, Connecticut

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