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469 Platt Hill Road

Winchester, Connecticut 06098

ACTIVE$895,000
Beds
4
Baths
2
SqFt
3,088
Acres
7.11
Year Built
1789
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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3 Fireplaces

About This Home

HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 , 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors, to the 12 over 12 Windows and Fireplaces, Displays the Charm & Character in this Residence! For a more Modern Twist, there is a Fully Remodeled Eat-in Kitchen with Quartz Counters, as well as Remodeled Bathrooms. 4 TO 5 Bedrooms, 3 Full Baths, Formal Dining Room & Comfortable Living Room. Spacious Sunken 20' x 21' Family Room with Cathedral Ceiling. Unique Loft offers a Birdseye View to the Family Room. Level 7 Acre Lot Enhanced by Stone Walls and Nice Plantings. Outbuildings include a 30' x 35' 4 Stall Horse Barn with Tack Room & Hayloft. 2 paddocks and a 25' X 30' Storage Building. Mechanicals include Oil Hot-Air Furnace, New propane heat in the sunken living room,200 AMP Electrical Service, Well Water & Septic System. A Quaint and Rural Atmosphere, but within Close Proximity to Major Shopping, access to State Parks, Lakes, Golf Courses, Ski Areas, and Local Arts and Cultural Venues. The Photo Library Partially tells the Story, but prospective Buyers need to Visit / Tour this Lovely Property in order to Appreciate its Attributes!!

Key Facts

City/Town
Winchester
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1789
Days on Market
87 days
Beds
4
Baths
2 full
Living Area
3,088 sq ft
Lot Size
7.11 acres
Property Taxes
$11,516 / Annually

Market Snapshot

The Winchester Market

Single Family · trailing 12 months

Median Days on Market

39

12 active listings

Median $ / Sq Ft

$265

12 active listings

Sale-to-List Ratio

100.0%

103 sales

How this home compares

List Price

$895,000

vs $524,900 median

70.5% above median

Price / Sq Ft

$290

vs $265 median

9.4% above median

Days on Market

87 days

vs 39 days median

48 days longer than median

Based on 12 active and 103 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of July 28, 2026.

Location

469 Platt Hill Road, Winchester, Connecticut

Property + 9 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,821

per month

  • Principal & Interest$4,563
  • Property Taxes$960
  • Insurance$298
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Winchester
Neighborhood
N/A
County
Litchfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1789
New Construction
No/Resale
Living Area
3,088 sq ft

Schools

Elementary
Per Board of Ed
High
Gilbert

Interior

Heating
Hot Air
Heat Fuel
OilPropane
Cooling
None
Fireplaces
3
Laundry
Main Level
Laundry Location
MAIN
Appliances
Oven/RangeRefrigeratorDishwasher
Basement
FullFull With Hatchway
Interior Features
Cable - Available
Additional Rooms
Mud Room

Exterior & Lot

Lot Size
7.11 acres
Zoning
RU-3
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Clapboard
Color
GREY
Roof
Asphalt Shingle
Foundation
Block
Exterior Features
Barn
Lot Description
Level LotOpen Lot

Listing & Financials

Property Taxes
$11,516 / Annually
Days on Market
87
MLS #
24172121
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Marshall Cohen

(860) 307-2594

Cohen Agency

(860) 618-5800

Co-Listed By

Wieslawa Fretto

Cohen Agency

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/28/2026 at 6:55 AM UTC.