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20 Cherry Lane

Wilton, Connecticut 06897

ACTIVE$2,679,000

Reduced from $2,850,000

Beds
6
Baths
6 | 1
SqFt
7,200
Acres
2.45
Year Built
1991
Matt Caiola

Matt Caiola

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Wine CellarPool4-Car Garage5 FireplacesPrice Reduced

About This Home

20 Cherry Lane is a rare Georgian Colonial estate set on nearly 2.5 flat, manicured acres bordering 50 acres of protected conservation land and hiking trails. Offering over 7200 sqft, with an additional 2100+ sqft lower level, this home combines exceptional scale, modern updates, and long-term value. Designed for entertaining and everyday living, the renovated chef's kitchen features double marble islands, double ovens, dual dishwashers, navy subway tile, and a custom coffee/wine bar, flowing into the oversized Great Room with a massive stone fireplace, full bar, and direct access to the resort style pool area. The flexible layout includes 6 bedrooms, a luxurious primary suite with private balcony and oversized walk-in closets, double office/conference spaces, library, homework zone, first floor guest suite, and a fully self contained in-law/au pair suite with private entrance, kitchen, and living area. The renovated lower level offers a gym space, wine cellar, oversized playroom with custom bunk beds. Outdoors enjoy a restored pool and spa, sports courts, playground, gazebo, fire pits, and multiple entertaining areas. Major upgrades include a new 2024 roof, updated HVAC, plumbing, electrical, and a renovated 4 car garage with smart-tech doors. Move in ready, this exceptional estate offers incredible space, infrastructure, and upside in a premier school district.

Key Facts

City/Town
Wilton
Neighborhood
South Wilton
Property / Style
Single Family · Colonial,Georgian Colonial
Year Built
1991
Days on Market
108 days
Beds
6
Baths
6 full · 1 half
Living Area
7,200 sq ft
Lot Size
2.45 acres
Garage / Parking
4 garage
Property Taxes
$34,687 / Annually

Market Snapshot

The Wilton Market

Single Family · trailing 12 months

View area

Median Days on Market

20

29 active listings

Median $ / Sq Ft

$407

29 active listings

Sale-to-List Ratio

105.4%

213 sales

How this home compares

List Price

$2.68M

vs $1.80M median

48.9% above median

Price / Sq Ft

$372

vs $407 median

8.6% below median

Days on Market

108 days

vs 20 days median

88 days longer than median

Based on 29 active and 213 closed sales (trailing 12 mo) of single family in Wilton. Source: SmartMLS · As of July 28, 2026.

Location

20 Cherry Lane, Wilton, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$17,443

per month

  • Principal & Interest$13,659
  • Property Taxes$2,891
  • Insurance$893
  • HOA$0

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

Location

City/Town
Wilton
Neighborhood
South Wilton
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial,Georgian Colonial
Year Built
1991
New Construction
No/Resale
Living Area
7,200 sq ft

Schools

Elementary
Miller-Driscoll
High
Wilton

Interior

Heating
Hot Air
Heat Fuel
OilPropane
Cooling
Central Air
Fireplaces
5
Laundry
Main Level
Appliances
Gas CooktopWall OvenMicrowaveRange HoodRefrigeratorFreezerDishwasherWasherDryerWine Chiller
Basement
FullStorageFully FinishedGarage AccessLiveable SpaceFull With Walk-Out
In-Law Apartment
YesFirst FloorSeparate Entry
Interior Features
Central VacuumSecurity System
Additional Rooms
Exercise RoomFoyerLaundry RoomWine Cellar

Exterior & Lot

Lot Size
2.45 acres
Zoning
R-2
Garage / Parking
4 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Pool
HeatedSpaIn Ground Pool
Construction
Brick
Color
Brick
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckPatio
Lot Description
Lightly WoodedLevel LotSloping LotProfessionally Landscaped

Listing & Financials

Property Taxes
$34,687 / Annually
Days on Market
108
MLS #
24165364
MLS Status
Active

Similar Properties

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

Listed By

Molly Rubins

(203) 216-3111

NestSeekers International

(203) 204-9555

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 7:01 AM UTC.