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27 Wooster Street

Ridgefield, Connecticut 06877

PENDING$1,295,000
Beds
4
Baths
2 | 1
SqFt
2,962
Acres
2.15
Year Built
1910
Matt Caiola

Matt Caiola

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Guest House2-Car Garage1 FireplaceVirtual Tour

About This Home

Extraordinary country compound just 1.5 miles to town center including exquisite turn of the century farmhouse, 2011 custom barn/guest house, detached 2 car garage, privacy fencing, & 2.15 level acres with scenic views of Wooster Mountain State Park. Total 3,762 sf with 5 BR, 3 full/1 half baths including 2,962 sf in the fully updated 1910 colonial w/4 BR & 2/1 baths, plus additional 800 sf in the state of the art barn with inviting front porch, copper leaders/gutters, radiant heated floors, timbered vaulted ceilings, massive great room with wet bar/fridge, plus private guest quarters w/full bath. Extensive improvements by former & current owners including: driveway w/cobblestone apron, stone walls, fencing, clearing & planting; windows; septic; built-in audio; mechanical upgrades - hot water heater, water tank/treatment, new well pump, insulation, plumbing, chimney flue; decks rebuilt w/top of line materials; kitchen updates; newly remodeled 2nd floor bath; plus full barn construction. Most picturesque sprawling yard w/ample outdoor living spaces including wrap around front porch; screened porch; rear deck, & stone terrace. Other gracious features include: private library w/French doors & built-ins; hardwood floors; crown moldings; elegant formal LR; formal DR w/built-in corner cupboard; casual breakfast room; beamed & vaulted FR w/brick fireplace; & relaxing MBR suite w/dressing room, balcony/sun deck, & private bath. One of a kind home & property, just 58 miles to Midtown.

Key Facts

City/Town
Ridgefield
Neighborhood
South Ridgefield
Property / Style
Single Family · Colonial,Farm House
Year Built
1910
Days on Market
1188 days
Beds
4
Baths
2 full · 1 half
Living Area
2,962 sq ft
Lot Size
2.15 acres
Garage / Parking
2 garage
Property Taxes
$19,064 / Annually

Market Snapshot

The Ridgefield Market

Single Family · trailing 12 months

View area

Median Days on Market

30

53 active listings

Median $ / Sq Ft

$422

53 active listings

Sale-to-List Ratio

101.6%

221 sales

How this home compares

List Price

$1.29M

vs $1.29M median

In line with median

Price / Sq Ft

$437

vs $422 median

In line with median

Days on Market

1188 days

vs 30 days median

1158 days longer than median

Based on 53 active and 221 closed sales (trailing 12 mo) of single family in Ridgefield. Source: SmartMLS · As of July 28, 2026.

Location

27 Wooster Street, Ridgefield, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,624

per month

  • Principal & Interest$6,603
  • Property Taxes$1,589
  • Insurance$432
  • HOA$0

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

Location

City/Town
Ridgefield
Neighborhood
South Ridgefield
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial,Farm House
Year Built
1910
Living Area
2,962 sq ft

Schools

Elementary
Scotland
High
Ridgefield

Interior

Heating
Hot WaterZoned
Cooling
Central AirZoned
Fireplaces
1
Laundry
Main Level
Basement
FullPartially FinishedWalk-out
Interior Features
Audio SystemSecurity System
Additional Rooms
Laundry RoomMud Room

Exterior & Lot

Lot Size
2.15 acres
Garage / Parking
2 garage spacesDetached Garage
Waterfront Details
Not Applicable
Construction
ClapboardWood
Roof
Asphalt Shingle
Foundation
ConcreteStone
Exterior Features
BalconyBarnDeckFrench DoorsGuest HouseLightingPorchPorch-ScreenedStone Wall
Lot Description
Level LotFence - StoneFence - WoodProfessionally Landscaped

Listing & Financials

Property Taxes
$19,064 / Annually
Days on Market
1188
MLS #
170565348
MLS Status
Under Contract

Similar Properties

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

Listed By

Laura Ancona

William Pitt Sotheby's Int'l

Co-Listed By

Robert McCullough

William Pitt Sotheby's Int'l

Buyer's Agent

Laurie Mortensen

William Pitt Sotheby's Int'l

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 6:01 AM UTC.