27 Wooster Street
Ridgefield, Connecticut 06877
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,962
- Acres
- 2.15
- Year Built
- 1910
- Neighborhood
- South Ridgefield
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
53
66 under contract
Median List Price
$1.29M
53 active listings
Median Closed Price
$1.20M
221 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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.