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100 Shortwoods Road

New Fairfield, Connecticut 06812

ACTIVE - NEW$649,000
Beds
3
Baths
2
SqFt
2,176
Acres
2.05
Year Built
1984
Matt Caiola

Matt Caiola

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2-Car Garage2 Fireplaces

About This Home

Step into easy living at this classic red barn-style home on two acres. Complete with cupola and stable door, it blends New England charm with many upgrades. The open main floor showcases exposed beams, a sunlit dining area, a kitchen with peninsula, and a living room anchored by a Lopi woodstove. An open staircase leads up to a cozy den, ready for movie nights. The adjacent bathroom includes a bathtub with shower and laundry closet. The 2nd floor primary is a spacious retreat with vaulted ceilings, wide plank floors, beams, WIC, and a retro Preway fireplace. The light-filled ensuite features a tiled shower and its own balcony. Two additional bedrooms complete the upper floor. Outside, a bluestone terrace is ready for grilling, alfresco dining, and stargazing among mature maples. Practicality abounds with an EV charger, shed and 2-car garage with walk-up attic. Nature lovers rejoice: steps to Pootatuck Forest and just up the hill from Squantz Pond swimming, boating, and fishing. Winter fun is around the corner at Thunder Ridge. Just 5 mins for small-town perks like groceries and other essentials, and 20 mins to all manner of options. Charming neighboring villages sit ready for jaunts. Access to NYC? 25 mins to Brewster station and just over an hour's drive to Henry Hudson bridge. Best of all? Recent updates include a new roof, renovated bathrooms, efficient mini-splits and professional landscaping, so just pack your bags and move right in!

Key Facts

City/Town
New Fairfield
Neighborhood
N/A
Property / Style
Single Family · Barn,Cottage
Year Built
1984
Days on Market
0 days
Beds
3
Baths
2 full
Living Area
2,176 sq ft
Lot Size
2.05 acres
Garage / Parking
2 garage · 8 total
Property Taxes
$9,080 / Annually

Market Snapshot

The New Fairfield Market

Single Family · trailing 12 months

Median Days on Market

62

31 active listings

Median $ / Sq Ft

$304

31 active listings

Sale-to-List Ratio

100.0%

149 sales

How this home compares

List Price

$649,000

vs $925,000 median

29.8% below median

Price / Sq Ft

$298

vs $304 median

In line with median

Days on Market

0 days

vs 62 days median

62 days fresher than median

Based on 31 active and 149 closed sales (trailing 12 mo) of single family in New Fairfield. Source: SmartMLS · As of August 5, 2026.

Location

100 Shortwoods Road, New Fairfield, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,310

per month

  • Principal & Interest$3,337
  • Property Taxes$757
  • Insurance$216
  • HOA$0

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

Location

City/Town
New Fairfield
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Barn,Cottage
Year Built
1984
New Construction
No/Resale
Living Area
2,176 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Per Board of Ed

Interior

Heating
BaseboardHeat PumpWood/Coal Stove
Heat Fuel
ElectricWood
Cooling
Ceiling FansDuctlessHeat PumpSplit System
Fireplaces
2
Laundry
Upper Level
Laundry Location
Guest bathroom
Appliances
Convection RangeRange HoodRefrigeratorDishwasherWasherElectric Dryer
Basement
Crawl SpacePartialStorageInterior Access
In-Law Apartment
No
Interior Features
Cable - AvailableOpen Floor Plan

Exterior & Lot

Lot Size
2.05 acres
Zoning
2
Garage / Parking
2 garage spaces8 total parking spacesDetached GaragePavedOff Street ParkingDrivewayPrivatePavedAsphalt
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
Vertical SidingWood
Color
Red
Roof
Asphalt Shingle
Foundation
ConcreteSlab
Exterior Features
BalconyShedGuttersStone WallFrench DoorsPatio
Lot Description
Lightly WoodedSloping LotProfessionally Landscaped

Listing & Financials

Property Taxes
$9,080 / Annually
Days on Market
0
MLS #
24196522
MLS Status
Active

Similar Properties

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Listed By

Richard Dalton

(646) 389-3701

Country House Realty CT Inc.

(845) 397-2590

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

The IDX display contains information sourced from SmartMLS, Inc. as of 8/5/2026. 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 8/5/2026 at 11:40 PM UTC.