100 Shortwoods Road
New Fairfield, Connecticut 06812
- Beds
- 3
- Baths
- 2
- SqFt
- 2,176
- Acres
- 2.05
- Year Built
- 1984
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
31
33 under contract
Median List Price
$925,000
31 active listings
Median Closed Price
$600,000
149 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 30, 2026per 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
Homes with a close match in area, property type, and price.
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.