101 Child Hill Road
Woodstock, Connecticut 06281
Reduced from $549,000
- Beds
- 4
- Baths
- 3
- SqFt
- 2,150
- Acres
- 0.90
- Year Built
- 1830
- Property Type
- Single Family

Matt Caiola
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About This Home
Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases its original door with full exterior shutters, a hallmark of Greek Revival style. The living room centers on a classic fireplace, and along the upstairs landing a wall of built-in bookshelves creates a welcoming library space. Three bedrooms are located on the second floor, with an additional first-floor room currently serving as a fourth bedroom. The primary includes a walk-in closet and bath with a clawfoot tub. The walk-up attic offers potential for an office, playroom, or studio. The kitchen features a custom layout paired with quality appliances (Sub-Zero fridge & Thor cooktop) and the warmth of a wood stove. Updates include new Trex decking and a newly finished three-season room off the dining room. Historic touches, such as unique wallcoverings and original details, remain intact, blending history, artistry, and the timeless charm of living in Woodstock, CT. Property to be sold in as-is condition.
Key Facts
- City/Town
- Woodstock
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1830
- Days on Market
- 393 days
- Beds
- 4
- Baths
- 3 full
- Living Area
- 2,150 sq ft
- Lot Size
- 0.90 acres
- Garage / Parking
- 1 garage
- Property Taxes
- $7,455 / Annually
Market Snapshot
The Woodstock Market
Single Family · trailing 12 months
Active Listings
21
13 under contract
Median List Price
$679,000
21 active listings
Median Closed Price
$425,000
105 sales
Median Days on Market
42
21 active listings
Median $ / Sq Ft
$261
21 active listings
Sale-to-List Ratio
100.0%
105 sales
How this home compares
List Price
$520,000
vs $679,000 median
23.4% below median
Price / Sq Ft
$242
vs $261 median
7.3% below median
Days on Market
393 days
vs 42 days median
351 days longer than median
Based on 21 active and 105 closed sales (trailing 12 mo) of single family in Woodstock. Source: SmartMLS · As of October 14, 2026.
Location
101 Child Hill Road, Woodstock, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$2,880
- Property Taxes$621
- Insurance$173
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodstock
- Neighborhood
- N/A
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1830
- New Construction
- No/Resale
- Living Area
- 2,150 sq ft
Schools
- Elementary
- Woodstock
- High
- Woodstock Academy
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Fireplaces
- 1
- Laundry
- Lower Level
- Laundry Location
- Basement
- Appliances
- Electric CooktopOven/RangeMicrowaveRefrigeratorDishwasherDisposalWasherDryer
- Basement
- FullGarage AccessInterior AccessConcrete FloorFull With Walk-Out
Exterior & Lot
- Lot Size
- 0.90 acres
- Zoning
- 0
- Garage / Parking
- 1 garage spaceUnder House Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- White
- Roof
- Shingle
- Foundation
- Stone
- Exterior Features
- Deck
- Lot Description
- Level LotCleared
Listing & Financials
- Property Taxes
- $7,455 / Annually
- Days on Market
- 393
- MLS #
- 24125003
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/14/2026. 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 10/14/2026 at 2:50 AM UTC.