Beautifully constructed and perched atop a scenic 3+ acre lot, this stately gambrel colonial is just a 5-minute drive from charming downtown Woodbury. Offering 4 to 5 bedrooms, this home features everything one would expect in almost 3400 square feet of living space; a formal dining room, a large front-to-back living room with a fireplace and hardwood floors, and a spacious eat-in kitchen with a center island. The generous family room is the heart of the home, boasting vaulted, beamed ceilings, a cozy fireplace, hardwood floors, and French doors leading to both the front and back yards. Upstairs, you'll find four bedrooms and two and a half bathrooms, along with a private au pair suite located above the garage-perfect for guests or extended family. Additional highlights include an oversized two-car garage, a walkout lower level with a third garage door, and enough space to accommodate three to four smaller vehicles. The exterior is impeccably maintained with expansive lawns, a pond with wild flowers, mature plantings, blue stone walkways and patios, classic stone walls, and a backyard pavilion- ideal for enjoying the outdoors while staying shaded from the sun. This ideal location is only a 5-minute drive to town parks, schools, and Woodbury's fabulous Main Street USA.
Sold for $750,000
$750,000
181 Railtree Hill Road, Woodbury, CT 06798
4beds
3,726sqft
Single Family Residence
Built in 1986
3.24 Acres Lot
$775,700 Zestimate®
$201/sqft
$6,679 Estimated rent
Home value
$775,700
$652,000 - $923,000
$6,679/mo
Zestimate® history
Loading...
Owner options
List your home for rent
$6,679/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
Learn more$6,679/mo
Rent Zestimate®
Refinance and save
$4,283/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
See today's rates$4,283/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Zillow last checked: 7 hours ago
Listing updated: September 07, 2025 at 05:08am
Listed by:
Timothy Drakeley 203-510-9184,
Drakeley Real Estate, Inc. 203-263-4336,
Rhonda Stokes 203-598-8992,
Drakeley Real Estate, Inc.
Bought with:
Dawn Puchala, REB.0792028
Key Realty of Connecticut
Source: Smart MLS,MLS#: 24096486
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: Cathedral Ceiling(s), Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Dining room
- Features: Hardwood Floor
- Level: Main
Family room
- Features: Vaulted Ceiling(s), Beamed Ceilings, Fireplace, Patio/Terrace, Hardwood Floor
- Level: Main
Kitchen
- Features: Eating Space, Kitchen Island
- Level: Main
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
Other
- Features: Vaulted Ceiling(s), Full Bath
- Level: Upper
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Cooktop, Oven, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Main Level
Features
- Open Floorplan
- Doors: French Doors
- Windows: Thermopane Windows
- Basement: Full,Partially Finished
- Attic: Pull Down Stairs
- Number of fireplaces: 2
Interior area
- Total structure area: 3,726
- Total interior livable area: 3,726 sqft
- Finished area above ground: 3,326
- Finished area below ground: 400
Property
Parking
- Total spaces: 3
- Parking features: Attached
- Attached garage spaces: 3
Features
- Patio & porch: Patio
- Exterior features: Sidewalk, Garden, Stone Wall
- Waterfront features: Waterfront, Pond
Lot
- Size: 3.24 Acres
- Features: Few Trees, Level, Rolling Slope
Details
- Parcel number: 934474
- Zoning: OS60
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1986
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Green energy
- Energy efficient items: Windows
Community & neighborhood
Community
- Community features: Golf, Library, Medical Facilities, Playground, Private School(s)
Location
- Region: Woodbury
- Subdivision: Good Hill
Price history
| Date | Event | Price |
|---|---|---|
| 9/7/2025 | Pending sale | $779,000+3.9%$209/sqft |
Source:  Smart MLS #24096486 Report a problem | ||
| 9/5/2025 | Sold | $750,000-3.7%$201/sqft |
Source: Smart MLS #24096486 Report a problem | ||
| 8/21/2025 | Price change | $779,000-2.5%$209/sqft |
Source: Smart MLS #24096486 Report a problem | ||
| 8/8/2025 | Price change | $799,000-3.1%$214/sqft |
Source: Smart MLS #24096486 Report a problem | ||
| 7/22/2025 | Price change | $824,900-1.8%$221/sqft |
Source: Smart MLS #24096486 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,001 +1.9% | $423,430 |
| 2024 | $9,811 +10.3% | $423,430 +38.3% |
| 2023 | $8,894 -0.4% | $306,070 |
Find assessor info on the county website
Neighborhood: 06798
Nearby schools
GreatSchools rating
- 5/10Mitchell Elementary SchoolGrades: PK-5Distance: 1.6 mi
- 6/10Woodbury Middle SchoolGrades: 6-8Distance: 1.4 mi
- 9/10Nonnewaug High SchoolGrades: 9-12Distance: 2.6 mi
Schools provided by the listing agent
- Elementary: Mitchell
- High: Nonnewaug
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get pre-qualified for a loan
At Zillow Home Loans, we can pre-qualify you in as little as 5 minutes with no impact to your credit score.An equal housing lender. NMLS #10287.
Sell for more on Zillow
Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
$775,700
2% more
+$15,514
With Zillow Showcase(estimated)
$791,214
- Connecticut
- Litchfield County
- Woodbury
- 06798
- 181 Railtree Hill Road