2 Judd Hill Road Woodbury, CT $ 599,900
2 Judd Hill Road
$ 599,900
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2 Judd Hill Road

Woodbury, CT, 06798
$ 599,900
Bedrooms3 Baths2.0 Sq 1,470

Monthly Estimate*

$ 3,694

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Single Family Home for sale in Woodbury, CT

for $599,900 with 3 bedrooms and 2 full baths. This 1,470 square foot home was built in 1958 on a lot size of 0.96.

Charm and modern comfort come together in this beautifully renovated 3-bedroom, 2-bath home set on nearly an acre along a quiet country road in Woodbury. Thoughtfully updated and move-in ready, this inviting home blends classic New England character with practical improvements throughout, including a fully insulated attic and insulated walls added by the current owner for enhanced comfort and efficiency. The main level features a warm living room with fireplace, a spacious first-floor bedroom, and a full bath, offering flexibility for guests or convenient one-level living. The newly updated kitchen opens to the dining area and leads directly to a brand-new deck overlooking a private, level backyard with distant pond and mountain views. The yard has been cleared and extends to a peaceful meadow that backs to a wooded preserve, creating a serene and private setting. A recent expansion added an oversized two-car garage, extra deep with high ceilings and potential for a loft, workshop, or additional storage. The full basement offers tall ceilings, ample storage, and rear exterior access to the leveled backyard. Adjacent to the basement door is an additional versatile room, ideal for outdoor storage, tools, hobbies, or a creative workspace. Additional highlights include a new furnace and septic tank installed in 2025, a newer whole-house propane generator, and a roof approximately 10 years old. This one-of-a-kind Woodbury retreat offers privacy, comfort, and thoughtful updates in a beautiful country setting. Come see it and don't miss the opportunity to own your own oasis in Woodbury.

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Single Family Active

Price

$ 599,900

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 3,988

Style

Lot Size

0.96

Year Built

1958

Town/City

Woodbury

MLS | Web ID

24172678

Features
General
Zoning OS80
Neighborhood N/A
County Litchfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 0.96
Directions Old Sherman to Judd Hill
High School Nonnewaug
City Woodbury
Elementary School Mitchell
Sq Ft Total 1470
DOM 0
Year Built 1958
Style Cape Cod
Year Built Source Public Records
Energy Features Generator
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Interior
Cooling System Window Unit
Total Rooms 7
Basement Description Full
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Exterior
Water Source Private Well
Lot Description Level Lot
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* Excluded Features
List By
Timothy Drakeley

Listing Agent

Drakeley Real Estate, Inc.

Broker

tim@drakeley.com

Email

Affordability Calculator

$4,026
Per Month
92%
8%
0%
Monthly Principal & Interest
$3,694
Monthly Property Taxes
$332
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
1233322 Elementary School
1232807 Middle School
Nonnewaug High School High School
Pricing History
DatePricePrice ChangeDescription
5/5/2026$599,900 Listed Price

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2 Judd Hill Road, Woodbury, CT, 06798 is a Single Family Home for sale at $599,900 with 1,470 sqft and a lot size of 0.96. 2 Judd Hill Road has 3 bedrooms, 2.0 baths, and was built in 1958. The property's zip code is 06798 which is in Woodbury, CT