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.
Accepting backups
Price cut: $25K (5/19)
$574,900
2 Judd Hill Road, Woodbury, CT 06798
3beds
1,470sqft
Single Family Residence
Built in 1958
0.96 Acres Lot
$567,900 Zestimate®
$391/sqft
$-- HOA
What's special
Serene and private settingSpacious first-floor bedroomNewly updated kitchen
- 38 days |
- 793 |
- 52 |
Zillow last checked:
Listing updated:
Listed by:
Timothy Drakeley (203)510-9184,
Drakeley Real Estate, Inc. 203-263-4336
Source: Smart MLS,MLS#: 24172678
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Hardwood Floor
- Level: Main
Bedroom
- Level: Upper
Bedroom
- Features: Softwood Floor
- Level: Upper
Den
- Features: Hardwood Floor
- Level: Main
Dining room
- Level: Main
Kitchen
- Features: Kitchen Island
- Level: Main
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
Heating
- Forced Air, Oil
Cooling
- Window Unit(s)
Appliances
- Included: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Main Level
Features
- Basement: Full
- Attic: Access Via Hatch
- Number of fireplaces: 1
Interior area
- Total structure area: 1,470
- Total interior livable area: 1,470 sqft
- Finished area above ground: 1,470
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 2
Features
- Patio & porch: Deck
Lot
- Size: 0.96 Acres
- Features: Level
Details
- Parcel number: 932289
- Zoning: OS80
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1958
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & HOA
Community
- Features: Golf, Lake, Library, Private School(s), Tennis Court(s)
HOA
- Has HOA: No
Location
- Region: Woodbury
Financial & listing details
- Price per square foot: $391/sqft
- Tax assessed value: $168,840
- Annual tax amount: $3,988
- Date on market: 5/5/2026
Estimated market value
$567,900
$540,000 - $596,000
$3,272/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/19/2026 | Price change | $574,900-4.2%$391/sqft |
Source: | ||
| 5/5/2026 | Listed for sale | $599,900+9.1%$408/sqft |
Source: | ||
| 1/9/2026 | Sold | $550,000-3.3%$374/sqft |
Source: | ||
| 12/7/2025 | Pending sale | $569,000$387/sqft |
Source: | ||
| 11/6/2025 | Price change | $569,000-5%$387/sqft |
Source: | ||
| 10/18/2025 | Listed for sale | $599,000+84.3%$407/sqft |
Source: | ||
| 2/28/2025 | Sold | $325,000+1.6%$221/sqft |
Source: | ||
| 2/3/2025 | Pending sale | $319,900$218/sqft |
Source: | ||
| 2/1/2025 | Listed for sale | $319,900$218/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $3,988 +3.3% | $168,840 +1.3% |
| 2024 | $3,860 +5.3% | $166,600 +32.1% |
| 2023 | $3,664 -0.4% | $126,080 |
| 2022 | $3,678 | $126,080 |
| 2021 | $3,678 | $126,080 |
| 2020 | $3,678 | $126,080 |
| 2019 | $3,678 +3.2% | $126,080 -6% |
| 2018 | $3,565 -2.1% | $134,130 |
| 2017 | $3,643 +3.3% | $134,130 |
| 2016 | $3,526 +0.8% | $134,130 |
| 2015 | $3,497 +1.5% | $134,130 |
| 2014 | $3,446 -11% | $134,130 -18.9% |
| 2013 | $3,872 -3.4% | $165,470 |
| 2012 | $4,009 +7.9% | $165,470 |
| 2011 | $3,716 +4.7% | $165,470 |
| 2010 | $3,549 +1.5% | $165,470 |
| 2009 | $3,496 +9.4% | $165,470 +26.1% |
| 2008 | $3,196 +1.6% | $131,260 |
| 2007 | $3,145 +5.1% | $131,260 |
| 2006 | $2,991 +6.4% | $131,260 |
| 2005 | $2,812 | $131,260 |
| 2004 | $2,812 +45.2% | $131,260 +84.7% |
| 2003 | $1,936 -23.2% | $71,050 -45.2% |
| 1997 | $2,521 | $129,620 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 06798
Nearby schools
GreatSchools rating
- 5/10Mitchell Elementary SchoolGrades: PK-5Distance: 3.3 mi
- 6/10Woodbury Middle SchoolGrades: 6-8Distance: 3.5 mi
- 9/10Nonnewaug High SchoolGrades: 9-12Distance: 3.4 mi
Schools provided by the listing agent
- Elementary: Mitchell
- Middle: Woodbury
- 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.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- Litchfield County
- Woodbury
- 06798
- 2 Judd Hill Road





