Charm and modern comfort come together in this beautifully renovated 3BR, 2BA home set on nearly an acre along a quiet country road in Woodbury. The inviting main level features a cozy living room with a fireplace, a spacious first-floor bedroom, and a full bath-perfect for guests or one-level living. A 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, seeded, and extends to a peaceful meadow that backs to a wooded preserve. The recent expansion includes an oversized two-car garage, extra deep with high ceilings offering loft or workshop potential. 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, or a creative workspace. Move-in ready and turn-key, this home blends New England charm with thoughtful updates and serene surroundings that will certainly delight everyone who walks through the door of this one of a kind home situated on an extremely private lot. Come see it and don't miss this opportunity to own an oasis in Woodbury. Added highlights include a new furnace (2025), new septic tank (2025), newer whole-house propane generator, and a roof approximately 10 years old.
Sold for $550,000
$550,000
2 Judd Hill Road, Woodbury, CT 06798
3beds
1,470sqft
Single Family Residence
Built in 1958
0.96 Acres Lot
$550,100 Zestimate®
$374/sqft
$3,334 Estimated rent
Home value
$550,100
$506,000 - $600,000
$3,334/mo
Zestimate® history
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What's special
Zillow last checked: 8 hours ago
Listing updated: January 09, 2026 at 12:55pm
Listed by:
Meg George (203)470-5267,
Higgins Group Bedford Square 203-226-0300
Bought with:
Timothy Drakeley, REB.0791885
Drakeley Real Estate, Inc.
Source: Smart MLS,MLS#: 24134430
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Level: Main
Bedroom
- Features: Wide Board Floor
- Level: Upper
Bedroom
- Features: Wide Board Floor
- Level: Upper
Family room
- Features: Fireplace, Hardwood Floor
- Level: Main
Kitchen
- Features: Balcony/Deck, Dining Area, Eating Space, Fireplace, Kitchen Island, Hardwood Floor
- Level: Main
Heating
- Forced Air, Oil
Cooling
- None
Appliances
- Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Electric Water Heater, Water Heater
- Laundry: Main Level
Features
- Open Floorplan, Smart Thermostat
- Basement: Full
- Attic: None
- Number of fireplaces: 1
Interior area
- Total structure area: 1,470
- Total interior livable area: 1,470 sqft
- Finished area above ground: 1,470
Property
Parking
- Total spaces: 6
- Parking features: Attached, Paved, Off Street, Driveway, Garage Door Opener, Private
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Deck
- Exterior features: Rain Gutters, Garden, Lighting, Stone Wall
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
Lot
- Size: 0.96 Acres
- Features: Corner Lot, Wetlands, Level, Cleared, Open Lot
Details
- Parcel number: 932289
- Zoning: OS80
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 & neighborhood
Location
- Region: Woodbury
- Subdivision: Quassapaug
Price history
| Date | Event | Price |
|---|---|---|
| 1/9/2026 | Sold | $550,000-3.3%$374/sqft |
Source:  Smart MLS #24134430 Report a problem | ||
| 12/7/2025 | Pending sale | $569,000$387/sqft |
Source: Smart MLS #24134430 Report a problem | ||
| 11/6/2025 | Price change | $569,000-5%$387/sqft |
Source: Smart MLS #24134430 Report a problem | ||
| 10/18/2025 | Listed for sale | $599,000+84.3%$407/sqft |
Source: Smart MLS #24134430 Report a problem | ||
| 2/28/2025 | Sold | $325,000+1.6%$221/sqft |
Source: Smart MLS #24071100 Report a problem | ||
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 |
Find assessor info on the county website
Neighborhood: 06798
Nearby schools
GreatSchools rating
- 5/10Mitchell Elementary SchoolGrades: PK-5Distance: 3.3 mi
- 6/10Woodbury Middle SchoolGrades: 6-8Distance: 3.6 mi
- 9/10Nonnewaug High SchoolGrades: 9-12Distance: 3.3 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.
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$550,100
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