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$599,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,470 Sq. Ft.
  • 2 Car Garage
  • Updated 1 hour ago
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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.

Full Property Details for 2 Judd Hill Rd

General

  • Price: $599,900
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24172678
  • Updated: Today (5/5/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 7
  • Interior Features: Auto Garage Door Opener
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Hardwood Floor, Main
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom - Softwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Island, Main
  • Dining Room: Dining Room, Main
  • Den: Den - Hardwood Floor, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Deck
  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Litchfield
  • Driving Directions: Old Sherman to Judd Hill

School Information

  • Elementary School: Mitchell
  • Middle School: Woodbury
  • High School: Nonnewaug

Heating & Cooling

  • Cooling Type: Window Unit
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Other

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Cape Cod
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 1,470
  • Above Ground: 1,470 Sq. Ft.
  • Year Built: 1958

Lot Features

  • Lot Size (Acres): 0.96
  • Zoning: OS80
  • Lot Description: Level Lot

Green Features

  • Energy Features: Generator

Financial Considerations

  • Assessment Amount: $168,840
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 932289

Listed by Drakeley Real Estate, Inc., Timothy Drakeley

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Listing agent

— 2 Judd Hill Rd —

  • Timothy Drakeley

    Drakeley Real Estate, Inc.

Agent Contact: (203) 510-9184 Office Contact: (203) 263-4336

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Price & Sales History for 2 Judd Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/05/2026
Listed
$599,900
9.07%
MLS
1/09/2026
Sold
$550,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2 Judd Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,988
3%
$168,840
1%
2023
$3,860
5%
$166,600
32%
2023
$3,664
—
$126,080
—
2022
$3,678
—
$126,080
—
2021
$3,678
—
$126,080
—
2020
$3,678
—
$126,080
—
2019
$3,678
3%
$126,080
-6%
2018
$3,565
-2%
$134,130
—
2017
$3,643
3%
$134,130
—
2016
$3,526
1%
$134,130
—
2015
$3,497
1%
$134,130
—
2014
$3,446
-11%
$134,130
-19%
2011
$3,872
—
$165,470
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Drakeley Real Estate, Inc., Timothy Drakeley

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2 Judd Hill Road, Woodbury, CT 06798 (MLS# 24172678) is a Single Family property with 3 bedrooms and 2 full bathrooms. 2 Judd Hill Road is currently listed for $599,900 and was received on May 05, 2026. Want to learn more about 2 Judd Hill Road? Do you have questions about finding other Single Family real estate for sale in Woodbury? You can browse all Woodbury real estate or contact a Coldwell Banker agent to request more information.

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