2 Judd Hill Road

Closed 7/2/26
Closed 7/2/26
Gallery Image 1
Sold
Last Sold Price
$575,000
3 beds1,470 sqft

2 Judd Hill Rd, Woodbury, CT 06798

Single FamilyProperty Type
0.96 acresLot Size
1958Year Built
$391/sq ftPrice per sq ft
2 carsParking Spaces

Description

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...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.
  • Listed by: Timothy Drakeley 203.510.9184 tim@drakeley.com • Drakeley Real Estate, Inc.
Listing closed: 07/02/2026 12:00 AM • Source: SMARTMLS, MLS#: 24172678
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Location

Listing Courtesy of Drakeley Real Estate, Inc., Timothy Drakeley

Sold By Houlihan Lawrence, Stephen Mele

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$3,402 per month

30 year fixed, 7.03% Interest

Principal and Interest

$3,070

Property Taxes

$332

HOA Dues

$0

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Property Information for 2 Judd Hill Road

Property Details

  • Taxes: $3,988 / year
  • MLS Type: Residential
  • County: Litchfield County
  • Basement Description: Full
  • Direct Waterfront: No
  • Garages Number: 2
  • Style: Cape Cod
  • Garage Parking Info: Attached Garage
  • Swimming Pool: No

Building Information

  • Year Built: 1958
  • Lot Size: 0.96 AC / 41,817 SF

Summary

Property and Location
  • Acres Source: Public Records
  • Directions: Old Sherman to Judd Hill
  • Elementary School: Mitchell
  • High School: Nonnewaug
  • Latitude: 41.515633
  • Longitude: -73.161629
  • Middle Jr High School: Woodbury
  • Neighborhood Amenities: Golf Course, Lake, Library, Private School(s), Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $3,988

Interior and Exterior Features

Exterior Features
  • Exterior Features: Deck
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Access Via Hatch
  • Cooling System: Window Unit
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Auto Garage Door Opener
  • Laundry Room Info: Main Level
  • Laundry Room Location: Stackable
  • Rooms Total: 7
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Den
Room 3
  • Room Entry Order: 3
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 4
  • Room Entry Order: 4
  • Room Level: Upper
  • Room Type: Bedroom
Room 5
  • Listing Key: 510376E14F778A21E063E201100AFF80
  • Room Entry Order: 5
  • Room Features: Softwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Level: Main
  • Room Type: Dining Room
Room 7
  • Room Entry Order: 7
  • Room Features: Island
  • Room Level: Main
  • Room Type: Eat-In Kitchen

Property

Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1958
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Sq Ft Description: Town records
  • Sq Ft Est Heated Below Grade: 0
  • Living Area SQFT Per Public Records: 884
Lot Information
  • Lot Description: Level Lot
  • Parcel Number: 932289
  • Sq Ft Est Heated Above Grade: 1470.0
  • Sq Ft Total: 1470.0
  • Zoning: OS80
Utilities
  • Energy Features: Generator
  • Heat Fuel Type: Oil
  • Hot Water Description: Other
  • Radon Mitigation Air: Unknown
  • Radon Mitigation Water: Unknown
  • Sewage System: Septic
  • Water Source: Private Well

Multi Family

Income and Expenses
  • Occupied By: Owner

Property History for 2 Judd Hill Road

DateEvent & SourcePriceAppreciation
Jun 25, 2026

Closed (Public Record)

Public Record #1945030537

$585,000

+14.4% / yr

Jan 9, 2026

Closed (Public Record)

Public Record #1926353765

$550,000

+82.6% / yr

Feb 24, 2025

Closed (Public Record)

Public Record #1552740048

$325,000—
DateEvent & SourcePrice
06/25/2026

Closed (Public Record)

Public Record #1945030537

$585,000

+14.4% / yr

01/09/2026

Closed (Public Record)

Public Record #1926353765

$550,000

+82.6% / yr

02/24/2025

Closed (Public Record)

Public Record #1552740048

$325,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public records

2 Judd Hill Road

Beds

2

Baths

1

Total Finished SqFt

884 SqFt

Above Grade Finished SqFt

884 SqFt

Unfinished Basement SqFt

608 SqFt

Stories

1

Schools near 2 Judd Hill Road

This home is within Regional School District 14.
Rating
School
Type
Grades
Distance
Bethlehem Elementary School
Public - PK to 5
Mitchell Elementary School
Public - PK to 5
Woodbury Middle School
Public - 6 to 8
Nonnewaug High School
Public - 9 to 12
Rating
School
Distance
Bethlehem Elementary School
PublicPK to 5

Mitchell Elementary School
PublicPK to 5

Woodbury Middle School
Public6 to 8

Nonnewaug High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Drakeley Real Estate, Inc., Timothy Drakeley

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.