249 Woodbury Rd

1,268 Sq. Ft.
$417 / Sq. Ft.
1,268
Sq. Ft.
$417
per Sq. Ft.

Description

This cozy 2-bedroom, 2 bath home features beautiful wide-board wood floors, a striking 2-story stone fireplace, and vaulted ceilings that fill the space with light. Set back from the road on 4.6 peaceful acres, it offers privacy, a welcoming front porch, and low taxes. Great starter home for those who love simple living with rustic charm and privacy without being secluded. Just minutes to Washington Depot, New Preston, The Mayflower Inn and the town beach on Lake Waramaug.This cozy 2-bedroom, 2 bath home features beautiful wide-board wood floors, a striking 2-story stone fireplace, and vaulted ceilings that fill the space with light. Set back from the road on 4.6 peaceful acres, it offers privacy, a welcoming front porch, and low taxes. Great starter home for those who love simple living with rustic charm and privacy without being secluded. Just minutes to Washington Depot, New Preston, The Mayflower Inn and the town beach on Lake Waramaug.
  1. Listed by Maria Taylor • Klemm Real Estate Inc
    P: (203)-578-0397 C: (203)-578-0397 mtaylor1800@aol.com
  2. Listed by Claudine McHugh • Klemm Real Estate Inc
    P: (203)-263-4040 C: (203)-228-7000 claudinemchugh17@gmail.com

Property Details for 249 Woodbury Road

Basement Description
Full, Unfinished, Full With Hatchway
Direct Waterfront
No
Garages Number
0
Neighborhood
N/A
Style
Cape Cod
Garage Parking Info
Driveway
Swimming Pool
No
LISTING UPDATED: 01/09/2026 08:14 PM

Property Details for 249 Woodbury Road

StatusClosed
MLS #24136860
Days on Market4
Taxes$3,842 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1998
Lot Size4.67 AC / 203,425 SF
CountyLitchfield County

Location

Listing Courtesy of Klemm Real Estate Inc, Maria Taylor; Klemm Real Estate Inc, Claudine McHugh

Sold By Klemm Real Estate Inc, Maria Taylor

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Building Information for 249 Woodbury Road

Stories-Year Built1998Building Size-Lot Size4.67 AC / 203,425 SF

Payment Calculator

$2,956 per month

30 year fixed, 6.36% Interest

Principal and Interest

$2,636

Property Taxes

$320

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 249 Woodbury Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Use Showingtime.
  • Elementary School: Per Board of Ed
  • High School: Shepaug
  • Latitude: 41.614728
  • Longitude: -73.292926
  • Middle Jr High School: Shepaug
  • State: Connecticut
Parking
  • Parking Total Spaces: 4
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $3,842
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Electric Range
  • Cooling System: None
  • Heat Type: Baseboard, Radiant
  • Attic YN: No
  • Fireplaces Total: 1
  • Interior Features: Cable - Available
  • Rooms Total: 6
Room 1
  • Room Entry Order: 1
  • Room Features: Vaulted Ceiling,Ceiling Fan,Fireplace,Wide Board Floor
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 11.0
Room 2
  • Room Entry Order: 2
  • Room Features: Wide Board Floor
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 11.0
Room 3
  • Room Entry Order: 3
  • Room Features: Pantry,Wide Board Floor
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 11.0
Room 4
  • Room Entry Order: 4
  • Room Features: Vaulted Ceiling,Hardwood Floor
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Loft
  • Room Width: 11.0
Room 5
  • Listing Key: 4253B9A1856B0656E063E201100AFB4E
  • Room Entry Order: 5
  • Room Features: Vaulted Ceiling,Full Bath,Walk-In Closet,Wide Board Floor
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 11.0
Room 6
  • Room Entry Order: 6
  • Room Features: Wide Board Floor
  • Room Length: 11.0
  • Room Level: Lower
  • Room Type: Bedroom
  • Room Width: 11.0
Property
Property and Assessments
  • Construction Description: Frame
  • Driveway Type: Shared, Unpaved
  • Exterior Siding: Clapboard, Wood
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1998
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 1268
Lot Information
  • Lot Description: Lightly Wooded, Level Lot
  • Parcel Number: 2139135
  • Sq Ft Est Heated Above Grade: 1268.0
  • Sq Ft Total: 1268.0
  • Zoning: R-1
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Electric, Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Vacant

Property History for 249 Woodbury Road

DateEvent & SourcePriceAppreciation
Jan 9, 2026

Closed (Public Record)

Public Record #1926943047

$529,000
DateEvent & SourcePrice
01/09/2026

Closed (Public Record)

Public Record #1926943047

$529,000

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

Public Records for 249 Woodbury Road

Taxable ValueLand$117,880Additions$236,180Total$354,060
Tax Record2024$3,842 ($320 / month)
Home Facts
Beds2Baths2Total Finished SqFt1,268 SqFtAbove Grade Finished SqFt1,268 SqFtUnfinished Basement SqFt816 SqFtStories2Lot Size203,425 SqFtStyleSingle Family ResidenceYear Built1998Year Renovated2010ZoningR-1CountyNORTHWEST HILLSAPNWGTN M:0003 B:0004 L:67Fireplace TypeHas Fireplace

Schools near 249 Woodbury Road

This home is within Regional School District 12.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 12
Public - K to 5
Private - 5 to 12
Rating
School
Distance
The Burnham School
PublicK to 5

Shepaug Valley School
Public6 to 12

Booth Free School
PublicK to 5

The Glenholme School
Private5 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 descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. 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 Klemm Real Estate Inc, Maria Taylor; Klemm Real Estate Inc, Claudine McHugh

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.