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$1,395,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,346 Sq. Ft.
  • 3 Car Garage
  • Updated 5 hours ago

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Open House: 1:00 PM - 3:00 PM

Saturday 7/25 1:00 PM - 3:00 PM

509 Weekeepeemee Road,Woodbury, CT 06798

509 Weekeepeemee RoadWoodburyCT06798

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Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for horses, chickens, and hosting friends and extended family.

Full Property Details for 509 Weekeepeemee Rd

General

  • Price: $1,395,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24192284
  • Updated: Today (7/24/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 6
  • Interior Features: Cable - Available, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Gas Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom, Upper
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Kitchen: Kitchen, Main
  • Dining Room: Dining Room, Main
  • Laundry: Lower Level
  • In-Law/Au Pair Suite: Yes

Exterior

  • Exterior Features: Grill, Shed, Porch, Barn, Gutters, Guest House, Stone Wall, Patio
  • Color: Gray Green

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Total Spaces: 6
  • Parking: Detached Garage, Driveway

Location

  • County: Litchfield
  • Driving Directions: Listing agent to accompany all showings. Notice of Video Recording at Ring camera.

School Information

  • Elementary School: Per Board of Ed
  • Middle School: Woodbury
  • High School: Nonnewaug

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Radiator, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic, 50 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Saltbox
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Unfinished, Storage, Concrete Floor, Full With Walk-Out
  • Roof: Wood Shingle
  • Attic: Yes
  • Square Feet: 2,346
  • Above Ground: 2,346 Sq. Ft.
  • Year Built: 1747

Lot Features

  • Lot Size (Acres): 5.19
  • Driveway/Sidewalk: Circular, Paved
  • Zoning: os100
  • Lot Description: Lightly Wooded, Treed, Dry, Sloping Lot, Professionally Landscaped

Financial Considerations

  • Assessment Amount: $436,800
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: See inc/excl sheet
  • Property ID: 933843

Listed by William Pitt Sotheby's Int'l, Carla Mascaro

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Listing agent

— 509 Weekeepeemee Rd —

  • Carla Mascaro

    William Pitt Sotheby's Int'l

Agent Contact: (650) 678-9912 Office Contact: (860) 868-6600

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

Schools serving 509 Weekeepeemee Rd

School District:Regional School District 14
NameGradesDistance
Bethlehem Elementary School
92 East Street, Bethlehem, CT 06751
PK-53.4 mi
Woodbury Middle School
67 Washington Avenue, Woodbury, CT 06798
6-83.4 mi
Nonnewaug High School
5 Minortown Road, Woodbury, CT 06798
9-123.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 509 Weekeepeemee Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/24/2026
Listed
$1,395,000
157.24%
MLS
11/01/2001
Sold
$542,300
—
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 509 Weekeepeemee Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,317
2%
$436,800
—
2023
$10,121
9%
$436,800
36%
2023
$9,328
—
$320,990
—
2022
$9,363
—
$320,990
—
2021
$9,363
—
$320,990
—
2020
$9,363
—
$320,990
—
2019
$9,363
-2%
$320,990
-11%
2018
$9,567
-2%
$359,930
—
2017
$9,776
3%
$359,930
—
2016
$9,463
1%
$359,930
—
2015
$9,383
1%
$359,930
—
2014
$9,247
1%
$359,930
-8%
2011
$9,144
—
$390,760
—
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.

Estimate the Cost for 509 Weekeepeemee Rd

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

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by William Pitt Sotheby's Int'l, Carla Mascaro

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509 Weekeepeemee Road, Woodbury, CT 06798 (MLS# 24192284) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 509 Weekeepeemee Road is currently listed for $1,395,000 and was received on July 24, 2026. Want to learn more about 509 Weekeepeemee 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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