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$1,837,500

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,640 Sq. Ft.
  • 2 Car Garage
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Many new renovations in this stunning antique home on a quiet country road. All flat usable land with gorgeous bank barn, gunite pool, Spectacular mature trees, and pond. Town has house listed as 5 bedrooms. The primary bedroom with walk in closet is on the main level. Upstairs is more efficiently used as 2 suites each with walk in closets or offices. Alternately, one of the larger bedrooms could be used as a shared play room with 3 bedrooms circulating it. Antique floors and hand hewn beams throughout. The large cooking fireplace has been revived to its former glory and the 2 smaller fireplaces have had propane inserts added. Recent upgrades include: Generator, new heating, interior and exterior paint, wood shingle roof, built ins, curtains etc. Tennis court was partially removed, foundation still in place. Buyers can rebuild it or scrape concrete and create additional lawn or gardens.

Full Property Details for 27 Wakelee Rd

General

  • Sold For: $1,837,500
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24034591
  • Added to Site: 541 day(s) ago

Interior

  • Number of Rooms: 9
  • Interior Features: Open Floor Plan
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Gas Cooktop, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - 9 ft+ Ceilings, Vaulted Ceiling, Hardwood Floor, Main
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper

Other Rooms

  • Living Room: Living Room - Beams, Fireplace, Hardwood Floor, Wide Board Floor, Main
  • Dining Room: Dining Room - Fireplace, Hardwood Floor, Wide Board Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Beams, Upper
  • Rec Room: Beams, Upper
  • Theater/Media: Media Room - Beams, Built-Ins, Fireplace, Main

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, In Ground Pool

Exterior

  • Exterior Features: Terrace, Barn, Stone Wall
  • Color: White

Parking

  • Garage Spaces: 2
  • Parking: Barn

Location

  • County: Litchfield
  • Driving Directions: Rt 199 to Wakelee #27

School Information

  • Elementary School: Booth Free
  • High School: Regional District 12

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Propane
  • Heating Fuel: Propane
  • Water Heater: Other

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Antique
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Wood
  • Basement Desc.: Full, Unfinished
  • Roof: Wood Shingle, Gable
  • Attic: Yes
  • Square Feet: 2,640
  • Above Ground: 2,640 Sq. Ft.
  • Year Built: 1815

Lot Features

  • Lot Size (Acres): 8.01
  • Zoning: C
  • Lot Description: Level Lot, Water View, Open Lot

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Pond

Financial Considerations

  • Assessment Amount: $819,420
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 867392

Listed by W. Raveis Lifestyles Realty, Stacey Matthews
Sold by William Pitt Sotheby's Int'l, THE KATHRYN CLAIR TEAM, Kathryn Bassett

Listing agent

— 27 Wakelee Rd —

  • Stacey Matthews

    W. Raveis Lifestyles Realty

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 27 Wakelee Rd

School District:Regional School District 12
NameGradesDistance
Shepaug Valley School
159 South Street, Washington, CT 06793
6-121.3 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 27 Wakelee Rd

Date
Details
Price
Change
Source
9/16/2025
Sold
$1,837,500
-7.89%
MLS
4/29/2025
Price Reduced
$1,995,000
-11.14%
MLS
11/11/2024
Price Reduced
$2,245,000
-5.27%
MLS
9/26/2024
Price Reduced
$2,370,000
-3.27%
MLS
7/24/2024
Listed
$2,450,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by W. Raveis Lifestyles Realty, Stacey Matthews
Sold by William Pitt Sotheby's Int'l, THE KATHRYN CLAIR TEAM, Kathryn Bassett

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27 Wakelee Road, Roxbury, CT 06783 (MLS# 24034591) is a Single Family property that was sold at $1,837,500 on September 16, 2025. Want to learn more about 27 Wakelee Road? Do you have questions about finding other Single Family real estate for sale in Roxbury? You can browse all Roxbury real estate or contact a Coldwell Banker agent to request more information.