27 Wakelee Rd

Roxbury, CT 06783

$1,837,500
Last Sold Price
4
Beds
2,640 Sq. Ft.
$696 / Sq. Ft.
2,640
Sq. Ft.
$696
per Sq. Ft.
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Closed 9/16/25
Closed 9/16/25

Description

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....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.
  1. Listed by Stacey Matthews • W. Raveis Lifestyles Realty
    P: (203)-671-9067 C: (203)-671-9067 stacey.matthews@raveis.com

Property Details for 27 Wakelee Road

Basement Description
Full, Unfinished
Direct Waterfront
Yes
Garages Number
2
Neighborhood
N/A
Style
Antique
Garage Parking Info
Barn
Swimming Pool
Yes
LISTING CLOSED: 09/16/2025 12:00 AM

Property Details for 27 Wakelee Road

StatusClosed
MLS #24034591
Days on Market336
Taxes$10,652 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1815
Lot Size8.01 AC / 348,915 SF
CountyLitchfield County
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Location

Listing Courtesy of W. Raveis Lifestyles Realty, Stacey Matthews

Sold By William Pitt Sotheby's Int'l, Kathryn C Bassett

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Building Information for 27 Wakelee Road

Stories-Year Built1815Building Size-Lot Size8.01 AC / 348,915 SF

Payment Calculator

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$10,044 per month

30 year fixed, 6.36% Interest

Principal and Interest

$9,156

Property Taxes

$888

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 27 Wakelee Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Rt 199 to Wakelee #27
  • Elementary School: Booth Free
  • High School: Regional District 12
  • Latitude: 41.589421
  • Longitude: -73.325348
  • Neighborhood Amenities: Golf Course, Health Club, Library, Park, Playground/Tot Lot, Private School(s), Stables/Riding, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $10,652
Interior and Exterior Features
Exterior Features
  • Exterior Features: Terrace, Barn, Stone Wall
  • Pool Description: Gunite, In Ground Pool
  • Waterfront Description: Pond
Interior Features
  • Appliances Included: Gas Cooktop, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Unfinished, Walk-up
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Interior Features: Open Floor Plan
  • Laundry Room Location: main level
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: Beams,Fireplace,Hardwood Floor,Wide Board Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Fireplace,Hardwood Floor,Wide Board Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Vaulted Ceiling,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: 1DEDE50EC90373ACE063D501100AB55C
  • Room Entry Order: 5
  • Room Level: Upper
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Features: Beams
  • Room Level: Upper
  • Room Type: Rec/Play Room
Room 8
  • Room Entry Order: 8
  • Room Features: Beams,Built-Ins,Fireplace
  • Room Level: Main
  • Room Type: Media Room
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Exterior Siding: Clapboard, Wood
  • Foundation Type: Stone
  • Fuel Tank Location: Above Ground
  • New Construction Type: No/Resale
  • Roof: Wood Shingle, Gable
  • Year Built: 1815
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Apartment: No
  • Sq Ft Est Heated Below Grade: 0
  • Living Area SQFT Per Public Records: 2640
Lot Information
  • Lot Description: Level Lot, Water View, Open Lot
  • Parcel Number: 867392
  • Sq Ft Est Heated Above Grade: 2640.0
  • Sq Ft Total: 2640.0
  • Zoning: C
Utilities
  • Heat Fuel Type: Propane
  • 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 27 Wakelee Road

DateEvent & SourcePriceAppreciation
Sep 8, 2025

Closed (Public Record)

Public Record #1914234517

$1,837,500

+2.5% / yr

Nov 14, 1991

Closed (Public Record)

Public Record #91920244

$810,000—
Oct 17, 1991

Closed (Public Record)

Public Record #91920239

$1,000,000—
DateEvent & SourcePrice
09/08/2025

Closed (Public Record)

Public Record #1914234517

$1,837,500

+2.5% / yr

11/14/1991

Closed (Public Record)

Public Record #91920244

$810,000
10/17/1991

Closed (Public Record)

Public Record #91920239

$1,000,000

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

Public Records for 27 Wakelee Road

Taxable ValueLand$317,310Additions$502,110Total$819,420
Tax Record2024$10,652 ($888 / month)
Home Facts
Beds5Baths2.5Total Finished SqFt2,640 SqFtAbove Grade Finished SqFt2,640 SqFtUnfinished Basement SqFt1,008 SqFtStories2Lot Size348,916 SqFtStyleSingle Family ResidenceYear Built1815Year Renovated1963ZoningCCountyNORTHWEST HILLSAPNRXBY M:11 L:2Fireplace TypeHas Fireplace

Schools near 27 Wakelee Road

This home is within Regional School District 12.
Rating
School
Type
Grades
Distance
Booth Free School
Public - K to 5
Shepaug Valley School
Public - 6 to 12
Washington Primary School
Public - PK to 5
The Burnham School
Public - K to 5
Rating
School
Distance
Booth Free School
PublicK to 5

Shepaug Valley School
Public6 to 12

Washington Primary School
PublicPK to 5

The Burnham School
PublicK to 5

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 W. Raveis Lifestyles Realty, Stacey Matthews

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.