
27 Wakelee Rd Roxbury, CT 06783
Highlights
- Barn
- Tennis Courts
- 8.01 Acre Lot
- Shepaug Valley School Rated A-
- Home fronts a pond
- Partially Wooded Lot
About This Home
As of February 2023Location, Historic, Architectural and Iconic. Rarely does such a superb property come to market. Located on one of the most beautiful country roads in Roxbury. This circa 1840’s Greek Revival type is perfectly sited to catch the sun, thus many of the rooms are bathed in light. The rooms are centered around the period fireplace. The front rooms consist of a generous formal dining room and handsome library with fireplace. The cook’s kitchen with center island and its abundance of windows, patio access, and post and beam construction is open to the main living areas of the home. This is an extraordinary space for easy entertaining. Ceiling are 9' 6” with wide board floors, architectural details reflecting the period, and a sense of historic integrity.
The main level primary bedroom is en-suite and has its own wing with all amenities and complete privacy. Also on the main level is powder room and laundry. Upstairs there are four additional bedrooms (one with a fireplace) and a large bathroom. The land, consisting of eight acres, is level and mostly open meadow providing pollinator pathways. An in-ground pool, a tennis court, a pond, a significant historic English Bank barn, established gardens, all amenities which create country living to perfection. The property is adjacent to Roxbury Land Trust. There have been thoughtful additions over the years combining architectural integrity with gracious modern living. Co-listing Agent/Owner.
Last Agent to Sell the Property
William Pitt Sotheby's Int'l License #REB.0629515 Listed on: 10/11/2021

Co-Listed By
Elizabeth Lacy
William Pitt Sotheby's Int'l License #RES.0825307
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $7,997
Year Built
- Built in 1840
Lot Details
- 8.01 Acre Lot
- Home fronts a pond
- Home fronts a stream
- Stone Wall
- Level Lot
- Open Lot
- Cleared Lot
- Partially Wooded Lot
- Garden
Parking
- Private Driveway
Home Design
- Antique Architecture
- Stone Foundation
- Frame Construction
- Wood Shingle Roof
- Wood Siding
Interior Spaces
- 2,640 Sq Ft Home
- 3 Fireplaces
- Basement Fills Entire Space Under The House
- Storage In Attic
Kitchen
- Oven or Range
- Dishwasher
Bedrooms and Bathrooms
- 5 Bedrooms
Laundry
- Laundry on main level
- Dryer
- Washer
Outdoor Features
- Gunite Pool
- Tennis Courts
- Patio
- Exterior Lighting
- Shed
Utilities
- Hot Water Heating System
- Heating System Uses Oil
- Heating System Uses Oil Above Ground
- Private Company Owned Well
- Hot Water Circulator
Additional Features
- Property is near a golf course
- Barn
Community Details
- No Home Owners Association
Ownership History
Purchase Details
Purchase Details
Purchase Details
Similar Homes in Roxbury, CT
Home Values in the Area
Average Home Value in this Area
Purchase History
Date | Type | Sale Price | Title Company |
---|---|---|---|
Warranty Deed | $810,000 | -- | |
Warranty Deed | $1,000,000 | -- | |
Warranty Deed | $1,000,000 | -- | |
Deed | $900,000 | -- |
Mortgage History
Date | Status | Loan Amount | Loan Type |
---|---|---|---|
Closed | $401,000 | No Value Available | |
Closed | $460,000 | No Value Available | |
Closed | $486,000 | No Value Available |
Property History
Date | Event | Price | Change | Sq Ft Price |
---|---|---|---|---|
07/16/2025 07/16/25 | Pending | -- | -- | -- |
04/30/2025 04/30/25 | Price Changed | $1,995,000 | -11.1% | $756 / Sq Ft |
11/11/2024 11/11/24 | Price Changed | $2,245,000 | -5.3% | $850 / Sq Ft |
09/26/2024 09/26/24 | Price Changed | $2,370,000 | -3.3% | $898 / Sq Ft |
08/01/2024 08/01/24 | For Sale | $2,450,000 | 0.0% | $928 / Sq Ft |
08/01/2024 08/01/24 | Off Market | $2,450,000 | -- | -- |
07/24/2024 07/24/24 | For Sale | $2,450,000 | +42.0% | $928 / Sq Ft |
02/03/2023 02/03/23 | Sold | $1,725,000 | -10.4% | $653 / Sq Ft |
10/04/2022 10/04/22 | Pending | -- | -- | -- |
08/10/2022 08/10/22 | Price Changed | $1,925,000 | -12.5% | $729 / Sq Ft |
05/11/2022 05/11/22 | For Sale | $2,200,000 | +27.5% | $833 / Sq Ft |
05/10/2022 05/10/22 | Off Market | $1,725,000 | -- | -- |
10/11/2021 10/11/21 | For Sale | $2,200,000 | -- | $833 / Sq Ft |
Tax History Compared to Growth
Tax History
Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
---|---|---|---|---|
2025 | $10,652 | $819,420 | $317,310 | $502,110 |
2024 | $10,325 | $819,420 | $317,310 | $502,110 |
2023 | $10,226 | $811,580 | $317,310 | $494,270 |
2022 | $7,997 | $524,370 | $247,290 | $277,080 |
2021 | $2,454 | $524,370 | $247,290 | $277,080 |
2020 | $3,721 | $524,370 | $247,290 | $277,080 |
2019 | $8,311 | $524,370 | $247,290 | $277,080 |
2018 | $8,311 | $524,370 | $247,290 | $277,080 |
2017 | $8,437 | $594,120 | $269,660 | $324,460 |
2016 | $7,968 | $581,590 | $269,660 | $311,930 |
2015 | $7,968 | $581,590 | $269,660 | $311,930 |
2014 | $7,793 | $581,590 | $269,660 | $311,930 |
Agents Affiliated with this Home
-
Seller's Agent in 2024
Stacey Matthews
W. Raveis Lifestyles Realty
(203) 671-9067
31 in this area
162 Total Sales
-
Seller's Agent in 2023
Karen Silk
William Pitt
(860) 488-3340
2 in this area
21 Total Sales
-
E
Seller Co-Listing Agent in 2023
Elizabeth Lacy
William Pitt
Map
Source: SmartMLS
MLS Number: 170443960

APN: ROXB-000011-000000-000002