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  4. Drakeley Real Estate, Inc.

Drakeley Real Estate, Inc.

256 Main Street South

Woodbury, CT

Team Members

Timothy Drakeley

Jeffrey Boucher

Joyce Drakeley

Mary Ann Bennett

Shelley Drakeley

Rhonda Stokes

John Dominello

Josh Harwood

Rhya Szymansky

Charles Cosgriff

Paige Porter

Kat Parlato

Taylor O'keefe-hamel

Matthew Amatruda

Ashley Stewart

Disclaimer: This page displays real estate agents and offices generated from active and closed MLS listings affiliated with this office. While we make every effort to provide accurate information, there may be inaccuracies due to factors such as fluctuating staff, office name changes, changes of address, and other varying circumstances. If you are the owner of the office or an agent listed here and would like to advertise, please fill out the form at https://www.realty.com/advertise.

Listings & Recent Sales (63)

Active Rental Sold

For Sale (22)

Address Bed / Bath Listing Price
Picture of Westover Drive
Westover Drive Naugatuck, CT
-, 0 Baths
$89,000
Picture of 439 Washington Road
439 Washington Road Woodbury, CT
Living Area: 960 Sqft.
2 Beds, 2 Baths
$314,900
Picture of 616 Main Street South
616 Main Street South Southbury, CT
Living Area: 4000 Sqft.
-, 2 Baths
$1,300,000
Picture of 75 Green Hill Road
75 Green Hill Road Washington, CT
Living Area: 3901 Sqft.
4 Beds, 4 Baths
$1,390,000
Picture of 6 Tulip Tree Lane South
6 Tulip Tree Lane South Bethlehem, CT
-, 0 Baths
$249,900
Picture of 18 Fieldstone Lane 18
18 Fieldstone Lane 18 Beacon Falls, CT
Living Area: 2719 Sqft.
2 Beds, 3 Baths
$599,000
Picture of 643 Heritage Village A
643 Heritage Village A Southbury, CT
Living Area: 1398 Sqft.
2 Beds, 2 Baths
$339,980
Picture of 233 Litchfield Turnpike
233 Litchfield Turnpike Washington, CT
Living Area: 5030 Sqft.
-, 3 Baths
$599,900
Picture of 6 Tulip Tree Lane South 6
6 Tulip Tree Lane South 6 Bethlehem, CT
-, 0 Baths
$59,900
Picture of 20 Cowles Road
20 Cowles Road Bethlehem, CT
Living Area: 3033 Sqft.
5 Beds, 4 Baths
$850,000
Picture of 114 Carmel Hill Road North
114 Carmel Hill Road North Bethlehem, CT
Living Area: 2430 Sqft.
3 Beds, 2 Baths
$749,900
Picture of 27 Middle Quarter Road
27 Middle Quarter Road Woodbury, CT
Living Area: 2042 Sqft.
3 Beds, 3 Baths
$999,900
Picture of 262 Stoddard Road
262 Stoddard Road Morris, CT
-, 0 Baths
$129,900
Picture of Minortown Road
Minortown Road Woodbury, CT
-, 0 Baths
$179,900
Picture of 1769 Goshen Road
1769 Goshen Road Torrington, CT
Living Area: 2428 Sqft.
3 Beds, 4 Baths
$485,000
Picture of 16 Jonathan Drive
16 Jonathan Drive Roxbury, CT
Living Area: 2028 Sqft.
3 Beds, 3 Baths
$995,000
Picture of 575 Heritage Village A
575 Heritage Village A Southbury, CT
Living Area: 1716 Sqft.
3 Beds, 2 Baths
$399,000
Picture of 182 Magnolia Hill Road
182 Magnolia Hill Road Bethlehem, CT
Living Area: 1757 Sqft.
3 Beds, 3 Baths
$899,000
Picture of 40 Main Street North
40 Main Street North Woodbury, CT
Living Area: 11804 Sqft.
-, 0 Baths
$1,300,000
Picture of 319 Thomaston Road 13
319 Thomaston Road 13 Watertown, CT
Living Area: 1224 Sqft.
2 Beds, 3 Baths
$330,000
Picture of 47 Woods Way 47
47 Woods Way 47 Woodbury, CT
Living Area: 1182 Sqft.
2 Beds, 2 Baths
$249,000
Picture of 103 Hollow Road
103 Hollow Road Watertown, CT
Living Area: 1747 Sqft.
3 Beds, 2 Baths
$375,000

Rentals (10)

Address Bed / Bath Listing Price
Picture of 466 Heritage Road 2
466 Heritage Road 2 Southbury, CT
Living Area: 1801 Sqft.
-, 0 Baths
$18
Picture of 73 Main Street South 1B
73 Main Street South 1B Woodbury, CT
Living Area: 1375 Sqft.
-, 0 Baths
$1,600
Picture of 466 Heritage Road 4
466 Heritage Road 4 Southbury, CT
Living Area: 9441 Sqft.
-, 0 Baths
$18
Picture of 4 Weekeepeemee Road
4 Weekeepeemee Road Woodbury, CT
Living Area: 4294 Sqft.
2 Beds, 1 Bath
$1,600
Picture of 533 Weekeepeemee Road
533 Weekeepeemee Road Woodbury, CT
Living Area: 2718 Sqft.
2 Beds, 1 Bath
$2,200
Picture of 220 Upper Grassy Hill Road
220 Upper Grassy Hill Road Woodbury, CT
Living Area: 1620 Sqft.
3 Beds, 3 Baths
$4,000
Picture of 524 Main Street South 1
524 Main Street South 1 Woodbury, CT
Living Area: 2000 Sqft.
-, 0 Baths
$4,000
Picture of 524 Main Street South 2
524 Main Street South 2 Woodbury, CT
Living Area: 1390 Sqft.
-, 0 Baths
$2,000
Picture of 524 Main Street South 3
524 Main Street South 3 Woodbury, CT
Living Area: 4320 Sqft.
-, 0 Baths
$3,000
Picture of 32 Lakeview Drive
32 Lakeview Drive Bethlehem, CT
Living Area: 1016 Sqft.
2 Beds, 1 Bath
$2,150

Sold (31)

Address Sold date Last List Price Represented
Picture of 2 Frisbie Circle
2 Frisbie Circle Wolcott, CT
Living Area: 1801 Sqft.
03/22/2026 $289,900 Listing
Picture of 65 Meyers Road
65 Meyers Road Plymouth, CT
Living Area: Sqft.
03/22/2026 $249,900 Listing
Picture of Main Street North
Main Street North Woodbury, CT
Living Area: Sqft.
03/22/2026 $399,900 Listing
Picture of 0 Tulip Tree Village
0 Tulip Tree Village Bethlehem, CT
Living Area: Sqft.
03/22/2026 $39,900 Selling
Picture of 32 Plumb Brook Road
32 Plumb Brook Road Woodbury, CT
Living Area: 2252 Sqft.
03/22/2026 $645,000 Listing
Picture of 70 Diamond Match Road
70 Diamond Match Road Southbury, CT
Living Area: 978 Sqft.
03/22/2026 $389,500 Listing
Picture of 101 Plumb Brook Road
101 Plumb Brook Road Woodbury, CT
Living Area: 1922 Sqft.
03/22/2026 $595,000 Selling
Picture of 18 Woodbury Hill 18
18 Woodbury Hill 18 Woodbury, CT
Living Area: 1796 Sqft.
03/22/2026 $559,900 Selling
Picture of 1088 Old Waterbury Road
1088 Old Waterbury Road Southbury, CT
Living Area: 1634 Sqft.
03/22/2026 $524,900 Listing
Picture of 280 Jeremy Swamp Road
280 Jeremy Swamp Road Southbury, CT
Living Area: Sqft.
03/22/2026 $139,900 Listing
Picture of 182 Magnolia Hill Road
182 Magnolia Hill Road Bethlehem, CT
Living Area: 1757 Sqft.
03/22/2026 $995,000 Listing
Picture of 33 Mountain Lane 2/upper
33 Mountain Lane 2/upper Woodbury, CT
Living Area: 1426 Sqft.
03/22/2026 $1,500 Selling
Picture of 151 Washington Avenue
151 Washington Avenue Woodbury, CT
Living Area: 2161 Sqft.
03/22/2026 $1,800 Selling
Picture of 69 Johnson Street
69 Johnson Street Naugatuck, CT
Living Area: 2547 Sqft.
03/22/2026 $410,000 Listing
Picture of 118 Good Hill Road
118 Good Hill Road Woodbury, CT
Living Area: 3196 Sqft.
03/22/2026 $769,900 Listing
Picture of 229 Bacon Pond Road APT 454
229 Bacon Pond Road APT 454 Woodbury, CT
Living Area: 913 Sqft.
03/22/2026 $185,000 Listing
Picture of 20 Heritage Circle B
20 Heritage Circle B Southbury, CT
Living Area: 1000 Sqft.
03/22/2026 $2,250 Selling
Picture of 2 Judd Hill Road
2 Judd Hill Road Woodbury, CT
Living Area: 1470 Sqft.
03/22/2026 $569,000 Selling
Picture of 183 Hulls Hill Road
183 Hulls Hill Road Southbury, CT
Living Area: 1294 Sqft.
03/22/2026 $475,000 Listing
Picture of 52 Scuppo Road
52 Scuppo Road Woodbury, CT
Living Area: 1247 Sqft.
03/22/2026 $499,900 Selling
Picture of 15 Lynns Corner Road
15 Lynns Corner Road Woodbury, CT
Living Area: 1696 Sqft.
03/22/2026 $489,900 Listing
Picture of 159 Main Street North
159 Main Street North Bethlehem, CT
Living Area: 2498 Sqft.
03/22/2026 $399,900 Listing
Picture of 57 Valley View Lane
57 Valley View Lane New Milford, CT
Living Area: 1654 Sqft.
03/22/2026 $304,500 Selling
Picture of 199 Hoop Pole Hill Road
199 Hoop Pole Hill Road Woodbury, CT
Living Area: 1710 Sqft.
03/22/2026 $1,650 Listing
Picture of 175 Arch Bridge Road D
175 Arch Bridge Road D Bethlehem, CT
Living Area: 800 Sqft.
03/22/2026 $1,300 Selling
Picture of 63 Water Street 22
63 Water Street 22 Torrington, CT
Living Area: 9876 Sqft.
03/22/2026 $1,300 Selling
Picture of 504 Heritage Village B
504 Heritage Village B Southbury, CT
Living Area: 928 Sqft.
03/22/2026 $2,150 Selling
Picture of 925 Oronoke Road 34G
925 Oronoke Road 34G Waterbury, CT
Living Area: 924 Sqft.
03/22/2026 $169,900 Colisting
Picture of 667 Upper Grassy Hill Road
667 Upper Grassy Hill Road Woodbury, CT
Living Area: 1987 Sqft.
03/22/2026 $550,000 Listing
Picture of 7 Woods Way 7
7 Woods Way 7 Woodbury, CT
Living Area: 1182 Sqft.
03/22/2026 $2,200 Selling
Picture of 237 Concord Drive
237 Concord Drive Watertown, CT
Living Area: 1990 Sqft.
03/22/2026 $480,000 Selling

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