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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 (60)

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
$289,000
Picture of 616 Main Street South
616 Main Street South Southbury, CT
Living Area: 4000 Sqft.
-, 2 Baths
$1,300,000
Picture of 523 Main Street North
523 Main Street North Woodbury, CT
Living Area: 2300 Sqft.
3 Beds, 2 Baths
$990,000
Picture of 6 Tulip Tree Lane South
6 Tulip Tree Lane South Bethlehem, CT
-, 0 Baths
$249,900
Picture of 643 Heritage Village A
643 Heritage Village A Southbury, CT
Living Area: 1398 Sqft.
2 Beds, 2 Baths
$314,900
Picture of 6 Tulip Tree Lane South 6
6 Tulip Tree Lane South 6 Bethlehem, CT
-, 0 Baths
$59,900
Picture of 114 Carmel Hill Road North
114 Carmel Hill Road North Bethlehem, CT
Living Area: 2430 Sqft.
3 Beds, 2 Baths
$699,900
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 14 Meadow Crest Drive
14 Meadow Crest Drive Woodbury, CT
Living Area: 2102 Sqft.
3 Beds, 2 Baths
$499,000
Picture of 16 Jonathan Drive
16 Jonathan Drive Roxbury, CT
Living Area: 2028 Sqft.
3 Beds, 3 Baths
$950,000
Picture of 575 Heritage Village A
575 Heritage Village A Southbury, CT
Living Area: 1716 Sqft.
3 Beds, 2 Baths
$399,000
Picture of 99 Plumb Brook Road
99 Plumb Brook Road Woodbury, CT
Living Area: 3330 Sqft.
4 Beds, 3 Baths
$849,900
Picture of 123 Cross Brook Road
123 Cross Brook Road Woodbury, CT
Living Area: 1564 Sqft.
1 Bed, 2 Baths
$585,000
Picture of 8 Curtiss Meadows
8 Curtiss Meadows Woodbury, CT
Living Area: 3865 Sqft.
4 Beds, 5 Baths
$949,900
Picture of 346 Westside Road
346 Westside Road Goshen, CT
Living Area: 1662 Sqft.
2 Beds, 2 Baths
$995,599
Picture of Brass Mill Dam Road
Brass Mill Dam Road Torrington, CT
-, 0 Baths
$100,000
Picture of 31 Hillcrest Avenue
31 Hillcrest Avenue Waterbury, CT
Living Area: 1326 Sqft.
3 Beds, 3 Baths
$425,000
Picture of Flanders Road
Flanders Road Woodbury, CT
-, 0 Baths
$1,150,000
Picture of 53 Hampton Road
53 Hampton Road Waterbury, CT
Living Area: 2194 Sqft.
3 Beds, 3 Baths
$439,000
Picture of Mount Mauwee Road
Mount Mauwee Road Kent, CT
-, 0 Baths
$525,000

Rentals (5)

Address Bed / Bath Listing Price
Picture of 34 Arrowhead Way A1
34 Arrowhead Way A1 Woodbury, CT
Living Area: 546 Sqft.
1 Bed, 1 Bath
$1,600
Picture of 4 Weekeepeemee Road
4 Weekeepeemee Road Woodbury, CT
Living Area: 4294 Sqft.
2 Beds, 1 Bath
$2,000
Picture of 39 Woodland Road
39 Woodland Road Bethlehem, CT
Living Area: 1248 Sqft.
3 Beds, 2 Baths
$3,000
Picture of 466 Heritage Road 4
466 Heritage Road 4 Southbury, CT
Living Area: 9441 Sqft.
-, 0 Baths
$15
Picture of 466 Heritage Road 2
466 Heritage Road 2 Southbury, CT
Living Area: 1801 Sqft.
-, 0 Baths
$13

Sold (33)

Address Sold date Last List Price Represented
Picture of 2 Frisbie Circle
2 Frisbie Circle Wolcott, CT
Living Area: 1801 Sqft.
06/04/2026 $289,900 Listing
Picture of 466 Heritage Road 2
466 Heritage Road 2 Southbury, CT
Living Area: 1801 Sqft.
06/04/2026 $18 Colisting
Picture of 75 Green Hill Road
75 Green Hill Road Washington, CT
Living Area: 3901 Sqft.
06/04/2026 $1,390,000 Listing
Picture of 73 Main Street South 1B
73 Main Street South 1B Woodbury, CT
Living Area: 1375 Sqft.
06/04/2026 $1,600 Selling
Picture of 18 Fieldstone Lane 18
18 Fieldstone Lane 18 Beacon Falls, CT
Living Area: 2719 Sqft.
06/04/2026 $599,000 Listing
Picture of 280 Jeremy Swamp Road
280 Jeremy Swamp Road Southbury, CT
Living Area: Sqft.
06/04/2026 $139,900 Listing
Picture of 233 Litchfield Turnpike
233 Litchfield Turnpike Washington, CT
Living Area: 5030 Sqft.
06/04/2026 $599,900 Listing
Picture of 69 Johnson Street
69 Johnson Street Naugatuck, CT
Living Area: 2547 Sqft.
06/04/2026 $410,000 Listing
Picture of 8 Main Street North
8 Main Street North Bethlehem, CT
Living Area: 1152 Sqft.
06/04/2026 $285,000 Listing
Picture of 20 Cowles Road
20 Cowles Road Bethlehem, CT
Living Area: 3033 Sqft.
06/04/2026 $850,000 Listing
Picture of 159 Main Street North
159 Main Street North Bethlehem, CT
Living Area: 2498 Sqft.
06/04/2026 $399,900 Listing
Picture of 667 Upper Grassy Hill Road
667 Upper Grassy Hill Road Woodbury, CT
Living Area: 1987 Sqft.
06/04/2026 $550,000 Listing
Picture of 65 Weekeepeemee Road
65 Weekeepeemee Road Bethlehem, CT
Living Area: 1126 Sqft.
06/04/2026 $349,900 Selling
Picture of 466 Heritage Road 4
466 Heritage Road 4 Southbury, CT
Living Area: 9441 Sqft.
06/04/2026 $18 Listing
Picture of Minortown Road
Minortown Road Woodbury, CT
Living Area: Sqft.
06/04/2026 $179,900 Selling
Picture of 1769 Goshen Road
1769 Goshen Road Torrington, CT
Living Area: 2428 Sqft.
06/04/2026 $485,000 Listing
Picture of 28 Oakcrest Road
28 Oakcrest Road Oxford, CT
Living Area: 1796 Sqft.
06/04/2026 $650,000 Selling
Picture of 115 Alain White Road
115 Alain White Road Morris, CT
Living Area: 2826 Sqft.
06/04/2026 $650,000 Selling
Picture of 142 Washington Road
142 Washington Road Woodbury, CT
Living Area: 1340 Sqft.
06/04/2026 $379,900 Listing
Picture of 4 Weekeepeemee Road
4 Weekeepeemee Road Woodbury, CT
Living Area: 4294 Sqft.
06/04/2026 $1,600 Selling
Picture of 182 Magnolia Hill Road
182 Magnolia Hill Road Bethlehem, CT
Living Area: 1757 Sqft.
06/04/2026 $899,000 Listing
Picture of 40 Main Street North
40 Main Street North Woodbury, CT
Living Area: 11804 Sqft.
06/04/2026 $1,300,000 Selling
Picture of 533 Weekeepeemee Road
533 Weekeepeemee Road Woodbury, CT
Living Area: 2718 Sqft.
06/04/2026 $2,200 Selling
Picture of 220 Upper Grassy Hill Road
220 Upper Grassy Hill Road Woodbury, CT
Living Area: 1620 Sqft.
06/04/2026 $3,600 Selling
Picture of 14 Fox Run 14
14 Fox Run 14 Woodbury, CT
Living Area: 1456 Sqft.
06/04/2026 $269,000 Listing
Picture of 319 Thomaston Road 13
319 Thomaston Road 13 Watertown, CT
Living Area: 1224 Sqft.
06/04/2026 $325,000 Listing
Picture of 47 Woods Way 47
47 Woods Way 47 Woodbury, CT
Living Area: 1182 Sqft.
06/04/2026 $214,900 Listing
Picture of 32 Lakeview Drive
32 Lakeview Drive Bethlehem, CT
Living Area: 1016 Sqft.
06/04/2026 $2,150 Selling
Picture of 25 Cross Road
25 Cross Road Plymouth, CT
Living Area: Sqft.
06/04/2026 $160,000 Listing
Picture of 193 Ridgewood Drive 193
193 Ridgewood Drive 193 Middlebury, CT
Living Area: 2658 Sqft.
06/04/2026 $649,900 Listing
Picture of 4 Main Street South 2
4 Main Street South 2 Woodbury, CT
Living Area: 2976 Sqft.
06/04/2026 $2,200 Listing
Picture of 136 Candee Hill Road
136 Candee Hill Road Watertown, CT
Living Area: 1286 Sqft.
06/04/2026 $295,000 Listing
Picture of 126 Triangle Street A41
126 Triangle Street A41 Danbury, CT
Living Area: 693 Sqft.
06/04/2026 $1,800 Selling

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Naugatuck, CT
Woodbury, CT
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Middlebury, CT
Danbury, CT

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