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78 HARTFORDBUSINESS.COM | 2025 BOOK OF LISTS R E A L E S TAT E LARGEST SINGLE-FAMILY HOME SALES IN CONNECTICUT Ranked by sale price, then by square feet in 2024 (1) Largest single-family home sales in Connecticut Ranked by sale price, then by squar e feet in 2024 ((11)) Address Sale price Square footage No. bedrooms/ no. full bathrooms No. days on market (2) Year built 1 22 Dairy Road Greenwich $16,250,000 14,689 7 9 162 2022 2 16 Windrose Way Greenwich $13,750,000 8,914 8 10 709 1985 3 400 5 1/2 Mile Road Cornwall $12,000,000 18,000 10 12 1050 1992 4 74 Lower Cross Road Greenwich $11,000,000 9,311 5 6 28 2000 5 279 Saugatuck Ave. Westport $11,000,000 8,246 4 5 91 1999 6 66 Beachside Ave. Westport $10,750,000 12,500 6 6 138 2019 7 1093 Pequot Ave. $10,650,000 9,092 5 6 67 2019 8 11 Pratt Island Darien $10,500,000 8,804 5 5 163 2007 9 18 Simmons Lane Greenwich $10,400,000 19,096 7 8 204 1924 10 1316 Pequot Ave. $9,750,000 7,415 5 4 57 1999 11 20 Ann St. Greenwich $9,650,000 7,059 7 6 25 2018 12 12 Butlers Island Road Darien $9,580,000 9,931 7 8 77 1957 13 25 Zaccheus Mead Lane Greenwich $8,900,000 10,383 6 7 30 1905 14 2 Owenoke Park Westport $8,795,000 4,820 5 5 349 2023 15 36 Mayfair Lane Greenwich $8,750,000 7,438 7 8 230 1932 16 53 Foxboro Road Essex $8,350,000 6,821 4 5 17 2004 17 161 Falcon Road Guilford $8,000,000 7,671 5 5 73 2016 18 36 French Road Greenwich $7,800,000 9,823 6 7 77 2000 19 158 Wykeham Road Washington $7,600,000 6,048 5 6 17 1989 20 248 Hillspoint Road Westport $7,500,000 4,136 5 3 11 2009 21 785 Oenoke Ridge New Canaan $7,295,000 13,062 7 7 203 2004 22 319 Bayberry Lane Westport $7,250,000 7,938 6 5 89 2020 23 8 Homewood Lane Darien $6,975,000 6,882 5 6 128 2022 24 727 Smith Ridge Road New Canaan $6,900,000 10,397 7 9 63 2005 Source: Data provided by Raveis Broder Team, West Hartford, 860-313-1300, with special thanks to Evan L. Berman. Note: Data originates from SmartMLS, which is deemed reliable but not guaranteed. Ranking private sales may not be included. (1) Sales from Jan. 1, 2024 to Nov. 12, 2024 were considered for this list. (2) operty may have been on market a greater number of days if previously listed. -Compiled by: Heide Martin, hmartin@nebusinessmedia.com