Winding Way, San Carlos, CA Property Records

San Mateo County property records for 75 addresses on Winding Way, San Carlos, CA · Last verified October 2026

Winding Way Highlights

Properties 75
Median Sale Price $1,875,000
Deeds and Mortgages on File 166
Median Price per Sqft $1,159
Owner Occupied 93%
Median Annual Tax Bill $16,192
Median Year Built 1966
Median Ownership Tenure 8 years

Properties on Winding Way

Address Details Last Sale Tax Bill Records Owner

1 Winding Way

60 bd · 6 ba · 1,560 sqft built 1966 · 0.164 acres $4,943 2025 Assessor + 2 Documents Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

7 Winding Way

3 bd · 2 ba · 2,810 sqft built 1933 · 0.233 acres $4,724 2025 Assessor Updated Jul 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

10 Winding Way

3 bd · 2.5 ba · 1,930 sqft built 2003 · 0.117 acres $2,780,000 Jan 2026 $27,401 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

12 Winding Way

4 bd · 3 ba · 1,030 sqft built 1939 · 0.109 acres $700,000 Dec 2008 $12,218 2025 Assessor Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

15 Winding Way

12 bd · 1.5 ba · 1,290 sqft built 1935 · 0.177 acres $1,300,000 May 2025 $6,464 2025 Assessor + 1 Document Updated Oct 2026 Owner on File
Address Details Last Sale Tax Bill Records Owner

19 Winding Way

3 bd · 2 ba · 1,370 sqft built 1967 · 0.297 acres $207,000 Jul 2014 $14,048 2025 Assessor + 1 Document Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

20 Winding Way

5 bd · 3.5 ba · 2,799 sqft built 1964 · 0.159 acres $2,425,000 Jan 2018 $34,921 2025 Assessor + 5 Documents Updated Aug 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

24 Winding Way

1 bd · 1 ba · 870 sqft built 1935 · 0.168 acres $565,000 Dec 2012 $9,847 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

27 Winding Way

2 bd · 1 ba · 1,650 sqft built 1981 · 0.202 acres $1,801,000 May 2024 $22,647 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

28 Winding Way

3 bd · 2 ba · 1,674 sqft built 1965 · 0.158 acres $1,635,000 Sep 2020 $21,897 2025 Assessor + 3 Documents Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

35 Winding Way

4 bd · 3 ba · 2,700 sqft built 1933 · 0.406 acres $3,185,000 Mar 2018 $39,997 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

36 Winding Way

3 bd · 2.5 ba · 2,250 sqft built 1979 · 0.142 acres $1,495,000 Jan 2019 $20,681 2025 Assessor + 3 Documents Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

38 Winding Way

4 bd · 3.5 ba · 2,387 sqft built 2018 · 0.168 acres $2,960,000 Jul 2021 $37,184 2025 Assessor + 4 Documents Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

44 Winding Way

4 bd · 2.5 ba · 2,230 sqft built 1977 · 0.112 acres $325,000 Jul 1993 $8,249 2025 Assessor + 3 Documents Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

47 Winding Way

3 bd · 1 ba · 1,010 sqft built 1935 · 0.12 acres $1,280,000 Nov 2025 $13,871 2025 Assessor + 4 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

48 Winding Way

3 bd · 2 ba · 1,900 sqft built 1966 · 0.086 acres $3,341 2025 Assessor Updated Sep 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

51 Winding Way

2 bd · 1 ba · 820 sqft built 1934 · 0.165 acres $5,442 2025 Assessor Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

52 Winding Way

2 bd · 1 ba · 1,860 sqft built 1935 · 0.088 acres $250,000 Oct 1999 $7,309 2025 Assessor + 4 Documents Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

55 Winding Way

4 bd · 4 ba · 3,150 sqft built 1992 · 0.122 acres $2,175,000 Aug 2024 $26,414 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

75 Winding Way

4 bd · 2.5 ba · 1,950 sqft built 2001 · 0.159 acres $1,700,000 Sep 2018 $23,230 2025 Assessor + 4 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

103 Winding Way

3 bd · 3 ba · 2,354 sqft built 1934 · 0.118 acres $3,100,000 Aug 2026 $11,575 2025 Assessor + 2 Documents Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

104 Winding Way

3 bd · 2 ba · 1,320 sqft built 1964 · 0.133 acres $1,715,000 Sep 2025 $21,459 2025 Assessor + 2 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

107 Winding Way

3 bd · 2.5 ba · 1,710 sqft built 2000 · 0.132 acres $2,795,000 Aug 2024 $33,325 2025 Assessor + 4 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

108 Winding Way

1 bd · 2 ba · 1,120 sqft built 1937 · 0.18 acres — Sep 1997 $6,246 2025 Assessor + 1 Document Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

111 Winding Way

3 bd · 2 ba · 1,620 sqft built 1966 · 0.243 acres $1,875,000 Mar 2020 $24,949 2025 Assessor + 3 Documents Updated Aug 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

112 Winding Way

5 bd · 3.5 ba · 2,620 sqft built 1933 · 0.17 acres $2,610,000 May 2018 $35,195 2025 Assessor + 3 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

116 Winding Way

3 bd · 3.5 ba · 2,840 sqft built 1965 · 0.103 acres $400,000 Feb 1994 $9,670 2025 Assessor + 1 Document Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

119 Winding Way

3 bd · 2.5 ba · 1,590 sqft built 1975 · 0.14 acres $800,000 Nov 2011 $13,292 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

120 Winding Way

4 bd · 3 ba · 1,900 sqft built 1964 · 0.094 acres $3,277 2025 Assessor Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

123 Winding Way

1 bd · 1 ba · 1,230 sqft built 1937 · 0.135 acres $1,670,000 Nov 2022 $21,535 2025 Assessor + 5 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

124 Winding Way

2 bd · 2 ba · 1,280 sqft built 1930 · 0.099 acres $1,488,000 Mar 2018 $20,964 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

128 Winding Way

4 bd · 2.5 ba · 1,690 sqft built 1934 · 0.169 acres $3,436 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

131 Winding Way

1 bd · 1 ba · 680 sqft built 1937 · 0.22 acres $5,815 2025 Assessor Updated Jul 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

132 Winding Way

1 bd · 1 ba · 930 sqft built 1947 · 0.116 acres $1,900,000 Oct 2022 $24,126 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

135 Winding Way

2 bd · 2.5 ba · 1,620 sqft built 1936 · 0.104 acres $315,000 Jul 1991 $8,005 2025 Assessor + 4 Documents Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

136 Winding Way

4 bd · 2 ba · 1,920 sqft built 1971 · 0.124 acres $1,654,545 Nov 2018 $23,593 2025 Assessor + 8 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

140 Winding Way

3 bd · 1 ba · 880 sqft built 1943 · 0.103 acres $1,250,000 Feb 2018 $18,024 2025 Assessor + 5 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

150 Winding Way

4 bd · 3.5 ba · 3,900 sqft built 1980 · 0.139 acres $2,868,000 Mar 2026 $22,759 2025 Assessor + 2 Documents Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

156 Winding Way

4 bd · 3.5 ba · 4,040 sqft built 1981 · 0.191 acres $600,000 May 1997 $12,984 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

160 Winding Way

5 bd · 3 ba · 3,065 sqft built 1999 · 0.135 acres $1,800,000 Oct 2016 $2,488 2025 Assessor Updated Aug 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

164 Winding Way

3 bd · 3 ba · 2,100 sqft built 1937 · 0.413 acres $3,510,000 May 2026 $36,938 2025 Assessor + 5 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

180 Winding Way

4 bd · 4 ba · 2,878 sqft built 1949 · 0.661 acres $750,000 Jul 2020 $43,479 2025 Assessor + 2 Documents Updated Jul 2026 2 Owners on File
Address Details Last Sale Tax Bill Records Owner

184 Winding Way

2 bd · 2 ba · 1,600 sqft built 1972 · 0.27 acres $1,528,000 Oct 2018 $22,892 2025 Assessor + 5 Documents Updated Aug 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

188 Winding Way

4 bd · 2.5 ba · 2,080 sqft built 1977 · 0.133 acres $1,750,000 May 2020 $23,426 2025 Assessor + 6 Documents Updated Aug 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

203 Winding Way

3 bd · 2.5 ba · 1,690 sqft built 1934 · 0.164 acres $980,000 Mar 2007 $16,805 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

208 Winding Way

3 bd · 3 ba · 1,680 sqft built 1968 · 0.185 acres $3,473 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

215 Winding Way

4 bd · 2.5 ba · 2,470 sqft built 2003 · 0.177 acres $1,310,000 Jan 2007 $21,656 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

216 Winding Way

3 bd · 2.5 ba · 1,590 sqft built 1989 · 0.095 acres $425,000 Oct 1996 $9,962 2025 Assessor + 1 Document Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

220 Winding Way

1 bd · 1 ba · 760 sqft built 1934 · 0.114 acres $1,265,000 Jun 2024 $16,475 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

221 Winding Way

3 bd · 2.5 ba · 2,250 sqft built 1979 · 0.119 acres $6,838 2025 Assessor + 3 Documents Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

227 Winding Way

3 bd · 2.5 ba · 1,940 sqft built 1966 · 0.112 acres $2,250,000 Oct 2025 $20,409 2025 Assessor + 2 Documents Updated Aug 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

228 Winding Way

3 bd · 2 ba · 2,820 sqft built 1981 · 0.295 acres $7,728 2025 Assessor + 1 Document Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

231 Winding Way

3 bd · 2 ba · 1,980 sqft built 1965 · 0.104 acres $1,500,000 Sep 2017 $21,195 2025 Assessor + 3 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

235 Winding Way

2 bd · 1 ba · 1,340 sqft built 1933 · 0.174 acres $1,740,000 Oct 2024 $21,565 2025 Assessor + 2 Documents Updated Aug 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

236 Winding Way

2 bd · 2 ba · 1,590 sqft built 1929 · 0.162 acres $625,000 Jun 2004 $12,439 2025 Assessor + 4 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

237 Winding Way

1 bd · 1 ba · 670 sqft built 1959 · 0.155 acres $1,000,000 Nov 2023 $13,540 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

239 Winding Way

3 bd · 2 ba · 1,580 sqft built 1965 · 0.136 acres $665,000 Jul 2003 $12,631 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

243 Winding Way

4 bd · 2 ba · 1,710 sqft built 1972 · 0.109 acres $723,500 Jul 2003 $13,636 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

247 Winding Way

3 bd · 2.5 ba · 2,170 sqft built 1976 · 0.085 acres $563,000 Jun 2012 $15,484 2025 Assessor + 2 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

251 Winding Way

4 bd · 3 ba · 2,140 sqft built 1979 · 0.117 acres $875,000 Jul 2004 $15,687 2025 Assessor + 2 Documents Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

255 Winding Way

3 bd · 2.5 ba · 1,380 sqft built 1966 · 0.128 acres $358,000 May 1991 $9,357 2025 Assessor Updated Jul 2026 2 Owners on File
Address Details Last Sale Tax Bill Records Owner

259 Winding Way

3 bd · 4.5 ba · 2,000 sqft built 1966 · 0.09 acres $1,550,000 Dec 2018 $21,443 2025 Assessor + 3 Documents Updated Jul 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

263 Winding Way

4 bd · 2.5 ba · 2,730 sqft built 1990 · 0.134 acres $3,100,000 May 2022 $31,074 2025 Assessor + 6 Documents Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

393 Winding Way

3 bd · 2.5 ba · 3,120 sqft built 1988 · 0.183 acres $438,500 Aug 1988 $11,264 2025 Assessor Updated Jul 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

399 Winding Way

2 bd · 1 ba · 780 sqft built 1933 · 0.37 acres $585,000 Feb 2012 $23,396 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

400 Winding Way

4 bd · 3.5 ba · 3,290 sqft built 1993 · 0.247 acres $3,140,000 Nov 2025 $20,993 2025 Assessor + 3 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

402 Winding Way

6 bd · 5 ba · 3,720 sqft built 1995 · 0.124 acres $1,167,500 Jul 2026 $33,498 2025 Assessor + 5 Documents Updated Sep 2026 2 Owners on File
Address Details Last Sale Tax Bill Records Owner

404 Winding Way

3 bd · 2.5 ba · 2,090 sqft built 1988 · 0.113 acres $478,000 Sep 1988 $11,756 2025 Assessor + 1 Document Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

408 Winding Way

4 bd · 3 ba · 2,610 sqft built 1965 · 0.101 acres $453,000 May 1997 $10,896 2025 Assessor + 1 Document Updated Jul 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

410 Winding Way

3 bd · 2 ba · 1,660 sqft built 1966 · 0.101 acres $550,000 May 2002 $11,226 2025 Assessor Updated Sep 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

412 Winding Way

3 bd · 2 ba · 1,785 sqft built 1966 · 0.101 acres $830,000 Oct 2004 $14,988 2025 Assessor + 3 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

414 Winding Way

4 bd · 2 ba · 2,040 sqft built 1970 · 0.142 acres $2,000,000 Dec 2023 $24,909 2025 Assessor + 2 Documents Updated Aug 2026 2 Owners on File
Address Details Last Sale Tax Bill Records Owner

416 Winding Way

3 bd · 2 ba · 1,400 sqft built 1967 · 0.124 acres $1,480,000 Sep 2019 $20,134 2025 Assessor + 4 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

418 Winding Way

4 bd · 2.5 ba · 2,440 sqft built 1966 · 0.143 acres $800,000 Jun 2010 $16,192 2025 Assessor + 3 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

420 Winding Way

3 bd · 3.5 ba · 3,240 sqft built 1976 · 0.214 acres $1,350,000 Nov 2014 $19,843 2025 Assessor + 1 Document Updated Sep 2026 2 Owners on File Owner Occupied

Property Records in Nearby Streets