Winter Harbor Dr, Ocean City, MD Property Records

Worcester County property records for 66 addresses on Winter Harbor Dr, Ocean City, MD · Last verified October 2026

Winter Harbor Dr Highlights

Properties 66
Median Sale Price $489,900
Deeds and Mortgages on File 56
Median Price per Sqft $312
Owner Occupied 36%
Median Annual Tax Bill $6,006
Median Year Built 1980
Median Ownership Tenure 13 years

Properties on Winter Harbor Dr

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

100 Winter Harbor Dr

2 ba · 1,504 sqft · built 1970 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$279,000Jul 2017 $5,7732026 Amount on Record Jun 2003 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

101 Winter Harbor Dr

3 ba · 1,252 sqft · built 1969 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$338,000Apr 2014 $6,3142026 Amount on Record Dec 2003 2 Owners on Record AssessorUpdated Oct 2026

102 Winter Harbor Dr

2 ba · 1,568 sqft · built 1966 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$489,900May 2021 $8,2622026 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

103 Winter Harbor Dr

2.5 ba · 1,775 sqft · built 2002 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Sep 2001 $7,6532026 2 Owners on Record AssessorUpdated Oct 2026

104 Winter Harbor Dr

5.5 ba · 3,657 sqft · built 2003 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$636,000Feb 2021 $9,6812026 Amount on Record Jan 2003 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

105 Winter Harbor Dr

2 ba · 1,848 sqft · built 1986 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$399,000Apr 2017 $7,3172026 —Jul 2011 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

106 Winter Harbor Dr

2 ba · 1,580 sqft · built 1966 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Sep 2003 $6,7412026 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

107 Winter Harbor Dr

2 ba · 1,272 sqft · built 1986 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$133,000Aug 1995 $6,5312026 Amount on Record Aug 1987 2 Owners on Record AssessorUpdated Oct 2026

108 Winter Harbor Dr

2 ba · 1,120 sqft · built 1981 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,7932026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

109 Winter Harbor Dr

1.5 ba · 1,104 sqft · built 1970 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2009 $5,9622026 —May 2002 2 Owners on Record AssessorUpdated Oct 2026

110 Winter Harbor Dr

2 ba · 1,738 sqft · built 1982 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2025 $7,2092026 Amount on Record Oct 2003 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

111 Winter Harbor Dr

2 ba · 1,772 sqft · built 2018 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,2752026 2 Owners on Record Assessor + 4 DocumentsUpdated Oct 2026

112 Winter Harbor Dr

2 ba · 1,809 sqft · built 1982 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$62,500Jun 1986 $5,3012025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

113 Winter Harbor Dr

2 ba · 1,012 sqft · built 1972 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$212,500Apr 2002 $6,0142026 Amount on Record Jul 2000 Owner on Record AssessorUpdated Oct 2026

114 Winter Harbor Dr

1 ba · 1,232 sqft · built 1981 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,7932025 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

115 Winter Harbor Dr

2 ba · 1,009 sqft · built 1967 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Aug 2015 $5,4602025 Amount on Record Jun 1990 2 Owners on Record AssessorUpdated Aug 2026

116 Winter Harbor Dr

2 ba · 1,559 sqft · built 1980 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$355,000Dec 2002 $6,8262026 Owner on Record AssessorUpdated Oct 2026

117 Winter Harbor Dr

2 ba · 1,680 sqft · built 1972 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
—May 1996 $6,2592025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

118 Winter Harbor Dr

2 ba · 1,248 sqft · built 1967 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$720,000Aug 2026 $6,5842026 Amount on Record Mar 2022 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

119 Winter Harbor Dr

2 ba · 1,880 sqft · built 1995 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$45,500Jul 1984 $4,5952025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

120 Winter Harbor Dr

2 ba · 1,260 sqft · built 1993 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$72,500Sep 1992 $6,2602025 Amount on Record Apr 1988 2 Owners on Record AssessorUpdated Aug 2026

121 Winter Harbor Dr

2 ba · 2,896 sqft · built 1991 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Jul 2015 $8,0742025 Amount on Record Mar 1994 2 Owners on Record AssessorUpdated Aug 2026

122 Winter Harbor Dr

4 ba · 1,792 sqft · built 1978 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000Apr 2001 $7,5232026 Amount on Record Apr 1995 Owner on Record AssessorUpdated Oct 2026

123 Winter Harbor Dr

2 ba · 1,334 sqft · built 1968 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$380,000Jun 2016 $6,6602026 Amount on Record May 2000 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

124 Winter Harbor Dr

4.5 ba · 4,476 sqft · built 1981 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$510,000Jul 2006 $11,3852026 Amount on Record Dec 1989 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

125 Winter Harbor Dr

2 ba · 1,232 sqft · built 1982 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$460,000Oct 2020 $6,2272025 Amount on Record Aug 2016 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

126 Winter Harbor Dr

3 ba · 2,765 sqft · built 2003 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$195,000Oct 2002 $8,3052026 Amount on Record Jan 1991 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

127 Winter Harbor Dr

1.5 ba · 1,232 sqft · built 1980 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,9892025 2 Owners on Record AssessorUpdated Aug 2026

128 Winter Harbor Dr

2 ba · 1,688 sqft · built 1978 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$440,000Jun 2020 $7,5452026 Amount on Record Oct 2001 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

129 Winter Harbor Dr

2 ba · 1,712 sqft · built 1981 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$155,000Oct 1984 $6,2542025 Owner on Record AssessorUpdated Aug 2026

130 Winter Harbor Dr

2 ba · 1,387 sqft · built 1997 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$68,000Mar 1996 $5,9672025 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

131 Winter Harbor Dr

2 ba · 1,332 sqft · built 1971 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$459,000Oct 2018 $6,3572026 Amount on Record Jun 2009 2 Owners on Record Assessor + 2 DocumentsUpdated Oct 2026

132 Winter Harbor Dr

2 ba · 1,360 sqft · built 1994 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000Dec 2012 $6,0702025 Amount on Record May 1992 2 Owners on Record AssessorUpdated Aug 2026

133 Winter Harbor Dr

2 ba · 1,568 sqft · built 1979 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,6222025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

134 Winter Harbor Dr

4 ba · 4,194 sqft · built 2006 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$355,000Nov 2004 $9,0542026 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

135 Winter Harbor Dr

2 ba · 1,456 sqft · built 1978 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2011 $5,9832025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

136 Winter Harbor Dr

0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Aug 2021 $3,7462025 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

137 Winter Harbor Dr

3 ba · 2,300 sqft · built 1968 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,6532025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

138 Winter Harbor Dr

2 ba · 1,568 sqft · built 1993 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$381,000Mar 2011 $5,1172025 Amount on Record Jul 1992 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

139 Winter Harbor Dr

2 ba · 1,369 sqft · built 1978 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$297,500May 2014 $6,1922026 —Aug 2001 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

140 Winter Harbor Dr

2 ba · 2,093 sqft · built 1969 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Apr 2020 $6,4512025 —Jan 2001 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

141 Winter Harbor Dr

3 ba · 2,488 sqft · built 1988 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$408,000May 2014 $7,6262025 Amount on Record Jun 1997 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

142 Winter Harbor Dr

2 ba · 1,564 sqft · built 1972 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$315,000Apr 2017 $5,9092025 —Jan 2004 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

143 Winter Harbor Dr

2.5 ba · 2,130 sqft · built 2001 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$545,000Nov 2019 $8,2522026 Amount on Record Jun 2000 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

144 Winter Harbor Dr

2 ba · 1,305 sqft · built 1978 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Jun 2018 $6,7762026 Amount on Record Apr 1999 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

145 Winter Harbor Dr

2 ba · 1,448 sqft · built 1979 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$365,000Jan 2013 $6,4522025 Amount on Record Jan 2012 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

146 Winter Harbor Dr

2 ba · 1,211 sqft · built 1994 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000May 2009 $6,1872026 Amount on Record Sep 2001 2 Owners on Record AssessorUpdated Oct 2026

147 Winter Harbor Dr

2 ba · 1,232 sqft · built 1977 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$549,999Jun 2021 $5,6712025 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

148 Winter Harbor Dr

2.5 ba · 2,070 sqft · built 1983 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$479,500May 2021 $6,4122025 Amount on Record Jul 1982 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

149 Winter Harbor Dr

2 ba · 1,926 sqft · built 1979 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Sep 2008 $5,1932026 Amount on Record Nov 1991 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

150 Winter Harbor Dr

1.5 ba · 1,606 sqft · built 1972 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$440,000Dec 2009 $6,6692026 Amount on Record Oct 2004 2 Owners on Record AssessorUpdated Oct 2026

151 Winter Harbor Dr

3.5 ba · 2,024 sqft · built 1978 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2007 $6,3622025 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

152 Winter Harbor Dr

3 ba · 2,352 sqft · built 2003 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Mar 2013 $5,8422026 Amount on Record Dec 2007 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

153 Winter Harbor Dr

4.5 ba · 3,234 sqft · built 2002 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$485,000Nov 2012 $8,5602025 Amount on Record Mar 1999 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

154 Winter Harbor Dr

2.5 ba · 4,443 sqft · built 2009 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$337,500Mar 2004 $7,8482026 —Apr 1997 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

155 Winter Harbor Dr

1.5 ba · 864 sqft · built 1972 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,6352025 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

156 Winter Harbor Dr

2.5 ba · 2,793 sqft · built 1986 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$55,000Aug 1985 $5,0882025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

157 Winter Harbor Dr

2 ba · 1,418 sqft · built 1972 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$600,000Dec 2023 $5,8822025 Amount on Record Mar 2013 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

158 Winter Harbor Dr

2.5 ba · 2,332 sqft · built 2001 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$388,000Mar 2015 $5,8452025 Amount on Record Mar 1997 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

159 Winter Harbor Dr

2 ba · 1,456 sqft · built 1979 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$153,000Apr 1998 $2,4372025 Amount on Record Sep 1995 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

160 Winter Harbor Dr

2 ba · 1,232 sqft · built 1973 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$368,200Jun 2014 $4,7272025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

161 Winter Harbor Dr

1.5 ba · 1,104 sqft · built 1973 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Dec 2015 $4,8342026 Amount on Record Jan 2015 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

162 Winter Harbor Dr

3 ba · 2,112 sqft · built 1972 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$660,000Sep 2022 $6,7222025 Amount on Record Apr 2020 Owner on Record Assessor + 3 DocumentsUpdated Aug 2026

163 Winter Harbor Dr

3 ba · 2,142 sqft · built 1987 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$340,000Sep 2019 $7,0792026 Amount on Record Feb 2019 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

164 Winter Harbor Dr

2.5 ba · 3,260 sqft · built 2010 · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$190,000Dec 2000 $7,2692026 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

165 Winter Harbor Dr

2 ba · 2,677 sqft · built 1994 · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$209,000Nov 1995 $8,9532026 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

Property Records in Nearby Streets