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Ocean Pines, MD 55+ active adult communities & homes for sale

32 communities near Ocean Pines

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5 rating (2 reviews) The Parke at Ocean Pines
$200Ks - $300Ks
The Parke at Ocean Pines, Ocean Pines, MD
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 503 homes
5 rating (2 reviews) Heritage Shores
$300Ks - $500Ks
Heritage Shores, Bridgeville, DE
New and Resale | 55+ age-restricted | Built 2004 - present | 1,816 homes
5 rating (2 reviews) Noble's Pond
$300Ks - $500Ks
Noble's Pond, Dover, DE
New and Resale | 55+ age-restricted | Built 2007 - present | 800 homes
2.8 rating (4 reviews) The Villages at Red Mill ...
$400Ks - $600Ks
The Villages at Red Mill ..., Lewes, DE
New and Resale | Age-targeted | Built 2009 - present | 520 homes
Roesville
$300Ks
Roesville, Felton, DE
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 470 homes
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Independence
$100Ks - $700Ks
Independence, Millsboro, DE
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 455 homes
5 rating (1 reviews) Bishop's Landing
$500Ks
Bishop's Landing, Millville, DE
New and Resale | Age-targeted | Built 2013 - present | 449 homes
3 rating (5 reviews) Heritage Creek
$400Ks - $500Ks
Heritage Creek, Milton, DE
New and Resale | Age-targeted | Built 2008 - present | 400 homes
Four Seasons at Hatteras ...
$400Ks - $500Ks
Four Seasons at Hatteras ..., Magnolia, DE
New Construction | 55+ age-restricted | Built 2023 - present | 400 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Champions' Club
$300Ks - $400Ks
Champions' Club, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Forest Landing at Bethany...
$400Ks - $500Ks
Forest Landing at Bethany..., Frankford, DE
New and Resale | Age-targeted | Built 2012 - present | 280 homes
Four Seasons at Belle Ter...
$600Ks - $700Ks
Four Seasons at Belle Ter..., Lewes, DE
New Construction | 55+ age-restricted | Built 2019 - present | 269 homes
Auburn Meadows
$400Ks
Auburn Meadows, Smyrna, DE
New Construction | 55+ age-restricted | Built 2022 - present | 262 homes
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3.3 rating (3 reviews) Windstone
$400Ks
Windstone, Milton, DE
Resale Only | Age-targeted | Built 2017 - 2022 | 260 homes
Bay Crossing
$500Ks - $600Ks
Bay Crossing, Lewes, DE
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 homes
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Longacre Village
$200Ks - $300Ks
Longacre Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 250 homes
5 rating (2 reviews) Spring Meadow
$300Ks - $400Ks
Spring Meadow, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 246 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
SummersGate
$400Ks
SummersGate, Salisbury, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 216 homes
5 rating (3 reviews) Village of Eastridge
$300Ks - $400Ks
Village of Eastridge, Smyrna, DE
New Construction | 55+ age-restricted | Built 2014 - present | 189 homes
The Village of Cinderberr...
$300Ks
The Village of Cinderberr..., Georgetown, DE
New and Resale | 55+ age-restricted | Built 2003 - present | 170 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Ashland
$400Ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
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Osprey Point
$400Ks
Osprey Point, Upper Township, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 149 homes
Verona Woods
$300Ks - $400Ks
Verona Woods, Dover, DE
Resale Only | 55+ age-restricted | Built 2020 - present | 148 homes
Legacy at Cape May
$400Ks - $500Ks
Legacy at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 141 homes
4.5 rating (2 reviews) Southern Meadow
$100Ks
Southern Meadow, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 120 homes
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Questions? Call us: (667) 843-7291
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Gatherings at Cape May
$400Ks - $500Ks
Gatherings at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 115 homes
1.7 rating (3 reviews) Silver Woods
$400Ks - $500Ks
Silver Woods, Ocean View, DE
New and Resale | Age-targeted | Built 2005 - present | 111 homes
Fieldstone Village
$300Ks
Fieldstone Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2002 - present | 98 homes
Cedar Bay
$200Ks - $300Ks
Cedar Bay, Ocean View, DE
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 72 homes
Gateway Shores
$200Ks - $300Ks
Gateway Shores, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 1996 - 2002 | 66 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Wynndemere
$400Ks
Wynndemere, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2011 | 62 homes
Four Seasons at Stone Har...
$600Ks
Four Seasons at Stone Har..., Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2009 | 60 homes
Village of Eastridge 100 NEW VILLAGE LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$479,500

3 beds

|

2 baths

|

1,842 sq ft

100 NEW VILLAGE LN, SMYRNA, DE, 19977
Silver Woods 220 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$459,990

3 beds

|

3 baths

|

2,088 sq ft

220 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
Silver Woods 222 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$448,990

3 beds

|

3 baths

|

2,088 sq ft

222 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
New Windstone 29522 FIELDSTONE DR, MILTON, DE, 19968, Milton, DE 19968
$499,999

4 beds

|

3 baths

|

2,300 sq ft

29522 FIELDSTONE DR, MILTON, DE, 19968
Community: Windstone
New Silver Woods 238 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$479,900

3 beds

|

3 baths

|

2,088 sq ft

238 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
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Questions? Call us: (667) 843-7291
Silver Woods 393 SCRANTON LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$449,900

3 beds

|

3 baths

|

2,178 sq ft

393 SCRANTON LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
New The Village of Cinderberry 27 BAYBERRY ST, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$365,000

2 beds

|

2 baths

|

1,649 sq ft

27 BAYBERRY ST, GEORGETOWN, DE, 19947
The Villages at Red Mill Pond 36396 BABBLING BROOK WAY, LEWES, DE, 199..., Lewes, DE 19958
$625,000

4 beds

|

3 baths

|

2,600 sq ft

36396 BABBLING BROOK WAY, LEWES, DE, 199...
Bay Crossing 34743 MARITIME WAY, LEWES, DE, 19958, Lewes, DE 19958
$539,900
|

2,125 sq ft

34743 MARITIME WAY, LEWES, DE, 19958
Community: Bay Crossing
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
New Spring Meadow 543 SORRELL CIR, SMYRNA, DE, 19977, Smyrna, DE 19977
$440,000

2 beds

|

2 baths

|

2,776 sq ft

543 SORRELL CIR, SMYRNA, DE, 19977
Community: Spring Meadow
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New Verona Woods 168 TYBALT LN, DOVER, DE, 19901, Dover, DE 19901
$420,000

3 beds

|

2 baths

|

1,404 sq ft

168 TYBALT LN, DOVER, DE, 19901
Community: Verona Woods
Windstone 29645 RIVERSTONE DR, MILTON, DE, 19968, Milton, DE 19968
$465,000

3 beds

|

2 baths

|

1,730 sq ft

29645 RIVERSTONE DR, MILTON, DE, 19968
Community: Windstone
Champions' Club 532 AUGUSTA NATIONAL DR, MAGNOLIA, DE, 1..., Magnolia, DE 19962
$338,000

2 beds

|

2 baths

|

1,696 sq ft

532 AUGUSTA NATIONAL DR, MAGNOLIA, DE, 1...
Community: Champions' Club
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Questions? Call us: (667) 843-7291
Longacre Village 39 STARFIRE CT, DOVER, DE, 19901, Dover, DE 19901
$315,000

2 beds

|

2 baths

|

1,198 sq ft

39 STARFIRE CT, DOVER, DE, 19901
Community: Longacre Village
Noble's Pond 812 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$449,320

3 beds

|

3 baths

|

2,151 sq ft

812 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
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Noble's Pond 786 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$416,380

2 beds

|

2 baths

|

1,728 sq ft

786 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 1175 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$357,800

2 beds

|

2 baths

|

1,518 sq ft

1175 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
New Forest Landing at Bethany Beach 37099 FAIRWAY DR, FRANKFORD, DE, 19945, Frankford, DE 19945
$599,000

4 beds

|

3 baths

|

2,400 sq ft

|

Condo

37099 FAIRWAY DR, FRANKFORD, DE, 19945
Noble's Pond 208 CARNEY CT, DOVER, DE, 19904, Dover, DE 19904
$359,990

3 beds

|

3 baths

|

2,142 sq ft

208 CARNEY CT, DOVER, DE, 19904
Community: Noble's Pond
Auburn Meadows 31 ARDMONT DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$405,050

2 beds

|

2 baths

|

1,936 sq ft

31 ARDMONT DR, SMYRNA, DE, 19977
Community: Auburn Meadows
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Auburn Meadows 43 ARDMONT DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$409,818

2 beds

|

2 baths

|

1,778 sq ft

43 ARDMONT DR, SMYRNA, DE, 19977
Community: Auburn Meadows
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Heritage Shores 103 WINGED FOOT DR, BRIDGEVILLE, DE, 199..., Bridgeville, DE 19933
$399,800

3 beds

|

2 baths

|

1,952 sq ft

103 WINGED FOOT DR, BRIDGEVILLE, DE, 199...
Community: Heritage Shores
Independence 24006 BENJAMIN HARRISON CIR, MILLSBORO, ..., Millsboro, DE 19966
$510,000

3 beds

|

2 baths

|

1,776 sq ft

24006 BENJAMIN HARRISON CIR, MILLSBORO, ...
Community: Independence
Heritage Shores 21 WHITE PELICAN CT, BRIDGEVILLE, DE, 19..., Bridgeville, DE 19933
$450,000

3 beds

|

3 baths

|

2,458 sq ft

21 WHITE PELICAN CT, BRIDGEVILLE, DE, 19...
Community: Heritage Shores
Heritage Shores 338 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$464,900

3 beds

|

2 baths

|

1,576 sq ft

338 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
Want to learn more about 55+ rental communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
New Auburn Meadows 999 VIRDIN DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$437,990

3 beds

|

3 baths

|

2,386 sq ft

999 VIRDIN DR, SMYRNA, DE, 19977
Community: Auburn Meadows
Auburn Meadows 303 VIRDIN DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$459,000

2 beds

|

2 baths

|

2,176 sq ft

303 VIRDIN DR, SMYRNA, DE, 19977
Community: Auburn Meadows
New Silver Woods 224 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$459,990

3 beds

|

3 baths

|

2,067 sq ft

224 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
Champions' Club 34 SAHALEE CT, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$415,000

3 beds

|

3 baths

|

2,109 sq ft

34 SAHALEE CT, MAGNOLIA, DE, 19962
Community: Champions' Club
Heritage Shores 134 WATERSIDE DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$324,900

2 beds

|

2 baths

|

1,320 sq ft

134 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Four Seasons at Hatteras Hills 103 WANCHESE DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$499,990

3 beds

|

2 baths

|

1,778 sq ft

103 WANCHESE DR, MAGNOLIA, DE, 19962
Four Seasons at Hatteras Hills 58 WANCHESE DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$564,900

4 beds

|

2 baths

|

2,344 sq ft

58 WANCHESE DR, MAGNOLIA, DE, 19962
Four Seasons at Hatteras Hills 74 WANCHESE DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$439,990

3 beds

|

2 baths

|

1,627 sq ft

74 WANCHESE DR, MAGNOLIA, DE, 19962
Four Seasons at Hatteras Hills 179 BUXTON CIR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$529,990

3 beds

|

2 baths

|

1,778 sq ft

179 BUXTON CIR, MAGNOLIA, DE, 19962
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Heritage Shores 33 WATERSIDE DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$415,000

2 beds

|

2 baths

|

1,952 sq ft

33 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Want to learn more about 55+ rental communities in Ocean Pines? 55places can help!
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Silver Woods 226 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$503,990

3 beds

|

3 baths

|

2,267 sq ft

226 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
Silver Woods 205 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$449,990

3 beds

|

3 baths

|

2,267 sq ft

205 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
Silver Woods 136 KINGSTON AVE, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$443,990

3 beds

|

3 baths

|

2,267 sq ft

136 KINGSTON AVE, OCEAN VIEW, DE, 19970
Community: Silver Woods
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
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Silver Woods 138 KINGSTON AVE, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$424,990

3 beds

|

3 baths

|

2,088 sq ft

138 KINGSTON AVE, OCEAN VIEW, DE, 19970
Community: Silver Woods
Cedar Bay 30611 CEDAR NECK RD UNIT 2204, OCEAN VIE..., Ocean View, DE 19970
$295,000

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

30611 CEDAR NECK RD UNIT 2204, OCEAN VIE...
Community: Cedar Bay

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