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

130 homes near Ocean Pines

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5 rating (2 reviews) The Parke at Ocean Pines
$200Ks - $600Ks
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 - $600Ks
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
Champions' Club
$300Ks - $400Ks
Champions' Club, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 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.
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
3.3 rating (3 reviews) Windstone
$400Ks
Windstone, Milton, DE
Resale Only | Age-targeted | Built 2017 - 2022 | 260 homes
Bay Crossing
$400Ks - $700Ks
Bay Crossing, Lewes, DE
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 homes
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Longacre Village
$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
SummersGate
$300Ks
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
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.
Ashland
$400Ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
Osprey Point
$400Ks
Osprey Point, Upper Township, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 149 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
Gatherings at Cape May
$400Ks - $500Ks
Gatherings at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 115 homes
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1.7 rating (3 reviews) Silver Woods
$400Ks
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
Wynndemere
$400Ks
Wynndemere, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2011 | 62 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.
Four Seasons at Stone Har...
$500Ks - $600Ks
Four Seasons at Stone Har..., Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2009 | 60 homes
The Villages at Red Mill Pond 31454 VIVID VIEW DR, LEWES, DE, 19958, Lewes, DE 19958
$624,900

3 beds

|

2 baths

|

2,392 sq ft

31454 VIVID VIEW DR, LEWES, DE, 19958
Independence 26446 COTTONTAIL CV, MILLSBORO, DE, 1996..., Millsboro, DE 19966
$150,000

3 beds

|

2 baths

|

1,344 sq ft

26446 COTTONTAIL CV, MILLSBORO, DE, 1996...
Community: Independence
Champions' Club 85 BAY HILL RD, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$325,000

2 beds

|

2 baths

|

1,967 sq ft

85 BAY HILL RD, MAGNOLIA, DE, 19962
Community: Champions' Club
Longacre Village 45 HARCREST CT, DOVER, DE, 19901, Dover, DE 19901
$359,900

3 beds

|

3 baths

|

2,010 sq ft

45 HARCREST CT, DOVER, DE, 19901
Community: Longacre Village
Windstone 29575 FIELDSTONE DR, MILTON, DE, 19968, Milton, DE 19968
$475,000

3 beds

|

2 baths

|

2,056 sq ft

29575 FIELDSTONE DR, MILTON, DE, 19968
Community: Windstone
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Questions? Call us: (667) 843-7291
Four Seasons at Belle Terre 21160 CONTI ST, LEWES, DE, 19958, Lewes, DE 19958
$759,900

5 beds

|

3 baths

|

3,630 sq ft

21160 CONTI ST, LEWES, DE, 19958
Heritage Shores 134 WATERSIDE DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$344,900

2 beds

|

2 baths

|

1,320 sq ft

134 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Bishop's Landing 19127 GREYS NECK CT, MILLVILLE, DE, 1996..., Millville, DE 19967
$622,000

5 beds

|

4 baths

|

3,010 sq ft

19127 GREYS NECK CT, MILLVILLE, DE, 1996...
Community: Bishop's Landing
Four Seasons at Belle Terre 21336 DAUPHINE ST, LEWES, DE, 19958, Lewes, DE 19958
$670,000

3 beds

|

2 baths

|

2,087 sq ft

21336 DAUPHINE ST, LEWES, DE, 19958
Silver Woods 380 SCRANTON LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$445,000

4 beds

|

3 baths

|

2,026 sq ft

380 SCRANTON LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
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.
Noble's Pond 122 CASSELBERRY LN, DOVER, DE, 19904, Dover, DE 19904
$349,900

2 beds

|

2 baths

|

1,379 sq ft

122 CASSELBERRY LN, DOVER, DE, 19904
Community: Noble's Pond
Champions' Club 673 AUGUSTA NATIONAL DR, MAGNOLIA, DE, 1..., Magnolia, DE 19962
$365,000

2 beds

|

2 baths

|

1,599 sq ft

673 AUGUSTA NATIONAL DR, MAGNOLIA, DE, 1...
Community: Champions' Club
Village of Eastridge 131 HENGST FARM LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$457,351

2 beds

|

2 baths

|

1,684 sq ft

131 HENGST FARM LN, SMYRNA, DE, 19977
Bishop's Landing 30195 BRANDYWINE DR, MILLVILLE, DE, 1996..., Millville, DE 19967
$665,000

4 beds

|

4 baths

|

3,152 sq ft

30195 BRANDYWINE DR, MILLVILLE, DE, 1996...
Community: Bishop's Landing
The Villages at Red Mill Pond 18682 GOLDEN SUNRISE PL, LEWES, DE, 1995..., Lewes, DE 19958
$489,900

3 beds

|

2 baths

|

1,498 sq ft

18682 GOLDEN SUNRISE PL, LEWES, DE, 1995...
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Questions? Call us: (667) 843-7291
The Villages at Red Mill Pond 17513 YELLOW BELL DR, LEWES, DE, 19958, Lewes, DE 19958
$614,900

3 beds

|

2 baths

|

2,100 sq ft

17513 YELLOW BELL DR, LEWES, DE, 19958
The Villages at Red Mill Pond 17547 CLOUD NINE DR, LEWES, DE, 19958, Lewes, DE 19958
$545,000

3 beds

|

2 baths

|

1,668 sq ft

17547 CLOUD NINE DR, LEWES, DE, 19958
Independence 24006 BENJAMIN HARRISON CIR, MILLSBORO, ..., Millsboro, DE 19966
$515,000

3 beds

|

2 baths

|

1,776 sq ft

24006 BENJAMIN HARRISON CIR, MILLSBORO, ...
Community: Independence
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 204 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$498,990

3 beds

|

3 baths

|

2,088 sq ft

204 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
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.
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
Noble's Pond 498 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$512,000

3 beds

|

3 baths

|

2,373 sq ft

498 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
The Village of Cinderberry 2 CASTLEBERRY LN, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$340,000

3 beds

|

2 baths

|

1,986 sq ft

2 CASTLEBERRY LN, GEORGETOWN, DE, 19947
Bay Crossing 34677 VILLA CIR 504, LEWES, DE, 19958, Lewes, DE 19958
$399,900

3 beds

|

2 baths

|

1,215 sq ft

34677 VILLA CIR 504, LEWES, DE, 19958
Community: Bay Crossing
Cedar Bay 30611 CEDAR NECK RD UNIT 2204, OCEAN VIE..., Ocean View, DE 19970
$314,900

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

30611 CEDAR NECK RD UNIT 2204, OCEAN VIE...
Community: Cedar Bay
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Champions' Club 314 AUGUSTA NATIONAL DR, MAGNOLIA, DE, 1..., Magnolia, DE 19962
$325,000

2 beds

|

2 baths

|

1,566 sq ft

314 AUGUSTA NATIONAL DR, MAGNOLIA, DE, 1...
Community: Champions' Club
Southern Meadow 104 LAVENDER DR # 10, MAGNOLIA, DE, 1996..., Magnolia, DE 19962
$185,000

2 beds

|

2 baths

|

1,750 sq ft

104 LAVENDER DR # 10, MAGNOLIA, DE, 1996...
Community: Southern Meadow
Heritage Creek 202 HAY ST, MILTON, DE, 19968, Milton, DE 19968
$448,900

3 beds

|

3 baths

|

2,046 sq ft

202 HAY ST, MILTON, DE, 19968
Community: Heritage Creek
Bay Crossing 34774 SCHOONER PASS, LEWES, DE, 19958, Lewes, DE 19958
$499,900

3 beds

|

3 baths

|

1,993 sq ft

34774 SCHOONER PASS, LEWES, DE, 19958
Community: Bay Crossing
The Villages at Red Mill Pond 17927 TORRY PINES PL, LEWES, DE, 19958, Lewes, DE 19958
$529,000

3 beds

|

3 baths

|

3,736 sq ft

17927 TORRY PINES PL, LEWES, DE, 19958
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 100 EMILYS PINTAIL DR, BRIDGEVILLE, DE, ..., Bridgeville, DE 19933
$424,900

3 beds

|

3 baths

|

2,912 sq ft

100 EMILYS PINTAIL DR, BRIDGEVILLE, DE, ...
Community: Heritage Shores
Village of Eastridge 00 FELIX VIEW CT ASTON, SMYRNA, DE, 1997..., Smyrna, DE 19977
$406,000

2 beds

|

2 baths

|

1,720 sq ft

00 FELIX VIEW CT ASTON, SMYRNA, DE, 1997...
Champions' Club 221 NICKLAUS LN, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$419,900

2 beds

|

2 baths

|

1,623 sq ft

221 NICKLAUS LN, MAGNOLIA, DE, 19962
Community: Champions' Club
Noble's Pond 135 CASSELBERRY LN, DOVER, DE, 19904, Dover, DE 19904
$365,000

2 beds

|

2 baths

|

1,283 sq ft

135 CASSELBERRY LN, DOVER, DE, 19904
Community: Noble's Pond
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
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Windstone 29635 RIVERSTONE DR, MILTON, DE, 19968, Milton, DE 19968
$399,900

3 beds

|

2 baths

|

1,732 sq ft

29635 RIVERSTONE DR, MILTON, DE, 19968
Community: Windstone
Independence 29432 ANDREW JACKSON DR, MILLSBORO, DE, ..., Millsboro, DE 19966
$715,000

3 beds

|

2 baths

|

2,900 sq ft

29432 ANDREW JACKSON DR, MILLSBORO, DE, ...
Community: Independence
Fieldstone Village 175 CLAYSTONE DR, DOVER, DE, 19901, Dover, DE 19901
$369,900

3 beds

|

2 baths

|

1,945 sq ft

175 CLAYSTONE DR, DOVER, DE, 19901
Community: Fieldstone Village
Heritage Shores 9 LINKS DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$425,000

3 beds

|

2 baths

|

1,810 sq ft

9 LINKS DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Four Seasons at Hatteras Hills 179 BUXTON CIR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$534,900

3 beds

|

2 baths

|

1,778 sq ft

179 BUXTON CIR, MAGNOLIA, DE, 19962
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130 homes near Ocean Pines
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