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Ocean Pines, MD 55+ active adult communities & homes for sale - Page 4

181 homes near Ocean Pines

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5 rating (2 reviews) Heritage Shores
$200ks - $500ks
Heritage Shores, Bridgeville, DE
New and Resale | 55+ age-restricted | Built 2004 - present | 1,816 homes
5 rating (2 reviews) Noble's Pond
$200ks - $300ks
Noble's Pond, Dover, DE
New and Resale | 55+ age-restricted | Built 2007 - present | 800 homes
The Village of Cinderberr...
$200ks - $300ks
The Village of Cinderberr..., Georgetown, DE
New and Resale | 55+ age-restricted | Built 2003 - present | 170 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
Four Seasons at Hatteras ...
$400ks - $500ks
Four Seasons at Hatteras ..., Magnolia, DE
New Construction | 55+ age-restricted | Built 2023 - present | 400 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
1.7 rating (3 reviews) Silver Woods
$400ks - $500ks
Silver Woods, Ocean View, DE
New and Resale | Age-targeted | Built 2005 - present | 111 homes
3 rating (5 reviews) Heritage Creek
$300ks - $500ks
Heritage Creek, Milton, DE
New and Resale | Age-targeted | Built 2008 - present | 400 homes
Independence
$400ks - $800ks
Independence, Millsboro, DE
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 455 homes
Liberty West
$400ks
Liberty West, Georgetown, DE
New Construction | Age-targeted | Built 2025 - present | 181 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
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.
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
Forest Landing at Bethany...
$300ks - $500ks
Forest Landing at Bethany..., Frankford, DE
New and Resale | Age-targeted | Built 2012 - present | 280 homes
Ashland
$300ks - $400ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
4.5 rating (2 reviews) Southern Meadow
$100ks - $200ks
Southern Meadow, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 120 homes
Verona Woods
$300ks - $400ks
Verona Woods, Dover, DE
Resale Only | 55+ age-restricted | Built 2020 - present | 148 homes
5 rating (1 reviews) Bishop's Landing
$300ks - $500ks
Bishop's Landing, Millville, DE
New and Resale | Age-targeted | Built 2013 - present | 449 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
3.7 rating (3 reviews) Spring Meadow
- $400ks
Spring Meadow, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 246 homes
3.3 rating (3 reviews) Windstone
$400ks
Windstone, Milton, DE
Resale Only | Age-targeted | Built 2017 - 2022 | 260 homes
Champions' Club
$300ks - $400ks
Champions' Club, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 homes
Legacy at Cape May
$400ks - $500ks
Legacy at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 141 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 Belle Ter...
$400ks - $600ks
Four Seasons at Belle Ter..., Lewes, DE
New Construction | 55+ age-restricted | Built 2019 - present | 269 homes
Four Seasons at Stone Har...
$600ks - $700ks
Four Seasons at Stone Har..., Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2009 | 60 homes
Osprey Point
$300ks - $400ks
Osprey Point, Upper Township, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 149 homes
Bay Crossing
$400ks - $600ks
Bay Crossing, Lewes, DE
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 homes
Auburn Meadows
$400ks - $500ks
Auburn Meadows, Smyrna, DE
New Construction | 55+ age-restricted | Built 2022 - present | 262 homes
Fieldstone Village
$200ks - $300ks
Fieldstone Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2002 - present | 98 homes
SummersGate
$300ks
SummersGate, Salisbury, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 216 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Roesville
$300ks
Roesville, Felton, DE
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 470 homes
Longacre Village
$300ks
Longacre Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 250 homes
Cedar Bay
$200ks - $300ks
Cedar Bay, Ocean View, DE
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 72 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.
Gatherings at Cape May
$500ks
Gatherings at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 115 homes
Wynndemere
$400ks
Wynndemere, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2011 | 62 homes
Gateway Shores
$200ks - $300ks
Gateway Shores, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 1996 - 2002 | 66 homes
Four Seasons at Hatteras Hills 30 FRISCO DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$479,990

3 beds

|

3 baths

|

1,778 sq ft

30 FRISCO DR, MAGNOLIA, DE, 19962
Champions' Club 295 NICKLAUS LN, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$449,900

3 beds

|

3 baths

|

3,058 sq ft

295 NICKLAUS LN, MAGNOLIA, DE, 19962
Community: Champions' Club
Wynndemere 1 WYNNDEMERE CT, CAPE MAY COURT HOUSE, N..., Cape May Court House, NJ 08210
$479,900

3 beds

|

2 baths

|

1,611 sq ft

|

House

1 WYNNDEMERE CT, CAPE MAY COURT HOUSE, N...
Community: Wynndemere
Noble's Pond 267 NOBLES POND XING, DOVER, DE, 19904, Dover, DE 19904
$400,000

3 beds

|

2 baths

|

1,824 sq ft

267 NOBLES POND XING, DOVER, DE, 19904
Community: Noble's Pond
Independence 33245 TIDEWATER CV, MILLSBORO, DE, 19966, Millsboro, DE 19966
$160,000

3 beds

|

2 baths

|

1,092 sq ft

33245 TIDEWATER CV, MILLSBORO, DE, 19966
Community: Independence
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Heritage Shores 109 WHISTLING DUCK DR, BRIDGEVILLE, DE, ..., Bridgeville, DE 19933
$319,400

2 beds

|

2 baths

|

1,659 sq ft

109 WHISTLING DUCK DR, BRIDGEVILLE, DE, ...
Community: Heritage Shores
Bishop's Landing 30255 BRANDYWINE DR, MILLVILLE, DE, 1996..., Millville, DE 19967
$629,000

4 beds

|

4 baths

|

2,900 sq ft

30255 BRANDYWINE DR, MILLVILLE, DE, 1996...
Community: Bishop's Landing
Four Seasons at Hatteras Hills 43 WANCHESE DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$469,990

3 beds

|

3 baths

|

1,778 sq ft

43 WANCHESE DR, MAGNOLIA, DE, 19962
Noble's Pond 212 SKIPPING STONE LN, DOVER, DE, 19904, Dover, DE 19904
$539,900

3 beds

|

3 baths

|

3,393 sq ft

212 SKIPPING STONE LN, DOVER, DE, 19904
Community: Noble's Pond
Four Seasons at Belle Terre 21153 CONTI ST, LEWES, DE, 19958, Lewes, DE 19958
$639,000

3 beds

|

2 baths

|

2,611 sq ft

21153 CONTI ST, 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.
The Village of Cinderberry 74 CINDER WAY, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$359,000

3 beds

|

2 baths

|

1,786 sq ft

74 CINDER WAY, GEORGETOWN, DE, 19947
Village of Eastridge 95 OSCAR MILL LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$390,000

2 beds

|

2 baths

|

1,584 sq ft

95 OSCAR MILL LN, SMYRNA, DE, 19977
Bay Crossing 34807 CAPSTAN LN, LEWES, DE, 19958, Lewes, DE 19958
$522,500

2 beds

|

3 baths

|

2,100 sq ft

|

Condo

34807 CAPSTAN LN, LEWES, DE, 19958
Community: Bay Crossing
Heritage Creek 305 PROSPECT ST, MILTON, DE, 19968, Milton, DE 19968
$475,000

3 beds

|

2 baths

|

1,661 sq ft

305 PROSPECT ST, MILTON, DE, 19968
Community: Heritage Creek
Independence 26453 COTTONTAIL CV, MILLSBORO, DE, 1996..., Millsboro, DE 19966
$189,900

3 beds

|

2 baths

|

1,755 sq ft

26453 COTTONTAIL CV, MILLSBORO, DE, 1996...
Community: Independence
Osprey Point 1731 ROUTE 9 11, SEAVILLE, NJ, 08230, Seaville, NJ 08230
$534,000

2 beds

|

2 baths

|

1,848 sq ft

|

Condo

1731 ROUTE 9 11, SEAVILLE, NJ, 08230
Community: Osprey Point
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Noble's Pond 11 KINSALE PL, DOVER, DE, 19904, Dover, DE 19904
$389,000

3 beds

|

3 baths

|

2,306 sq ft

11 KINSALE PL, DOVER, DE, 19904
Community: Noble's Pond
Ashland 26 CYCLOPS TRL, SMYRNA, DE, 19977, Smyrna, DE 19977
$425,000

3 beds

|

3 baths

|

1,848 sq ft

26 CYCLOPS TRL, SMYRNA, DE, 19977
Community: Ashland
The Parke at Ocean Pines 11427 MANKLIN CREEK RD 7, OCEAN PINES, M..., Ocean Pines, MD 21811
$295,000

3 beds

|

2 baths

|

1,181 sq ft

|

Condo

11427 MANKLIN CREEK RD 7, OCEAN PINES, M...
Bay Crossing 34825 CAPSTAN LN, LEWES, DE, 19958, Lewes, DE 19958
$650,000

4 beds

|

3 baths

|

2,400 sq ft

34825 CAPSTAN LN, 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.
Heritage Shores 105 WHISTLING DUCK DR, BRIDGEVILLE, DE, ..., Bridgeville, DE 19933
$299,900

2 beds

|

2 baths

|

1,481 sq ft

105 WHISTLING DUCK DR, BRIDGEVILLE, DE, ...
Community: Heritage Shores
Heritage Creek 215 MILL POND AVE, MILTON, DE, 19968, Milton, DE 19968
$444,900

3 beds

|

2 baths

|

1,979 sq ft

215 MILL POND AVE, MILTON, DE, 19968
Community: Heritage Creek
Noble's Pond 04 FAIRMONT LN, DOVER, DE, 19904, Dover, DE 19904
$450,900

2 beds

|

2 baths

|

1,820 sq ft

04 FAIRMONT LN, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 03 FAIRMONT LN, DOVER, DE, 19904, Dover, DE 19904
$442,900

2 beds

|

2 baths

|

1,750 sq ft

03 FAIRMONT LN, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 02 FAIRMONT LN, DOVER, DE, 19904, Dover, DE 19904
$423,900

2 beds

|

2 baths

|

1,510 sq ft

02 FAIRMONT LN, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 01 FAIRMONT LN, DOVER, DE, 19904, Dover, DE 19904
$392,900

2 beds

|

2 baths

|

1,260 sq ft

01 FAIRMONT LN, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 498 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$492,000

3 beds

|

3 baths

|

2,373 sq ft

498 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Noble's Pond 643 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$459,900

2 beds

|

2 baths

|

1,575 sq ft

643 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 05 FAIRMONT LN, DOVER, DE, 19904, Dover, DE 19904
$456,900

3 beds

|

2 baths

|

1,820 sq ft

05 FAIRMONT LN, DOVER, DE, 19904
Community: Noble's Pond
Village of Eastridge 115 HENGST FARM LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$467,489

2 beds

|

2 baths

|

1,760 sq ft

115 HENGST FARM LN, SMYRNA, DE, 19977
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.
Village of Eastridge 131 HENGST FARM LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$449,900

2 beds

|

2 baths

|

1,684 sq ft

131 HENGST FARM LN, SMYRNA, DE, 19977
The Village of Cinderberry 3 BAYBERRY ST 2, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$335,000

2 beds

|

2 baths

|

1,359 sq ft

3 BAYBERRY ST 2, GEORGETOWN, DE, 19947
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
Verona Woods 168 TYBALT LN, DOVER, DE, 19901, Dover, DE 19901
$415,000

3 beds

|

2 baths

|

1,404 sq ft

168 TYBALT LN, DOVER, DE, 19901
Community: Verona Woods
Heritage Shores 21 WHITE PELICAN CT, BRIDGEVILLE, DE, 19..., Bridgeville, DE 19933
$429,900

3 beds

|

3 baths

|

2,458 sq ft

21 WHITE PELICAN CT, BRIDGEVILLE, DE, 19...
Community: Heritage Shores
The Village of Cinderberry 14 MULBERRY ST, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$345,000

2 beds

|

2 baths

|

1,591 sq ft

14 MULBERRY ST, GEORGETOWN, DE, 19947
Silver Woods 218 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$438,990

3 beds

|

3 baths

|

2,267 sq ft

218 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
Southern Meadow 116 LAVENDER DR 4, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$194,900

2 beds

|

2 baths

|

1,720 sq ft

116 LAVENDER DR 4, MAGNOLIA, DE, 19962
Community: Southern Meadow
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Heritage Shores 16 BLUE HERON CT, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$399,900

3 beds

|

2 baths

|

1,890 sq ft

16 BLUE HERON CT, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Bishop's Landing 33298 LONE CEDAR LANDING LNDG 5802, MILL..., Millville, DE 19967
$489,900

4 beds

|

3 baths

|

2,600 sq ft

33298 LONE CEDAR LANDING LNDG 5802, MILL...
Community: Bishop's Landing
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.
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