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Ocean Pines, MD 55+ active adult communities & homes for sale - Page 2

118 homes 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
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
$400Ks - $700Ks
Bay Crossing, Lewes, DE
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 homes
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
Ashland
$400Ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
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Questions? Call us: (667) 843-7291
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
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.
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
Wynndemere
$400Ks
Wynndemere, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2011 | 62 homes
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Questions? Call us: (667) 843-7291
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
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
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
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
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
$334,900

2 beds

|

2 baths

|

1,320 sq ft

134 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
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Questions? Call us: (667) 843-7291
Noble's Pond 213 NOBLES POND XING, DOVER, DE, 19904, Dover, DE 19904
$424,900

3 beds

|

2 baths

|

2,535 sq ft

213 NOBLES POND XING, DOVER, DE, 19904
Community: Noble's Pond
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
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 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
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 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
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
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
Village of Eastridge 131 LUPINE DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$430,000

2 beds

|

2 baths

|

2,303 sq ft

131 LUPINE DR, SMYRNA, DE, 19977
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Bishop's Landing 25512 FOX POINT LN, MILLVILLE, DE, 19967, Millville, DE 19967
$689,000

4 beds

|

3 baths

|

2,982 sq ft

25512 FOX POINT LN, MILLVILLE, DE, 19967
Community: Bishop's Landing
Heritage Shores 99 EMILYS PINTAIL DR, BRIDGEVILLE, DE, 1..., Bridgeville, DE 19933
$417,500

4 beds

|

3 baths

|

3,091 sq ft

99 EMILYS PINTAIL DR, BRIDGEVILLE, DE, 1...
Community: Heritage Shores
Forest Landing at Bethany Beach HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE..., Ocean View, DE 19970
$479,990

3 beds

|

3 baths

|

2,070 sq ft

HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE...
Silver Woods HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE..., Ocean View, DE 19970
$479,990

3 beds

|

3 baths

|

2,070 sq ft

HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE...
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 185 MERRICK WAY, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$419,990

3 beds

|

3 baths

|

2,201 sq ft

185 MERRICK WAY, OCEAN VIEW, DE, 19970
Community: Silver Woods
Silver Woods 342 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$514,990

4 beds

|

4 baths

|

2,443 sq ft

342 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Forest Landing at Bethany Beach 342 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$514,990

4 beds

|

4 baths

|

2,443 sq ft

342 GALLAGHER DR, OCEAN VIEW, DE, 19970
Bishop's Landing 17010 BELLEVUE CT, MILLVILLE, DE, 19967, Millville, DE 19967
$614,000

5 beds

|

4 baths

|

3,010 sq ft

17010 BELLEVUE CT, MILLVILLE, DE, 19967
Community: Bishop's Landing
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Four Seasons at Hatteras Hills 103 WANCHESE DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$502,900

3 beds

|

2 baths

|

1,778 sq ft

103 WANCHESE DR, MAGNOLIA, DE, 19962
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
Independence 26603 WHITEWATER CV, MILLSBORO, DE, 1996..., Millsboro, DE 19966
$175,000

3 beds

|

2 baths

|

1,550 sq ft

26603 WHITEWATER CV, MILLSBORO, DE, 1996...
Community: Independence
Spring Meadow 200 SPRING MEADOW DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$334,900

2 beds

|

2 baths

|

1,509 sq ft

200 SPRING MEADOW DR, SMYRNA, DE, 19977
Community: Spring Meadow
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 8 HARLEQUIN LOOP, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$345,900

3 beds

|

2 baths

|

1,845 sq ft

8 HARLEQUIN LOOP, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Bay Crossing 34775 SCHOONER PASS, LEWES, DE, 19958, Lewes, DE 19958
$460,000

3 beds

|

3 baths

|

1,600 sq ft

34775 SCHOONER PASS, LEWES, DE, 19958
Community: Bay Crossing
Heritage Shores 33 WATERSIDE DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$425,000

2 beds

|

2 baths

|

1,952 sq ft

33 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Independence 23792 SAMUEL ADAMS CIR, MILLSBORO, DE, 1..., Millsboro, DE 19966
$715,000

4 beds

|

3 baths

|

3,142 sq ft

23792 SAMUEL ADAMS CIR, MILLSBORO, DE, 1...
Community: Independence
The Village of Cinderberry 23 FRANKENBERRY DR, GEORGETOWN, DE, 1994..., Georgetown, DE 19947
$340,000

2 beds

|

2 baths

|

1,565 sq ft

|

Condo

23 FRANKENBERRY DR, GEORGETOWN, DE, 1994...
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
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
Heritage Shores 318 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$449,990

3 beds

|

2 baths

|

2,018 sq ft

318 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
Heritage Shores 16 BLUE HERON CT, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$419,900

3 beds

|

2 baths

|

1,890 sq ft

16 BLUE HERON CT, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Bay Crossing 34953 COMPASS CV, LEWES, DE, 19958, Lewes, DE 19958
$725,000

4 beds

|

4 baths

|

4,061 sq ft

34953 COMPASS CV, 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 3 AMANDAS TEAL DR, BRIDGEVILLE, DE, 1993..., Bridgeville, DE 19933
$399,900

3 beds

|

2 baths

|

2,420 sq ft

3 AMANDAS TEAL DR, BRIDGEVILLE, DE, 1993...
Community: Heritage Shores
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
The Village of Cinderberry 25 BAYBERRY ST # 13, GEORGETOWN, DE, 199..., Georgetown, DE 19947
$310,000

3 beds

|

2 baths

|

1,690 sq ft

|

Condo

25 BAYBERRY ST # 13, GEORGETOWN, DE, 199...
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
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Silver Woods 207 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$424,990

3 beds

|

3 baths

|

2,178 sq ft

207 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
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
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