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

189 homes near Ocean Pines

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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
$200ks - $300ks
Noble's Pond, Dover, DE
New and Resale | 55+ age-restricted | Built 2007 - present | 800 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
The Village of Cinderberr...
$200ks - $300ks
The Village of Cinderberr..., Georgetown, DE
New and Resale | 55+ age-restricted | Built 2003 - present | 170 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
5 rating (3 reviews) Village of Eastridge
$300ks - $400ks
Village of Eastridge, Smyrna, DE
New Construction | 55+ age-restricted | Built 2014 - present | 189 homes
Sundance Club
$500ks - $800ks
Sundance Club, Frankford, DE
New Construction | 55+ age-restricted | Built 2026 - present | 180 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
Longacre Village
$300ks
Longacre Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 250 homes
Liberty West
$400ks
Liberty West, Georgetown, DE
New Construction | Age-targeted | Built 2025 - present | 181 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
Auburn Meadows
$400ks - $500ks
Auburn Meadows, Smyrna, DE
New Construction | 55+ age-restricted | Built 2022 - present | 262 homes
Ashland
$300ks - $400ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
3.7 rating (3 reviews) Spring Meadow
$300ks - $400ks
Spring Meadow, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 246 homes
3 rating (5 reviews) Heritage Creek
$300ks - $500ks
Heritage Creek, Milton, DE
New and Resale | Age-targeted | Built 2008 - present | 400 homes
Osprey Point
$300ks - $400ks
Osprey Point, Upper Township, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 149 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Legacy at Cape May
$400ks - $500ks
Legacy at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 141 homes
3.3 rating (3 reviews) Windstone
$400ks
Windstone, Milton, DE
Resale Only | Age-targeted | Built 2017 - 2022 | 260 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
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.
Independence
$400ks - $800ks
Independence, Millsboro, DE
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 455 homes
Bay Crossing
$400ks - $600ks
Bay Crossing, Lewes, DE
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 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
Four Seasons at Belle Ter...
$400ks - $600ks
Four Seasons at Belle Ter..., Lewes, DE
New Construction | 55+ age-restricted | Built 2019 - present | 269 homes
Champions' Club
$300ks - $400ks
Champions' Club, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 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
Wynndemere
$400ks
Wynndemere, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2011 | 62 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Fieldstone Village
$200ks - $300ks
Fieldstone Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2002 - present | 98 homes
Gateway Shores
$200ks - $300ks
Gateway Shores, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 1996 - 2002 | 66 homes
Gatherings at Cape May
$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.
Forest Landing at Bethany...
$300ks - $500ks
Forest Landing at Bethany..., Frankford, DE
New and Resale | Age-targeted | Built 2012 - present | 280 homes
SummersGate
$300ks
SummersGate, Salisbury, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 216 homes
Cedar Bay
$200ks - $300ks
Cedar Bay, Ocean View, DE
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 72 homes
Roesville
$300ks
Roesville, Felton, DE
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 470 homes
The Village of Cinderberry 14 MULBERRY ST, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$342,000

2 beds

|

2 baths

|

1,591 sq ft

14 MULBERRY ST, GEORGETOWN, DE, 19947
Silver Woods 309 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$487,990

3 beds

|

3 baths

|

2,088 sq ft

309 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Bishop's Landing 38652 LONGS CHAPEL LN, MILLVILLE, DE, 19..., Millville, DE 19967
$699,900

5 beds

|

3 baths

|

2,900 sq ft

38652 LONGS CHAPEL LN, MILLVILLE, DE, 19...
Community: Bishop's Landing
The Villages at Red Mill Pond 18680 GOLDEN SUNRISE PL, LEWES, DE, 1995..., Lewes, DE 19958
$799,900

5 beds

|

4 baths

|

3,902 sq ft

18680 GOLDEN SUNRISE PL, LEWES, DE, 1995...
Silver Woods 321 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$460,990

3 beds

|

3 baths

|

2,088 sq ft

321 GALLAGHER DR, 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
Silver Woods 317 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$451,990

3 beds

|

3 baths

|

2,088 sq ft

317 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Silver Woods 333 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$435,990

3 beds

|

3 baths

|

2,088 sq ft

333 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Silver Woods 315 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$439,990

3 beds

|

3 baths

|

2,267 sq ft

315 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Silver Woods 329 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$447,990

3 beds

|

3 baths

|

2,267 sq ft

329 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Windstone 16272 ASHLAR LOOP, MILTON, DE, 19968, Milton, DE 19968
$515,000

4 beds

|

3 baths

|

2,372 sq ft

16272 ASHLAR LOOP, MILTON, DE, 19968
Community: Windstone
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.
Sundance Club 36034 LOOKOUT RUN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$769,900

3 beds

|

3 baths

|

2,720 sq ft

|

Condo

36034 LOOKOUT RUN, OCEAN VIEW, DE, 19970
Community: Sundance Club
Sundance Club 36030 LOOKOUT RUN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$704,900

4 beds

|

3 baths

|

2,720 sq ft

|

Condo

36030 LOOKOUT RUN, OCEAN VIEW, DE, 19970
Community: Sundance Club
Sundance Club 36026 LOOKOUT RUN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$684,900

4 beds

|

3 baths

|

2,156 sq ft

|

Condo

36026 LOOKOUT RUN, OCEAN VIEW, DE, 19970
Community: Sundance Club
Sundance Club 36014 LOOKOUT RUN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$654,900

3 beds

|

3 baths

|

2,082 sq ft

|

Condo

36014 LOOKOUT RUN, OCEAN VIEW, DE, 19970
Community: Sundance Club
Sundance Club 36020 LOOKOUT RUN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$654,900

3 beds

|

3 baths

|

2,193 sq ft

|

Condo

36020 LOOKOUT RUN, OCEAN VIEW, DE, 19970
Community: Sundance Club
Sundance Club 32276 SUNDANCE CIR, OCEAN VIEW, DE, 1997..., Ocean View, DE 19970
$579,900

3 beds

|

2 baths

|

1,567 sq ft

|

Condo

32276 SUNDANCE CIR, OCEAN VIEW, DE, 1997...
Community: Sundance Club
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Sundance Club 32280 SUNDANCE CIR, OCEAN VIEW, DE, 1997..., Ocean View, DE 19970
$549,900

2 beds

|

2 baths

|

1,411 sq ft

|

Condo

32280 SUNDANCE CIR, OCEAN VIEW, DE, 1997...
Community: Sundance Club
Sundance Club 32274 SUNDANCE CIR, OCEAN VIEW, DE, 1997..., Ocean View, DE 19970
$604,900

3 beds

|

2 baths

|

1,661 sq ft

|

Condo

32274 SUNDANCE CIR, OCEAN VIEW, DE, 1997...
Community: Sundance Club
Village of Eastridge 74 FELIX VIEW CT, SMYRNA, DE, 19977, Smyrna, DE 19977
$379,900

2 beds

|

2 baths

|

1,584 sq ft

74 FELIX VIEW CT, SMYRNA, DE, 19977
Wynndemere 26 WYNNDEMERE CT, CAPE MAY COURT HOUSE, ..., Cape May Court House, NJ 08210
$550,000

3 beds

|

2 baths

|

1,644 sq ft

|

Other

26 WYNNDEMERE CT, CAPE MAY COURT HOUSE, ...
Community: Wynndemere
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 336 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$445,000

3 beds

|

2 baths

|

1,533 sq ft

336 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
Longacre Village 216 N RED HAVEN LN, DOVER, DE, 19901, Dover, DE 19901
$385,000

2 beds

|

2 baths

|

1,764 sq ft

216 N RED HAVEN LN, DOVER, DE, 19901
Community: Longacre Village
Spring Meadow 594 SORRELL CIR, SMYRNA, DE, 19977, Smyrna, DE 19977
$319,900

2 beds

|

2 baths

|

1,323 sq ft

594 SORRELL CIR, SMYRNA, DE, 19977
Community: Spring Meadow
Heritage Shores 305 WATERSIDE SQ, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$349,900

2 beds

|

2 baths

|

1,508 sq ft

305 WATERSIDE SQ, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Ashland 145 E CLARENDON DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$385,000

2 beds

|

2 baths

|

1,796 sq ft

145 E CLARENDON DR, SMYRNA, DE, 19977
Community: Ashland
Bishop's Landing 30243 BRANDYWINE DR, MILLVILLE, DE, 1996..., Millville, DE 19967
$649,900

5 beds

|

4 baths

|

3,300 sq ft

30243 BRANDYWINE DR, MILLVILLE, DE, 1996...
Community: Bishop's Landing
Longacre Village 103 CANDOR LN, DOVER, DE, 19901, Dover, DE 19901
$330,000

3 beds

|

3 baths

|

2,231 sq ft

103 CANDOR LN, DOVER, DE, 19901
Community: Longacre Village
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Independence 29664 PATRICK HENRY CIR, MILLSBORO, DE, ..., Millsboro, DE 19966
$650,000

3 beds

|

3 baths

|

2,244 sq ft

29664 PATRICK HENRY CIR, MILLSBORO, DE, ...
Community: Independence
Heritage Shores 322 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$489,990

3 beds

|

3 baths

|

2,292 sq ft

322 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
Village of Eastridge 101 HENGST FARM LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$459,322

2 beds

|

3 baths

|

1,645 sq ft

101 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.
The Village of Cinderberry 13 FRANKENBERRY DR, GEORGETOWN, DE, 1994..., Georgetown, DE 19947
$380,000

3 beds

|

2 baths

|

1,372 sq ft

|

Condo

13 FRANKENBERRY DR, GEORGETOWN, DE, 1994...
Auburn Meadows 106 BERKS RD, SMYRNA, DE, 19977, Smyrna, DE 19977
$453,000

3 beds

|

3 baths

|

2,246 sq ft

106 BERKS RD, SMYRNA, DE, 19977
Community: Auburn Meadows
Osprey Point 1731 ROUTE 9 9, SEAVILLE, NJ, 08250, Seaville, NJ 08250
$539,900

2 beds

|

2 baths

|

2,002 sq ft

|

Other

1731 ROUTE 9 9, SEAVILLE, NJ, 08250
Community: Osprey Point
Longacre Village 118 WINESAP LN, DOVER, DE, 19901, Dover, DE 19901
$469,900

3 beds

|

3 baths

|

3,089 sq ft

118 WINESAP LN, DOVER, DE, 19901
Community: Longacre Village
The Villages at Red Mill Pond 16512 GREENSPRING AVE, LEWES, DE, 19958, Lewes, DE 19958
$629,900

3 beds

|

3 baths

|

2,400 sq ft

16512 GREENSPRING AVE, LEWES, DE, 19958
The Village of Cinderberry 4 FRANKENBERRY DR 138, GEORGETOWN, DE, 1..., Georgetown, DE 19947
$360,000

2 beds

|

2 baths

|

1,868 sq ft

|

Condo

4 FRANKENBERRY DR 138, GEORGETOWN, DE, 1...
Silver Woods 246 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$499,990

4 beds

|

4 baths

|

2,500 sq ft

246 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
The Parke at Ocean Pines 11421 MANKLIN CREEK RD 1, BERLIN, MD, 21..., Berlin, MD 21811
$295,000

3 beds

|

2 baths

|

1,181 sq ft

|

Condo

11421 MANKLIN CREEK RD 1, BERLIN, MD, 21...
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
The Villages at Red Mill Pond 17563 CLOUD NINE DR, LEWES, DE, 19958, Lewes, DE 19958
$549,900

3 beds

|

2 baths

|

2,228 sq ft

17563 CLOUD NINE DR, LEWES, DE, 19958
Liberty West 36802 W OLD GATE DR, GEORGETOWN, DE, 199..., Georgetown, DE 19947
$469,990

3 beds

|

2 baths

|

1,976 sq ft

36802 W OLD GATE DR, GEORGETOWN, DE, 199...
Community: Liberty West
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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