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Middletown, MD 55+ active adult communities & homes for sale - Page 6

415 homes near Middletown

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The Village at Foxfield
$500Ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes
5 rating (1 reviews) Leisure World® of Marylan...
<$100k - $500Ks
Leisure World® of Marylan..., Silver Spring, MD
Resale Only | 55+ age-restricted | Built 1966 - 2009 | 5,600 homes
4.3 rating (11 reviews) Amblebrook
$300Ks - $600Ks
Amblebrook, Gettysburg, PA
New Construction | 55+ age-restricted | Built 2018 - present | 2,000 homes
5 rating (3 reviews) Heritage Hunt
$400Ks - $800Ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
2 rating (1 reviews) Birchwood at Brambleton
$400Ks - $900Ks
Birchwood at Brambleton, Ashburn, VA
New and Resale | 55+ age-restricted | Built 2016 - present | 1,502 homes
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5 rating (2 reviews) Potomac Green
$600Ks - $800Ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
5 rating (31 reviews) Lansdowne Woods of Virgin...
$300Ks - $500Ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 homes
Penn National
$200Ks - $600Ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
5 rating (2 reviews) Trilogy® at Lake Frederic...
$400Ks - $1Ms
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale | 55+ age-restricted | Built 2006 - present | 950 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 (1 reviews) Regency at Dominion Valle...
$400Ks - $500Ks
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes
5 rating (1 reviews) Four Seasons at Historic ...
$600Ks
Four Seasons at Historic ..., Dumfries, VA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 homes
5 rating (1 reviews) Two Rivers
$500Ks - $700Ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes
Cameron Grove
$200Ks - $400Ks
Cameron Grove, Upper Marlboro, MD
Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 homes
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5 rating (2 reviews) Central Parke at Victoria...
$400Ks - $600Ks
Central Parke at Victoria..., Laurel, MD
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 609 homes
Parklands
$300Ks - $600Ks
Parklands, White Plains, MD
New Construction | 55+ age-restricted | Built 2025 - present | 586 homes
The Woodlands of Urbana
$400Ks - $600Ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
5 rating (1 reviews) Crestwood Village
$300Ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 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.
Traditions of America at ...
$400Ks - $500Ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 517 homes
Carter's Mill
$400Ks - $700Ks
Carter's Mill, Haymarket, VA
New Construction | 55+ age-restricted | Built 2020 - present | 480 homes
3 rating (2 reviews) Dunbarton
$600Ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
The Courtyards at Waverly...
$300Ks - $800Ks
The Courtyards at Waverly..., Marriottsville, MD
Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 homes
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5 rating (1 reviews) Carroll Vista
$300Ks - $500Ks
Carroll Vista, Taneytown, MD
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 453 homes
Cedar Ridge at Piney Orch...
$300Ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes
Montebello
$600Ks - $1Ms
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
Village Crest
$300Ks
Village Crest, Ellicott City, MD
New and Resale | 55+ age-restricted | Built 2005 - 2010 | 406 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.
Courtyards at Waverly Woo...
$400Ks
Courtyards at Waverly Woo..., Woodstock, MD
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 383 homes
5 rating (1 reviews) Snowden Overlook
$400Ks - $700Ks
Snowden Overlook, Columbia, MD
Resale Only | 55+ age-restricted | Built 2005 - 2010 | 350 homes
Creek View
$100Ks - $200Ks
Creek View, Carlisle, PA
New and Resale | 55+ age-restricted | Built 2004 - present | 305 homes
Longstown Village
$100Ks - $200Ks
Longstown Village, York, PA
Resale Only | Age-targeted | Built 1997 - 2000 | 304 homes
Heritage at St. Charles
$400Ks - $500Ks
Heritage at St. Charles, White Plains, MD
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 300 homes
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Questions? Call us: (240) 663-8229
Willow Run
$400Ks - $600Ks
Willow Run, Winchester, VA
New Construction | 55+ age-restricted | 300 homes
The Villages At Woodholme
$400Ks - $500Ks
The Villages At Woodholme, Baltimore, MD
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 286 homes
Spring Hill
$500Ks - $800Ks
Spring Hill, Lorton, VA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes
The Enclave at Ellicott H...
$300Ks - $600Ks
The Enclave at Ellicott H..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 280 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.
Regency at Ashburn
$800Ks - $900Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
The Crest of Alexandria
$900Ks
The Crest of Alexandria, Alexandria, VA
New and Resale | 55+ age-restricted | Built 2017 - present | 250 homes
Emerald Pointe
$300Ks - $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
Colonial Charles
$400Ks
Colonial Charles, Waldorf, MD
Resale Only | 55+ age-restricted | Built 2006 - 2018 | 240 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
River Ridge
$500Ks
River Ridge, Woodbridge, VA
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 238 homes
Signature Club at Greenvi...
$400Ks - $600Ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes
Two Rivers 1219 BEAVER TREE DR, ODENTON, MD, 21113, Odenton, MD 21113
$519,000

2 beds

|

3 baths

|

1,410 sq ft

1219 BEAVER TREE DR, ODENTON, MD, 21113
Community: Two Rivers
Parklands 3958 KATMAI ST, WHITE PLAINS, MD, 20695, White Plains, MD 20695
$649,999

4 beds

|

4 baths

|

4,111 sq ft

3958 KATMAI ST, WHITE PLAINS, MD, 20695
Community: Parklands
Liberty Place 40 LIBERTY RD T, SYKESVILLE, MD, 21784, Sykesville, MD 21784
$334,900

2 beds

|

2 baths

|

1,186 sq ft

|

Condo

40 LIBERTY RD T, SYKESVILLE, MD, 21784
Community: Liberty Place
Leisure World® of Maryland 15401 BASSETT LN 45-2E, SILVER SPRING, M..., Silver Spring, MD 20906
$215,000

2 beds

|

2 baths

|

1,157 sq ft

|

Condo

15401 BASSETT LN 45-2E, SILVER SPRING, M...
Cedar Ridge at Piney Orchard 8615 WANDERING FOX TRL UNIT 405, ODENTON..., Odenton, MD 21113
$384,900

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

8615 WANDERING FOX TRL UNIT 405, ODENTON...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Leisure World® of Maryland 14507 ELMHAN CT # 182-B, SILVER SPRING, ..., Silver Spring, MD 20906
$434,000

3 beds

|

2 baths

|

1,193 sq ft

|

Condo

14507 ELMHAN CT # 182-B, SILVER SPRING, ...
Gatherings at Lyndwood 6155 SHADYWOOD RD 204, ELKRIDGE, MD, 210..., Elkridge, MD 21075
$419,500

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

6155 SHADYWOOD RD 204, ELKRIDGE, MD, 210...
The Enclave at Ellicott Hills 2550 KENSINGTON GDNS 205, ELLICOTT CITY,..., Ellicott City, MD 21043
$400,000

3 beds

|

2 baths

|

1,740 sq ft

|

Condo

2550 KENSINGTON GDNS 205, ELLICOTT CITY,...
Cameron Grove 14000 NEW ACADIA LN APT 106, UPPER MARLB..., Upper Marlboro, MD 20774
$285,000

1 beds

|

1 baths

|

1,020 sq ft

|

Condo

14000 NEW ACADIA LN APT 106, UPPER MARLB...
Community: Cameron Grove
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.
Ellicott Meadows 12022 WINDSOR MOSS 102, ELLICOTT CITY, M..., Ellicott City, MD 21042
$749,999

4 beds

|

4 baths

|

3,931 sq ft

|

Condo

12022 WINDSOR MOSS 102, ELLICOTT CITY, M...
Community: Ellicott Meadows
The Courtyards at Waverly Woods 2231 JOHN GRAVEL RD L, MARRIOTTSVILLE, M..., Marriottsville, MD 21104
$397,000

2 beds

|

2 baths

|

1,438 sq ft

|

Condo

2231 JOHN GRAVEL RD L, MARRIOTTSVILLE, M...
Leisure World® of Maryland 2900 N LEISURE WORLD BLVD 301, SILVER SP..., Silver Spring, MD 20906
$215,000

2 beds

|

2 baths

|

1,149 sq ft

|

Condo

2900 N LEISURE WORLD BLVD 301, SILVER SP...
Central Parke at Victoria Falls 13106 OLD FIELD TER, LAUREL, MD, 20707, Laurel, MD 20707
$614,900

4 beds

|

3 baths

|

3,304 sq ft

13106 OLD FIELD TER, LAUREL, MD, 20707
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Leisure World® of Maryland 3388 CHISWICK CT # 49-A, SILVER SPRING, ..., Silver Spring, MD 20906
$215,900

2 beds

|

3 baths

|

1,600 sq ft

|

Condo

3388 CHISWICK CT # 49-A, SILVER SPRING, ...
Parklands 5332 KINGS CANYON CT, WHITE PLAINS, MD, ..., White Plains, MD 20695
$450,000

4 beds

|

3 baths

|

2,728 sq ft

5332 KINGS CANYON CT, WHITE PLAINS, MD, ...
Community: Parklands
Cameron Grove 13507 LEESBURG PL, UPPER MARLBORO, MD, 2..., Upper Marlboro, MD 20774
$395,000

2 beds

|

2 baths

|

1,469 sq ft

13507 LEESBURG PL, UPPER MARLBORO, MD, 2...
Community: Cameron Grove
Gatherings at Lyndwood 6150 SHADYWOOD RD UNIT 401, ELKRIDGE, MD..., Elkridge, MD 21075
$425,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

6150 SHADYWOOD RD UNIT 401, ELKRIDGE, MD...
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.
Emerald Pointe 13336 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$424,900

2 beds

|

2 baths

|

2,615 sq ft

13336 MARQUISE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD APT 514, SILVE..., Silver Spring, MD 20906
$250,000

2 beds

|

2 baths

|

1,035 sq ft

|

Condo

3200 N LEISURE WORLD BLVD APT 514, SILVE...
Village Crest 8115 YELLOW PINE DR L, ELLICOTT CITY, MD..., Ellicott City, MD 21043
$385,000

2 beds

|

2 baths

|

1,574 sq ft

|

Condo

8115 YELLOW PINE DR L, ELLICOTT CITY, MD...
Community: Village Crest
Parklands 10147 SHENANDOAH LN, WHITE PLAINS, MD, 2..., White Plains, MD 20695
$567,490

3 beds

|

3 baths

|

2,593 sq ft

10147 SHENANDOAH LN, WHITE PLAINS, MD, 2...
Community: Parklands
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Leisure World® of Maryland 2901 S LEISURE WORLD BLVD 304, SILVER SP..., Silver Spring, MD 20906
$299,900

2 beds

|

2 baths

|

1,229 sq ft

|

Condo

2901 S LEISURE WORLD BLVD 304, SILVER SP...
Leisure World® of Maryland 3500 FOREST EDGE DR 15-2E, SILVER SPRING..., Silver Spring, MD 20906
$159,900

2 beds

|

2 baths

|

1,157 sq ft

|

Condo

3500 FOREST EDGE DR 15-2E, SILVER SPRING...
Ellicott's Retreat 8911 CARLS CT Q, ELLICOTT CITY, MD, 2104..., Ellicott City, MD 21043
$455,000

2 beds

|

2 baths

|

1,624 sq ft

|

Condo

8911 CARLS CT Q, ELLICOTT CITY, MD, 2104...
Community: Ellicott's Retreat
The Villages At Woodholme 8402 PRAIRIE ROSE PL # 8402, PIKESVILLE,..., Pikesville, MD 21208
$456,900

3 beds

|

4 baths

|

3,800 sq ft

|

Condo

8402 PRAIRIE ROSE PL # 8402, PIKESVILLE,...
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.
Watershed 1202 CRESTED WOOD DR, LAUREL, MD, 20724, Laurel, MD 20724
$664,990

4 beds

|

4 baths

|

2,660 sq ft

1202 CRESTED WOOD DR, LAUREL, MD, 20724
Community: Watershed
Leisure World® of Maryland 3310 N LEISURE WORLD BLVD 124, SILVER SP..., Silver Spring, MD 20906
$250,000

2 beds

|

2 baths

|

1,195 sq ft

|

Condo

3310 N LEISURE WORLD BLVD 124, SILVER SP...
Carroll Vista 172 SADDLETOP DR # 364, TANEYTOWN, MD, 2..., Taneytown, MD 21787
$329,900

1 beds

|

2 baths

|

1,419 sq ft

|

Condo

172 SADDLETOP DR # 364, TANEYTOWN, MD, 2...
Community: Carroll Vista
Leisure World® of Maryland 3005 S LEISURE WORLD BLVD APT 702, SILVE..., Silver Spring, MD 20906
$289,900

2 beds

|

2 baths

|

1,093 sq ft

|

Condo

3005 S LEISURE WORLD BLVD APT 702, SILVE...
Parklands 10628 GREAT BASIN PL, WHITE PLAINS, MD, ..., White Plains, MD 20695
$419,990

3 beds

|

4 baths

|

1,915 sq ft

10628 GREAT BASIN PL, WHITE PLAINS, MD, ...
Community: Parklands
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
The Enclave at Ellicott Hills 2530 KENSINGTON GDNS UNIT 406, ELLICOTT ..., Ellicott City, MD 21043
$415,000

3 beds

|

2 baths

|

1,750 sq ft

|

Condo

2530 KENSINGTON GDNS UNIT 406, ELLICOTT ...
Winifred Manor 2010 RUDY SERRA DR C, SYKESVILLE, MD, 21..., Sykesville, MD 21784
$275,000

2 beds

|

2 baths

|

1,080 sq ft

|

Condo

2010 RUDY SERRA DR C, SYKESVILLE, MD, 21...
Community: Winifred Manor
Leisure World® of Maryland 15115 INTERLACHEN DR 3-1020, SILVER SPRI..., Silver Spring, MD 20906
$235,000

2 beds

|

2 baths

|

980 sq ft

|

Condo

15115 INTERLACHEN DR 3-1020, SILVER SPRI...
Parklands 10635 GREAT BASIN PL, WHITE PLAINS, MD, ..., White Plains, MD 20695
$423,890

3 beds

|

3 baths

|

2,195 sq ft

10635 GREAT BASIN PL, WHITE PLAINS, MD, ...
Community: Parklands
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.
Parklands 10609 GREAT BASIN PL, WHITE PLAINS, MD, ..., White Plains, MD 20695
$409,990

3 beds

|

3 baths

|

1,917 sq ft

10609 GREAT BASIN PL, WHITE PLAINS, MD, ...
Community: Parklands
Emerald Pointe 13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742
$429,000

2 beds

|

3 baths

|

2,739 sq ft

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...
Community: Emerald Pointe
Parklands 10632 GREAT BASIN PL, WHITE PLAINS, MD, ..., White Plains, MD 20695
$399,990

3 beds

|

3 baths

|

1,918 sq ft

10632 GREAT BASIN PL, WHITE PLAINS, MD, ...
Community: Parklands
New Birchwood at Brambleton 23630 HAVELOCK WALK TER UNIT 405, ASHBUR..., Ashburn, VA 20148
$435,000

2 beds

|

2 baths

|

1,059 sq ft

|

Condo

23630 HAVELOCK WALK TER UNIT 405, ASHBUR...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Four Seasons at Historic Virginia 16040 DANCING LEAF PL, DUMFRIES, VA, 220..., Dumfries, VA 22025
$600,000

3 beds

|

2 baths

|

2,727 sq ft

16040 DANCING LEAF PL, DUMFRIES, VA, 220...
Regency at Dominion Valley 15251 ROYAL CREST DR APT 306, HAYMARKET,..., Haymarket, VA 20169
$500,000

3 beds

|

2 baths

|

1,833 sq ft

|

Condo

15251 ROYAL CREST DR APT 306, HAYMARKET,...

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