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

440 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 - $500Ks
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 - $1Ms
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 - $400Ks
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
5 rating (1 reviews) Regency at Dominion Valle...
$400Ks - $700Ks
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 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) 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 - $500Ks
Cameron Grove, Upper Marlboro, MD
Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 homes
5 rating (2 reviews) Central Parke at Victoria...
$300Ks - $600Ks
Central Parke at Victoria..., Laurel, MD
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 609 homes
The Woodlands of Urbana
$600Ks
The Woodlands of Urbana, Urbana, MD
New Construction | 55+ age-restricted | Built 2019 - present | 565 homes
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5 rating (1 reviews) Crestwood Village
$300Ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
Traditions of America at ...
$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 - $600Ks
The Courtyards at Waverly..., Marriottsville, MD
Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 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) Carroll Vista
$300Ks - $500Ks
Carroll Vista, Taneytown, MD
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 453 homes
Cedar Ridge at Piney Orch...
$300Ks - $400Ks
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 - $400Ks
Village Crest, Ellicott City, MD
New and Resale | 55+ age-restricted | Built 2005 - 2010 | 406 homes
Courtyards at Waverly Woo...
$300Ks - $400Ks
Courtyards at Waverly Woo..., Woodstock, MD
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 383 homes
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Questions? Call us: (240) 663-8229
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
Heritage at St. Charles, White Plains, MD
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 300 homes
Willow Run
$400Ks - $600Ks
Willow Run, Winchester, VA
New Construction | 55+ age-restricted | 300 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.
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
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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
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
River Ridge
$500Ks - $700Ks
River Ridge, Woodbridge, VA
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 238 homes
Signature Club at Greenvi...
$400Ks - $900Ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes
Eden Brook
$300Ks
Eden Brook, Odenton, MD
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 224 homes
Amblebrook 39 REEDGRASS WAY, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$665,000

3 beds

|

3 baths

|

2,421 sq ft

39 REEDGRASS WAY, GETTYSBURG, PA, 17325
Community: Amblebrook
Country Manor 21 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$190,000

2 beds

|

2 baths

|

1,322 sq ft

21 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
Amblebrook 118 ELDERBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$411,990

3 beds

|

2 baths

|

1,736 sq ft

118 ELDERBERRY WAY, GETTYSBURG, PA, 1732...
Community: Amblebrook
Country Manor 81 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$205,000

2 beds

|

2 baths

|

1,550 sq ft

81 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
Traditions of America at Silver Spring 86 PRESIDENTS DR, MECHANICSBURG, PA, 170..., Mechanicsburg, PA 17050
$515,000

2 beds

|

2 baths

|

2,036 sq ft

|

Condo

86 PRESIDENTS DR, MECHANICSBURG, PA, 170...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Amblebrook 118 NEW VISTA WAY, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$484,900

2 beds

|

2 baths

|

1,733 sq ft

118 NEW VISTA WAY, GETTYSBURG, PA, 17325
Community: Amblebrook
Amblebrook 126 ELDERBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$399,990

3 beds

|

2 baths

|

1,736 sq ft

126 ELDERBERRY WAY, GETTYSBURG, PA, 1732...
Community: Amblebrook
Cortland Park 787 AURORA DR, MECHANICSBURG, PA, 17055, Mechanicsburg, PA 17055
$489,900

3 beds

|

3 baths

|

2,360 sq ft

787 AURORA DR, MECHANICSBURG, PA, 17055
Community: Cortland Park
Penn National 5860 FAIRWAY DR W APT 4, FAYETTEVILLE, P..., Fayetteville, PA 17222
$204,000

2 beds

|

2 baths

|

1,598 sq ft

|

Condo

5860 FAIRWAY DR W APT 4, FAYETTEVILLE, P...
Community: Penn National
Carmella 110 BLUEBELL DR, MECHANICSBURG, PA, 1705..., Mechanicsburg, PA 17050
$415,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

110 BLUEBELL DR, MECHANICSBURG, PA, 1705...
Community: Carmella
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.
Amblebrook 85 QUIET CREEK DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$599,990

2 beds

|

2 baths

|

2,220 sq ft

85 QUIET CREEK DR, GETTYSBURG, PA, 17325
Community: Amblebrook
Creek View 118 GLENRIDGE DR, CARLISLE, PA, 17015, Carlisle, PA 17015
$269,710

2 beds

|

2 baths

|

1,408 sq ft

118 GLENRIDGE DR, CARLISLE, PA, 17015
Community: Creek View
Amblebrook 294 RUSTIC WOOD DR, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$574,900

2 beds

|

2 baths

|

2,474 sq ft

294 RUSTIC WOOD DR, GETTYSBURG, PA, 1732...
Community: Amblebrook
Cherry Tree 679 CYPRESS DR # 76, HANOVER, PA, 17331, Hanover, PA 17331
$324,900

3 beds

|

2 baths

|

1,568 sq ft

679 CYPRESS DR # 76, HANOVER, PA, 17331
Community: Cherry Tree
Sagebrook 880 SHADOWBROOKE DR, DOVER, PA, 17315, Dover, PA 17315
$379,990

2 beds

|

2 baths

880 SHADOWBROOKE DR, DOVER, PA, 17315
Community: Sagebrook
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Penn National 6352 PENN NATIONAL DR, CHAMBERSBURG, PA,..., Chambersburg, PA 17201
$495,000

3 beds

|

2 baths

|

2,173 sq ft

6352 PENN NATIONAL DR, CHAMBERSBURG, PA,...
Community: Penn National
Penn National 6357 9TH VW, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222
$329,900

3 beds

|

2 baths

|

1,958 sq ft

|

Condo

6357 9TH VW, FAYETTEVILLE, PA, 17222
Community: Penn National
Country Manor 84 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$184,900

2 beds

|

2 baths

|

1,438 sq ft

84 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
Winchester Landing 100 MAURY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602
$385,000

3 beds

|

3 baths

|

1,678 sq ft

100 MAURY WAY, WINCHESTER, VA, 22602
Community: Winchester Landing
New Cedar Ridge at Piney Orchard 8615 WANDERING FOX TRL 208, ODENTON, MD,..., Odenton, MD 21113
$350,000

2 beds

|

2 baths

|

1,400 sq ft

|

Condo

8615 WANDERING FOX TRL 208, ODENTON, 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.
Cameron Grove 13216 FOX BOW DR 403, UPPER MARLBORO, MD..., Upper Marlboro, MD 20774
$333,900

2 beds

|

2 baths

|

1,298 sq ft

|

Condo

13216 FOX BOW DR 403, UPPER MARLBORO, MD...
Community: Cameron Grove
Leisure World® of Maryland 15301 PINE ORCHARD DR 86-3E, SILVER SPRI..., Silver Spring, MD 20906
$269,999

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15301 PINE ORCHARD DR 86-3E, SILVER SPRI...
Leisure World® of Maryland 3210 N LEISURE WORLD BLVD 1001, SILVER S..., Silver Spring, MD 20906
$449,000

3 beds

|

2 baths

|

1,544 sq ft

|

Condo

3210 N LEISURE WORLD BLVD 1001, SILVER S...
Central Parke at Victoria Falls 13401 BELLE CHASSE BLVD 411, LAUREL, MD,..., Laurel, MD 20707
$385,000

2 beds

|

2 baths

|

1,673 sq ft

|

Condo

13401 BELLE CHASSE BLVD 411, LAUREL, MD,...
Gatherings at Forest Glen 8603 WINTERGREEN CT UNIT 201, ODENTON, M..., Odenton, MD 21113
$340,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

8603 WINTERGREEN CT UNIT 201, ODENTON, M...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Gatherings at Cabin Branch 13240 PETREL ST # 106, CLARKSBURG, MD, 2..., Clarksburg, MD 20871
$399,990

1 beds

|

1 baths

|

1,203 sq ft

|

Condo

13240 PETREL ST # 106, CLARKSBURG, MD, 2...
The Village at Cabin Branch 13240 PETREL ST # 106, CLARKSBURG, MD, 2..., Clarksburg, MD 20871
$399,990

1 beds

|

1 baths

|

1,203 sq ft

|

Condo

13240 PETREL ST # 106, CLARKSBURG, MD, 2...
Leisure World® of Maryland 3210 N LEISURE WORLD BLVD 308, SILVER SP..., Silver Spring, MD 20906
$339,900

2 beds

|

2 baths

|

1,335 sq ft

|

Condo

3210 N LEISURE WORLD BLVD 308, SILVER SP...
New Leisure World® of Maryland 15107 INTERLACHEN DR 2-215, SILVER SPRIN..., Silver Spring, MD 20906
$240,000

2 beds

|

2 baths

|

1,120 sq ft

|

Condo

15107 INTERLACHEN DR 2-215, SILVER SPRIN...
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD 115, SILVER SP..., Silver Spring, MD 20906
$300,000

3 beds

|

2 baths

|

1,489 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 115, SILVER SP...
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.
Bethany Glen 9987 CALMING CT, ELLICOTT CITY, MD, 2104..., Ellicott City, MD 21042
$768,990

3 beds

|

3 baths

|

2,734 sq ft

9987 CALMING CT, ELLICOTT CITY, MD, 2104...
Community: Bethany Glen
Leisure World® of Maryland 2904 N LEISURE WORLD BLVD 211, SILVER SP..., Silver Spring, MD 20906
$228,500

2 beds

|

2 baths

|

1,041 sq ft

|

Condo

2904 N LEISURE WORLD BLVD 211, SILVER SP...
The Village at Cabin Branch 13444 PETREL ST, CLARKSBURG, MD, 20871, Clarksburg, MD 20871
$564,999

3 beds

|

3 baths

|

1,933 sq ft

13444 PETREL ST, CLARKSBURG, MD, 20871
Gatherings at Cabin Branch 13444 PETREL ST, CLARKSBURG, MD, 20871, Clarksburg, MD 20871
$564,999

3 beds

|

3 baths

|

1,933 sq ft

13444 PETREL ST, CLARKSBURG, MD, 20871
Cedar Ridge at Piney Orchard 8612 FLUTTERING LEAF TRL 203, ODENTON, M..., Odenton, MD 21113
$399,900

2 beds

|

2 baths

|

1,700 sq ft

|

Condo

8612 FLUTTERING LEAF TRL 203, ODENTON, M...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Leisure World® of Maryland 15101 INTERLACHEN DR 1-123, SILVER SPRIN..., Silver Spring, MD 20906
$234,900

2 beds

|

2 baths

|

1,225 sq ft

|

Condo

15101 INTERLACHEN DR 1-123, SILVER SPRIN...
Heritage at St. Charles 4909 KESWICK CT, WHITE PLAINS, MD, 20695, White Plains, MD 20695
$475,000

4 beds

|

3 baths

|

2,081 sq ft

4909 KESWICK CT, WHITE PLAINS, MD, 20695
Snowden Overlook 8740 ENDLESS OCEAN WAY 26, COLUMBIA, MD,..., Columbia, MD 21045
$729,900

3 beds

|

4 baths

|

3,540 sq ft

|

Condo

8740 ENDLESS OCEAN WAY 26, COLUMBIA, MD,...
Community: Snowden Overlook
Leisure World® of Maryland 3500 FOREST EDGE DR 15-2F, SILVER SPRING..., Silver Spring, MD 20906
$185,000

1 beds

|

2 baths

|

946 sq ft

3500 FOREST EDGE DR 15-2F, SILVER SPRING...
Gatherings at Lyndwood 7305 MAPLECREST RD 207, ELKRIDGE, MD, 21..., Elkridge, MD 21075
$459,000

3 beds

|

2 baths

|

1,900 sq ft

|

Condo

7305 MAPLECREST RD 207, ELKRIDGE, MD, 21...

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440 homes near Middletown
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