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

489 homes near Middletown

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No reviews yet The Village at Foxfield
$300Ks - $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 - $1Ms
Amblebrook, Gettysburg, PA
New Construction | 55+ age-restricted | Built 2018 - present | 2,000 homes
5 rating (3 reviews) Heritage Hunt
$600Ks - $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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
5 rating (2 reviews) Potomac Green
$700Ks - $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
No reviews yet Penn National
$200Ks - $800Ks
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 - $800Ks
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 - $700Ks
Four Seasons at Historic ..., Dumfries, VA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 homes
5 rating (1 reviews) Two Rivers
$500Ks - $800Ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes
No reviews yet Cameron Grove
$300Ks - $400Ks
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
No reviews yet The Woodlands of Urbana
$600Ks - $700Ks
The Woodlands of Urbana, Urbana, MD
New Construction | 55+ age-restricted | Built 2019 - present | 565 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
5 rating (1 reviews) Crestwood Village
$300Ks - $300Ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
No reviews yet Traditions of America at ...
$400Ks - $500Ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 517 homes
No reviews yet 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 - $600Ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
No reviews yet 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
No reviews yet Cedar Ridge at Piney Orch...
$300Ks - $400Ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes
No reviews yet Montebello
$600Ks - $1Ms
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
No reviews yet Village Crest
$400Ks - $600Ks
Village Crest, Ellicott City, MD
New and Resale | 55+ age-restricted | Built 2005 - 2010 | 406 homes
No reviews yet Courtyards at Waverly Woo...
$300Ks - $400Ks
Courtyards at Waverly Woo..., Woodstock, MD
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 383 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
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
No reviews yet Creek View
$100Ks - $200Ks
Creek View, Carlisle, PA
New and Resale | 55+ age-restricted | Built 2004 - present | 305 homes
No reviews yet Longstown Village
$100Ks - $200Ks
Longstown Village, York, PA
Resale Only | Age-targeted | Built 1997 - 2000 | 304 homes
No reviews yet Heritage at St. Charles
$400Ks - $500Ks
Heritage at St. Charles, White Plains, MD
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 300 homes
No reviews yet The Villages At Woodholme
$400Ks - $500Ks
The Villages At Woodholme, Baltimore, MD
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 286 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.
No reviews yet Spring Hill
$500Ks - $800Ks
Spring Hill, Lorton, VA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes
No reviews yet The Enclave at Ellicott H...
$400Ks - $400Ks
The Enclave at Ellicott H..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 280 homes
No reviews yet Regency at Ashburn
$500Ks - $600Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
No reviews yet Emerald Pointe
$300Ks - $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
No reviews yet The Crest of Alexandria
$900Ks - $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
No reviews yet Colonial Charles
$400Ks - $400Ks
Colonial Charles, Waldorf, MD
Resale Only | 55+ age-restricted | Built 2006 - 2018 | 240 homes
No reviews yet River Ridge
$600Ks - $600Ks
River Ridge, Woodbridge, VA
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 238 homes
No reviews yet Signature Club at Greenvi...
$400Ks - $900Ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes
No reviews yet Eden Brook
$300Ks - $300Ks
Eden Brook, Odenton, MD
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 224 homes
No reviews yet Roth's Farm Village
$200Ks - $200Ks
Roth's Farm Village, Spring Grove, PA
New and Resale | 55+ age-restricted | Built 2006 - present | 224 homes
Leisure World® of Maryland 2 FINSBURY PARK CT # 47-A, SILVER SPRING..., Silver Spring, MD 20906
$445,000

3 beds

|

2 baths

|

1,193 sq ft

|

Condo

2 FINSBURY PARK CT # 47-A, SILVER SPRING...
Courts of Clarksburg 825 BUTTERFLY WEED DR, GERMANTOWN, MD, 2..., Germantown, MD 20876
$740,000

2 beds

|

2 baths

|

1,806 sq ft

825 BUTTERFLY WEED DR, GERMANTOWN, MD, 2...
Cameron Grove 13200 WRIGHT PL, UPPER MARLBORO, MD, 207..., Upper Marlboro, MD 20774
$475,000

3 beds

|

3 baths

|

2,100 sq ft

13200 WRIGHT PL, UPPER MARLBORO, MD, 207...
Community: Cameron Grove
Snowden Overlook 8656 VAST ROSE DR 23, COLUMBIA, MD, 2104..., Columbia, MD 21045
$775,000

4 beds

|

5 baths

|

3,719 sq ft

|

Condo

8656 VAST ROSE DR 23, COLUMBIA, MD, 2104...
Community: Snowden Overlook
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,...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Leisure World® of Maryland 3100 N LEISURE WORLD BLVD 812, SILVER SP..., Silver Spring, MD 20906
$339,900

2 beds

|

2 baths

|

1,325 sq ft

|

Condo

3100 N LEISURE WORLD BLVD 812, SILVER SP...
Carroll Vista 419 CLUBSIDE DR # 296, TANEYTOWN, MD, 21..., Taneytown, MD 21787
$425,000

3 beds

|

3 baths

|

1,697 sq ft

|

Condo

419 CLUBSIDE DR # 296, TANEYTOWN, MD, 21...
Community: Carroll Vista
Cedar Ridge at Piney Orchard 8610 FLUTTERING LEAF TRL 208, ODENTON, M..., Odenton, MD 21113
$385,000

2 beds

|

2 baths

|

1,400 sq ft

|

Condo

8610 FLUTTERING LEAF TRL 208, ODENTON, M...
Leisure World® of Maryland 3101 FARNBOROUGH CT # 257B, SILVER SPRIN..., Silver Spring, MD 20906
$275,000

2 beds

|

2 baths

|

998 sq ft

3101 FARNBOROUGH CT # 257B, SILVER SPRIN...
Leisure World® of Maryland 3525 TARKINGTON LN # 63-B, SILVER SPRING..., Silver Spring, MD 20906
$415,000

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

3525 TARKINGTON LN # 63-B, SILVER SPRING...
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.
Leisure World® of Maryland 3434 GLENEAGLES DR # 78-B, SILVER SPRING..., Silver Spring, MD 20906
$262,000

2 beds

|

3 baths

|

1,600 sq ft

|

Condo

3434 GLENEAGLES DR # 78-B, SILVER SPRING...
Snowden Overlook 8820 SHINING OCEANS WAY UNIT 407, COLUMB..., Columbia, MD 21045
$520,000

3 beds

|

2 baths

|

1,924 sq ft

|

Condo

8820 SHINING OCEANS WAY UNIT 407, COLUMB...
Community: Snowden Overlook
Leisure World® of Maryland 15003 CANDOVER CT # 281-C, SILVER SPRING..., Silver Spring, MD 20906
$259,900

2 beds

|

3 baths

|

1,359 sq ft

|

Condo

15003 CANDOVER CT # 281-C, SILVER SPRING...
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...
Carroll Vista 172 SADDLETOP DR # 364, TANEYTOWN, MD, 2..., Taneytown, MD 21787
$334,900

1 beds

|

2 baths

|

1,419 sq ft

|

Condo

172 SADDLETOP DR # 364, TANEYTOWN, MD, 2...
Community: Carroll Vista
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 ...
Leisure World® of Maryland 3311 S LEISURE WORLD BLVD 99-3D, SILVER ..., Silver Spring, MD 20906
$100,000

1 beds

|

1 baths

|

800 sq ft

|

Condo

3311 S LEISURE WORLD BLVD 99-3D, SILVER ...
Leisure World® of Maryland 3005 S LEISURE WORLD BLVD 821, SILVER SP..., Silver Spring, MD 20906
$375,000

2 beds

|

2 baths

|

1,601 sq ft

|

Condo

3005 S LEISURE WORLD BLVD 821, SILVER SP...
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 2904 N LEISURE WORLD BLVD APT 514, SILVE..., Silver Spring, MD 20906
$199,500

1 beds

|

1 baths

|

888 sq ft

|

Condo

2904 N LEISURE WORLD BLVD APT 514, SILVE...
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 Woodlands of Urbana 2928 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704
$725,000

3 beds

|

4 baths

|

3,634 sq ft

2928 HERB GARDEN DR, FREDERICK, MD, 2170...
Leisure World® of Maryland 2904 N LEISURE WORLD BLVD 501, SILVER SP..., Silver Spring, MD 20906
$289,000

2 beds

|

2 baths

|

1,111 sq ft

|

Condo

2904 N LEISURE WORLD BLVD 501, SILVER SP...
Villas at Cattail Creek 15236 CALLAWAY CT 32, GLENWOOD, MD, 2173..., Glenwood, MD 21738
$647,000

4 beds

|

4 baths

|

4,223 sq ft

|

Condo

15236 CALLAWAY CT 32, GLENWOOD, MD, 2173...
Leisure World® of Maryland 15311 BEAVERBROOK CT 90-2E, SILVER SPRIN..., Silver Spring, MD 20906
$270,000

3 beds

|

2 baths

|

1,340 sq ft

|

Condo

15311 BEAVERBROOK CT 90-2E, SILVER SPRIN...
Leisure World® of Maryland 3330 N LEISURE WORLD BLVD 5-1012, SILVER..., Silver Spring, MD 20906
$189,999

2 beds

|

2 baths

|

980 sq ft

|

Condo

3330 N LEISURE WORLD BLVD 5-1012, SILVER...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Leisure World® of Maryland 3310 N LEISURE WORLD BLVD 520, SILVER SP..., Silver Spring, MD 20906
$179,700

2 beds

|

2 baths

|

980 sq ft

|

Condo

3310 N LEISURE WORLD BLVD 520, SILVER SP...
The Courtyards at Waverly Woods 2350 ADAM DAVID WAY, MARRIOTTSVILLE, MD,..., Marriottsville, MD 21104
$670,000

3 beds

|

3 baths

|

3,444 sq ft

2350 ADAM DAVID WAY, MARRIOTTSVILLE, MD,...
Carroll Vista 152 SADDLETOP DR # 354, TANEYTOWN, MD, 2..., Taneytown, MD 21787
$362,500

2 beds

|

2 baths

|

1,679 sq ft

|

Condo

152 SADDLETOP DR # 354, TANEYTOWN, MD, 2...
Community: Carroll Vista
Gatherings at Jefferson Place 8801 BOSLEY RD UNIT 401, ELLICOTT CITY, ..., Ellicott City, MD 21043
$400,000

2 beds

|

2 baths

|

1,480 sq ft

|

Condo

8801 BOSLEY RD UNIT 401, ELLICOTT CITY, ...
Snowden Overlook 8820 SHINING OCEANS WAY 410, COLUMBIA, M..., Columbia, MD 21045
$499,000

2 beds

|

2 baths

|

1,787 sq ft

|

Condo

8820 SHINING OCEANS WAY 410, COLUMBIA, M...
Community: Snowden Overlook
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 Woods East 11110 CHAMBERS CT A, WOODSTOCK, MD, 2116..., Woodstock, MD 21163
$385,000

2 beds

|

2 baths

|

1,595 sq ft

|

Condo

11110 CHAMBERS CT A, WOODSTOCK, MD, 2116...
Leisure World® of Maryland 15101 INTERLACHEN DR 1-823, SILVER SPRIN..., Silver Spring, MD 20906
$210,000

2 beds

|

2 baths

|

1,225 sq ft

|

Condo

15101 INTERLACHEN DR 1-823, SILVER SPRIN...
Cameron Grove 13712 NEW ACADIA LN, UPPER MARLBORO, MD,..., Upper Marlboro, MD 20774
$455,000

2 beds

|

2 baths

|

1,720 sq ft

13712 NEW ACADIA LN, UPPER MARLBORO, MD,...
Community: Cameron Grove
Cedar Ridge at Piney Orchard 8600 ROAMING RIDGE WAY UNIT 106, ODENTON..., Odenton, MD 21113
$415,000

2 beds

|

2 baths

|

1,600 sq ft

|

Condo

8600 ROAMING RIDGE WAY UNIT 106, ODENTON...
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 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...
Leisure World® of Maryland 14801 PENNFIELD CIR 412, SILVER SPRING, ..., Silver Spring, MD 20906
$349,900

2 beds

|

2 baths

|

1,361 sq ft

|

Condo

14801 PENNFIELD CIR 412, SILVER SPRING, ...
Courtyards at Waverly Woods East 11150 CHAMBERS CT H, WOODSTOCK, MD, 2116..., Woodstock, MD 21163
$410,000

2 beds

|

2 baths

|

1,610 sq ft

|

Condo

11150 CHAMBERS CT H, WOODSTOCK, MD, 2116...
Gatherings at Forest Glen 8612 WINTERGREEN CT 105, ODENTON, MD, 21..., Odenton, MD 21113
$365,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

8612 WINTERGREEN CT 105, ODENTON, MD, 21...
Leisure World® of Maryland 3005 S LEISURE WORLD BLVD 802, SILVER SP..., Silver Spring, MD 20906
$265,000

2 beds

|

2 baths

|

1,093 sq ft

|

Condo

3005 S LEISURE WORLD BLVD 802, SILVER SP...

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489 homes near Middletown
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