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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
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
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
New The Atrium at MetroWest 9555 SAINTSBURY DR UNIT 503, FAIRFAX, VA..., Fairfax, VA 22031
$799,000

2 beds

|

2 baths

|

1,546 sq ft

|

Condo

9555 SAINTSBURY DR UNIT 503, FAIRFAX, VA...
Four Seasons at Ashburn Village 44465 CHAMBERLAIN TER UNIT 103, ASHBURN,..., Ashburn, VA 20147
$429,900

2 beds

|

2 baths

|

1,612 sq ft

|

Condo

44465 CHAMBERLAIN TER UNIT 103, ASHBURN,...
River Ridge 12221 SEAFORD CT, WOODBRIDGE, VA, 22192, Woodbridge, VA 22192
$584,900

3 beds

|

3 baths

|

1,962 sq ft

12221 SEAFORD CT, WOODBRIDGE, VA, 22192
Community: River Ridge
Heritage Hunt 17680 GLASS RIDGE PL, GAINESVILLE, VA, 2..., Gainesville, VA 20155
$650,000

3 beds

|

3 baths

|

2,920 sq ft

17680 GLASS RIDGE PL, GAINESVILLE, VA, 2...
Community: Heritage Hunt
Birchwood at Brambleton 23731 SEPTEMBER SUN SQ, ASHBURN, VA, 201..., Ashburn, VA 20148
$989,900

4 beds

|

4 baths

|

4,071 sq ft

23731 SEPTEMBER SUN SQ, ASHBURN, VA, 201...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Potomac Green 20389 OYSTER REEF PL, ASHBURN, VA, 20147, Ashburn, VA 20147
$875,000

3 beds

|

3 baths

|

2,404 sq ft

20389 OYSTER REEF PL, ASHBURN, VA, 20147
Community: Potomac Green
Potomac Green 44385 MALTESE FALCON SQ, ASHBURN, VA, 20..., Ashburn, VA 20147
$635,000

2 beds

|

3 baths

|

2,060 sq ft

44385 MALTESE FALCON SQ, ASHBURN, VA, 20...
Community: Potomac Green
Heritage Hunt 13753 TUSCARORA CT, GAINESVILLE, VA, 201..., Gainesville, VA 20155
$695,000

3 beds

|

3 baths

|

3,338 sq ft

13753 TUSCARORA CT, GAINESVILLE, VA, 201...
Community: Heritage Hunt
Central Parke at Lowes Island 20810 NOBLE TER 205, STERLING, VA, 20165, Sterling, VA 20165
$494,000

3 beds

|

2 baths

|

1,989 sq ft

|

Condo

20810 NOBLE TER 205, STERLING, VA, 20165
Heritage Hunt 6880 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$749,000

2 beds

|

3 baths

|

3,087 sq ft

6880 SADDLE RUN WAY, GAINESVILLE, VA, 20...
Community: Heritage Hunt
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 Hunt 6868 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$675,000

3 beds

|

3 baths

|

2,528 sq ft

6868 SADDLE RUN WAY, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Belmont Bay 680 WATERMANS DR APT 505, WOODBRIDGE, VA..., Woodbridge, VA 22191
$419,900

2 beds

|

3 baths

|

1,457 sq ft

|

Condo

680 WATERMANS DR APT 505, WOODBRIDGE, VA...
Community: Belmont Bay
Birchwood at Brambleton 43016 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$881,457

3 beds

|

4 baths

|

2,742 sq ft

43016 DEBONAIR TER, ASHBURN, VA, 20148
Birchwood at Brambleton 43089 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148
$949,990

3 beds

|

3 baths

|

2,491 sq ft

43089 GREELEY SQ, ASHBURN, VA, 20148
Regency at Dominion Valley 15110 HEATHER MILL LN APT 201, HAYMARKET..., Haymarket, VA 20169
$455,000

2 beds

|

2 baths

|

1,551 sq ft

|

Condo

15110 HEATHER MILL LN APT 201, HAYMARKET...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Gatherings at Potomac Station 750 MOUNT AIRY TER NE UNIT 304, LEESBURG..., Leesburg, VA 20176
$499,999

2 beds

|

2 baths

|

1,532 sq ft

|

Condo

750 MOUNT AIRY TER NE UNIT 304, LEESBURG...
Gatherings at Potomac Station 750 MOUNT AIRY TER NE UNIT 206A, LEESBUR..., Leesburg, VA 20176
$449,999

2 beds

|

2 baths

|

1,532 sq ft

|

Condo

750 MOUNT AIRY TER NE UNIT 206A, LEESBUR...
Gatherings at Potomac Station 750 MOUNT AIRY TER NE UNIT 403A, LEESBUR..., Leesburg, VA 20176
$484,999

2 beds

|

2 baths

|

1,410 sq ft

|

Condo

750 MOUNT AIRY TER NE UNIT 403A, LEESBUR...
Heritage Hunt 13154 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155
$725,000

3 beds

|

4 baths

|

3,195 sq ft

13154 TRIPLE CROWN LOOP, GAINESVILLE, VA...
Community: Heritage Hunt
Regency at Dominion Valley 5484 RODRIQUEZ LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$739,900

3 beds

|

3 baths

|

2,598 sq ft

5484 RODRIQUEZ LN, HAYMARKET, VA, 20169
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.
Trilogy® at Lake Frederick 105 BAYHILL TER, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$359,900

3 beds

|

3 baths

|

1,962 sq ft

105 BAYHILL TER, LAKE FREDERICK, VA, 226...
Woodbrook Village 222 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$369,000

2 beds

|

2 baths

|

1,260 sq ft

222 CRESTWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
Birchwood at Brambleton 42788 MACBETH TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$799,000

3 beds

|

3 baths

|

2,669 sq ft

42788 MACBETH TER, ASHBURN, VA, 20148
Woodbrook Village 105 TANGLEWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$375,000

2 beds

|

2 baths

|

1,372 sq ft

105 TANGLEWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
Birchwood at Brambleton 43044 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148
$1,050,000

4 beds

|

3 baths

|

3,753 sq ft

43044 GREELEY SQ, ASHBURN, VA, 20148
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Potomac Green 44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147
$895,500

4 beds

|

4 baths

|

2,709 sq ft

44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,...
Community: Potomac Green
Saintsbury Plaza 2905 SAINTSBURY PLZ APT 312, FAIRFAX, VA..., Fairfax, VA 22031
$599,000

3 beds

|

3 baths

|

1,718 sq ft

|

Condo

2905 SAINTSBURY PLZ APT 312, FAIRFAX, VA...
Community: Saintsbury Plaza
Regency at Dominion Valley 15100 HEATHER MILL LN APT 407, HAYMARKET..., Haymarket, VA 20169
$450,000

2 beds

|

2 baths

|

1,538 sq ft

|

Condo

15100 HEATHER MILL LN APT 407, HAYMARKET...
The Village at Harvest Ridge 147 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601
$655,000

3 beds

|

3 baths

|

3,153 sq ft

147 HARVEST RIDGE DR, WINCHESTER, VA, 22...
Trilogy® at Lake Frederick 102 BETONY CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$785,990

3 beds

|

3 baths

|

3,434 sq ft

102 BETONY CT, LAKE FREDERICK, VA, 22630
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 Atrium at MetroWest 2960 VADEN DR # 2-307, FAIRFAX, VA, 2203..., Fairfax, VA 22031
$749,900

2 beds

|

2 baths

|

1,546 sq ft

|

Condo

2960 VADEN DR # 2-307, FAIRFAX, VA, 2203...
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,...
Gatherings at Wellington 9202 CHARLESTON DR 307, MANASSAS, VA, 20..., Manassas, VA 20110
$421,000

3 beds

|

2 baths

|

2,006 sq ft

|

Condo

9202 CHARLESTON DR 307, MANASSAS, VA, 20...
Trilogy® at Lake Frederick 118 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$650,000

3 beds

|

3 baths

|

2,523 sq ft

118 VICEROY WAY, LAKE FREDERICK, VA, 226...
Saintsbury Plaza 2903 SAINTSBURY PLZ 310, FAIRFAX, VA, 22..., Fairfax, VA 22031
$384,000

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2903 SAINTSBURY PLZ 310, FAIRFAX, VA, 22...
Community: Saintsbury Plaza
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Suffield Meadows 6704 HOLLY FARM LN UNIT 109, WARRENTON, ..., Warrenton, VA 20187
$375,000

2 beds

|

2 baths

|

Condo

6704 HOLLY FARM LN UNIT 109, WARRENTON, ...
Community: Suffield Meadows
Birchwood at Brambleton 23707 KINSTON FERRY TER, ASHBURN, VA, 20..., Ashburn, VA 20148
$767,500

4 beds

|

3 baths

|

2,676 sq ft

23707 KINSTON FERRY TER, ASHBURN, VA, 20...
Heritage Hunt 6135 FERRIER CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155
$835,000

4 beds

|

4 baths

|

3,965 sq ft

6135 FERRIER CT, GAINESVILLE, VA, 20155
Community: Heritage Hunt
Heritage Hunt 13879 CRABTREE WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155
$725,000

4 beds

|

3 baths

|

3,151 sq ft

13879 CRABTREE WAY, GAINESVILLE, VA, 201...
Community: Heritage Hunt
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 815, LEESBURG, V..., Leesburg, VA 20176
$498,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

19385 CYPRESS RIDGE TER 815, LEESBURG, V...

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440 homes near Middletown
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