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Middletown, MD 55+ active adult communities & homes for sale - Page 8

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
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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
Lansdowne Woods of Virginia 19365 CYPRESS RIDGE TER UNIT 1102, LEESB..., Leesburg, VA 20176
$389,000

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

19365 CYPRESS RIDGE TER UNIT 1102, LEESB...
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER UNIT 522, LEESBU..., Leesburg, VA 20176
$370,000

2 beds

|

2 baths

|

1,101 sq ft

|

Condo

19385 CYPRESS RIDGE TER UNIT 522, LEESBU...
Heritage Hunt 7065 HERITAGE HUNT DR 203, GAINESVILLE, ..., Gainesville, VA 20155
$440,000

2 beds

|

2 baths

|

1,421 sq ft

|

Condo

7065 HERITAGE HUNT DR 203, GAINESVILLE, ...
Community: Heritage Hunt
New The Atrium at MetroWest 2960 VADEN DR UNIT 413, FAIRFAX, VA, 220..., Fairfax, VA 22031
$745,000

2 beds

|

2 baths

|

1,391 sq ft

|

Condo

2960 VADEN DR UNIT 413, FAIRFAX, VA, 220...
The Village at Harvest Ridge 147 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601
$639,000

3 beds

|

3 baths

|

3,153 sq ft

147 HARVEST RIDGE DR, WINCHESTER, VA, 22...
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Questions? Call us: (240) 663-8229
New Spring Hill 8410 STARGAZER LILY CT, LORTON, VA, 2207..., Lorton, VA 22079
$869,950

3 beds

|

3 baths

|

2,546 sq ft

8410 STARGAZER LILY CT, LORTON, VA, 2207...
Community: Spring Hill
Four Seasons at Virginia Crossing 13970 ENGLEFIELD DR UNIT 303, WOODBRIDGE..., Woodbridge, VA 22193
$525,000

2 beds

|

2 baths

|

1,801 sq ft

|

Condo

13970 ENGLEFIELD DR UNIT 303, WOODBRIDGE...
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER UNIT 708, LEESBU..., Leesburg, VA 20176
$399,000

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

19375 CYPRESS RIDGE TER UNIT 708, LEESBU...
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...
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.
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 901, LEESBURG, V..., Leesburg, VA 20176
$515,000

3 beds

|

2 baths

|

1,534 sq ft

|

Condo

19375 CYPRESS RIDGE TER 901, LEESBURG, V...
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER UNIT 920, LEESBU..., Leesburg, VA 20176
$450,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

19385 CYPRESS RIDGE TER UNIT 920, LEESBU...
Trilogy® at Lake Frederick 105 BAYHILL TER, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$369,900

3 beds

|

3 baths

|

1,962 sq ft

105 BAYHILL TER, LAKE FREDERICK, VA, 226...
Cottage Glen 129 DOONBEG CT, WINCHESTER, VA, 22602, Winchester, VA 22602
$450,000

4 beds

|

3 baths

|

2,072 sq ft

129 DOONBEG CT, WINCHESTER, VA, 22602
Community: Cottage Glen
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Heritage Hunt 6920 NETHERSTONE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$625,000

2 beds

|

3 baths

|

2,745 sq ft

6920 NETHERSTONE CT, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Woodbrook Village 203 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$379,000

2 beds

|

2 baths

|

1,590 sq ft

203 CRESTWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
Gatherings at Potomac Station 750 MOUNT AIRY TER NE UNIT 403B, LEESBUR..., Leesburg, VA 20176
$484,999

2 beds

|

2 baths

|

1,410 sq ft

|

Condo

750 MOUNT AIRY TER NE UNIT 403B, LEESBUR...
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER UNIT 503, LEESBU..., Leesburg, VA 20176
$379,900

2 beds

|

2 baths

|

1,251 sq ft

|

Condo

19355 CYPRESS RIDGE TER UNIT 503, LEESBU...
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.
Gatherings at Wellington 10273 FOUNTAIN CIR 202, MANASSAS, VA, 20..., Manassas, VA 20110
$415,000

3 beds

|

2 baths

|

2,006 sq ft

|

Condo

10273 FOUNTAIN CIR 202, MANASSAS, VA, 20...
Gatherings at Wellington 9202 CHARLESTON DR 307, MANASSAS, VA, 20..., Manassas, VA 20110
$425,000

3 beds

|

2 baths

|

2,006 sq ft

|

Condo

9202 CHARLESTON DR 307, MANASSAS, VA, 20...
Willow Run 113 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602
$509,990

4 beds

|

3 baths

|

2,168 sq ft

113 TRELLIS VIEW LN, WINCHESTER, VA, 226...
Community: Willow Run
Heritage Hunt 7065 HERITAGE HUNT DR 108, GAINESVILLE, ..., Gainesville, VA 20155
$410,000

2 beds

|

2 baths

|

1,292 sq ft

|

Condo

7065 HERITAGE HUNT DR 108, GAINESVILLE, ...
Community: Heritage Hunt
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Regency at Dominion Valley 15251 ROYAL CREST DR APT 103, HAYMARKET,..., Haymarket, VA 20169
$464,900

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

15251 ROYAL CREST DR APT 103, HAYMARKET,...
Montebello 21630 HAWKSBILL HIGH CIR UNIT 403, STERL..., Sterling, VA 20164
$545,000

2 beds

|

2 baths

|

1,435 sq ft

|

Condo

21630 HAWKSBILL HIGH CIR UNIT 403, STERL...
Community: Montebello
Four Seasons at Virginia Crossing 13970 ENGLEFIELD DR UNIT 207, WOODBRIDGE..., Woodbridge, VA 22193
$525,000

2 beds

|

3 baths

|

1,811 sq ft

|

Condo

13970 ENGLEFIELD DR UNIT 207, WOODBRIDGE...
Trilogy® at Lake Frederick 112 BETONY CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$759,990

3 beds

|

3 baths

|

3,434 sq ft

112 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.
Montebello 21630 HAWKSBILL HIGH CIR UNIT 204, STERL..., Sterling, VA 20164
$620,000

2 beds

|

2 baths

|

1,640 sq ft

|

Condo

21630 HAWKSBILL HIGH CIR UNIT 204, STERL...
Community: Montebello
Winchester Landing 140 MCCORMICK CIR APT 302, WINCHESTER, V..., Winchester, VA 22602
$314,900

2 beds

|

2 baths

|

1,156 sq ft

140 MCCORMICK CIR APT 302, WINCHESTER, V...
Community: Winchester Landing
Four Seasons at Virginia Crossing 14035 MADRONA LN, WOODBRIDGE, VA, 22193, Woodbridge, VA 22193
$669,900

3 beds

|

3 baths

|

2,192 sq ft

14035 MADRONA LN, WOODBRIDGE, VA, 22193
Willow Run 113 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602
$599,990

4 beds

|

3 baths

|

2,909 sq ft

113 SCENTED ROSE WAY, WINCHESTER, VA, 22...
Community: Willow Run
Spring Hill 8970 FASCINATION CT APT 315, LORTON, VA,..., Lorton, VA 22079
$525,000

2 beds

|

2 baths

|

1,558 sq ft

|

Condo

8970 FASCINATION CT APT 315, LORTON, VA,...
Community: Spring Hill
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 612, LEESBURG, V..., Leesburg, VA 20176
$575,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

19355 CYPRESS RIDGE TER 612, LEESBURG, V...
Cadence at Lansdowne 43917 MARITIME SONG TER, LEESBURG, VA, 2..., Leesburg, VA 20176
$765,000

3 beds

|

3 baths

|

2,389 sq ft

43917 MARITIME SONG TER, LEESBURG, VA, 2...
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
Willow Run 111 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602
$629,990

4 beds

|

3 baths

|

2,865 sq ft

111 SCENTED ROSE WAY, WINCHESTER, VA, 22...
Community: Willow Run
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 103 BURKWOOD TER, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$410,000

3 beds

|

3 baths

|

2,376 sq ft

103 BURKWOOD TER, LAKE FREDERICK, VA, 22...
The Retreat at Poland Hill 43441 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152
$945,000

4 beds

|

4 baths

|

3,553 sq ft

43441 BETTYS FARM DR, CHANTILLY, VA, 201...
Lexington Square 44510 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$795,526

3 beds

|

3 baths

|

3,058 sq ft

44510 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington Square
Lexington 7 44510 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$795,526

3 beds

|

3 baths

|

3,058 sq ft

44510 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington 7
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
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
Lexington Square 44508 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$818,236

3 beds

|

3 baths

|

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington Square

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