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

401 homes near Middletown

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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

3.7 rating (6 reviews)

Amblebrook

$300Ks - $700Ks

Amblebrook, Gettysburg, PA

New Construction | 55+ age-restricted | Built 2018 - present | 2,000 homes

5 rating (3 reviews)

Heritage Hunt

$300Ks - $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

$300Ks - $900Ks

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 - $800Ks

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 ...

$500Ks - $600Ks

Four Seasons at Historic ..., Dumfries, VA

Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 homes

5 rating (1 reviews)

Two Rivers

$700Ks - $800Ks

Two Rivers, Odenton, MD

New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes

No reviews yet

Cameron Grove

$300Ks - $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 - $400Ks

Central Parke at Victoria..., Laurel, MD

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 609 homes

No reviews yet

The Woodlands of Urbana

$400Ks - $900Ks

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 ...

$500Ks - $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

1 rating (1 reviews)

Dunbarton

$600Ks - $600Ks

Dunbarton, Bristow, VA

Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes

No reviews yet

The Courtyards at Waverly...

$600Ks - $600Ks

The Courtyards at Waverly..., Marriottsville, MD

Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 homes

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

$300Ks - $300Ks

Village Crest, Ellicott City, MD

New and Resale | 55+ age-restricted | Built 2005 - 2010 | 406 homes

No reviews yet

Courtyards at Waverly Woo...

$400Ks - $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

$600Ks - $600Ks

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

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

$600Ks - $600Ks

Regency at Ashburn, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes

No reviews yet

The Crest of Alexandria

$900Ks - $1Ms

The Crest of Alexandria, Alexandria, VA

New and Resale | 55+ age-restricted | Built 2017 - present | 250 homes

No reviews yet

Emerald Pointe

$300Ks - $400Ks

Emerald Pointe, Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2008 - 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 - $500Ks

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...

$500Ks - $600Ks

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

1 2 3...4

Lexington Square

44486 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$827,046

3 beds

3 baths

3,128 sq ft

44486 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington Square

Four Seasons at Virginia Crossing

13970 ENGLEFIELD DR UNIT 207, WOODBRIDGE..., Woodbridge, VA 22193

$539,000

2 beds

3 baths

1,811 sq ft

Condo

13970 ENGLEFIELD DR UNIT 207, WOODBRIDGE...

Community: Four Seasons at Virginia Crossing

Birchwood at Brambleton

42788 MACBETH TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$849,990

3 beds

3 baths

2,669 sq ft

42788 MACBETH TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Four Seasons at Historic Virginia

16453 SPARKLING BROOK LOOP, DUMFRIES, VA..., Dumfries, VA 22025

$629,900

3 beds

3 baths

2,468 sq ft

16453 SPARKLING BROOK LOOP, DUMFRIES, VA...

Community: Four Seasons at Historic Virginia

Four Seasons at Historic Virginia

3750 CHINA GROVE MEWS, DUMFRIES, VA, 220..., Dumfries, VA 22025

$599,999

2 beds

2 baths

2,107 sq ft

3750 CHINA GROVE MEWS, DUMFRIES, VA, 220...

Community: Four Seasons at Historic Virginia

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 903, LEESBURG, V..., Leesburg, VA 20176

$449,000

2 beds

2 baths

1,251 sq ft

Condo

19355 CYPRESS RIDGE TER 903, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Woodbrook Village

101 ROSEWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602

$390,000

2 beds

2 baths

1,692 sq ft

101 ROSEWOOD LN, WINCHESTER, VA, 22602

Community: Woodbrook Village

The Village at Harvest Ridge

143 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601

$575,000

3 beds

2 baths

2,233 sq ft

143 HARVEST RIDGE DR, WINCHESTER, VA, 22...

Community: The Village at Harvest Ridge

Four Seasons at Virginia Crossing

13970 ENGLEFIELD DR UNIT 303, WOODBRIDGE..., Woodbridge, VA 22193

$530,000

2 beds

2 baths

1,801 sq ft

Condo

13970 ENGLEFIELD DR UNIT 303, WOODBRIDGE...

Community: Four Seasons at Virginia Crossing

Trilogy® at Lake Frederick

116 GROSBEAK CT, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$574,000

2 beds

2 baths

2,047 sq ft

116 GROSBEAK CT, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Four Seasons at Historic Virginia

16916 FOUR SEASONS DR, DUMFRIES, VA, 220..., Dumfries, VA 22025

$560,000

2 beds

2 baths

1,797 sq ft

16916 FOUR SEASONS DR, DUMFRIES, VA, 220...

Community: Four Seasons at Historic Virginia

Regency at Ashburn

44589 YORK CREST TER APT 200, ASHBURN, V..., Ashburn, VA 20147

$609,000

3 beds

2 baths

1,894 sq ft

Condo

44589 YORK CREST TER APT 200, ASHBURN, V...

Community: Regency at Ashburn

Cedar Meadows

124 BLUETS DR, WHITE POST, VA, 22663, White Post, VA 22663

$415,000

2 beds

2 baths

1,509 sq ft

124 BLUETS DR, WHITE POST, VA, 22663

Community: Cedar Meadows

Four Seasons at Vint Hill

3680 OSBORNE DR, WARRENTON, VA, 20187, Warrenton, VA 20187

$650,000

4 beds

3 baths

3,562 sq ft

3680 OSBORNE DR, WARRENTON, VA, 20187

Community: Four Seasons at Vint Hill

Regency at Dominion Valley

15201 ROYAL CREST DR APT 303, HAYMARKET,..., Haymarket, VA 20169

$445,000

2 beds

2 baths

1,499 sq ft

Condo

15201 ROYAL CREST DR APT 303, HAYMARKET,...

Community: Regency at Dominion Valley

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (240) 663-8229

Birchwood at Brambleton

23640 BOLTON CRESCENT TER # 13-304, ASHB..., Ashburn, VA 20148

$549,990

2 beds

2 baths

1,419 sq ft

Condo

23640 BOLTON CRESCENT TER # 13-304, ASHB...

Community: Birchwood at Brambleton

Belmont Bay

645 ANGELFISH WAY, WOODBRIDGE, VA, 22191, Woodbridge, VA 22191

$836,090

4 beds

4 baths

2,705 sq ft

645 ANGELFISH WAY, WOODBRIDGE, VA, 22191

Community: Belmont Bay

Birchwood at Brambleton

42785 CUMULUS TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$799,900

3 beds

3 baths

2,669 sq ft

42785 CUMULUS TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Four Seasons at Historic Virginia

3839 MULBERRY POINT CT, DUMFRIES, VA, 22..., Dumfries, VA 22025

$679,950

4 beds

3 baths

3,424 sq ft

3839 MULBERRY POINT CT, DUMFRIES, VA, 22...

Community: Four Seasons at Historic Virginia

Four Seasons at Ashburn Village

44485 CHAMBERLAIN TER UNIT 205, ASHBURN,..., Ashburn, VA 20147

$435,000

2 beds

2 baths

1,612 sq ft

Condo

44485 CHAMBERLAIN TER UNIT 205, ASHBURN,...

Community: Four Seasons at Ashburn Village

Potomac Green

44516 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147

$920,000

3 beds

3 baths

2,703 sq ft

44516 BLUERIDGE MEADOWS DR, ASHBURN, VA,...

Community: Potomac Green

Montebello

21729 HAWKSBILL HIGH CIR, STERLING, VA, ..., Sterling, VA 20164

$950,000

2 beds

3 baths

2,302 sq ft

21729 HAWKSBILL HIGH CIR, STERLING, VA, ...

Community: Montebello

Spring Hill

8435 PEACE LILY CT APT 314, LORTON, VA, ..., Lorton, VA 22079

$539,000

2 beds

2 baths

1,621 sq ft

Condo

8435 PEACE LILY CT APT 314, LORTON, VA, ...

Community: Spring Hill

Trilogy® at Lake Frederick

102 PHACELIA WAY, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$410,000

3 beds

4 baths

2,200 sq ft

102 PHACELIA WAY, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Lexington Square

44494 COALPORT TER, ASHBURN, VA, 20147, Ashburn, VA 20147

$976,316

4 beds

4 baths

4,109 sq ft

44494 COALPORT TER, ASHBURN, VA, 20147

Community: Lexington Square

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (240) 663-8229

Lexington 7

$976,316

4 beds

4 baths

4,109 sq ft

44494 COALPORT TER, ASHBURN, VA, 20147

Community: Lexington 7

Cedar Meadows

109 BLEEDING HEART DR, WHITE POST, VA, 2..., White Post, VA 22663

$450,000

3 beds

2 baths

1,765 sq ft

109 BLEEDING HEART DR, WHITE POST, VA, 2...

Community: Cedar Meadows

Regency at Dominion Valley

15209 BRIER CREEK DR, HAYMARKET, VA, 201..., Haymarket, VA 20169

$730,000

2 beds

3 baths

2,842 sq ft

15209 BRIER CREEK DR, HAYMARKET, VA, 201...

Community: Regency at Dominion Valley

Cedar Meadows

107 BLUETS DR, WHITE POST, VA, 22663, White Post, VA 22663

$450,000

3 beds

2 baths

1,609 sq ft

107 BLUETS DR, WHITE POST, VA, 22663

Community: Cedar Meadows

Abrams Chase

112 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$479,500

2 beds

2 baths

1,609 sq ft

112 AMBERFIELD CT, WINCHESTER, VA, 22602

Community: Abrams Chase

Willow Lawn Cottages

1826 KERSHAW LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$387,900

2 beds

2 baths

1,431 sq ft

1826 KERSHAW LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 503, LEESBURG, V..., Leesburg, VA 20176

$435,000

2 beds

2 baths

1,509 sq ft

Condo

19385 CYPRESS RIDGE TER 503, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Birchwood at Brambleton

42743 CUMULUS TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$875,000

3 beds

3 baths

2,832 sq ft

42743 CUMULUS TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Belmont Bay

620 ANGELFISH WAY, WOODBRIDGE, VA, 22191, Woodbridge, VA 22191

$849,950

3 beds

4 baths

3,240 sq ft

620 ANGELFISH WAY, WOODBRIDGE, VA, 22191

Community: Belmont Bay

Birchwood at Brambleton

23675 HARDESTY TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$859,315

2 beds

4 baths

2,742 sq ft

23675 HARDESTY TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (240) 663-8229

Birchwood at Brambleton

23631 HAVELOCK WALK TER 220, ASHBURN, VA..., Ashburn, VA 20148

$550,000

3 beds

2 baths

1,971 sq ft

Condo

23631 HAVELOCK WALK TER 220, ASHBURN, VA...

Community: Birchwood at Brambleton

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 203, LEESBURG, V..., Leesburg, VA 20176

$399,000

2 beds

2 baths

1,251 sq ft

Condo

19355 CYPRESS RIDGE TER 203, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Cadence at Lansdowne

18989 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176

$755,000

3 beds

3 baths

2,649 sq ft

18989 CORAL REEF SQ, LEESBURG, VA, 20176

Community: Cadence at Lansdowne

Central Parke at Lowes Island

20804 NOBLE TER 208, STERLING, VA, 20165, Sterling, VA 20165

$455,000

2 beds

2 baths

1,692 sq ft

Condo

20804 NOBLE TER 208, STERLING, VA, 20165

Community: Central Parke at Lowes Island

Trilogy® at Lake Frederick

111 WAKE ROBIN CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$450,000

4 beds

4 baths

2,248 sq ft

111 WAKE ROBIN CT, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

1 2 3 4 5 6 7 8 9 10…11

Frequently Asked Questions

What size 55+ communities are there in Middletown?

In Middletown, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Middletown?

The smallest 55+ community in Middletown has 81 homes, the largest has 81 homes, and the average community consists of 81 homes.

Are there gated 55+ communities in Middletown?

No, there are no gated 55+ communities in Middletown.

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401 homes near Middletown

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

125 communities near Middletown

401 homes near Middletown

3 beds

3 baths

3,128 sq ft

2 beds

3 baths

1,811 sq ft

Condo

3 beds

3 baths

2,669 sq ft

3 beds

3 baths

2,468 sq ft

2 beds

2 baths

2,107 sq ft

2 beds

2 baths

1,251 sq ft

Condo

2 beds

2 baths

1,692 sq ft

3 beds

2 baths

2,233 sq ft

2 beds

2 baths

1,801 sq ft

Condo

2 beds

2 baths

2,047 sq ft

2 beds

2 baths

1,797 sq ft

3 beds

2 baths

1,894 sq ft

Condo

2 beds

2 baths

1,509 sq ft

4 beds

3 baths

3,562 sq ft

2 beds

2 baths

1,499 sq ft

Condo

2 beds

2 baths

1,419 sq ft

Condo

4 beds

4 baths

2,705 sq ft

3 beds

3 baths

2,669 sq ft

4 beds

3 baths

3,424 sq ft

2 beds

2 baths

1,612 sq ft

Condo

3 beds

3 baths

2,703 sq ft

2 beds

3 baths

2,302 sq ft

2 beds

2 baths

1,621 sq ft

Condo