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

413 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 - $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 - $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

$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

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

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

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

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

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

1 2 3...4

New Winchester Landing

122 HARDY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$375,000

3 beds

3 baths

1,630 sq ft

122 HARDY WAY, WINCHESTER, VA, 22602

Community: Winchester Landing

Four Seasons at Virginia Crossing

13950 ENGLEFIELD DR UNIT 302, WOODBRIDGE..., Woodbridge, VA 22193

$515,000

2 beds

3 baths

1,811 sq ft

Condo

13950 ENGLEFIELD DR UNIT 302, WOODBRIDGE...

Community: Four Seasons at Virginia Crossing

New Birchwood at Brambleton

23669 GOLDEN EMBERS SQ UNIT 303, ASHBURN..., Ashburn, VA 20148

$724,900

3 beds

2 baths

2,148 sq ft

Condo

23669 GOLDEN EMBERS SQ UNIT 303, ASHBURN...

Community: Birchwood at Brambleton

Birchwood at Brambleton

23631 HAVELOCK WALK TER 404, ASHBURN, VA..., Ashburn, VA 20148

$569,000

2 beds

2 baths

1,959 sq ft

Condo

23631 HAVELOCK WALK TER 404, ASHBURN, VA...

Community: Birchwood at Brambleton

New Winchester Landing

151 MCCORMICK CIR APT 203, WINCHESTER, V..., Winchester, VA 22602

$315,000

2 beds

2 baths

1,156 sq ft

Condo

151 MCCORMICK CIR APT 203, WINCHESTER, V...

Community: Winchester Landing

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Birchwood at Brambleton

23595 GOLDEN EMBERS SQ, ASHBURN, VA, 201..., Ashburn, VA 20148

$860,000

3 beds

4 baths

3,637 sq ft

23595 GOLDEN EMBERS SQ, ASHBURN, VA, 201...

Community: Birchwood at Brambleton

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

Carmella

$599,000

3 beds

4 baths

3,848 sq ft

Condo

427 CARMELLA DR, MECHANICSBURG, PA, 1705...

Community: Carmella

Leisure World® of Maryland

3200 N LEISURE WORLD BLVD APT 514, SILVE..., Silver Spring, MD 20906

$250,000

2 beds

2 baths

1,035 sq ft

Condo

3200 N LEISURE WORLD BLVD APT 514, SILVE...

Community: Leisure World® of Maryland

Village Crest

8115 YELLOW PINE DR L, ELLICOTT CITY, MD..., Ellicott City, MD 21043

$385,000

2 beds

2 baths

1,574 sq ft

Condo

8115 YELLOW PINE DR L, ELLICOTT CITY, MD...

Community: Village Crest

Trilogy® at Lake Frederick

108 GADWELL LN, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$714,900

3 beds

4 baths

3,464 sq ft

108 GADWELL LN, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

New Lansdowne Woods of Virginia

19350 MAGNOLIA SQ 308, LEESBURG, VA, 201..., Leesburg, VA 20176

$435,000

2 beds

2 baths

1,444 sq ft

Condo

19350 MAGNOLIA SQ 308, LEESBURG, VA, 201...

Community: Lansdowne Woods of Virginia

New Trilogy® at Lake Frederick

118 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$600,000

3 beds

3 baths

2,523 sq ft

118 VICEROY WAY, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (240) 663-8229

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

Potomac Green

44420 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$749,000

3 beds

3 baths

2,447 sq ft

44420 SUNSET MAPLE DR, ASHBURN, VA, 2014...

Community: Potomac Green

Birchwood at Brambleton

43221 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148

$1,228,000

3 beds

4 baths

4,124 sq ft

43221 GREELEY SQ, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

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,...

Community: Four Seasons at Ashburn Village

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 207, LEESBURG, V..., Leesburg, VA 20176

$399,900

2 beds

2 baths

1,380 sq ft

Condo

19375 CYPRESS RIDGE TER 207, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Four Seasons at Virginia Crossing

13950 ENGLEFIELD DR UNIT 408, WOODBRIDGE..., Woodbridge, VA 22193

$415,000

2 beds

2 baths

1,329 sq ft

Condo

13950 ENGLEFIELD DR UNIT 408, WOODBRIDGE...

Community: Four Seasons at Virginia Crossing

Trilogy® at Lake Frederick

117 MALLARD DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$799,998

3 beds

4 baths

3,601 sq ft

117 MALLARD DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

117 HARVESTER DR, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$899,000

4 beds

5 baths

6,096 sq ft

117 HARVESTER DR, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

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Willow Run

111 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602

$459,990

4 beds

3 baths

2,168 sq ft

111 TRELLIS VIEW LN, WINCHESTER, VA, 226...

Community: Willow Run

Parklands

10147 SHENANDOAH LN, WHITE PLAINS, MD, 2..., White Plains, MD 20695

$567,490

3 beds

3 baths

2,593 sq ft

10147 SHENANDOAH LN, WHITE PLAINS, MD, 2...

Community: Parklands

Trilogy® at Lake Frederick

114 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$729,900

3 beds

4 baths

3,333 sq ft

114 TURNSTONE LN, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Heritage Highlands

67 HARPERS MILL WAY, LOVETTSVILLE, VA, 2..., Lovettsville, VA 20180

$499,999

2 beds

3 baths

2,119 sq ft

67 HARPERS MILL WAY, LOVETTSVILLE, VA, 2...

Community: Heritage Highlands

Heritage Hunt

13612 RYTON RIDGE LN, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$859,900

4 beds

3 baths

4,486 sq ft

13612 RYTON RIDGE LN, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Four Seasons at Virginia Crossing

3720 HAVERTILL LN UNIT 407, WOODBRIDGE, ..., Woodbridge, VA 22193

$499,000

2 beds

3 baths

1,811 sq ft

Condo

3720 HAVERTILL LN UNIT 407, WOODBRIDGE, ...

Community: Four Seasons at Virginia Crossing

New The Highlands at Blue Ridge Shadows

47 HICKORY SHAFT CT, FRONT ROYAL, VA, 22..., Front Royal, VA 22630

$585,000

4 beds

4 baths

3,482 sq ft

47 HICKORY SHAFT CT, FRONT ROYAL, VA, 22...

Community: The Highlands at Blue Ridge Shadows

Regency at Dominion Valley

15201 ROYAL CREST DR APT 407, HAYMARKET,..., Haymarket, VA 20169

$435,000

2 beds

2 baths

1,538 sq ft

Condo

15201 ROYAL CREST DR APT 407, HAYMARKET,...

Community: Regency at Dominion Valley

The Atrium at MetroWest

2960 VADEN DR # 2-312, FAIRFAX, VA, 2203..., Fairfax, VA 22031

$768,980

2 beds

2 baths

1,546 sq ft

Condo

2960 VADEN DR # 2-312, FAIRFAX, VA, 2203...

Community: The Atrium at MetroWest

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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,...

Community: Regency at Dominion Valley

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

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

Heritage Hunt

13963 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$599,990

3 beds

3 baths

2,090 sq ft

13963 CHELMSFORD DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 114, LEESBURG, V..., Leesburg, VA 20176

$350,000

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 114, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Regency at Belmont

43921 HURLEYS HUNT TER, ASHBURN, VA, 201..., Ashburn, VA 20147

$1,075,000

4 beds

4 baths

3,255 sq ft

43921 HURLEYS HUNT TER, ASHBURN, VA, 201...

Community: Regency at Belmont

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

Four Seasons at Historic Virginia

16040 DANCING LEAF PL, DUMFRIES, VA, 220..., Dumfries, VA 22025

$600,000

3 beds

2 baths

2,727 sq ft

16040 DANCING LEAF PL, DUMFRIES, VA, 220...

Community: Four Seasons at Historic Virginia

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

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Regency at Dominion Valley

5429 TREVINO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169

$735,000

3 beds

3 baths

2,524 sq ft

5429 TREVINO DR, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

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...

Community: Lansdowne Woods of Virginia

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.

How long do listings in 55+ communities in Middletown typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ community in Middletown stay on the market for around 58 days. The average price of homes for sale in this community is approximately $550,000, though prices can range widely based on the size, location, and amenities of the community. For example, homes in The Village at Foxfield average around $550,000.

Want more information about active adult communities around Middletown?

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413 homes

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

135 communities near Middletown

413 homes near Middletown

3 beds

3 baths

1,630 sq ft

2 beds

3 baths

1,811 sq ft

Condo

3 beds

2 baths

2,148 sq ft

Condo

2 beds

2 baths

1,959 sq ft

Condo

2 beds

2 baths

1,156 sq ft

Condo

3 beds

4 baths

3,637 sq ft

2 beds

3 baths

2,060 sq ft

3 beds

4 baths

3,848 sq ft

Condo

2 beds

2 baths

1,035 sq ft

Condo

2 beds

2 baths

1,574 sq ft

Condo

3 beds

4 baths

3,464 sq ft

2 beds

2 baths

1,444 sq ft

Condo

3 beds

3 baths

2,523 sq ft

2 beds

2 baths

1,260 sq ft

3 beds

3 baths

2,447 sq ft

3 beds

4 baths

4,124 sq ft

2 beds

2 baths

1,612 sq ft

Condo

2 beds

2 baths

1,380 sq ft

Condo

2 beds

2 baths

1,329 sq ft

Condo

3 beds

4 baths

3,601 sq ft

4 beds

5 baths

6,096 sq ft

4 beds

3 baths

2,168 sq ft