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Middletown, MD 55+ active adult communities & homes for sale - Page 2

141 communities near Middletown

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The Villages At Woodholme
$400ks - $500ks
The Villages At Woodholme, Baltimore, MD
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 286 homes
Walden Woods
$500ks - $600ks
Walden Woods, Laurel, MD
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 97 homes
The Courtyards at Waverly...
$300ks - $1Ms
The Courtyards at Waverly..., Marriottsville, MD
Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 homes
5 rating (1 reviews) Regency at Dominion Valle...
$300ks - $1Ms
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes
Maple Highlands
$900ks - $800ks
Maple Highlands, Fulton, MD
New Construction | 55+ age-restricted | Built 2024 - present | 34 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Gatherings at Ellicott Mi...
$300ks
Gatherings at Ellicott Mi..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2013 - 2018 | 127 homes
Crawfords Ridge
$500ks - $600ks
Crawfords Ridge, Odenton, MD
Resale Only | 55+ age-restricted | Built 2006 - 2006 | 27 homes
Village Crest
$300ks
Village Crest, Ellicott City, MD
New and Resale | 55+ age-restricted | Built 2005 - 2010 | 406 homes
Eden Brook
$200ks - $300ks
Eden Brook, Odenton, MD
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 224 homes
3.7 rating (3 reviews) Four Seasons at Ashburn V...
$300ks - $400ks
Four Seasons at Ashburn V..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 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.
Montebello
$500ks - $700ks
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
5 rating (1 reviews) Carroll Vista
$300ks
Carroll Vista, Taneytown, MD
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 453 homes
5 rating (1 reviews) Willow Lawn Cottages
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes
5 rating (1 reviews) Gatherings at Wellington
$300ks - $400ks
Gatherings at Wellington, Manassas, VA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes
5 rating (1 reviews) Ellicott's Retreat
$300ks - $400ks
Ellicott's Retreat, Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2017 - 2022 | 160 homes
Suffield Meadows
$400ks
Suffield Meadows, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Cedar Ridge at Piney Orch...
$200ks - $300ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes
Blue Ridge
$300ks - $400ks
Blue Ridge, Harrisburg, PA
New and Resale | Age-targeted | Built 2020 - present | 130 homes
Cadence at Lansdowne
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes
The Village at Harvest Ri...
$400ks - $500ks
The Village at Harvest Ri..., Winchester, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 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.
Creek View
$100ks - $200ks
Creek View, Carlisle, PA
New and Resale | 55+ age-restricted | Built 2004 - present | 305 homes
Cross Creek Village
$300ks
Cross Creek Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 homes
Central Parke at Lowes Is...
$300ks - $600ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes
River Ridge
$400ks - $600ks
River Ridge, Woodbridge, VA
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 238 homes
3 rating (2 reviews) Dunbarton
$300ks - $500ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
5 rating (1 reviews) Four Seasons at Historic ...
$400ks - $600ks
Four Seasons at Historic ..., Dumfries, VA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 homes
Spring Hill
$400ks - $600ks
Spring Hill, Lorton, VA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Regency at Creekside
$700ks - $800ks
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes
Cottage Glen
$400ks
Cottage Glen, Winchester, VA
New and Resale | Age-targeted | Built 2018 - present | 25 homes
Railroad Cottages
$700ks - $900ks
Railroad Cottages, Falls Church, VA
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 10 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.
Abrams Chase
$400ks - $500ks
Abrams Chase, Winchester, VA
New Construction | 55+ age-restricted | Built 2020 - present | 13 homes
Ellicott Meadows
$600ks - $700ks
Ellicott Meadows, Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 160 homes
Patapsco Overlook
$400ks
Patapsco Overlook, Catonsville, MD
Resale Only | 55+ age-restricted | Built 2010 - 2017 | 80 homes
JerMae Estates
$300ks - $400ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
Guilford Mews
$300ks - $400ks
Guilford Mews, Jessup, MD
New and Resale | 55+ age-restricted | Built 2010 - present | 26 homes
Gatherings at Forest Glen
$300ks
Gatherings at Forest Glen, Odenton, MD
Resale Only | 55+ age-restricted | Built 2008 - 2013 | 189 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
CobbleStone Estates
$400ks - $500ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Boxwood Villas
$500ks - $600ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
Hawthorne Greene
$400ks - $500ks
Hawthorne Greene, La Plata, MD
Resale Only | 55+ age-restricted | Built 2018 - 2022 | 74 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.
New Suffield Meadows 6708 STREAM VIEW LN, WARRENTON, VA, 2018..., Warrenton, VA 20187
$619,900

3 beds

|

3 baths

|

3,701 sq ft

|

Condo

6708 STREAM VIEW LN, WARRENTON, VA, 2018...
Community: Suffield Meadows
New Regency at Dominion Valley 15508 HAGEN WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169
$929,900

3 beds

|

3 baths

|

3,810 sq ft

15508 HAGEN WAY, HAYMARKET, VA, 20169
New Cortland Park 770 AURORA DR, MECHANICSBURG, PA, 17055, Mechanicsburg, PA 17055
$534,900

4 beds

|

4 baths

|

2,256 sq ft

770 AURORA DR, MECHANICSBURG, PA, 17055
Community: Cortland Park
New The Courtyards at Waverly Woods 2241 JOHN GRAVEL RD M, MARRIOTTSVILLE, M..., Marriottsville, MD 21104
$400,000

2 beds

|

2 baths

|

1,438 sq ft

|

Condo

2241 JOHN GRAVEL RD M, MARRIOTTSVILLE, M...
New Heritage Hunt 13749 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155
$730,000

3 beds

|

3 baths

|

2,626 sq ft

13749 HERITAGE VALLEY WAY, GAINESVILLE, ...
Community: Heritage Hunt
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
New Birchwood at Brambleton 23640 BOLTON CRESCENT TER 403, ASHBURN, ..., Ashburn, VA 20148
$759,900

3 beds

|

2 baths

|

1,908 sq ft

|

Condo

23640 BOLTON CRESCENT TER 403, ASHBURN, ...
New Heritage at St. Charles 11271 YELLOWSTONE CT, WHITE PLAINS, MD, ..., White Plains, MD 20695
$490,000

3 beds

|

2 baths

|

2,066 sq ft

11271 YELLOWSTONE CT, WHITE PLAINS, MD, ...
New HiddenBrooke 7880 ROLLING WOODS CT 2103, SPRINGFIELD,..., Springfield, VA 22152
$485,000

2 beds

|

2 baths

|

1,366 sq ft

|

Condo

7880 ROLLING WOODS CT 2103, SPRINGFIELD,...
Community: HiddenBrooke
New Leisure World® of Maryland 15101 GLADE DR 10-3G, SILVER SPRING, MD,..., Silver Spring, MD 20906
$295,000

3 beds

|

2 baths

|

1,415 sq ft

|

Condo

15101 GLADE DR 10-3G, SILVER SPRING, MD,...
New Traditions of America at Silver Spring 411 GENERAL DR, MECHANICSBURG, PA, 17050, Mechanicsburg, PA 17050
$550,000

2 beds

|

2 baths

|

2,370 sq ft

|

Condo

411 GENERAL DR, MECHANICSBURG, PA, 17050
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.
New Amblebrook 43 CHOKEBERRY WAY, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$349,900

3 beds

|

2 baths

|

1,430 sq ft

43 CHOKEBERRY WAY, GETTYSBURG, PA, 17325
Community: Amblebrook
New The Courtyards at Waverly Woods 2415 ANDERSON HILL ST, MARRIOTTSVILLE, M..., Marriottsville, MD 21104
$900,000

3 beds

|

3 baths

|

5,380 sq ft

|

Condo

2415 ANDERSON HILL ST, MARRIOTTSVILLE, M...
New Traditions of America at Silver Spring 254 COLONIAL DR, MECHANICSBURG, PA, 1705..., Mechanicsburg, PA 17050
$499,500

2 beds

|

3 baths

|

2,529 sq ft

|

Condo

254 COLONIAL DR, MECHANICSBURG, PA, 1705...
New Snowden Overlook 8633 VAST ROSE DR 14, COLUMBIA, MD, 2104..., Columbia, MD 21045
$679,000

2 beds

|

4 baths

|

3,542 sq ft

|

Condo

8633 VAST ROSE DR 14, COLUMBIA, MD, 2104...
Community: Snowden Overlook
New Potomac Green 44480 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147
$885,000

3 beds

|

3 baths

|

2,817 sq ft

44480 BLUERIDGE MEADOWS DR, ASHBURN, VA,...
Community: Potomac Green
New Potomac Green 44397 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147
$760,000

3 beds

|

3 baths

|

2,118 sq ft

44397 OAKMONT MANOR SQ, ASHBURN, VA, 201...
Community: Potomac Green
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
New Courtyards at Waverly Woods East 11185 CHAMBERS CT G, WOODSTOCK, MD, 2116..., Woodstock, MD 21163
$385,500

2 beds

|

2 baths

|

1,358 sq ft

|

Condo

11185 CHAMBERS CT G, WOODSTOCK, MD, 2116...
New Ellicott's Retreat 8505 SUNELL LN, ELLICOTT CITY, MD, 21043, Ellicott City, MD 21043
$1,175,000

5 beds

|

5 baths

|

4,201 sq ft

8505 SUNELL LN, ELLICOTT CITY, MD, 21043
Community: Ellicott's Retreat
New Boxwood Villas 3816 FULHAM RD, FREDERICK, MD, 21704, Frederick, MD 21704
$759,900

3 beds

|

4 baths

|

3,383 sq ft

3816 FULHAM RD, FREDERICK, MD, 21704
Community: Boxwood Villas
New River Ridge 12357 ROMNEY MEWS, WOODBRIDGE, VA, 22192, Woodbridge, VA 22192
$719,900

3 beds

|

3 baths

|

3,760 sq ft

12357 ROMNEY MEWS, WOODBRIDGE, VA, 22192
Community: River Ridge
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.
New Maple Highlands 8511 LALLYBROCH LN, FULTON, MD, 20759, Fulton, MD 20759
$1,150,000

4 beds

|

4 baths

|

4,098 sq ft

|

Condo

8511 LALLYBROCH LN, FULTON, MD, 20759
Community: Maple Highlands
New Cameron Grove 13220 FOX BOW DR 104, UPPER MARLBORO, MD..., Upper Marlboro, MD 20774
$299,999

1 beds

|

1 baths

|

1,015 sq ft

|

Condo

13220 FOX BOW DR 104, UPPER MARLBORO, MD...
Community: Cameron Grove
New Village Crest 8220 ACADEMY RD 22, ELLICOTT CITY, MD, 2..., Ellicott City, MD 21043
$649,900

4 beds

|

4 baths

|

3,329 sq ft

|

Condo

8220 ACADEMY RD 22, ELLICOTT CITY, MD, 2...
Community: Village Crest
New Roth's Farm Village 1332 PLEASANT VIEW DR 75, SPRING GROVE, ..., Spring Grove, PA 17362
$245,000

2 beds

|

2 baths

|

1,104 sq ft

1332 PLEASANT VIEW DR 75, SPRING GROVE, ...
Community: Roth's Farm Village
New Regency at Belmont 43927 HURLEYS HUNT TER, ASHBURN, VA, 201..., Ashburn, VA 20147
$1,099,000

3 beds

|

4 baths

|

3,255 sq ft

43927 HURLEYS HUNT TER, ASHBURN, VA, 201...
Community: Regency at Belmont
New Scot's Glen 10737 MCGREGOR DR, COLUMBIA, MD, 21044, Columbia, MD 21044
$895,000

4 beds

|

5 baths

|

5,200 sq ft

|

Condo

10737 MCGREGOR DR, COLUMBIA, MD, 21044
Community: Scot's Glen
New Leisure World® of Maryland 3200 N LEISURE WORLD BLVD 712, SILVER SP..., Silver Spring, MD 20906
$310,000

2 beds

|

2 baths

|

1,260 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 712, SILVER SP...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
New Leisure World® of Maryland 14805 PENNFIELD CIR 309, SILVER SPRING, ..., Silver Spring, MD 20906
$375,000

2 beds

|

2 baths

|

1,709 sq ft

|

Condo

14805 PENNFIELD CIR 309, SILVER SPRING, ...
New Bloomfields 55+ 2644 BLAZING STAR ST, FREDERICK, MD, 217..., Frederick, MD 21702
$665,990

2 beds

|

2 baths

|

2,915 sq ft

2644 BLAZING STAR ST, FREDERICK, MD, 217...
Community: Bloomfields 55+
New Bloomfields 55+ 2619 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702
$809,990

4 beds

|

4 baths

|

4,034 sq ft

2619 BROADLEAF DR, FREDERICK, MD, 21702
Community: Bloomfields 55+
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.
New Bloomfields 55+ 2617 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702
$779,990

4 beds

|

4 baths

|

3,591 sq ft

2617 BROADLEAF DR, FREDERICK, MD, 21702
Community: Bloomfields 55+
New Bloomfields 55+ 2615 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702
$729,990

3 beds

|

3 baths

|

3,357 sq ft

2615 BROADLEAF DR, FREDERICK, MD, 21702
Community: Bloomfields 55+
New Bloomfields 55+ 2613 BROADLEAF, FREDERICK, MD, 21702, Frederick, MD 21702
$699,990

3 beds

|

3 baths

|

2,915 sq ft

2613 BROADLEAF, FREDERICK, MD, 21702
Community: Bloomfields 55+
New Montebello 21914 HAWKSBILL HIGH CIR 204, STERLING, ..., Sterling, VA 20164
$599,999

2 beds

|

2 baths

|

1,419 sq ft

|

Condo

21914 HAWKSBILL HIGH CIR 204, STERLING, ...
Community: Montebello
New Montebello 21630 HAWKSBILL HIGH CIR 202, STERLING, ..., Sterling, VA 20164
$735,999

3 beds

|

2 baths

|

1,940 sq ft

|

Condo

21630 HAWKSBILL HIGH CIR 202, STERLING, ...
Community: Montebello
New Heritage Hunt 13191 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155
$785

4 beds

|

5 baths

|

4,664 sq ft

13191 TRIPLE CROWN LOOP, GAINESVILLE, VA...
Community: Heritage Hunt
New Two Rivers 3068 SPRING PEEPER CT, ODENTON, MD, 2111..., Odenton, MD 21113
$545,000

2 beds

|

2 baths

|

1,614 sq ft

3068 SPRING PEEPER CT, ODENTON, MD, 2111...
Community: Two Rivers
New The Preserves at Cumberland Village 120 WOODHAVEN DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$475,000

2 beds

|

2 baths

|

1,718 sq ft

120 WOODHAVEN DR, GETTYSBURG, PA, 17325
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
New Trilogy® at Lake Frederick 134 ATLANTIS LN, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$635,000

3 beds

|

3 baths

|

2,173 sq ft

134 ATLANTIS LN, LAKE FREDERICK, VA, 226...
New Two Rivers 2859 DRAGON FLY WAY, ODENTON, MD, 21113, Odenton, MD 21113
$805,000

4 beds

|

4 baths

|

3,870 sq ft

2859 DRAGON FLY WAY, ODENTON, MD, 21113
Community: Two Rivers
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.

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