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Middletown, MD 55+ active adult communities & homes for sale - Page 3

133 communities near Middletown

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Cherry Tree
$300Ks
Cherry Tree, Hanover, PA
New Construction | 55+ age-restricted | Built 2018 - present | 100 homes
Albert Courts
$100Ks - $200Ks
Albert Courts, Thurmont, MD
Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 homes
5 rating (1 reviews) Four Seasons at Vint Hill
$600Ks
Four Seasons at Vint Hill, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 100 homes
Walden Woods
$600Ks - $700Ks
Walden Woods, Laurel, MD
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 97 homes
5 rating (1 reviews) Villas at Cattail Creek
$600Ks
Villas at Cattail Creek, Glenwood, MD
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 93 homes
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The Preserves at Cumberla...
$300Ks - $500Ks
The Preserves at Cumberla..., Gettysburg, PA
Resale Only | 55+ age-restricted | Built 2010 - present | 93 homes
Boxwood Villas
$500Ks - $600Ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
HiddenBrooke
$500Ks
HiddenBrooke, West Springfield, VA
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 91 homes
Cross Creek Village
$300Ks - $400Ks
Cross Creek Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 homes
Hickory Crest
$400Ks - $500Ks
Hickory Crest, Columbia, MD
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 88 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.
Watershed
$500Ks - $600Ks
Watershed, Laurel, MD
New Construction | 55+ age-restricted | 84 homes
The Reserve at New Windso...
$400Ks
The Reserve at New Windso..., New Windsor, MD
Resale Only | 55+ age-restricted | Built 2016 - 2021 | 83 homes
The Village at Harvest Ri...
$500Ks - $600Ks
The Village at Harvest Ri..., Winchester, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes
Woodbrook Village
$300Ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
Heritage Highlands
$300Ks - $400Ks
Heritage Highlands, Lovettsville, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes
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3.7 rating (3 reviews) Four Seasons at Ashburn V...
$400Ks
Four Seasons at Ashburn V..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 homes
Patapsco Overlook
$400Ks
Patapsco Overlook, Catonsville, MD
Resale Only | 55+ age-restricted | Built 2010 - 2017 | 80 homes
The Villages at Broadland...
$400Ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
Washington Square
$200Ks - $300Ks
Washington Square, La Plata, MD
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 78 homes
Hawthorne Greene
$400Ks
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.
Gatherings at Jefferson P...
$400Ks
Gatherings at Jefferson P..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 74 homes
Cadence at Lansdowne
$700Ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes
Scot's Glen
$700Ks - $800Ks
Scot's Glen, Columbia, MD
Resale Only | 55+ age-restricted | Built 2006 - 2012 | 73 homes
The Enclave at Ellicott S...
$400Ks - $500Ks
The Enclave at Ellicott S..., Ellicott City, MD
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 69 homes
The Village at Freedom Hi...
$300Ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes
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Questions? Call us: (240) 663-8229
CobbleStone Estates
$400Ks - $500Ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
Greenvale Mews
$400Ks - $500Ks
Greenvale Mews, Westminster, MD
Resale Only | 55+ age-restricted | Built 2013 - 2016 | 65 homes
The Enclave at Hines Farm
The Enclave at Hines Farm, Laurel, MD
Resale Only | 55+ age-restricted | Built 2025 - present | 63 homes
Liberty Grove
$300Ks
Liberty Grove, Manassas, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 homes
Gatherings at Potomac Sta...
$400Ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 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.
Liberty Place
$300Ks
Liberty Place, Sykesville, MD
Resale Only | 55+ age-restricted | Built 2023 - present | 54 homes
Castlefield
$400Ks - $500Ks
Castlefield, Manchester, MD
Resale Only | 55+ age-restricted | Built 2008 - 2022 | 53 homes
Robinson Manor
$600Ks - $700Ks
Robinson Manor, Gainesville, VA
New Construction | 55+ age-restricted | Built 2023 - present | 50 homes
Villas at Cattail
$300Ks - $400Ks
Villas at Cattail, Hanover, PA
Resale Only | 55+ age-restricted | Built 2007 - 2013 | 48 homes
The Signature at Broadlan...
$300Ks - $400Ks
The Signature at Broadlan..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 45 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Enclave at Park Forest
$500Ks - $600Ks
Enclave at Park Forest, Elkridge, MD
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 45 homes
The Highlands at Blue Rid...
$400Ks - $700Ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 42 homes
The Villas of Rock Oak
$400Ks
The Villas of Rock Oak, Odenton, MD
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 38 homes
Ballenger Run
$500Ks
Ballenger Run, Frederick, MD
Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes
Maple Highlands
$900Ks - $800Ks
Maple Highlands, Fulton, MD
New Construction | 55+ age-restricted | Built 2024 - present | 34 homes
New Cherry Tree 652 CYPRESS DR # 31, HANOVER, PA, 17331, Hanover, PA 17331
$339,900

3 beds

|

2 baths

|

1,821 sq ft

652 CYPRESS DR # 31, HANOVER, PA, 17331
Community: Cherry Tree
Bent Creek Crossing 22 BLUE MOUNTAIN VIS, MECHANICSBURG, PA,..., Mechanicsburg, PA 17050
$324,900

3 beds

|

3 baths

|

1,309 sq ft

22 BLUE MOUNTAIN VIS, MECHANICSBURG, PA,...
Community: Bent Creek Crossing
New Cortland Park 2097 HILL SIDE DR, MECHANICSBURG, PA, 17..., Mechanicsburg, PA 17055
$609,900

2 beds

|

2 baths

|

1,794 sq ft

2097 HILL SIDE DR, MECHANICSBURG, PA, 17...
Community: Cortland Park
Amblebrook 104 CHOKEBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$369,990

3 beds

|

2 baths

|

1,402 sq ft

104 CHOKEBERRY WAY, GETTYSBURG, PA, 1732...
Community: Amblebrook
Amblebrook 93 ELDERBERRY WAY, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$370,990

3 beds

|

2 baths

|

1,402 sq ft

93 ELDERBERRY WAY, GETTYSBURG, PA, 17325
Community: Amblebrook
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Amblebrook 114 ELDERBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$396,990

3 beds

|

2 baths

|

1,736 sq ft

114 ELDERBERRY WAY, GETTYSBURG, PA, 1732...
Community: Amblebrook
Longstown Village 1027 HASTINGS BLVD # 1027, YORK, PA, 174..., York, PA 17402
$275,000

2 beds

|

2 baths

|

1,494 sq ft

|

Condo

1027 HASTINGS BLVD # 1027, YORK, PA, 174...
Community: Longstown Village
Penn National 6135 MERION DR, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222
$535,000

5 beds

|

4 baths

|

4,494 sq ft

6135 MERION DR, FAYETTEVILLE, PA, 17222
Community: Penn National
Penn National 3821 CLUB HOUSE DR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$229,000

3 beds

|

3 baths

|

2,023 sq ft

3821 CLUB HOUSE DR, FAYETTEVILLE, PA, 17...
Community: Penn National
Penn National 6127 GREENBRIAR DR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$339,900

4 beds

|

3 baths

|

1,536 sq ft

6127 GREENBRIAR DR, FAYETTEVILLE, PA, 17...
Community: Penn National
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.
Penn National 6071 GREENBRIAR CT, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$349,900

4 beds

|

3 baths

|

3,486 sq ft

6071 GREENBRIAR CT, FAYETTEVILLE, PA, 17...
Community: Penn National
Penn National 6788 SAINT ANNES DR, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222
$649,900

4 beds

|

3 baths

|

4,310 sq ft

6788 SAINT ANNES DR, FAYETTEVILLE, PA, 1...
Community: Penn National
Penn National 7010 FAIRWAY OAKS, FAYETTEVILLE, PA, 172..., Fayetteville, PA 17222
$365,000

3 beds

|

2 baths

7010 FAIRWAY OAKS, FAYETTEVILLE, PA, 172...
Community: Penn National
Penn National 2375 ARONIMINK CIR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$274,000

2 beds

|

2 baths

2375 ARONIMINK CIR, FAYETTEVILLE, PA, 17...
Community: Penn National
Penn National 2365 ARONIMINK CIR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$239,000

2 beds

|

2 baths

|

1,254 sq ft

2365 ARONIMINK CIR, FAYETTEVILLE, PA, 17...
Community: Penn National
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Penn National 3891 ALFALFA LN, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222
$289,900

2 beds

|

2 baths

|

1,576 sq ft

3891 ALFALFA LN, FAYETTEVILLE, PA, 17222
Community: Penn National
Meadowview Village 130 LEONARD LN, HARRISBURG, PA, 17111, Harrisburg, PA 17111
$275,000

2 beds

|

2 baths

|

1,312 sq ft

|

Condo

130 LEONARD LN, HARRISBURG, PA, 17111
Community: Meadowview Village
Spring Valley Estates 11845 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$364,900

3 beds

|

3 baths

|

1,800 sq ft

11845 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Spring Valley Estates 11798 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$388,900

4 beds

|

3 baths

|

2,035 sq ft

11798 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Spring Valley Estates 11823 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$364,900

3 beds

|

3 baths

|

1,800 sq ft

11823 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
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.
Spring Valley Estates 11819 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$364,900

3 beds

|

3 baths

|

1,800 sq ft

11819 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Penn National 6881 OLD COURSE RD, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$554,000

3 beds

|

3 baths

|

3,089 sq ft

6881 OLD COURSE RD, FAYETTEVILLE, PA, 17...
Community: Penn National
Traditions of America at Silver Spring 75 PRESIDENTS DR, MECHANICSBURG, PA, 170..., Mechanicsburg, PA 17050
$545,000

3 beds

|

3 baths

|

2,978 sq ft

|

Condo

75 PRESIDENTS DR, MECHANICSBURG, PA, 170...
Amblebrook 113 GENTLE SLOPE WAY GENTLE SLOPE WAY 29..., Gettysburg, PA 17325
$450,562

3 beds

|

2 baths

|

1,370 sq ft

113 GENTLE SLOPE WAY GENTLE SLOPE WAY 29...
Community: Amblebrook
Amblebrook 97 CHOKEBERRY WAY, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$404,990

3 beds

|

2 baths

|

1,813 sq ft

97 CHOKEBERRY WAY, GETTYSBURG, PA, 17325
Community: Amblebrook
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Amblebrook 122 ELDERBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$416,990

3 beds

|

2 baths

|

1,813 sq ft

122 ELDERBERRY WAY, GETTYSBURG, PA, 1732...
Community: Amblebrook
Amblebrook 211 GRAND OVERLOOK DR, GETTYSBURG, PA, 1..., Gettysburg, PA 17325
$369,990

2 beds

|

2 baths

|

1,518 sq ft

211 GRAND OVERLOOK DR, GETTYSBURG, PA, 1...
Community: Amblebrook
Carmella 226 CARMELLA DR, MECHANICSBURG, PA, 1705..., Mechanicsburg, PA 17050
$430,000

2 beds

|

2 baths

|

1,615 sq ft

|

Condo

226 CARMELLA DR, MECHANICSBURG, PA, 1705...
Community: Carmella
Penn National 3826 FARMSTEAD DR, FAYETTEVILLE, PA, 172..., Fayetteville, PA 17222
$339,900

3 beds

|

4 baths

|

3,106 sq ft

3826 FARMSTEAD DR, FAYETTEVILLE, PA, 172...
Community: Penn National
Amblebrook 33 ROLLING HILLS WAY, GETTYSBURG, PA, 17..., Gettysburg, PA 17325
$450,000

2 beds

|

2 baths

|

1,852 sq ft

33 ROLLING HILLS WAY, GETTYSBURG, PA, 17...
Community: Amblebrook
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.
Amblebrook 52 TULIP TREE WAY, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$345,900

2 beds

|

2 baths

|

1,500 sq ft

52 TULIP TREE WAY, GETTYSBURG, PA, 17325
Community: Amblebrook
Carmella 427 CARMELLA DR, MECHANICSBURG, PA, 1705..., Mechanicsburg, PA 17050
$599,000

3 beds

|

4 baths

|

3,848 sq ft

|

Condo

427 CARMELLA DR, MECHANICSBURG, PA, 1705...
Community: Carmella
Spring Valley Estates 11802 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$388,900

4 beds

|

3 baths

|

2,035 sq ft

11802 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Penn National 6611 CONGRESSIONAL TER, FAYETTEVILLE, PA..., Fayetteville, PA 17222
$399,900

3 beds

|

3 baths

|

2,564 sq ft

6611 CONGRESSIONAL TER, FAYETTEVILLE, PA...
Community: Penn National
Amblebrook 318 RUSTIC WOOD DR, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$475,000

3 beds

|

2 baths

|

1,860 sq ft

318 RUSTIC WOOD DR, GETTYSBURG, PA, 1732...
Community: Amblebrook
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Penn National 5985 GREENBRIAR TER, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222
$344,900

2 beds

|

3 baths

|

1,724 sq ft

5985 GREENBRIAR TER, FAYETTEVILLE, PA, 1...
Community: Penn National
Traditions of America at Silver Spring 228 LOYAL DR, MECHANICSBURG, PA, 17050, Mechanicsburg, PA 17050
$539,900

3 beds

|

3 baths

|

3,230 sq ft

228 LOYAL DR, MECHANICSBURG, PA, 17050
Penn National 6041 GREENBRIAR TER, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222
$325,000

3 beds

|

2 baths

|

1,974 sq ft

6041 GREENBRIAR TER, FAYETTEVILLE, PA, 1...
Community: Penn National
Amblebrook 23 HIGHLAND VIEW LN, GETTYSBURG, PA, 173..., Gettysburg, PA 17325
$449,900

2 beds

|

2 baths

|

1,733 sq ft

23 HIGHLAND VIEW LN, GETTYSBURG, PA, 173...
Community: Amblebrook
Traditions of America at Silver Spring 265 FOUNDERS WAY, MECHANICSBURG, PA, 170..., Mechanicsburg, PA 17050
$525,000

2 beds

|

2 baths

|

2,189 sq ft

|

Condo

265 FOUNDERS WAY, MECHANICSBURG, PA, 170...

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133 communities near Middletown
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