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Middletown, MD 55+ active adult communities & homes for sale - Page 9

572 homes near Middletown

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5 rating (1 reviews) Leisure World® of Marylan...
<$100k - $800ks
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 - $700ks
Amblebrook, Gettysburg, PA
New Construction | 55+ age-restricted | Built 2018 - present | 2,000 homes
5 rating (2 reviews) Trilogy® at Lake Frederic...
- $900ks
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
The Flats at Heathcote Vi...
$300ks - $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction | 55+ age-restricted | Built 2026 - present | 500 homes
Parklands
$300ks - $500ks
Parklands, White Plains, MD
New Construction | 55+ age-restricted | Built 2025 - present | 586 homes
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Questions? Call us: (240) 663-8229
Willow Run
$500ks - $600ks
Willow Run, Winchester, VA
New Construction | 55+ age-restricted | 300 homes
Cameron Grove
$200ks - $400ks
Cameron Grove, Upper Marlboro, MD
Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 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
The Flats at Northside
$600ks - $1Ms
The Flats at Northside, Potomac, MD
New Construction | Age-targeted | Built 2025 - present | 143 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 (3 reviews) Heritage Hunt
$400ks - $600ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
5 rating (31 reviews) Lansdowne Woods of Virgin...
$200ks - $500ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 homes
Beechfield Manors
$200ks - $400ks
Beechfield Manors, Bowie, MD
New Construction | 55+ age-restricted | Built 2024 - present
Penn National
$100ks - $600ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
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Questions? Call us: (240) 663-8229
Emerald Pointe
$300ks - $500ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
The Village at Cabin Bran...
$500ks
The Village at Cabin Bran..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2021 - present
The Atrium at MetroWest
$600ks - $700ks
The Atrium at MetroWest, Fairfax, VA
New Construction | 55+ age-restricted | Built 2018 - present | 206 homes
Gatherings at Cabin Branc...
$400ks - $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2024 - present | 135 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.
The Gatherings at Lakevie...
$300ks - $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction | 55+ age-restricted | Built 2025 - present | 122 homes
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
Bloomfields 55+
$700ks - $800ks
Bloomfields 55+, Frederick, MD
New Construction | 55+ age-restricted | Built 2026 - present
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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
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 (2 reviews) Potomac Green
$400ks - $800ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
Spring Valley Estates
$300ks - $400ks
Spring Valley Estates, Waynesboro, PA
New Construction | 55+ age-restricted | Built 2019 - present | 140 homes
5 rating (1 reviews) Carroll Vista
$200ks - $300ks
Carroll Vista, Taneytown, MD
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 453 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) Two Rivers
$500ks - $700ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes
Cedar Ridge at Piney Orch...
$200ks - $300ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes
Winifred Manor
$200ks
Winifred Manor, Eldersburg, MD
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 152 homes
5 rating (2 reviews) Central Parke at Victoria...
$300ks - $500ks
Central Parke at Victoria..., Laurel, MD
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 609 homes
Blue Ridge
$300ks - $400ks
Blue Ridge, Harrisburg, PA
New and Resale | Age-targeted | Built 2020 - present | 130 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Carroll's Creek
$300ks
Carroll's Creek, Gambrills, MD
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 162 homes
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 homes
Signature Club at Greenvi...
$400ks - $500ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes
Traditions of America at ...
$400ks - $600ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 517 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) Gatherings at Lyndwood
$300ks - $400ks
Gatherings at Lyndwood, Elkridge, MD
Resale Only | 55+ age-restricted | Built 2005 - 2008 | 216 homes
Four Seasons at Virginia ...
$400ks - $500ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction | 55+ age-restricted | Built 2021 - present | 185 homes
Sagebrook
$300ks - $400ks
Sagebrook, Dover, PA
New and Resale | 55+ age-restricted | Built 2020 - present | 194 homes
The Crest of Alexandria
$400ks - $800ks
The Crest of Alexandria, Alexandria, VA
New and Resale | 55+ age-restricted | Built 2017 - present | 250 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
The Village at Freedom Hi...
$300ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes
5 rating (1 reviews) Crestwood Village
$200ks - $500ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
123...4
Amblebrook 57 GENTLE SLOPE WAY, GETTYSBURG, PA, 173..., Gettysburg, PA 17325
$564,990

5 beds

|

3 baths

|

2,637 sq ft

57 GENTLE SLOPE WAY, GETTYSBURG, PA, 173...
Community: Amblebrook
The Gatherings at Lakeview Community 590 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136
$374,990

3 beds

|

3 baths

|

1,569 sq ft

|

Condo

590 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
Winifred Manor 2013 RUDY SERRA DR 3D, ELDERSBURG, MD, 2..., Eldersburg, MD 21784
$239,900

2 beds

|

2 baths

|

1,025 sq ft

|

Condo

2013 RUDY SERRA DR 3D, ELDERSBURG, MD, 2...
Community: Winifred Manor
Hawthorne Greene 56 CAMDEN CIR, LA PLATA, MD, 20646, La Plata, MD 20646
$387,000

2 beds

|

2 baths

|

1,485 sq ft

56 CAMDEN CIR, LA PLATA, MD, 20646
Community: Hawthorne Greene
Leisure World® of Maryland 15115 INTERLACHEN DR 3-815, SILVER SPRIN..., Silver Spring, MD 20906
$185,000

2 beds

|

2 baths

|

1,115 sq ft

|

Condo

15115 INTERLACHEN DR 3-815, SILVER SPRIN...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Suffield Meadows 6696 CLUB HOUSE LN 206, WARRENTON, VA, 2..., Warrenton, VA 20187
$375,000

2 beds

|

2 baths

|

1,372 sq ft

|

Condo

6696 CLUB HOUSE LN 206, WARRENTON, VA, 2...
Community: Suffield Meadows
Crestwood Village 5693 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703
$364,900

2 beds

|

2 baths

|

1,148 sq ft

5693 CRABAPPLE DR, FREDERICK, MD, 21703
Community: Crestwood Village
Four Seasons at Virginia Crossing 13970 ENGLEFIELD DR 404, WOODBRIDGE, VA,..., Woodbridge, VA 22193
$449,990

2 beds

|

2 baths

|

1,437 sq ft

|

Condo

13970 ENGLEFIELD DR 404, WOODBRIDGE, VA,...
Leisure World® of Maryland 15100 INTERLACHEN DR 4-407, SILVER SPRIN..., Silver Spring, MD 20906
$389,900

3 beds

|

3 baths

|

1,530 sq ft

|

Condo

15100 INTERLACHEN DR 4-407, SILVER SPRIN...
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.
Leisure World® of Maryland 15115 INTERLACHEN DR 3-716, SILVER SPRIN..., Silver Spring, MD 20906
$169,000

1 beds

|

1 baths

|

850 sq ft

|

Condo

15115 INTERLACHEN DR 3-716, SILVER SPRIN...
Amblebrook 328 HIGHLAND WAY 170, GETTYSBURG, PA, 17..., Gettysburg, PA 17325
$499,990

2 beds

|

2 baths

|

1,661 sq ft

328 HIGHLAND WAY 170, GETTYSBURG, PA, 17...
Community: Amblebrook
Trilogy® at Lake Frederick 136 MALLARD DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630
$625,000

2 beds

|

2 baths

|

2,089 sq ft

136 MALLARD DR, LAKE FREDERICK, VA, 2263...
Willow Run LOT 0057 HYDRANGEA WAY, WINCHESTER, VA, ..., Winchester, VA 22602
$564,990

3 beds

|

2 baths

|

1,748 sq ft

LOT 0057 HYDRANGEA WAY, WINCHESTER, VA, ...
Community: Willow Run
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Willow Run LOT 0055 HYDRANGEA WAY, WINCHESTER, VA, ..., Winchester, VA 22602
$576,990

3 beds

|

2 baths

|

1,865 sq ft

LOT 0055 HYDRANGEA WAY, WINCHESTER, VA, ...
Community: Willow Run
Carroll Vista 314 BUTTERFLY DR 72, TANEYTOWN, MD, 2178..., Taneytown, MD 21787
$321,500

2 beds

|

2 baths

|

1,419 sq ft

|

Condo

314 BUTTERFLY DR 72, TANEYTOWN, MD, 2178...
Community: Carroll Vista
Four Seasons at Historic Virginia 3618 SECRET GROVE CT, DUMFRIES, VA, 2202..., Dumfries, VA 22025
$590,000

3 beds

|

2 baths

|

2,092 sq ft

3618 SECRET GROVE CT, DUMFRIES, VA, 2202...
Eden Brook 1009 SAMANTHA LN 201, ODENTON, MD, 21113, Odenton, MD 21113
$325,000

2 beds

|

2 baths

|

1,613 sq ft

|

Condo

1009 SAMANTHA LN 201, ODENTON, MD, 21113
Community: Eden Brook
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.
Four Seasons at Historic Virginia 4030 GREAT HARVEST CT, DUMFRIES, VA, 220..., Dumfries, VA 22025
$694,900

4 beds

|

3 baths

|

3,569 sq ft

4030 GREAT HARVEST CT, DUMFRIES, VA, 220...
Heritage Hunt 13170 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155
$779,900

3 beds

|

3 baths

|

2,848 sq ft

13170 TRIPLE CROWN LOOP, GAINESVILLE, VA...
Community: Heritage Hunt
The Village at Cabin Branch 13210 PETREL ST 3105, CLARKSBURG, MD, 20..., Clarksburg, MD 20871
$529,900

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST 3105, CLARKSBURG, MD, 20...
Gatherings at Cabin Branch 13210 PETREL ST 3105, CLARKSBURG, MD, 20..., Clarksburg, MD 20871
$529,900

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST 3105, CLARKSBURG, MD, 20...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Heritage Hunt 14025 BREEDERS CUP DR, GAINESVILLE, VA, ..., Gainesville, VA 20155
$699,000

3 beds

|

3 baths

|

2,714 sq ft

14025 BREEDERS CUP DR, GAINESVILLE, VA, ...
Community: Heritage Hunt
Spring Hill 8909 YELLOW DAISY PL, LORTON, VA, 22079, Lorton, VA 22079
$879,900

3 beds

|

3 baths

|

2,546 sq ft

8909 YELLOW DAISY PL, LORTON, VA, 22079
Community: Spring Hill
Birchwood at Brambleton 23631 HAVELOCK WALK TER 421, ASHBURN, VA..., Ashburn, VA 20148
$555,000

3 beds

|

2 baths

|

1,906 sq ft

|

Condo

23631 HAVELOCK WALK TER 421, ASHBURN, VA...
Heritage Hunt 6932 WALNUT HILL DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$575,000

4 beds

|

3 baths

|

2,126 sq ft

6932 WALNUT HILL DR, GAINESVILLE, VA, 20...
Community: Heritage Hunt
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.
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 7, HAYMARKET, VA, 201..., Haymarket, VA 20169
$474,990

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

5800 MOONSTONE WAY 7, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 6, HAYMARKET, VA, 201..., Haymarket, VA 20169
$374,990

1 beds

|

2 baths

|

995 sq ft

|

Condo

5800 MOONSTONE WAY 6, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 5, HAYMARKET, VA, 201..., Haymarket, VA 20169
$589,990

3 beds

|

2 baths

|

1,850 sq ft

|

Condo

5800 MOONSTONE WAY 5, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 4, HAYMARKET, VA, 201..., Haymarket, VA 20169
$539,990

2 beds

|

2 baths

|

1,520 sq ft

|

Condo

5800 MOONSTONE WAY 4, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 3, HAYMARKET, VA, 201..., Haymarket, VA 20169
$574,990

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

5800 MOONSTONE WAY 3, HAYMARKET, VA, 201...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 2, HAYMARKET, VA, 201..., Haymarket, VA 20169
$429,990

2 beds

|

2 baths

|

1,345 sq ft

|

Condo

5800 MOONSTONE WAY 2, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 1, HAYMARKET, VA, 201..., Haymarket, VA 20169
$494,990

2 beds

|

2 baths

|

1,475 sq ft

|

Condo

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201...
Bloomfields 55+ 2619 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702
$809,990

3 beds

|

3 baths

|

4,034 sq ft

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

3 beds

|

3 baths

|

3,591 sq ft

2617 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.
Bloomfields 55+ 2615 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702
$729,990

2 beds

|

2 baths

|

3,357 sq ft

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

2 beds

|

2 baths

|

2,915 sq ft

2613 BROADLEAF DR, FREDERICK, MD, 21702
Community: Bloomfields 55+
Amblebrook 80 BONESET DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325
$412,000

4 beds

|

4 baths

|

2,692 sq ft

80 BONESET DR, GETTYSBURG, PA, 17325
Community: Amblebrook
Country Manor 14 COLONIAL CT, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$209,500

3 beds

|

2 baths

|

1,708 sq ft

14 COLONIAL CT, SHIPPENSBURG, PA, 17257
Community: Country Manor
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Cameron Grove 13502 VANDIVER CT, UPPER MARLBORO, MD, 2..., Upper Marlboro, MD 20774
$430,000

2 beds

|

2 baths

|

1,658 sq ft

13502 VANDIVER CT, UPPER MARLBORO, MD, 2...
Community: Cameron Grove
Potomac Green 20763 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147
$850,000

3 beds

|

3 baths

|

2,810 sq ft

20763 CRESCENT POINTE PL, ASHBURN, VA, 2...
Community: Potomac Green

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