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Middletown, MD 55+ active adult communities & homes for sale - Page 16

627 homes near Middletown

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2.3 rating (3 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
5 rating (2 reviews) Trilogy® at Lake Frederic...
$300ks - $1Ms
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale | 55+ age-restricted | Built 2006 - present | 950 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 (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
The Flats at Heathcote Vi...
$300ks - $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction | 55+ age-restricted | Built 2026 - present | 500 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Parklands
$300ks - $500ks
Parklands, White Plains, MD
New Construction | 55+ age-restricted | Built 2025 - present | 586 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
Penn National
$100ks - $600ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
5 rating (1 reviews) Two Rivers
$500ks - $700ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 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
Gatherings at Cabin Branc...
$400ks - $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2024 - present | 135 homes
The Village at Cabin Bran...
$500ks
The Village at Cabin Bran..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2021 - present
The Gatherings at Lakevie...
$300ks - $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction | 55+ age-restricted | Built 2025 - present | 122 homes
Cameron Grove
$200ks - $400ks
Cameron Grove, Upper Marlboro, MD
Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Traditions of America at ...
$400ks - $600ks
Traditions of America at ..., Mechanicsburg, PA
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 517 homes
Willow Run
$500ks - $600ks
Willow Run, Winchester, VA
New Construction | 55+ age-restricted | 300 homes
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
5 rating (1 reviews) Snowden Overlook
$300ks - $600ks
Snowden Overlook, Columbia, MD
Resale Only | 55+ age-restricted | Built 2005 - 2010 | 350 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 Atrium at MetroWest
$600ks - $700ks
The Atrium at MetroWest, Fairfax, VA
New Construction | 55+ age-restricted | Built 2018 - present | 206 homes
Spring Valley Estates
$300ks - $400ks
Spring Valley Estates, Waynesboro, PA
New Construction | 55+ age-restricted | Built 2019 - present | 140 homes
Signature Club at Greenvi...
$400ks - $500ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 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
Bloomfields 55+
$700ks - $800ks
Bloomfields 55+, Frederick, MD
New Construction | 55+ age-restricted | Built 2026 - present
Emerald Pointe
$300ks - $500ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Cadence at Lansdowne
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes
Carroll's Creek
$300ks
Carroll's Creek, Gambrills, MD
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 162 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
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.
Cromwell 55+
$300ks - $900ks
Cromwell 55+, Ijamsville, MD
New Construction | 55+ age-restricted | Built 2024 - present | 488 homes
Winchester Landing
$300ks - $400ks
Winchester Landing, Winchester, VA
Resale Only | 55+ age-restricted | Built 2023 - 2025
Four Seasons at Virginia ...
$400ks - $500ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction | 55+ age-restricted | Built 2021 - present | 185 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
Beechfield Manors
$200ks - $400ks
Beechfield Manors, Bowie, MD
New Construction | 55+ age-restricted | Built 2024 - present
3 rating (2 reviews) Dunbarton
$300ks - $500ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
Country Manor
$200ks
Country Manor, Shippensburg, PA
Resale Only | 55+ age-restricted | Built 2000 - 2018 | 130 homes
5 rating (1 reviews) Willow Lawn Cottages
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Sagebrook
$300ks - $400ks
Sagebrook, Dover, PA
New and Resale | 55+ age-restricted | Built 2020 - present | 194 homes
The Courtyards at Waverly...
$300ks - $1Ms
The Courtyards at Waverly..., Marriottsville, MD
Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 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.
123...4
Cindy Certified
255 W FALLS STATION BLVD 607, FALLS CHUR..., Falls Church, VA 22046
$1,145,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

255 W FALLS STATION BLVD 607, FALLS CHUR...
Cindy Certified
255 W FALLS STATION BLVD 911, FALLS CHUR..., Falls Church, VA 22046
$899,000

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

255 W FALLS STATION BLVD 911, FALLS CHUR...
Leisure World® of Maryland 15107 INTERLACHEN DR 2-321, SILVER SPRIN..., Silver Spring, MD 20906
$184,500

2 beds

|

2 baths

|

990 sq ft

15107 INTERLACHEN DR 2-321, SILVER SPRIN...
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 920, LEESBURG, V..., Leesburg, VA 20176
$450,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

19385 CYPRESS RIDGE TER 920, LEESBURG, V...
Four Seasons at Virginia Crossing 3703 HAVERTILL LN, WOODBRIDGE, VA, 22193, Woodbridge, VA 22193
$625,000

3 beds

|

3 baths

|

2,215 sq ft

3703 HAVERTILL LN, WOODBRIDGE, VA, 22193
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Birchwood at Brambleton 42972 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$853,586

3 beds

|

4 baths

|

2,742 sq ft

42972 TRUMAN TER, ASHBURN, VA, 20148
Leisure World® of Maryland 3500 FOREST EDGE DR 15-2E, SILVER SPRING..., Silver Spring, MD 20906
$180,000

2 beds

|

2 baths

|

1,157 sq ft

|

Condo

3500 FOREST EDGE DR 15-2E, SILVER SPRING...
Willow Run 118 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602
$529,990

3 beds

|

2 baths

|

1,958 sq ft

118 SCENTED ROSE WAY, WINCHESTER, VA, 22...
Community: Willow Run
Leisure World® of Maryland 15300 BEAVERBROOK CT 88-2B, SILVER SPRIN..., Silver Spring, MD 20906
$268,888

2 beds

|

2 baths

|

1,043 sq ft

|

Condo

15300 BEAVERBROOK CT 88-2B, SILVER SPRIN...
Beechfield Manors 4003 SEASIDE ALDER RD 0208 - ROSE, BOWIE..., Bowie, MD 20720
$383,850

2 beds

|

2 baths

|

1,294 sq ft

|

Condo

4003 SEASIDE ALDER RD 0208 - ROSE, BOWIE...
Community: Beechfield Manors
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.
Beechfield Manors 4003 SEASIDE ALDER RD 0204 - VIOLET, BOW..., Bowie, MD 20720
$349,990

2 beds

|

2 baths

|

1,288 sq ft

|

Condo

4003 SEASIDE ALDER RD 0204 - VIOLET, BOW...
Community: Beechfield Manors
Emerald Pointe 13357 DIAMOND POINTE DR V120, HAGERSTOWN..., Hagerstown, MD 21742
$499,900

2 beds

|

2 baths

|

1,850 sq ft

13357 DIAMOND POINTE DR V120, HAGERSTOWN...
Community: Emerald Pointe
The Gatherings at Lakeview Community 626 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136
$470,990

3 beds

|

3 baths

|

2,475 sq ft

|

Condo

626 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
The Gatherings at Lakeview Community 624 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136
$362,990

3 beds

|

3 baths

|

1,569 sq ft

|

Condo

624 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
Sagebrook 907 SHADOWBROOKE DR, DOVER, PA, 17315, Dover, PA 17315
$401,990

2 beds

|

2 baths

907 SHADOWBROOKE DR, DOVER, PA, 17315
Community: Sagebrook
Cindy Certified
255 W FALLS STATION BLVD 206, FALLS CHUR..., Falls Church, VA 22046
$899,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

255 W FALLS STATION BLVD 206, FALLS CHUR...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Beechfield Manors 4005 SEASIDE ALDER RD D- DAISY - 9101, B..., Bowie, MD 20720
$324,990

1 beds

|

1 baths

|

1,005 sq ft

|

Condo

4005 SEASIDE ALDER RD D- DAISY - 9101, B...
Community: Beechfield Manors
Cindy Certified
255 W FALLS STATION BLVD 205, FALLS CHUR..., Falls Church, VA 22046
$699,000

2 beds

|

2 baths

|

1,235 sq ft

|

Condo

255 W FALLS STATION BLVD 205, FALLS CHUR...
Cindy Certified
255 W FALLS STATION BLVD 6, FALLS CHURCH..., Falls Church, VA 22046
$1,340,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

255 W FALLS STATION BLVD 6, FALLS CHURCH...
Cindy Certified
255 W FALLS STATION BLVD 1, FALLS CHURCH..., Falls Church, VA 22046
$1,470,000

3 beds

|

3 baths

|

1,690 sq ft

|

Condo

255 W FALLS STATION BLVD 1, FALLS CHURCH...
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.
Cindy Certified
255 W FALLS STATION BLVD 9, FALLS CHURCH..., Falls Church, VA 22046
$1,620,000

2 beds

|

3 baths

|

1,565 sq ft

|

Condo

255 W FALLS STATION BLVD 9, FALLS CHURCH...
Cindy Certified
255 W FALLS STATION BLVD 5, FALLS CHURCH..., Falls Church, VA 22046
$990,000

2 beds

|

2 baths

|

1,235 sq ft

|

Condo

255 W FALLS STATION BLVD 5, FALLS CHURCH...
Cindy Certified
255 W FALLS STATION BLVD 3, FALLS CHURCH..., Falls Church, VA 22046
$1,005,000

2 beds

|

2 baths

|

1,275 sq ft

|

Condo

255 W FALLS STATION BLVD 3, FALLS CHURCH...
Cindy Certified
255 W FALLS STATION BLVD 2, FALLS CHURCH..., Falls Church, VA 22046
$1,110,000

2 beds

|

2 baths

|

1,325 sq ft

|

Condo

255 W FALLS STATION BLVD 2, FALLS CHURCH...
The Village at Cabin Branch 13210 PETREL ST 3304, CLARKSBURG, MD, 20..., Clarksburg, MD 20871
$474,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST 3304, CLARKSBURG, MD, 20...
Gatherings at Cabin Branch 13210 PETREL ST 3304, CLARKSBURG, MD, 20..., Clarksburg, MD 20871
$474,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST 3304, CLARKSBURG, MD, 20...
Cindy Certified
255 W FALLS STATION BLVD 302, FALLS CHUR..., Falls Church, VA 22046
$775,000

2 beds

|

2 baths

|

1,325 sq ft

|

Condo

255 W FALLS STATION BLVD 302, FALLS CHUR...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229

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