Winchester Area, VA 55+ active adult communities & homes for sale - Page 2

150 homes near Winchester Area

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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 Heathcote Vi...

$300ks - $500ks

The Flats at Heathcote Vi..., Haymarket, VA

New Construction | 55+ age-restricted | Built 2026 - present | 500 homes

5 rating (2 reviews)

Trilogy® at Lake Frederic...

$400ks - $800ks

Trilogy® at Lake Frederic..., Lake Frederick, VA

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

5 rating (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes

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

Questions? Call us: (540) 452-4199

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 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 (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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

Resale Only | 55+ age-restricted | Built 2023 - 2025

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes

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

Questions? Call us: (540) 452-4199

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

New Construction | 55+ age-restricted | Built 2024 - present | 23 homes

Montebello

$500ks - $600ks

Montebello, Sterling, VA

New and Resale | 55+ age-restricted | Built 2022 - present | 450 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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

New Construction | 55+ age-restricted | Built 2023 - present | 50 homes

The Retreat at Poland Hil...

$800ks

The Retreat at Poland Hil..., Chantilly, VA

Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 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

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

Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes

CobbleStone Estates

$400ks - $500ks

CobbleStone Estates, Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 homes

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

New and Resale | Age-targeted | Built 2018 - present | 25 homes

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes

The Highlands at Blue Rid...

$400ks - $600ks

The Highlands at Blue Rid..., Front Royal, VA

Resale Only | 55+ age-restricted | Built 2017 - 2019 | 42 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

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

Questions? Call us: (540) 452-4199

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 homes

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

New Construction | 55+ age-restricted | Built 2020 - present | 13 homes

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

New Construction | 55+ age-restricted | Built 2021 - present | 145 homes

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 homes

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

Questions? Call us: (540) 452-4199

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 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

1...2

Potomac Green

44397 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147

$725,000

3 beds

3 baths

2,118 sq ft

44397 OAKMONT MANOR SQ, ASHBURN, VA, 201...

Community: Potomac Green

Willow Run

121 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602

$604,990

4 beds

3 baths

2,818 sq ft

121 SCENTED ROSE WAY, WINCHESTER, VA, 22...

Community: Willow Run

Willow Run

117 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602

$604,990

4 beds

3 baths

2,865 sq ft

117 SCENTED ROSE WAY, WINCHESTER, VA, 22...

Community: Willow Run

Trilogy® at Lake Frederick

109 BAYHILL TER, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$425,000

3 beds

4 baths

2,304 sq ft

109 BAYHILL TER, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Cadence at Lansdowne

18989 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176

$747,800

3 beds

3 baths

2,649 sq ft

18989 CORAL REEF SQ, LEESBURG, VA, 20176

Community: Cadence at Lansdowne

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

Questions? Call us: (540) 452-4199

Birchwood at Brambleton

23642 WINTERDAY DR, ASHBURN, VA, 20148, Ashburn, VA 20148

$799,990

3 beds

4 baths

2,742 sq ft

23642 WINTERDAY DR, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Potomac Green

20655 HOPE SPRING TER 104, ASHBURN, VA, ..., Ashburn, VA 20147

$350,000

2 beds

2 baths

876 sq ft

Condo

20655 HOPE SPRING TER 104, ASHBURN, VA, ...

Community: Potomac Green

Crestwood Village

5798 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$526,000

2 beds

2 baths

2,044 sq ft

5798 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

Crestwood Village

7046 CATALPA RD, FREDERICK, MD, 21703, Frederick, MD 21703

$339,900

2 beds

2 baths

1,226 sq ft

7046 CATALPA RD, FREDERICK, MD, 21703

Community: Crestwood Village

Central Parke at Lowes Island

20816 NOBLE TER 312, STERLING, VA, 20165, Sterling, VA 20165

$485,000

2 beds

2 baths

1,989 sq ft

Condo

20816 NOBLE TER 312, STERLING, VA, 20165

Community: Central Parke at Lowes Island

Trilogy® at Lake Frederick

117 PINTAIL WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$867,900

4 beds

4 baths

4,804 sq ft

117 PINTAIL WAY, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Regency at Dominion Valley

5375 TREVINO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169

$779,000

4 beds

4 baths

3,527 sq ft

5375 TREVINO DR, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

JerMae Estates

6 SYLVIA CIR, THURMONT, MD, 21788, Thurmont, MD 21788

$485,000

4 beds

3 baths

2,766 sq ft

6 SYLVIA CIR, THURMONT, MD, 21788

Community: JerMae Estates

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

109 TUTELO LN, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$625,000

2 beds

3 baths

3,505 sq ft

109 TUTELO LN, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Lexington Square

44490 COALPORT TER, ASHBURN, VA, 20147, Ashburn, VA 20147

$1,050,000

4 beds

4 baths

4,109 sq ft

44490 COALPORT TER, ASHBURN, VA, 20147

Community: Lexington Square

Lexington 7

$1,050,000

4 beds

4 baths

4,109 sq ft

44490 COALPORT TER, ASHBURN, VA, 20147

Community: Lexington 7

Rosehill Manor Villas

13354 SNAP DRAGON WAY, HAGERSTOWN, MD, 2..., Hagerstown, MD 21742

$379,990

3 beds

2 baths

1,466 sq ft

13354 SNAP DRAGON WAY, HAGERSTOWN, MD, 2...

Community: Rosehill Manor Villas

Rosehill Manor Villas

13352 SNAP DRAGON WAY, HAGERSTOWN, MD, 2..., Hagerstown, MD 21742

$397,646

3 beds

2 baths

1,687 sq ft

13352 SNAP DRAGON WAY, HAGERSTOWN, MD, 2...

Community: Rosehill Manor Villas

Winchester Landing

116 MAURY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$395,000

3 beds

3 baths

1,630 sq ft

116 MAURY WAY, WINCHESTER, VA, 22602

Community: Winchester Landing

Birchwood at Brambleton

42874 FIREFLY SONATA TER APT 206, ASHBUR..., Ashburn, VA 20148

$579,000

3 beds

2 baths

1,850 sq ft

Condo

42874 FIREFLY SONATA TER APT 206, ASHBUR...

Community: Birchwood at Brambleton

Heritage Hunt

13141 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$799,900

2 beds

4 baths

3,494 sq ft

13141 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

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

Questions? Call us: (540) 452-4199

The Highlands at Blue Ridge Shadows

87 ALBATROSS CT, FRONT ROYAL, VA, 22630, Front Royal, VA 22630

$689,999

4 beds

5 baths

3,379 sq ft

87 ALBATROSS CT, FRONT ROYAL, VA, 22630

Community: The Highlands at Blue Ridge Shadows

Heritage Hunt

6029 CALUMET CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$700,000

2 beds

4 baths

3,198 sq ft

6029 CALUMET CT, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Lexington 7

44508 LOWESTOFT SQ HOMESITE 22, ASHBURN,..., Ashburn, VA 20147

$794,236

3 beds

3 baths

3,036 sq ft

44508 LOWESTOFT SQ HOMESITE 22, ASHBURN,...

Community: Lexington 7

Lexington Square

$794,236

3 beds

3 baths

3,036 sq ft

44508 LOWESTOFT SQ HOMESITE 22, ASHBURN,...

Community: Lexington Square

The Village at Harvest Ridge

435 MIKEY CT, WINCHESTER, VA, 22601, Winchester, VA 22601

$549,900

3 beds

2 baths

1,800 sq ft

435 MIKEY CT, WINCHESTER, VA, 22601

Community: The Village at Harvest Ridge

Heritage Hunt

6159 FERRIER CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$785,000

3 beds

3 baths

2,846 sq ft

6159 FERRIER CT, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Heritage Hunt

6767 DERBY RUN WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$750,000

3 beds

3 baths

2,713 sq ft

6767 DERBY RUN WAY, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Potomac Green

44452 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147

$680,000

2 beds

2 baths

1,667 sq ft

44452 OAKMONT MANOR SQ, ASHBURN, VA, 201...

Community: Potomac Green

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

Questions? Call us: (540) 452-4199

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 114, LEESBURG, V..., Leesburg, VA 20176

$389,000

2 beds

2 baths

1,446 sq ft

Condo

19375 CYPRESS RIDGE TER 114, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Regency at Creekside

5934 BOWES CREEK PL, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$1,255,000

4 beds

5 baths

4,873 sq ft

5934 BOWES CREEK PL, GAINESVILLE, VA, 20...

Community: Regency at Creekside

The Retreat at Poland Hill

43441 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152

$939,900

4 beds

4 baths

3,553 sq ft

43441 BETTYS FARM DR, CHANTILLY, VA, 201...

Community: The Retreat at Poland Hill

Crestwood Village

5640 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703

$465,000

2 beds

2 baths

1,199 sq ft

5640 CRABAPPLE DR, FREDERICK, MD, 21703

Community: Crestwood Village

Gatherings at Wellington

9200 CHARLESTON DR 301, MANASSAS, VA, 20..., Manassas, VA 20110

$380,000

2 beds

2 baths

1,441 sq ft

Condo

9200 CHARLESTON DR 301, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Potomac Green

20850 ADAMS MILL PL, ASHBURN, VA, 20147, Ashburn, VA 20147

$790,000

3 beds

3 baths

2,452 sq ft

20850 ADAMS MILL PL, ASHBURN, VA, 20147

Community: Potomac Green

Trilogy® at Lake Frederick

105 CHECKERSPOT WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$424,900

3 beds

4 baths

2,227 sq ft

105 CHECKERSPOT WAY, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

124 PIMPERNEL PL, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$869,700

3 beds

4 baths

3,768 sq ft

124 PIMPERNEL PL, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Crestwood Village

6996 BASSWOOD RD H, FREDERICK, MD, 21703, Frederick, MD 21703

$239,900

2 beds

1 baths

941 sq ft

Condo

6996 BASSWOOD RD H, FREDERICK, MD, 21703

Community: Crestwood Village

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

Questions? Call us: (540) 452-4199

Willow Run

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

$509,990

4 beds

3 baths

2,168 sq ft

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

Community: Willow Run

Willow Run

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

$469,990

4 beds

3 baths

2,168 sq ft

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

Community: Willow Run

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Winchester Area

Frequently Asked Questions

What size 55+ communities are there in the Winchester Area?

In the Winchester Area, there are no large communities, 1 medium community with 500-1000 homes, and 9 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in the Winchester Area?

The smallest 55+ communities in the Winchester Area has 13 homes, the largest has 950 homes, and the average communities consists of 161 homes.

Are there new 55+ homes available in the Winchester Area?

Yes, there are new 55+ homes available in the Winchester Area. The most recent communities started in the Winchester Area include Abrams Chase, Cottage Glen, The Highlands at Blue Ridge Shadows. There are also 3 communities in the Winchester Area that offer new construction homes, including Abrams Chase, Trilogy® at Lake Frederick, Cottage Glen.

Are there gated 55+ communities in the Winchester Area?

Yes, there are gated 55+ communities in the Winchester Area. Approximately 30.0% of 55+ communities in the area are gated. For instance, Cedar Meadows is a gated communities with 129 homes, and Trilogy® at Lake Frederick is another gated communities with 950 homes.

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

On average, listings in 55+ communities in the Winchester Area stay on the market for around 602 days. The average price of homes for sale in these communities is approximately $484,040, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Highlands at Blue Ridge Shadows average around $615,000, while homes in Cottage Glen average around $479,500.

Want to learn more about 55+ communities in the Winchester Area?

Insights and market stats
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Answers from local 55+ experts

Want to learn more about 55+ communities in Winchester Area?

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150 homes

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© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Feb 24, 2026.
This application does not include information on all of the properties available for sale at this time.

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Winchester Area, VA 55+ active adult communities & homes for sale - Page 2

50 communities near Winchester Area

150 homes near Winchester Area

3 beds

3 baths

2,118 sq ft

4 beds

3 baths

2,818 sq ft

4 beds

3 baths

2,865 sq ft

3 beds

4 baths

2,304 sq ft

3 beds

3 baths

2,649 sq ft

3 beds

4 baths

2,742 sq ft

2 beds

2 baths

876 sq ft

Condo

2 beds

2 baths

2,044 sq ft

2 beds

2 baths

1,226 sq ft

2 beds

2 baths

1,989 sq ft

Condo

4 beds

4 baths

4,804 sq ft

4 beds

4 baths

3,527 sq ft

4 beds

3 baths

2,766 sq ft

2 beds

3 baths

3,505 sq ft

4 beds

4 baths

4,109 sq ft

4 beds

4 baths

4,109 sq ft

3 beds

2 baths

1,466 sq ft

3 beds

2 baths

1,687 sq ft

3 beds

3 baths

1,630 sq ft

3 beds

2 baths

1,850 sq ft

Condo

2 beds

4 baths

3,494 sq ft

4 beds

5 baths

3,379 sq ft

2 beds

4 baths

3,198 sq ft

3 beds

3 baths

3,036 sq ft

3 beds

3 baths