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

51 communities near Winchester Area

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5 rating (2 reviews)

Trilogy® at Lake Frederic...

- $1Ms

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

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

5 rating (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

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

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

Questions? Call us: (540) 452-4199

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

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

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

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)

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

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 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 Winchester Area? 55places can help!

Questions? Call us: (540) 452-4199

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 homes

Montebello

$500ks - $1Ms

Montebello, Sterling, VA

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

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

The Retreat at Poland Hil...

$800ks

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

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

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

Questions? Call us: (540) 452-4199

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

CobbleStone Estates

$400ks - $500ks

CobbleStone Estates, Hagerstown, MD

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

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

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

Albert Courts

$100ks - $200ks

Albert Courts, Thurmont, MD

Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 homes

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

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

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes

1...2

Cedar Meadows

126 FORGET ME NOT DR, WHITE POST, VA, 22..., White Post, VA 22663

$459,900

3 beds

2 baths

1,659 sq ft

126 FORGET ME NOT DR, WHITE POST, VA, 22...

Community: Cedar Meadows

Regency at Belmont

43909 EVELYN PATH TER, ASHBURN, VA, 2014..., Ashburn, VA 20147

$999,990

4 beds

4 baths

3,243 sq ft

43909 EVELYN PATH TER, ASHBURN, VA, 2014...

Community: Regency at Belmont

Trilogy® at Lake Frederick

109 EMPEROR DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$625,000

4 beds

4 baths

3,859 sq ft

109 EMPEROR DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Abrams Chase

105 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$464,900

2 beds

2 baths

1,800 sq ft

105 AMBERFIELD CT, WINCHESTER, VA, 22602

Community: Abrams Chase

New Potomac Green

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

$729,000

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 Winchester Area? 55places can help!

Questions? Call us: (540) 452-4199

New Crestwood Village

6864 SNOWBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703

$474,900

2 beds

2 baths

1,749 sq ft

6864 SNOWBERRY CT, FREDERICK, MD, 21703

Community: Crestwood Village

New Central Parke at Lowes Island

20891 ROYAL VILLA TER, STERLING, VA, 201..., Sterling, VA 20165

$750,000

4 beds

3 baths

2,521 sq ft

20891 ROYAL VILLA TER, STERLING, VA, 201...

Community: Central Parke at Lowes Island

New The Village at Foxfield

4 LAMAR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769

$489,900

2 beds

2 baths

1,359 sq ft

4 LAMAR LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

New Emerald Pointe

19404 AMETHYST DR V59, HAGERSTOWN, MD, 2..., Hagerstown, MD 21742

$649,900

4 beds

3 baths

2,559 sq ft

19404 AMETHYST DR V59, HAGERSTOWN, MD, 2...

Community: Emerald Pointe

New Heritage Hunt

13465 VICTORY GALLOP WAY, GAINESVILLE, V..., Gainesville, VA 20155

$630,000

2 beds

3 baths

1,987 sq ft

13465 VICTORY GALLOP WAY, GAINESVILLE, V...

Community: Heritage Hunt

New Crestwood Village

6979 ARBOR DR, FREDERICK, MD, 21703, Frederick, MD 21703

$379,000

2 beds

2 baths

1,225 sq ft

6979 ARBOR DR, FREDERICK, MD, 21703

Community: Crestwood Village

Ballenger Run

5311 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703

$525,000

3 beds

4 baths

2,868 sq ft

5311 CRAPE MYRTLE DR, FREDERICK, MD, 217...

Community: Ballenger Run

Cadence at Lansdowne

43865 CASTAWAY CAY TER, LEESBURG, VA, 20..., Leesburg, VA 20176

$899,990

3 beds

3 baths

2,643 sq ft

43865 CASTAWAY CAY TER, LEESBURG, VA, 20...

Community: Cadence at Lansdowne

Potomac Green

44398 MALTESE FALCON SQ, ASHBURN, VA, 20..., Ashburn, VA 20147

$740,000

3 beds

3 baths

2,118 sq ft

44398 MALTESE FALCON SQ, ASHBURN, VA, 20...

Community: Potomac Green

Liberty Grove

9970 WELLINGTON RD, MANASSAS, VA, 20110, Manassas, VA 20110

$565,000

3 beds

4 baths

2,404 sq ft

Condo

9970 WELLINGTON RD, MANASSAS, VA, 20110

Community: Liberty Grove

Birchwood at Brambleton

23600 RAYTOWN TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$846,046

3 beds

4 baths

2,742 sq ft

23600 RAYTOWN TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

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

Questions? Call us: (540) 452-4199

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 809, LEESBURG, V..., Leesburg, VA 20176

$399,900

2 beds

2 baths

1,246 sq ft

Condo

19385 CYPRESS RIDGE TER 809, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Birchwood at Brambleton

42874 FIREFLY SONATA TER 403, ASHBURN, V..., Ashburn, VA 20148

$574,900

3 beds

2 baths

1,712 sq ft

Condo

42874 FIREFLY SONATA TER 403, ASHBURN, V...

Community: Birchwood at Brambleton

The Flats at Heathcote Village by Del Webb

6091 AZURITE WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$797,540

3 beds

3 baths

2,625 sq ft

6091 AZURITE WAY, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

6099 AZURITE WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$752,083

3 beds

3 baths

2,763 sq ft

6099 AZURITE WAY, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5926 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$839,324

3 beds

3 baths

2,763 sq ft

5926 SUNSTONE LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5928 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$809,871

3 beds

4 baths

2,763 sq ft

5928 SUNSTONE LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Village at Harvest Ridge

116 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601

$625,000

3 beds

3 baths

3,573 sq ft

116 HARVEST RIDGE DR, WINCHESTER, VA, 22...

Community: The Village at Harvest Ridge

Dunbarton

$749,999

5 beds

3 baths

3,322 sq ft

12975 DUNBARTON DR, BRISTOW, VA, 20136

Community: Dunbarton

Liberty Grove

8609 LIBERTY TRL, MANASSAS, VA, 20110, Manassas, VA 20110

$595,000

3 beds

4 baths

2,404 sq ft

Condo

8609 LIBERTY TRL, MANASSAS, VA, 20110

Community: Liberty Grove

Winchester Landing

120 GABRIEL CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$524,900

3 beds

3 baths

2,072 sq ft

120 GABRIEL CT, WINCHESTER, VA, 22602

Community: Winchester Landing

Dunbarton

13244 ORMOND DR, BRISTOW, VA, 20136, Bristow, VA 20136

$529,900

2 beds

2 baths

1,763 sq ft

13244 ORMOND DR, BRISTOW, VA, 20136

Community: Dunbarton

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

184 TROUT LILY DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$419,000

3 beds

4 baths

2,439 sq ft

184 TROUT LILY DR, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

Heritage Hunt

13728 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$725,000

3 beds

3 baths

2,320 sq ft

13728 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Montebello

21630 HAWKSBILL HIGH CIR 405, STERLING, ..., Sterling, VA 20164

$545,000

2 beds

2 baths

1,296 sq ft

Condo

21630 HAWKSBILL HIGH CIR 405, STERLING, ...

Community: Montebello

The Woodlands of Urbana

3264 STARLIGHT ST, FREDERICK, MD, 21704, Frederick, MD 21704

$549,990

3 beds

3 baths

1,817 sq ft

3264 STARLIGHT ST, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

Heritage Hunt

6817 DERBY RUN WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$699,000

2 beds

2 baths

1,588 sq ft

6817 DERBY RUN WAY, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Trilogy® at Lake Frederick

110 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$675,000

3 beds

3 baths

3,555 sq ft

110 VICEROY WAY, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Potomac Green

44442 CRUDEN BAY DR, ASHBURN, VA, 20147, Ashburn, VA 20147

$739,900

3 beds

3 baths

2,255 sq ft

44442 CRUDEN BAY DR, ASHBURN, VA, 20147

Community: Potomac Green

Potomac Green

44406 ADARE MANOR SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$700,000

2 beds

2 baths

1,667 sq ft

44406 ADARE MANOR SQ, ASHBURN, VA, 20147

Community: Potomac Green

Dunbarton

13199 ORMOND DR, BRISTOW, VA, 20136, Bristow, VA 20136

$790,000

4 beds

4 baths

3,216 sq ft

13199 ORMOND DR, BRISTOW, VA, 20136

Community: Dunbarton

Trilogy® at Lake Frederick

120 CHOKE CHERRY CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$485,000

4 beds

4 baths

3,008 sq ft

120 CHOKE CHERRY CT, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

The Woodlands of Urbana

9311 SORREL LN, FREDERICK, MD, 21704, Frederick, MD 21704

$725,000

3 beds

4 baths

3,292 sq ft

9311 SORREL LN, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

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

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Potomac Green

44426 CRUDEN BAY DR, ASHBURN, VA, 20147, Ashburn, VA 20147

$745,000

3 beds

3 baths

2,253 sq ft

44426 CRUDEN BAY DR, ASHBURN, VA, 20147

Community: Potomac Green

Regency at Dominion Valley

5219 ARMOUR CT, HAYMARKET, VA, 20169, Haymarket, VA 20169

$725,000

3 beds

3 baths

2,358 sq ft

5219 ARMOUR CT, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

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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 10 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 173 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 Winchester Landing, Abrams Chase, Cottage Glen. There are also 4 communities in the Winchester Area that offer new construction homes, including Cottage Glen, Trilogy® at Lake Frederick, Willow Run.

Are there gated 55+ communities in the Winchester Area?

Yes, there are gated 55+ communities in the Winchester Area. Approximately 33.3% of 55+ communities in the area are gated. For instance, Cottage Glen is a gated communities with 25 homes, and Cedar Meadows is another gated communities with 129 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 620 days. The average price of homes for sale in these communities is approximately $480,385, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Village at Harvest Ridge average around $625,881, while homes in Cottage Glen average around $464,750.

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

Insights and market stats
Instant new home alerts
Answers from local 55+ experts

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

Call us: (540) 452-4199

51 communities

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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 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: Jun 22, 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

51 communities near Winchester Area

227 homes near Winchester Area

3 beds

2 baths

1,659 sq ft

4 beds

4 baths

3,243 sq ft

4 beds

4 baths

3,859 sq ft

2 beds

2 baths

1,800 sq ft

3 beds

3 baths

2,118 sq ft

2 beds

2 baths

1,749 sq ft

4 beds

3 baths

2,521 sq ft

2 beds

2 baths

1,359 sq ft

4 beds

3 baths

2,559 sq ft

2 beds

3 baths

1,987 sq ft

2 beds

2 baths

1,225 sq ft

3 beds

4 baths

2,868 sq ft

3 beds

3 baths

2,643 sq ft

3 beds

3 baths

2,118 sq ft

3 beds

4 baths

2,404 sq ft

Condo

3 beds

4 baths

2,742 sq ft

2 beds

2 baths

1,246 sq ft

Condo

3 beds

2 baths

1,712 sq ft

Condo

3 beds

3 baths

2,625 sq ft

3 beds

3 baths

2,763 sq ft

3 beds

3 baths

2,763 sq ft

3 beds

4 baths

2,763 sq ft

3 beds

3 baths

3,573 sq ft

5 beds

3 baths

3,322 sq ft

3 beds

4 baths