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

202 homes near Winchester Area

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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

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 (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

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

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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

New Construction | 55+ age-restricted | Built 2022 - present | 177 homes

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2008 - present | 250 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.

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Montebello

$500ks - $1Ms

Montebello, Sterling, VA

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

The Retreat at Poland Hil...

$800ks

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

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

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

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

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

The Villages at Broadland...

$400ks

The Villages at Broadland..., Ashburn, VA

New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes

Albert Courts

$100ks - $200ks

Albert Courts, Thurmont, MD

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

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

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

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

Questions? Call us: (540) 452-4199

CobbleStone Estates

$400ks - $500ks

CobbleStone Estates, Hagerstown, MD

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

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

1...2

Heritage Hunt

6845 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$740,000

4 beds

3 baths

2,068 sq ft

6845 SADDLE RUN WAY, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Vistas at Lansdowne

44238 SILVERPALM GROVE TER, LEESBURG, VA..., Leesburg, VA 20176

$865,000

3 beds

5 baths

3,891 sq ft

44238 SILVERPALM GROVE TER, LEESBURG, VA...

Community: Vistas at Lansdowne

Trilogy® at Lake Frederick

111 SWITCHGRASS WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$619,000

3 beds

3 baths

2,530 sq ft

111 SWITCHGRASS WAY, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Ballenger Run

5307 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703

$529,900

3 beds

4 baths

2,669 sq ft

5307 CRAPE MYRTLE DR, FREDERICK, MD, 217...

Community: Ballenger Run

Dunbarton

12904 FETLAR WAY, BRISTOW, VA, 20136, Bristow, VA 20136

$589,500

2 beds

2 baths

2,008 sq ft

12904 FETLAR WAY, BRISTOW, VA, 20136

Community: Dunbarton

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

Questions? Call us: (540) 452-4199

Regency at Dominion Valley

5245 ARMOUR CT, HAYMARKET, VA, 20169, Haymarket, VA 20169

$735,000

2 beds

3 baths

2,782 sq ft

5245 ARMOUR CT, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Regency at Ashburn

20851 SABER JET PL, ASHBURN, VA, 20147, Ashburn, VA 20147

$1,015,000

3 beds

3 baths

2,493 sq ft

20851 SABER JET PL, ASHBURN, VA, 20147

Community: Regency at Ashburn

Crestwood Village

5675 BARBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703

$355,000

2 beds

2 baths

1,148 sq ft

5675 BARBERRY CT, FREDERICK, MD, 21703

Community: Crestwood Village

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 903, LEESBURG, V..., Leesburg, VA 20176

$439,900

2 beds

2 baths

1,509 sq ft

Condo

19385 CYPRESS RIDGE TER 903, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Winchester Landing

106 HARDY, WINCHESTER, VA, 22602, Winchester, VA 22602

$374,900

3 beds

3 baths

1,630 sq ft

106 HARDY, WINCHESTER, VA, 22602

Community: Winchester Landing

Regency at Ashburn

44589 YORK CREST TER 405, ASHBURN, VA, 2..., Ashburn, VA 20147

$500,000

2 beds

2 baths

1,491 sq ft

Condo

44589 YORK CREST TER 405, ASHBURN, VA, 2...

Community: Regency at Ashburn

Potomac Green

20590 HOPE SPRING TER 203, ASHBURN, VA, ..., Ashburn, VA 20147

$465,000

2 beds

2 baths

1,347 sq ft

Condo

20590 HOPE SPRING TER 203, ASHBURN, VA, ...

Community: Potomac Green

Winchester Landing

113 WERTLAND PL, WINCHESTER, VA, 22602, Winchester, VA 22602

$435,000

3 beds

3 baths

1,634 sq ft

113 WERTLAND PL, WINCHESTER, VA, 22602

Community: Winchester Landing

Regency at Dominion Valley

5217 ADDLERFIELD WAY, HAYMARKET, VA, 201..., Haymarket, VA 20169

$800,000

3 beds

3 baths

3,315 sq ft

5217 ADDLERFIELD WAY, HAYMARKET, VA, 201...

Community: Regency at Dominion Valley

Potomac Green

20610 HOPE SPRING TER 104, ASHBURN, VA, ..., Ashburn, VA 20147

$315,000

2 beds

2 baths

876 sq ft

Condo

20610 HOPE SPRING TER 104, ASHBURN, VA, ...

Community: Potomac Green

Lexington 7

19847 SILVERY BLUE TER, ASHBURN, VA, 201..., Ashburn, VA 20147

$875,000

3 beds

4 baths

3,408 sq ft

19847 SILVERY BLUE TER, ASHBURN, VA, 201...

Community: Lexington 7

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

Questions? Call us: (540) 452-4199

Potomac Green

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

$699,000

3 beds

3 baths

2,118 sq ft

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

Community: Potomac Green

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

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

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

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

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

Ballenger Run

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

$519,900

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

$815,000

3 beds

3 baths

2,643 sq ft

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

Community: Cadence at Lansdowne

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

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

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

Questions? Call us: (540) 452-4199

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

$739,999

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

$514,900

3 beds

3 baths

2,072 sq ft

120 GABRIEL CT, WINCHESTER, VA, 22602

Community: Winchester Landing

Heritage Hunt

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

$699,000

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

Potomac Green

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

$690,000

2 beds

2 baths

1,667 sq ft

44406 ADARE MANOR SQ, ASHBURN, VA, 20147

Community: Potomac Green

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

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Dunbarton

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

$699,999

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

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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

202 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: Jul 21, 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

51 communities near Winchester Area

202 homes near Winchester Area

4 beds

3 baths

2,068 sq ft

3 beds

5 baths

3,891 sq ft

3 beds

3 baths

2,530 sq ft

3 beds

4 baths

2,669 sq ft

2 beds

2 baths

2,008 sq ft

2 beds

3 baths

2,782 sq ft

3 beds

3 baths

2,493 sq ft

2 beds

2 baths

1,148 sq ft

2 beds

2 baths

1,509 sq ft

Condo

3 beds

3 baths

1,630 sq ft

2 beds

2 baths

1,491 sq ft

Condo

2 beds

2 baths

1,347 sq ft

Condo

3 beds

3 baths

1,634 sq ft

3 beds

3 baths

3,315 sq ft

2 beds

2 baths

876 sq ft

Condo

3 beds

4 baths

3,408 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

3 beds

4 baths

2,868 sq ft

3 beds

3 baths

2,643 sq ft

3 beds