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

46 communities near Winchester Area

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5 rating (2 reviews)

Trilogy® at Lake Frederic...

$400Ks - $1Ms

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

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

Cedar Meadows

$400Ks

Cedar Meadows, White Post, VA

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

5 rating (1 reviews)

Willow Lawn Cottages

$300Ks

Willow Lawn Cottages, Winchester, VA

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

Cross Creek Village

$300Ks - $400Ks

Cross Creek Village, Winchester, VA

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

The Village at Harvest Ri...

$500Ks - $600Ks

The Village at Harvest Ri..., Winchester, VA

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes

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

Questions? Call us: (540) 452-4199

Woodbrook Village

$300Ks

Woodbrook Village, Winchester, VA

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

Heritage Highlands

$300Ks - $400Ks

Heritage Highlands, Lovettsville, VA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes

The Highlands at Blue Rid...

$400Ks - $700Ks

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

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

Cottage Glen

$400Ks

Cottage Glen, Winchester, VA

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

Abrams Chase

$500Ks

Abrams Chase, Winchester, VA

New Construction | 55+ age-restricted | Built 2020 - present | 13 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 - $800Ks

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

5 rating (2 reviews)

Potomac Green

$700Ks - $800Ks

Potomac Green, Ashburn, VA

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

5 rating (31 reviews)

Lansdowne Woods of Virgin...

$300Ks - $400Ks

Lansdowne Woods of Virgin..., Lansdowne, VA

Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 homes

5 rating (1 reviews)

Regency at Dominion Valle...

$400Ks - $700Ks

Regency at Dominion Valle..., Haymarket, VA

Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes

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

Questions? Call us: (540) 452-4199

The Woodlands of Urbana

$600Ks

The Woodlands of Urbana, Urbana, MD

New Construction | 55+ age-restricted | Built 2019 - present | 565 homes

5 rating (1 reviews)

Crestwood Village

$300Ks

Crestwood Village, Frederick, MD

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

Carter's Mill

$400Ks - $700Ks

Carter's Mill, Haymarket, VA

New Construction | 55+ age-restricted | Built 2020 - present | 480 homes

3 rating (2 reviews)

Dunbarton

$600Ks

Dunbarton, Bristow, VA

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

Montebello

$600Ks - $1Ms

Montebello, Sterling, VA

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

Regency at Ashburn

$800Ks - $900Ks

Regency at Ashburn, Ashburn, VA

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

Emerald Pointe

$300Ks - $400Ks

Emerald Pointe, Hagerstown, MD

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

The Retreat at Poland Hil...

$700Ks - $900Ks

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

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

Regency at Creekside

$900Ks

Regency at Creekside, Gainesville, VA

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

Central Parke at Lowes Is...

$400Ks - $700Ks

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

Regency at Belmont

$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

Vistas at Lansdowne

$500Ks - $800Ks

Vistas at Lansdowne, Lansdowne, VA

Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes

Lexington 7

$800Ks

Lexington 7, Ashburn, VA

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

Suffield Meadows

$300Ks - $400Ks

Suffield Meadows, Warrenton, VA

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

JerMae Estates

$400Ks - $500Ks

JerMae Estates, Thurmont, MD

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

Albert Courts

$100Ks - $200Ks

Albert Courts, Thurmont, MD

Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 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 Village at Foxfield

$500Ks

The Village at Foxfield, Middletown, MD

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

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

Questions? Call us: (540) 452-4199

3.7 rating (3 reviews)

Four Seasons at Ashburn V...

$400Ks

Four Seasons at Ashburn V..., Ashburn, VA

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 homes

The Villages at Broadland...

$400Ks

The Villages at Broadland..., Ashburn, VA

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

Cadence at Lansdowne

$700Ks

Cadence at Lansdowne, Lansdowne, VA

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

CobbleStone Estates

$400Ks - $500Ks

CobbleStone Estates, Hagerstown, MD

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

1...2

Emerald Pointe

13366 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$434,900

2 beds

2 baths

2,826 sq ft

13366 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Albert Courts

215 STULL CT, THURMONT, MD, 21788, Thurmont, MD 21788

$305,000

3 beds

3 baths

1,532 sq ft

215 STULL CT, THURMONT, MD, 21788

Community: Albert Courts

Crestwood Village

5722 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$349,000

2 beds

2 baths

1,264 sq ft

5722 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

Crestwood Village

6905 CHOKEBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703

$324,900

2 beds

1 baths

1,160 sq ft

6905 CHOKEBERRY CT, FREDERICK, MD, 21703

Community: Crestwood Village

Emerald Pointe

13336 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$424,900

2 beds

2 baths

2,615 sq ft

13336 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

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

Questions? Call us: (540) 452-4199

The Woodlands of Urbana

3207 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704

$609,900

3 beds

3 baths

1,677 sq ft

3207 THORNAPPLE DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

The Village at Freedom Hills

13946 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$379,900

2 beds

2 baths

1,484 sq ft

13946 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

The Woodlands of Urbana

3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704

$615,000

3 beds

3 baths

1,816 sq ft

3225 THORNAPPLE DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

The Village at Foxfield

1 KELLER LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769

$574,900

3 beds

3 baths

3,161 sq ft

1 KELLER LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

Crestwood Village

7043 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703

$339,999

2 beds

2 baths

1,225 sq ft

7043 BASSWOOD RD, FREDERICK, MD, 21703

Community: Crestwood Village

The Woodlands of Urbana

2928 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704

$725,000

3 beds

4 baths

3,634 sq ft

2928 HERB GARDEN DR, FREDERICK, MD, 2170...

Community: The Woodlands of Urbana

Emerald Pointe

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$359,900

2 beds

2 baths

1,834 sq ft

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Emerald Pointe

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742

$429,000

2 beds

3 baths

2,739 sq ft

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...

Community: Emerald Pointe

Emerald Pointe

19554 TURQUOISE DR V219, HAGERSTOWN, MD,..., Hagerstown, MD 21742

$484,900

2 beds

2 baths

19554 TURQUOISE DR V219, HAGERSTOWN, MD,...

Community: Emerald Pointe

New Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 1006, LEESBURG, ..., Leesburg, VA 20176

$529,000

3 beds

3 baths

1,720 sq ft

Condo

19355 CYPRESS RIDGE TER 1006, LEESBURG, ...

Community: Lansdowne Woods of Virginia

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

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

$650,000

3 beds

3 baths

2,523 sq ft

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

Community: Trilogy® at Lake Frederick

Heritage Hunt

13753 TUSCARORA CT, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$695,000

3 beds

3 baths

3,338 sq ft

13753 TUSCARORA CT, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Heritage Hunt

6135 FERRIER CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$835,000

4 beds

4 baths

3,965 sq ft

6135 FERRIER CT, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Suffield Meadows

6704 HOLLY FARM LN UNIT 109, WARRENTON, ..., Warrenton, VA 20187

$375,000

2 beds

2 baths

Condo

6704 HOLLY FARM LN UNIT 109, WARRENTON, ...

Community: Suffield Meadows

Heritage Hunt

13879 CRABTREE WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155

2 beds

2 baths

1,959 sq ft

Condo

23631 HAVELOCK WALK TER 404, ASHBURN, VA...

Community: Birchwood at Brambleton

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

Questions? Call us: (540) 452-4199

The Retreat at Poland Hill

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

$945,000

4 beds

4 baths

3,553 sq ft

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

Community: The Retreat at Poland Hill

Trilogy® at Lake Frederick

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

$359,900

3 beds

3 baths

1,962 sq ft

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

Community: Trilogy® at Lake Frederick

Heritage Hunt

13612 RYTON RIDGE LN, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$864,900

4 beds

3 baths

4,486 sq ft

13612 RYTON RIDGE LN, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Birchwood at Brambleton

23707 KINSTON FERRY TER, ASHBURN, VA, 20..., Ashburn, VA 20148

$767,500

4 beds

3 baths

2,676 sq ft

23707 KINSTON FERRY TER, ASHBURN, VA, 20...

Community: Birchwood at Brambleton

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 815, LEESBURG, V..., Leesburg, VA 20176

$498,000

3 beds

2 baths

1,475 sq ft

Condo

19385 CYPRESS RIDGE TER 815, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Regency at Dominion Valley

15428 CHAMPIONSHIP DR, HAYMARKET, VA, 20..., Haymarket, VA 20169

$750,000

3 beds

3 baths

3,309 sq ft

15428 CHAMPIONSHIP DR, HAYMARKET, VA, 20...

Community: Regency at Dominion Valley

Birchwood at Brambleton

23688 BOLTON CRESCENT TER APT 204, ASHBU..., Ashburn, VA 20148

$470,000

2 beds

2 baths

1,280 sq ft

Condo

23688 BOLTON CRESCENT TER APT 204, ASHBU...

Community: Birchwood at Brambleton

Regency at Dominion Valley

15100 HEATHER MILL LN APT 407, HAYMARKET..., Haymarket, VA 20169

$450,000

2 beds

102 PHOEBE CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$915,000

5 beds

4 baths

4,267 sq ft

102 PHOEBE CT, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Regency at Dominion Valley

15110 HEATHER MILL LN APT 201, HAYMARKET..., Haymarket, VA 20169

$469,000

2 beds

2 baths

1,551 sq ft

Condo

15110 HEATHER MILL LN APT 201, HAYMARKET...

Community: Regency at Dominion Valley

Regency at Dominion Valley

5484 RODRIQUEZ LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$745,000

3 beds

3 baths

2,598 sq ft

5484 RODRIQUEZ LN, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Trilogy® at Lake Frederick

105 CABBAGE WHITE DR, LAKE FREDERICK, VA..., Lake Frederick, VA 22630

$639,000

3 beds

4 baths

2,700 sq ft

105 CABBAGE WHITE DR, LAKE FREDERICK, VA...

Community: Trilogy® at Lake Frederick

Heritage Hunt

$450,000

2 beds

2 baths

1,421 sq ft

Condo

7065 HERITAGE HUNT DR 203, GAINESVILLE, ...

Community: Heritage Hunt

1 2 3…4

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Virginia
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?

Call us: (540) 452-4199

46 communities near Winchester Area

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REIN updates its listings on a daily basis. Data last updated: Dec 03, 2025.
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

46 communities near Winchester Area

127 homes near Winchester Area

2 beds

2 baths

2,826 sq ft

3 beds

3 baths

1,532 sq ft

2 beds

2 baths

1,264 sq ft

2 beds

1 baths

1,160 sq ft

2 beds

2 baths

2,615 sq ft

3 beds

3 baths

1,677 sq ft

2 beds

2 baths

1,484 sq ft

3 beds

3 baths

1,816 sq ft

3 beds

3 baths

3,161 sq ft

2 beds

2 baths

1,225 sq ft

3 beds

4 baths

3,634 sq ft

2 beds

2 baths

1,834 sq ft

2 beds

3 baths

2,739 sq ft

2 beds

2 baths

3 beds

3 baths

1,720 sq ft

Condo

3 beds

3 baths

2,523 sq ft

3 beds

3 baths

3,338 sq ft

4 beds

4 baths

3,965 sq ft

2 beds

2 baths

Condo

4 beds

3 baths

3,151 sq ft

3 beds

2 baths

1,833 sq ft

Condo

2 beds

2 baths

1,410 sq ft

Condo

2 beds

2 baths

1,532 sq ft

Condo

2 beds

2 baths

1,532 sq ft

Condo

2 beds