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...

- $900ks

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

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

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

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

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

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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 Freedom Hi...

$300ks

The Village at Freedom Hi..., Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Montebello

$500ks - $800ks

Montebello, Sterling, VA

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

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

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

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

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

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

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

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

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

CobbleStone Estates

$400ks - $500ks

CobbleStone Estates, Hagerstown, MD

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

Vistas at Lansdowne

$800ks

Vistas at Lansdowne, Lansdowne, VA

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

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

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

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

Questions? Call us: (540) 452-4199

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

1...2

New Lexington 7

19877 SILVERY BLUE TER, ASHBURN, VA, 201..., Ashburn, VA 20147

$898,000

4 beds

4 baths

3,865 sq ft

19877 SILVERY BLUE TER, ASHBURN, VA, 201...

Community: Lexington 7

New Regency at Dominion Valley

5117 FALDO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169

$925,000

4 beds

3 baths

3,428 sq ft

5117 FALDO DR, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

New Birchwood at Brambleton

42760 LITTLEHALES TER, ASHBURN, VA, 2014..., Ashburn, VA 20148

$1,200,000

4 beds

4 baths

3,838 sq ft

42760 LITTLEHALES TER, ASHBURN, VA, 2014...

Community: Birchwood at Brambleton

New Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 314, LEESBURG, V..., Leesburg, VA 20176

$334,990

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 314, LEESBURG, V...

Community: Lansdowne Woods of Virginia

New The Woodlands of Urbana

3411 ANGELICA WAY 401, FREDERICK, MD, 21..., Frederick, MD 21704

$525,000

2 beds

2 baths

1,785 sq ft

Condo

3411 ANGELICA WAY 401, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

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

Questions? Call us: (540) 452-4199

New Trilogy® at Lake Frederick

102 PEREGRINE CT, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$775,000

3 beds

3 baths

3,051 sq ft

102 PEREGRINE CT, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

New Heritage Hunt

13001 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$850,000

4 beds

3 baths

4,074 sq ft

13001 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

New Birchwood at Brambleton

42729 AUTUMN DAY TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$1,050,000

3 beds

3 baths

2,802 sq ft

42729 AUTUMN DAY TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

New Rosehill Manor Villas

19642 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$399,900

3 beds

2 baths

1,712 sq ft

19642 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

New Suffield Meadows

6704 HOLLY FARM LN 112, WARRENTON, VA, 2..., Warrenton, VA 20187

$440,000

2 beds

2 baths

1,754 sq ft

Condo

6704 HOLLY FARM LN 112, WARRENTON, VA, 2...

Community: Suffield Meadows

New Heritage Hunt

13520 NORWICK PL, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$687,500

3 beds

3 baths

2,153 sq ft

13520 NORWICK PL, GAINESVILLE, VA, 20155

Community: Heritage Hunt

New Trilogy® at Lake Frederick

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

$409,900

3 beds

4 baths

2,327 sq ft

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

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

120 LEATHER FLOWER DR, LAKE FREDERICK, V..., Lake Frederick, VA 22630

$445,000

3 beds

4 baths

2,202 sq ft

120 LEATHER FLOWER DR, LAKE FREDERICK, V...

Community: Trilogy® at Lake Frederick

Heritage Hunt

13514 RYTON RIDGE LN, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$950,000

4 beds

4 baths

4,376 sq ft

13514 RYTON RIDGE LN, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Regency at Ashburn

44605 YORK CREST TER 300, ASHBURN, VA, 2..., Ashburn, VA 20147

$615,000

3 beds

2 baths

1,825 sq ft

Condo

44605 YORK CREST TER 300, ASHBURN, VA, 2...

Community: Regency at Ashburn

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 306, LEESBURG, V..., Leesburg, VA 20176

$365,000

2 beds

2 baths

1,315 sq ft

Condo

19365 CYPRESS RIDGE TER 306, LEESBURG, V...

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

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

$589,900

2 beds

3 baths

3,505 sq ft

109 TUTELO LN, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Heritage Hunt

6004 GALLANT FOX CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$724,900

3 beds

3 baths

2,618 sq ft

6004 GALLANT FOX CT, GAINESVILLE, VA, 20...

Community: Heritage Hunt

The Village at Harvest Ridge

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

$625,000

3 beds

2 baths

2,444 sq ft

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

Community: The Village at Harvest Ridge

Regency at Dominion Valley

15471 CHAMPIONSHIP DR, HAYMARKET, VA, 20..., Haymarket, VA 20169

$985,000

3 beds

3 baths

3,160 sq ft

15471 CHAMPIONSHIP DR, HAYMARKET, VA, 20...

Community: Regency at Dominion Valley

Trilogy® at Lake Frederick

117 MALLARD DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$780,000

3 beds

4 baths

3,601 sq ft

117 MALLARD DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Gatherings at Potomac Station

700 MOUNT AIRY TER 301, LEESBURG, VA, 20..., Leesburg, VA 20176

$609,000

2 beds

2 baths

1,809 sq ft

Condo

700 MOUNT AIRY TER 301, LEESBURG, VA, 20...

Community: Gatherings at Potomac Station

The Woodlands of Urbana

2913 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704

$870,000

3 beds

3 baths

2,712 sq ft

2913 HERB GARDEN DR, FREDERICK, MD, 2170...

Community: The Woodlands of Urbana

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 907, LEESBURG, V..., Leesburg, VA 20176

$585,000

3 beds

3 baths

1,720 sq ft

Condo

19365 CYPRESS RIDGE TER 907, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Crestwood Village

5811 BOX ELDER CT B, FREDERICK, MD, 2170..., Frederick, MD 21703

$265,000

2 beds

1 baths

Condo

5811 BOX ELDER CT B, FREDERICK, MD, 2170...

Community: Crestwood Village

Trilogy® at Lake Frederick

128 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$680,000

2 beds

4 baths

3,696 sq ft

128 TURNSTONE LN, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

152 MILKWEED DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$530,000

3 beds

2 baths

1,804 sq ft

152 MILKWEED DR, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

Rosehill Manor Villas

19704 OLEANDER CT, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$459,990

3 beds

3 baths

1,895 sq ft

19704 OLEANDER CT, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Rosehill Manor Villas

19702 OLEANDER CT, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$399,990

2 beds

2 baths

1,819 sq ft

19702 OLEANDER CT, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

CobbleStone Estates

18208 WISTERIA WAY, HAGERSTOWN, MD, 2174..., Hagerstown, MD 21740

$389,900

2 beds

2 baths

1,432 sq ft

18208 WISTERIA WAY, HAGERSTOWN, MD, 2174...

Community: CobbleStone Estates

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 103, LEESBURG, V..., Leesburg, VA 20176

$374,999

2 beds

2 baths

1,251 sq ft

Condo

19355 CYPRESS RIDGE TER 103, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Regency at Dominion Valley

15231 ROYAL CREST DR 204, HAYMARKET, VA,..., Haymarket, VA 20169

$460,000

2 beds

2 baths

1,499 sq ft

Condo

15231 ROYAL CREST DR 204, HAYMARKET, VA,...

Community: Regency at Dominion Valley

Suffield Meadows

6715 HOLLY FARM LN, WARRENTON, VA, 20187, Warrenton, VA 20187

$585,000

3 beds

4 baths

3,350 sq ft

Condo

6715 HOLLY FARM LN, WARRENTON, VA, 20187

Community: Suffield Meadows

Regency at Dominion Valley

15550 ALDERBROOK DR, HAYMARKET, VA, 2016..., Haymarket, VA 20169

$800,000

2 beds

3 baths

3,741 sq ft

15550 ALDERBROOK DR, HAYMARKET, VA, 2016...

Community: Regency at Dominion Valley

Potomac Green

20789 ADAMS MILL PL, ASHBURN, VA, 20147, Ashburn, VA 20147

$745,000

3 beds

3 baths

2,447 sq ft

20789 ADAMS MILL PL, ASHBURN, VA, 20147

Community: Potomac Green

Dunbarton

$550,000

2 beds

2 baths

1,884 sq ft

12984 DUNBARTON DR, BRISTOW, VA, 20136

Community: Dunbarton

The Village at Foxfield

7 DERR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769

$675,000

3 beds

3 baths

2,208 sq ft

7 DERR LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

Heritage Hunt

6922 WALNUT HILL DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$535,000

2 beds

2 baths

1,432 sq ft

6922 WALNUT HILL DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

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

5800 MOONSTONE WAY 202, HAYMARKET, VA, 2..., Haymarket, VA 20169

$622,140

3 beds

2 baths

1,850 sq ft

Condo

5800 MOONSTONE WAY 202, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 203, HAYMARKET, VA, 2..., Haymarket, VA 20169

$520,005

2 beds

2 baths

1,445 sq ft

Condo

5800 MOONSTONE WAY 203, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

Home
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
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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© 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: May 01, 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

204 homes near Winchester Area

4 beds

4 baths

3,865 sq ft

4 beds

3 baths

3,428 sq ft

4 beds

4 baths

3,838 sq ft

2 beds

2 baths

1,038 sq ft

Condo

2 beds

2 baths

1,785 sq ft

Condo

3 beds

3 baths

3,051 sq ft

4 beds

3 baths

4,074 sq ft

3 beds

3 baths

2,802 sq ft

3 beds

2 baths

1,712 sq ft

2 beds

2 baths

1,754 sq ft

Condo

3 beds

3 baths

2,153 sq ft

3 beds

4 baths

2,327 sq ft

3 beds

4 baths

2,202 sq ft

4 beds

4 baths

4,376 sq ft

3 beds

2 baths

1,825 sq ft

Condo

2 beds

2 baths

1,315 sq ft

Condo

2 beds

3 baths

3,505 sq ft

3 beds

3 baths

2,618 sq ft

3 beds

2 baths

2,444 sq ft

3 beds

3 baths

3,160 sq ft

3 beds

4 baths

3,601 sq ft

2 beds

2 baths

1,809 sq ft

Condo

3 beds

3 baths

2,712 sq ft

3 beds

3 baths