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

219 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

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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

Montebello

$500ks - $700ks

Montebello, Sterling, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

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

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

Albert Courts

$100ks - $200ks

Albert Courts, Thurmont, MD

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

1...2

Four Seasons at Ashburn Village

21007 ROCKY KNOLL SQ 205, ASHBURN, VA, 2..., Ashburn, VA 20147

$529,900

2 beds

2 baths

1,491 sq ft

Condo

21007 ROCKY KNOLL SQ 205, ASHBURN, VA, 2...

Community: Four Seasons at Ashburn Village

Heritage Hunt

13293 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$724,989

3 beds

3 baths

2,520 sq ft

13293 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Rosehill Manor Villas

19601 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$374,900

3 beds

2 baths

1,735 sq ft

19601 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Birchwood at Brambleton

23630 HAVELOCK WALK TER 200, ASHBURN, VA..., Ashburn, VA 20148

$529,990

3 beds

2 baths

1,742 sq ft

Condo

23630 HAVELOCK WALK TER 200, ASHBURN, VA...

Community: Birchwood at Brambleton

Cedar Meadows

104 POPPY DR, WHITE POST, VA, 22663, White Post, VA 22663

$470,000

3 beds

2 baths

1,633 sq ft

104 POPPY DR, WHITE POST, VA, 22663

Community: Cedar Meadows

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 519, LEESBURG, V..., Leesburg, VA 20176

$325,000

2 beds

2 baths

1,038 sq ft

Condo

19385 CYPRESS RIDGE TER 519, LEESBURG, V...

Community: Lansdowne Woods of Virginia

The Village at Harvest Ridge

407 MIKEY CT, WINCHESTER, VA, 22601, Winchester, VA 22601

$699,900

3 beds

3 baths

3,280 sq ft

407 MIKEY CT, WINCHESTER, VA, 22601

Community: The Village at Harvest Ridge

Heritage Hunt

6840 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155

$750,000

3 beds

3 baths

2,626 sq ft

6840 TRED AVON PL, GAINESVILLE, VA, 2015...

Community: Heritage Hunt

Crestwood Village

7006 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703

$295,500

2 beds

1 baths

924 sq ft

7006 BASSWOOD RD, FREDERICK, MD, 21703

Community: Crestwood Village

Regency at Dominion Valley

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

$824,500

3 beds

3 baths

3,179 sq ft

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

Community: Regency at Dominion Valley

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 621, LEESBURG, V..., Leesburg, VA 20176

$449,900

2 beds

2 baths

1,509 sq ft

Condo

19375 CYPRESS RIDGE TER 621, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Dunbarton

9716 SEAFIELD PL, BRISTOW, VA, 20136, Bristow, VA 20136

$675,000

3 beds

3 baths

2,760 sq ft

9716 SEAFIELD PL, BRISTOW, VA, 20136

Community: Dunbarton

Trilogy® at Lake Frederick

124 YELLOW BIRCH, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$1,199,000

4 beds

5 baths

4,933 sq ft

124 YELLOW BIRCH, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

122 FOAM FLOWER DR, LAKE FREDERICK, VA, ..., Lake Frederick, VA 22630

$564,900

3 beds

2 baths

1,980 sq ft

122 FOAM FLOWER DR, LAKE FREDERICK, VA, ...

Community: Trilogy® at Lake Frederick

JerMae Estates

5 GEOLEY CT, THURMONT, MD, 21788, Thurmont, MD 21788

$519,999

4 beds

3 baths

2,038 sq ft

5 GEOLEY CT, THURMONT, MD, 21788

Community: JerMae Estates

Regency at Dominion Valley

15100 HEATHER MILL LN 301, HAYMARKET, VA..., Haymarket, VA 20169

$499,000

3 beds

2 baths

1,833 sq ft

Condo

15100 HEATHER MILL LN 301, HAYMARKET, VA...

Community: Regency at Dominion Valley

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

Questions? Call us: (540) 452-4199

Regency at Dominion Valley

5416 ZOYSIA CT, HAYMARKET, VA, 20169, Haymarket, VA 20169

$915,000

4 beds

4 baths

3,962 sq ft

5416 ZOYSIA CT, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Willow Lawn Cottages

1856 MELVOR LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$369,900

2 beds

2 baths

1,219 sq ft

1856 MELVOR LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

Potomac Green

44367 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147

$685,000

2 beds

3 baths

2,060 sq ft

44367 OAKMONT MANOR SQ, ASHBURN, VA, 201...

Community: Potomac Green

Heritage Hunt

6877 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$660,000

3 beds

2 baths

1,809 sq ft

6877 SADDLE RUN WAY, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 1021, LEESBURG, ..., Leesburg, VA 20176

$480,000

2 beds

2 baths

1,509 sq ft

Condo

19355 CYPRESS RIDGE TER 1021, LEESBURG, ...

Community: Lansdowne Woods of Virginia

Potomac Green

44394 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147

$699,990

2 beds

2 baths

1,667 sq ft

44394 OAKMONT MANOR SQ, ASHBURN, VA, 201...

Community: Potomac Green

Dunbarton

9712 SEAFIELD PL, BRISTOW, VA, 20136, Bristow, VA 20136

$650,000

2 beds

3 baths

3,882 sq ft

9712 SEAFIELD PL, BRISTOW, VA, 20136

Community: Dunbarton

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

Heritage Hunt

13641 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155

$720,000

2 beds

2 baths

1,904 sq ft

13641 HERITAGE VALLEY WAY, GAINESVILLE, ...

Community: Heritage Hunt

Heritage Hunt

13618 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155

$850,000

3 beds

3 baths

3,320 sq ft

13618 HERITAGE VALLEY WAY, GAINESVILLE, ...

Community: Heritage Hunt

Birchwood at Brambleton

23664 CHALMERS CROSSING TER, ASHBURN, VA..., Ashburn, VA 20148

$875,000

4 beds

4 baths

2,798 sq ft

23664 CHALMERS CROSSING TER, 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

Regency at Dominion Valley

15110 HEATHER MILL LN 404, HAYMARKET, VA..., Haymarket, VA 20169

$475,000

2 beds

2 baths

1,499 sq ft

Condo

15110 HEATHER MILL LN 404, HAYMARKET, VA...

Community: Regency at Dominion Valley

Trilogy® at Lake Frederick

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

$639,900

4 beds

4 baths

3,859 sq ft

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

Community: Trilogy® at Lake Frederick

Heritage Hunt

6901 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$650,000

3 beds

3 baths

2,618 sq ft

6901 SADDLE RUN WAY, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Potomac Green

44360 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$649,999

2 beds

3 baths

2,060 sq ft

44360 SUNSET MAPLE DR, ASHBURN, VA, 2014...

Community: Potomac Green

The Village at Freedom Hills

13928 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

2 beds

2 baths

1,345 sq ft

Condo

5800 MOONSTONE WAY 2, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

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The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201..., Haymarket, VA 20169

$494,990

2 beds

2 baths

1,475 sq ft

Condo

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

Trilogy® at Lake Frederick

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

$570,000

2 beds

2 baths

1,791 sq ft

110 SWITCHGRASS WAY, 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 Trilogy® at Lake Frederick, Cottage Glen, Abrams Chase.

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, Trilogy® at Lake Frederick is a gated communities with 950 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 614 days. The average price of homes for sale in these communities is approximately $482,668, 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 $631,008, 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

219 homes

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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: May 31, 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

219 homes near Winchester Area

2 beds

2 baths

1,491 sq ft

Condo

3 beds

3 baths

2,520 sq ft

3 beds

2 baths

1,735 sq ft

3 beds

2 baths

1,742 sq ft

Condo

3 beds

2 baths

1,633 sq ft

2 beds

2 baths

1,038 sq ft

Condo

3 beds

3 baths

3,280 sq ft

3 beds

3 baths

2,626 sq ft

2 beds

1 baths

924 sq ft

3 beds

3 baths

3,179 sq ft

2 beds

2 baths

1,509 sq ft

Condo

3 beds

3 baths

2,760 sq ft

4 beds

5 baths

4,933 sq ft

3 beds

2 baths

1,980 sq ft

4 beds

3 baths

2,038 sq ft

3 beds

2 baths

1,833 sq ft

Condo

4 beds

4 baths

3,962 sq ft

2 beds

2 baths

1,219 sq ft

2 beds

3 baths

2,060 sq ft

3 beds

2 baths

1,809 sq ft

2 beds

2 baths

1,509 sq ft

Condo

2 beds

2 baths

1,667 sq ft

2 beds

3 baths

3,882 sq ft

4 beds

4 baths