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

51 communities near Winchester Area

Sort by:

Relevance

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 (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

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

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2008 - present | 250 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 (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

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.

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

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

Vistas at Lansdowne

$800ks

Vistas at Lansdowne, Lansdowne, VA

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

Montebello

$500ks - $900ks

Montebello, Sterling, VA

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

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

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

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

CobbleStone Estates

$400ks - $500ks

CobbleStone Estates, Hagerstown, MD

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

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

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

Carter's Mill

$400ks - $700ks

Carter's Mill, Haymarket, VA

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

The Retreat at Poland Hil...

$800ks

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

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

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

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

1...2

New Dunbarton

12984 DUNBARTON DR, BRISTOW, VA, 20136, Bristow, VA 20136

$550,000

2 beds

2 baths

1,884 sq ft

12984 DUNBARTON DR, BRISTOW, VA, 20136

Community: Dunbarton

New The Village at Foxfield

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

$675,000

3 beds

2 baths

2,208 sq ft

7 DERR LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

New 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

New The Flats at Heathcote Village by Del Webb

5840 MOONSTONE WAY 202, HAYMARKET, VA, 2..., Haymarket, VA 20169

$622,140

3 beds

2 baths

1,850 sq ft

Condo

5840 MOONSTONE WAY 202, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

New 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

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

Questions? Call us: (540) 452-4199

New The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 104, HAYMARKET, VA, 2..., Haymarket, VA 20169

$456,065

2 beds

2 baths

1,345 sq ft

Condo

5800 MOONSTONE WAY 104, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

New Heritage Hunt

17657 GLASS RIDGE PL, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$585,000

4 beds

3 baths

2,156 sq ft

17657 GLASS RIDGE PL, GAINESVILLE, VA, 2...

Community: Heritage Hunt

New Heritage Hunt

7065 HERITAGE HUNT DR, GAINESVILLE, VA, ..., Gainesville, VA 20155

$400,000

2 beds

2 baths

1,292 sq ft

Condo

7065 HERITAGE HUNT DR, GAINESVILLE, VA, ...

Community: Heritage Hunt

New Robinson Manor

14714 GRAND CRU LOOP, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$750,000

4 beds

4 baths

2,651 sq ft

14714 GRAND CRU LOOP, GAINESVILLE, VA, 2...

Community: Robinson Manor

New Heritage Hunt

7055 HERITAGE HUNT DR 210, GAINESVILLE, ..., Gainesville, VA 20155

$435,000

3 beds

2 baths

1,424 sq ft

Condo

7055 HERITAGE HUNT DR 210, GAINESVILLE, ...

Community: Heritage Hunt

New Regency at Ashburn

44568 GRANITE RUN TER, ASHBURN, VA, 2014..., Ashburn, VA 20147

$895,000

2 beds

3 baths

3,392 sq ft

44568 GRANITE RUN TER, ASHBURN, VA, 2014...

Community: Regency at Ashburn

New Woodbrook Village

200 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602

$415,000

2 beds

2 baths

1,692 sq ft

200 CRESTWOOD LN, WINCHESTER, VA, 22602

Community: Woodbrook Village

New Birchwood at Brambleton

42734 CUMULUS TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$895,000

4 beds

4 baths

3,026 sq ft

42734 CUMULUS TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

New Regency at Dominion Valley

15296 WESTHAM CT, HAYMARKET, VA, 20169, Haymarket, VA 20169

$570,000

3 beds

4 baths

2,133 sq ft

Condo

15296 WESTHAM CT, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

New Dunbarton

12974 DUNBARTON DR, BRISTOW, VA, 20136, Bristow, VA 20136

$525,000

2 beds

2 baths

1,896 sq ft

12974 DUNBARTON DR, BRISTOW, VA, 20136

Community: Dunbarton

New Heritage Hunt

6921 NETHERSTONE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$719,999

3 beds

3 baths

2,520 sq ft

6921 NETHERSTONE CT, 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

New Potomac Green

20369 OYSTER REEF PL, ASHBURN, VA, 20147, Ashburn, VA 20147

$875,000

3 beds

3 baths

2,452 sq ft

20369 OYSTER REEF PL, ASHBURN, VA, 20147

Community: Potomac Green

New Regency at Creekside

6202 CHANCELLORSVILLE DR, GAINESVILLE, V..., Gainesville, VA 20155

$1,125,000

3 beds

3 baths

3,510 sq ft

6202 CHANCELLORSVILLE DR, GAINESVILLE, V...

Community: Regency at Creekside

New Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 514, LEESBURG, V..., Leesburg, VA 20176

$515,000

2 beds

2 baths

1,509 sq ft

Condo

19385 CYPRESS RIDGE TER 514, LEESBURG, V...

Community: Lansdowne Woods of Virginia

New Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 604, LEESBURG, V..., Leesburg, VA 20176

$340,000

2 beds

2 baths

1,038 sq ft

Condo

19375 CYPRESS RIDGE TER 604, LEESBURG, V...

Community: Lansdowne Woods of Virginia

New Heritage Hunt

13972 REAL QUITE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$810,000

4 beds

4 baths

3,256 sq ft

13972 REAL QUITE CT, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Birchwood at Brambleton

23651 HAVELOCK WALK TER 304, ASHBURN, VA..., Ashburn, VA 20148

$469,900

2 beds

2 baths

1,229 sq ft

Condo

23651 HAVELOCK WALK TER 304, ASHBURN, VA...

Community: Birchwood at Brambleton

Liberty Grove

8600 LIBERTY TRL 204, MANASSAS, VA, 2011..., Manassas, VA 20110

$322,700

2 beds

3 baths

1,743 sq ft

Condo

8600 LIBERTY TRL 204, MANASSAS, VA, 2011...

Community: Liberty Grove

Heritage Hunt

6907 BROADLEAF TER, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$775,000

3 beds

3 baths

2,653 sq ft

6907 BROADLEAF TER, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Birchwood at Brambleton

23665 HAVELOCK WALK TER 406, ASHBURN, VA..., Ashburn, VA 20148

$525,000

1 beds

2 baths

1,229 sq ft

Condo

23665 HAVELOCK WALK TER 406, ASHBURN, VA...

Community: Birchwood at Brambleton

Potomac Green

44351 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147

$675,000

2 beds

3 baths

2,060 sq ft

44351 OAKMONT MANOR SQ, ASHBURN, VA, 201...

Community: Potomac Green

Potomac Green

44435 CRUDEN BAY DR, ASHBURN, VA, 20147, Ashburn, VA 20147

$725,000

3 beds

3 baths

2,255 sq ft

44435 CRUDEN BAY DR, ASHBURN, VA, 20147

Community: Potomac Green

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

Questions? Call us: (540) 452-4199

The Retreat at Poland Hill

25614 PRESTON PARK TER, CHANTILLY, VA, 2..., Chantilly, VA 20152

$785,000

3 beds

3 baths

2,450 sq ft

25614 PRESTON PARK TER, CHANTILLY, VA, 2...

Community: The Retreat at Poland Hill

The Flats at Heathcote Village by Del Webb

6156 AMBER LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$699,990

3 beds

3 baths

2,625 sq ft

6156 AMBER LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

6156 AMBER LN 2, HAYMARKET, VA, 20169, Haymarket, VA 20169

$734,990

3 beds

3 baths

3,424 sq ft

6156 AMBER LN 2, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

6152 AMBER LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$709,990

3 beds

3 baths

2,763 sq ft

6152 AMBER LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

6152 AMBER LN 2, HAYMARKET, VA, 20169, Haymarket, VA 20169

$744,990

3 beds

3 baths

3,531 sq ft

6152 AMBER LN 2, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

Regency at Creekside

6198 CHANCELLORSVILLE DR, GAINESVILLE, V..., Gainesville, VA 20155

$1,075,000

3 beds

3 baths

3,247 sq ft

6198 CHANCELLORSVILLE DR, GAINESVILLE, V...

Community: Regency at Creekside

Crestwood Village

5738 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$336,000

2 beds

2 baths

1,264 sq ft

5738 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

Heritage Hunt

13891 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$435,000

3 beds

2 baths

1,424 sq ft

Condo

13891 CHELMSFORD DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Cedar Meadows

103 BLEEDING HEART DR, WHITE POST, VA, 2..., White Post, VA 22663

$475,000

3 beds

2 baths

1,493 sq ft

103 BLEEDING HEART DR, WHITE POST, VA, 2...

Community: Cedar Meadows

The Woodlands of Urbana

3234 STARLIGHT ST, FREDERICK, MD, 21704, Frederick, MD 21704

$649,990

3 beds

4 baths

2,276 sq ft

3234 STARLIGHT ST, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

Potomac Green

44348 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$649,999

2 beds

3 baths

2,060 sq ft

44348 SUNSET MAPLE DR, ASHBURN, VA, 2014...

Community: Potomac Green

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

Questions? Call us: (540) 452-4199

Potomac Green

44345 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$749,999

2 beds

2 baths

1,591 sq ft

44345 SUNSET MAPLE DR, ASHBURN, VA, 2014...

Community: Potomac Green

Trilogy® at Lake Frederick

104 GROSBEAK CT, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$637,800

3 beds

3 baths

2,933 sq ft

104 GROSBEAK CT, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

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

Remove Boundaries ×

Map Satellite

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: Apr 18, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

51 communities near Winchester Area

209 homes near Winchester Area

2 beds

2 baths

1,884 sq ft

3 beds

2 baths

2,208 sq ft

2 beds

2 baths

1,432 sq ft

3 beds

2 baths

1,850 sq ft

Condo

2 beds

2 baths

1,445 sq ft

Condo

2 beds

2 baths

1,345 sq ft

Condo

4 beds

3 baths

2,156 sq ft

2 beds

2 baths

1,292 sq ft

Condo

4 beds

4 baths

2,651 sq ft

3 beds

2 baths

1,424 sq ft

Condo

2 beds

3 baths

3,392 sq ft

2 beds

2 baths

1,692 sq ft

4 beds

4 baths

3,026 sq ft

3 beds

4 baths

2,133 sq ft

Condo

2 beds

2 baths

1,896 sq ft

3 beds

3 baths

2,520 sq ft

3 beds

3 baths

2,452 sq ft

3 beds

3 baths

3,510 sq ft

2 beds

2 baths

1,509 sq ft

Condo

2 beds

2 baths

1,038 sq ft

Condo

4 beds

4 baths

3,256 sq ft

2 beds

2 baths

1,229 sq ft

Condo

2 beds

3 baths