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

125 homes near Winchester Area

Sort by:

Relevance

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

Willow Run

$400Ks - $600Ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 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

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

Questions? Call us: (540) 452-4199

The Village at Harvest Ri...

$500Ks - $600Ks

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

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

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

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.

Abrams Chase

$500Ks

Abrams Chase, Winchester, VA

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

Winchester Landing

$300Ks

Winchester Landing, Winchester, VA

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

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

$600Ks - $800Ks

Potomac Green, Ashburn, VA

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

$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

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

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

Questions? Call us: (540) 452-4199

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

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

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

Questions? Call us: (540) 452-4199

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

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

1...2

Heritage Hunt

6880 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$749,000

2 beds

3 baths

3,087 sq ft

6880 SADDLE RUN WAY, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Heritage Hunt

6868 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$675,000

3 beds

3 baths

2,528 sq ft

6868 SADDLE RUN WAY, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Birchwood at Brambleton

43016 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$881,457

3 beds

4 baths

2,742 sq ft

43016 DEBONAIR TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Birchwood at Brambleton

43089 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148

$949,990

3 beds

3 baths

2,491 sq ft

43089 GREELEY SQ, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Regency at Dominion Valley

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

$455,000

2 beds

2 baths

1,551 sq ft

Condo

15110 HEATHER MILL LN APT 201, HAYMARKET...

Community: Regency at Dominion Valley

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

Questions? Call us: (540) 452-4199

Gatherings at Potomac Station

750 MOUNT AIRY TER NE UNIT 304, LEESBURG..., Leesburg, VA 20176

$499,999

2 beds

2 baths

1,532 sq ft

Condo

750 MOUNT AIRY TER NE UNIT 304, LEESBURG...

Community: Gatherings at Potomac Station

Gatherings at Potomac Station

750 MOUNT AIRY TER NE UNIT 206A, LEESBUR..., Leesburg, VA 20176

$449,999

2 beds

2 baths

1,532 sq ft

Condo

750 MOUNT AIRY TER NE UNIT 206A, LEESBUR...

Community: Gatherings at Potomac Station

Gatherings at Potomac Station

750 MOUNT AIRY TER NE UNIT 403A, LEESBUR..., Leesburg, VA 20176

$484,999

2 beds

2 baths

1,410 sq ft

Condo

750 MOUNT AIRY TER NE UNIT 403A, LEESBUR...

Community: Gatherings at Potomac Station

Heritage Hunt

13154 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$725,000

3 beds

4 baths

3,195 sq ft

13154 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

Regency at Dominion Valley

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

$739,900

3 beds

3 baths

2,598 sq ft

5484 RODRIQUEZ LN, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

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

Woodbrook Village

222 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602

$369,000

2 beds

2 baths

1,260 sq ft

222 CRESTWOOD LN, WINCHESTER, VA, 22602

Community: Woodbrook Village

Birchwood at Brambleton

42788 MACBETH TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$799,000

3 beds

3 baths

2,669 sq ft

42788 MACBETH TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Birchwood at Brambleton

43044 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148

$1,050,000

4 beds

3 baths

3,753 sq ft

43044 GREELEY SQ, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Potomac Green

44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147

$895,500

4 beds

4 baths

2,709 sq ft

44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,...

Community: Potomac Green

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

Questions? Call us: (540) 452-4199

Regency at Dominion Valley

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

$450,000

2 beds

2 baths

1,538 sq ft

Condo

15100 HEATHER MILL LN APT 407, HAYMARKET...

Community: Regency at Dominion Valley

Trilogy® at Lake Frederick

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

3 beds

3 baths

2,523 sq ft

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

Community: Trilogy® at Lake Frederick

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

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

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

Heritage Hunt

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

$725,000

4 beds

3 baths

3,151 sq ft

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

Community: Heritage Hunt

Trilogy® at Lake Frederick

103 PLANETREE CT, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$825,000

3 beds

3 baths

3,589 sq ft

103 PLANETREE CT, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

Winchester Landing

100 MAURY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$385,000

3 beds

3 baths

1,678 sq ft

100 MAURY WAY, WINCHESTER, VA, 22602

Community: Winchester Landing

Trilogy® at Lake Frederick

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

$799,998

3 beds

4 baths

3,601 sq ft

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

Community: Trilogy® at Lake Frederick

Regency at Dominion Valley

15201 ROYAL CREST DR APT 407, HAYMARKET,..., Haymarket, VA 20169

$440,000

2 beds

2 baths

1,538 sq ft

Condo

15201 ROYAL CREST DR APT 407, HAYMARKET,...

Community: Regency at Dominion Valley

Heritage Hunt

6159 FERRIER CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155

3 beds

3 baths

2,640 sq ft

13746 HERITAGE VALLEY WAY, GAINESVILLE, ...

Community: Heritage Hunt

Gatherings at Wellington

10273 FOUNTAIN CIR 306, MANASSAS, VA, 20..., Manassas, VA 20110

$375,000

2 beds

2 baths

1,558 sq ft

Condo

10273 FOUNTAIN CIR 306, MANASSAS, VA, 20...

Community: Gatherings at Wellington

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

Questions? Call us: (540) 452-4199

Willow Run

115 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602

$629,990

4 beds

3 baths

2,818 sq ft

115 SCENTED ROSE WAY, WINCHESTER, VA, 22...

Community: Willow Run

Willow Run

113 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602

$509,990

4 beds

3 baths

2,168 sq ft

113 TRELLIS VIEW LN, WINCHESTER, VA, 226...

Community: Willow Run

Willow Run

111 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602

$509,990

4 beds

3 baths

2,168 sq ft

111 TRELLIS VIEW LN, WINCHESTER, VA, 226...

Community: Willow Run

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 207, LEESBURG, V..., Leesburg, VA 20176

$399,900

2 beds

2 baths

1,380 sq ft

Condo

19375 CYPRESS RIDGE TER 207, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER UNIT 522, LEESBU..., Leesburg, VA 20176

$370,000

2 beds

2 baths

1,101 sq ft

Condo

19385 CYPRESS RIDGE TER UNIT 522, LEESBU...

Community: Lansdowne Woods of Virginia

1 2 3…4

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

125 homes near Winchester Area

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.
© 2025 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: Dec 11, 2025.
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

48 communities near Winchester Area

125 homes near Winchester Area

2 beds

3 baths

3,087 sq ft

3 beds

3 baths

2,528 sq ft

3 beds

4 baths

2,742 sq ft

3 beds

3 baths

2,491 sq ft

2 beds

2 baths

1,551 sq ft

Condo

2 beds

2 baths

1,532 sq ft

Condo

2 beds

2 baths

1,532 sq ft

Condo

2 beds

2 baths

1,410 sq ft

Condo

3 beds

4 baths

3,195 sq ft

3 beds

3 baths

2,598 sq ft

3 beds

3 baths

1,962 sq ft

2 beds

2 baths

1,260 sq ft

3 beds

3 baths

2,669 sq ft

4 beds

3 baths

3,753 sq ft

4 beds

4 baths

2,709 sq ft

2 beds

2 baths

1,538 sq ft

Condo

3 beds

3 baths

3,434 sq ft

3 beds

2 baths

1,833 sq ft

Condo

3 beds

2 baths

2,006 sq ft

Condo

3 beds

3 baths

2,523 sq ft

2 beds

2 baths

Condo

4 beds

3 baths

2,676 sq ft

4 beds

4 baths

3,965 sq ft

4 beds