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

116 homes 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

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

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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

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

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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

5 rating (2 reviews)

Potomac Green

$600Ks - $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 - $500Ks

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 - $500Ks

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

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

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

Questions? Call us: (540) 452-4199

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

Rosehill Manor Villas

$300Ks

Rosehill Manor Villas, Hagerstown, MD

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

Regency at Belmont

$900Ks

Regency at Belmont, Ashburn, VA

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

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

Questions? Call us: (540) 452-4199

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

$700Ks - $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

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

Albert Courts

$100Ks - $200Ks

Albert Courts, Thurmont, MD

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

1...2

New Winchester Landing

122 HARDY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$375,000

3 beds

3 baths

1,630 sq ft

122 HARDY WAY, WINCHESTER, VA, 22602

Community: Winchester Landing

New Birchwood at Brambleton

23669 GOLDEN EMBERS SQ UNIT 303, ASHBURN..., Ashburn, VA 20148

$724,900

3 beds

2 baths

2,148 sq ft

Condo

23669 GOLDEN EMBERS SQ UNIT 303, ASHBURN...

Community: Birchwood at Brambleton

Birchwood at Brambleton

23631 HAVELOCK WALK TER 404, ASHBURN, VA..., Ashburn, VA 20148

$569,000

2 beds

2 baths

1,959 sq ft

Condo

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

Community: Birchwood at Brambleton

New Winchester Landing

151 MCCORMICK CIR APT 203, WINCHESTER, V..., Winchester, VA 22602

$315,000

2 beds

2 baths

1,156 sq ft

Condo

151 MCCORMICK CIR APT 203, WINCHESTER, V...

Community: Winchester Landing

Birchwood at Brambleton

23595 GOLDEN EMBERS SQ, ASHBURN, VA, 201..., Ashburn, VA 20148

$860,000

3 beds

4 baths

3,637 sq ft

23595 GOLDEN EMBERS SQ, ASHBURN, VA, 201...

Community: Birchwood at Brambleton

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

Questions? Call us: (540) 452-4199

Potomac Green

44385 MALTESE FALCON SQ, ASHBURN, VA, 20..., Ashburn, VA 20147

$635,000

2 beds

3 baths

2,060 sq ft

44385 MALTESE FALCON SQ, ASHBURN, VA, 20...

Community: Potomac Green

Trilogy® at Lake Frederick

108 GADWELL LN, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$714,900

3 beds

4 baths

3,464 sq ft

108 GADWELL LN, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

New Lansdowne Woods of Virginia

19350 MAGNOLIA SQ 308, LEESBURG, VA, 201..., Leesburg, VA 20176

$435,000

2 beds

2 baths

1,444 sq ft

Condo

19350 MAGNOLIA SQ 308, LEESBURG, VA, 201...

Community: Lansdowne Woods of Virginia

New Trilogy® at Lake Frederick

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

$600,000

3 beds

3 baths

2,523 sq ft

118 VICEROY WAY, 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

Potomac Green

44420 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$749,000

3 beds

3 baths

2,447 sq ft

44420 SUNSET MAPLE DR, ASHBURN, VA, 2014...

Community: Potomac Green

Birchwood at Brambleton

43221 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148

$1,228,000

3 beds

4 baths

4,124 sq ft

43221 GREELEY SQ, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Four Seasons at Ashburn Village

44465 CHAMBERLAIN TER UNIT 103, ASHBURN,..., Ashburn, VA 20147

$429,900

2 beds

2 baths

1,612 sq ft

Condo

44465 CHAMBERLAIN TER UNIT 103, ASHBURN,...

Community: Four Seasons at Ashburn Village

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

Questions? Call us: (540) 452-4199

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

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

Trilogy® at Lake Frederick

117 HARVESTER DR, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$899,000

4 beds

5 baths

6,096 sq ft

117 HARVESTER DR, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Willow Run

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

$459,990

4 beds

3 baths

2,168 sq ft

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

Community: Willow Run

Trilogy® at Lake Frederick

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

$729,900

3 beds

4 baths

3,333 sq ft

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

Community: Trilogy® at Lake Frederick

Heritage Highlands

67 HARPERS MILL WAY, LOVETTSVILLE, VA, 2..., Lovettsville, VA 20180

$499,999

2 beds

3 baths

2,119 sq ft

67 HARPERS MILL WAY, LOVETTSVILLE, VA, 2...

Community: Heritage Highlands

Heritage Hunt

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

$859,900

4 beds

3 baths

4,486 sq ft

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

Community: Heritage Hunt

New The Highlands at Blue Ridge Shadows

47 HICKORY SHAFT CT, FRONT ROYAL, VA, 22..., Front Royal, VA 22630

$585,000

4 beds

4 baths

3,482 sq ft

47 HICKORY SHAFT CT, FRONT ROYAL, VA, 22...

Community: The Highlands at Blue Ridge Shadows

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

Questions? Call us: (540) 452-4199

Regency at Dominion Valley

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

$435,000

2 beds

2 baths

1,538 sq ft

Condo

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

Community: Regency at Dominion Valley

Regency at Dominion Valley

15251 ROYAL CREST DR APT 306, HAYMARKET,..., Haymarket, VA 20169

$500,000

3 beds

2 baths

1,833 sq ft

Condo

15251 ROYAL CREST DR APT 306, HAYMARKET,...

Community: Regency at Dominion Valley

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

Heritage Hunt

13963 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$599,990

3 beds

3 baths

2,090 sq ft

13963 CHELMSFORD DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 114, LEESBURG, V..., Leesburg, VA 20176

$350,000

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 114, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Regency at Belmont

43921 HURLEYS HUNT TER, ASHBURN, VA, 201..., Ashburn, VA 20147

$1,075,000

4 beds

4 baths

3,255 sq ft

43921 HURLEYS HUNT TER, ASHBURN, VA, 201...

Community: Regency at Belmont

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

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Regency at Dominion Valley

5429 TREVINO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169

$735,000

3 beds

3 baths

2,524 sq ft

5429 TREVINO DR, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER UNIT 1102, LEESB..., Leesburg, VA 20176

$389,000

2 beds

2 baths

1,105 sq ft

Condo

19365 CYPRESS RIDGE TER UNIT 1102, LEESB...

Community: Lansdowne Woods of Virginia

Birchwood at Brambleton

42783 FIREFLY SONATA TER, ASHBURN, VA, 2..., Ashburn, VA 20148

$760,000

2 beds

3 baths

2,406 sq ft

42783 FIREFLY SONATA TER, ASHBURN, VA, 2...

Community: Birchwood at Brambleton

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

Heritage Hunt

$440,000

2 beds

2 baths

1,421 sq ft

Condo

7065 HERITAGE HUNT DR 203, GAINESVILLE, ...

Community: Heritage Hunt

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER UNIT 821, LEESBU..., Leesburg, VA 20176

$367,000

2 beds

2 baths

1,246 sq ft

Condo

19385 CYPRESS RIDGE TER UNIT 821, LEESBU...

Community: Lansdowne Woods of Virginia

The Village at Harvest Ridge

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

$639,000

3 beds

3 baths

3,153 sq ft

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

Community: The Village at Harvest Ridge

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER UNIT 708, LEESBU..., Leesburg, VA 20176

$399,000

2 beds

2 baths

1,315 sq ft

Condo

19375 CYPRESS RIDGE TER UNIT 708, LEESBU...

Community: Lansdowne Woods of Virginia

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 901, LEESBURG, V..., Leesburg, VA 20176

$515,000

3 beds

2 baths

1,534 sq ft

Condo

19375 CYPRESS RIDGE TER 901, LEESBURG, V...

Community: Lansdowne Woods of Virginia

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

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Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER UNIT 920, LEESBU..., Leesburg, VA 20176

$450,000

3 beds

2 baths

1,475 sq ft

Condo

19385 CYPRESS RIDGE TER UNIT 920, LEESBU...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

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

$369,900

3 beds

3 baths

1,962 sq ft

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

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 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

116 homes

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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: Jan 09, 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

49 communities near Winchester Area

116 homes near Winchester Area

3 beds

3 baths

1,630 sq ft

3 beds

2 baths

2,148 sq ft

Condo

2 beds

2 baths

1,959 sq ft

Condo

2 beds

2 baths

1,156 sq ft

Condo

3 beds

4 baths

3,637 sq ft

2 beds

3 baths

2,060 sq ft

3 beds

4 baths

3,464 sq ft

2 beds

2 baths

1,444 sq ft

Condo

3 beds

3 baths

2,523 sq ft

2 beds

2 baths

1,260 sq ft

3 beds

3 baths

2,447 sq ft

3 beds

4 baths

4,124 sq ft

2 beds

2 baths

1,612 sq ft

Condo

2 beds

2 baths

1,380 sq ft

Condo

3 beds

4 baths

3,601 sq ft

4 beds

5 baths

6,096 sq ft

4 beds

3 baths

2,168 sq ft

3 beds

4 baths

3,333 sq ft

2 beds

3 baths

2,119 sq ft

4 beds

3 baths

4,486 sq ft

4 beds

4 baths

3,482 sq ft

2 beds

2 baths

1,538 sq ft

Condo

3 beds

2 baths

1,833 sq ft

Condo