Winchester Area, VA 55+ active adult communities & homes for sale - Page 4

150 homes near Winchester Area

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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 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 (2 reviews)

Trilogy® at Lake Frederic...

$400ks - $800ks

Trilogy® at Lake Frederic..., Lake Frederick, VA

New and Resale | 55+ age-restricted | Built 2006 - present | 950 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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

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

Questions? Call us: (540) 452-4199

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

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

Montebello

$500ks - $600ks

Montebello, Sterling, VA

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

The Retreat at Poland Hil...

$800ks

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

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

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

CobbleStone Estates

$400ks - $500ks

CobbleStone Estates, Hagerstown, MD

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

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

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

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

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

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

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

Questions? Call us: (540) 452-4199

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

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

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

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

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

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

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

Cross Creek Village

$300ks

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

1...2

The Woodlands of Urbana

3520 STARLIGHT ST 302, FREDERICK, MD, 21..., Frederick, MD 21704

$436,900

$445,000

2 beds

2 baths

1,538 sq ft

Condo

15100 HEATHER MILL LN APT 407, 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

Potomac Green

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

$885,000

4 beds

4 baths

2,709 sq ft

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

Community: Potomac Green

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

Heritage Hunt

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

3 beds

2 baths

1,630 sq ft

Condo

42920 FIREFLY SONATA TER UNIT 307, ASHBU...

Community: Birchwood at Brambleton

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

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

$849,900

4 beds

5 baths

6,096 sq ft

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

Community: Trilogy® at Lake Frederick

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

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

Rosehill Manor Villas

19710 OLEANDER CT, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$374,990

2 beds

2 baths

1,811 sq ft

19710 OLEANDER CT, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Birchwood at Brambleton

42972 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$853,586

4 beds

4 baths

2,742 sq ft

42972 TRUMAN TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Gatherings at Wellington

10273 FOUNTAIN CIR 202, MANASSAS, VA, 20..., Manassas, VA 20110

$415,000

3 beds

2 baths

2,006 sq ft

Condo

10273 FOUNTAIN CIR 202, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Lansdowne Woods of Virginia

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

$365,000

2 beds

2 baths

1,105 sq ft

Condo

19365 CYPRESS RIDGE TER UNIT 1102, LEESB...

Community: Lansdowne Woods of Virginia

Birchwood at Brambleton

43011 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$799,990

3 beds

4 baths

2,742 sq ft

43011 DEBONAIR TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

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 UNIT 522, LEESBU..., Leesburg, VA 20176

$365,000

2 beds

2 baths

1,101 sq ft

Condo

19385 CYPRESS RIDGE TER UNIT 522, LEESBU...

Community: Lansdowne Woods of Virginia

Gatherings at Wellington

9202 CHARLESTON DR 405, MANASSAS, VA, 20..., Manassas, VA 20110

$359,990

2 beds

2 baths

1,504 sq ft

Condo

9202 CHARLESTON DR 405, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Willow Run

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

$599,990

4 beds

3 baths

2,818 sq ft

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

Community: Willow Run

Willow Run

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

$549,990

3 beds

2 baths

1,958 sq ft

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

Community: Willow Run

Emerald Pointe

19554 TURQUOISE DR V219, HAGERSTOWN, MD,..., Hagerstown, MD 21742

$484,900

2 beds

2 baths

19554 TURQUOISE DR V219, HAGERSTOWN, MD,...

Community: Emerald Pointe

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

Winchester Landing

140 MCCORMICK CIR APT 403, WINCHESTER, V..., Winchester, VA 22602

$305,000

2 beds

2 baths

1,156 sq ft

Condo

140 MCCORMICK CIR APT 403, WINCHESTER, V...

Community: Winchester Landing

Emerald Pointe

13336 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$424,900

2 beds

2 baths

2,615 sq ft

13336 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

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

Questions? Call us: (540) 452-4199

Emerald Pointe

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742

$429,000

2 beds

3 baths

2,739 sq ft

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...

Community: Emerald Pointe

1 2 3 4

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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

150 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: Feb 24, 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 4

50 communities near Winchester Area

150 homes near Winchester Area

2 beds

2 baths

1,489 sq ft

Condo

2 beds

3 baths

2,745 sq ft

2 beds

1 baths

1,160 sq ft

2 beds

2 baths

1,264 sq ft

2 beds

2 baths

1,538 sq ft

Condo

4 beds

4 baths

2,709 sq ft

3 beds

3 baths

2,090 sq ft

4 beds

3 baths

4,486 sq ft

2 beds

2 baths

1,612 sq ft

Condo

2 beds

2 baths

1,421 sq ft

Condo

2 beds

2 baths

1,538 sq ft

Condo

2 beds

2 baths

1,509 sq ft

Condo

3 beds

2 baths

1,630 sq ft

Condo

4 beds

5 baths

6,096 sq ft

3 beds

4 baths

3,601 sq ft

3 beds

2 baths

1,475 sq ft

Condo

2 beds

2 baths

1,811 sq ft

4 beds

4 baths

2,742 sq ft

3 beds

2 baths

2,006 sq ft

Condo

2 beds

2 baths

1,105 sq ft

Condo

3 beds

4 baths

2,742 sq ft

2 beds

2 baths

1,101 sq ft

Condo