Winchester Area, VA 55+ active adult communities & homes for sale - Page 3

202 homes near Winchester Area

Sort by:

Relevance

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

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 (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

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 (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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

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

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.

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Montebello

$500ks - $1Ms

Montebello, Sterling, VA

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

Regency at Belmont

$600ks - $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

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

The Retreat at Poland Hil...

$800ks

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

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

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

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

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

The Villages at Broadland...

$400ks

The Villages at Broadland..., Ashburn, VA

New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes

Albert Courts

$100ks - $200ks

Albert Courts, Thurmont, MD

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

CobbleStone Estates

$400ks - $500ks

CobbleStone Estates, Hagerstown, MD

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

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

1...2

Regency at Dominion Valley

5219 ARMOUR CT, HAYMARKET, VA, 20169, Haymarket, VA 20169

$719,000

3 beds

3 baths

2,358 sq ft

5219 ARMOUR CT, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Lansdowne Woods of Virginia

19350 MAGNOLIA GROVE SQ 201, LEESBURG, V..., Leesburg, VA 20176

$399,000

2 beds

2 baths

1,387 sq ft

Condo

19350 MAGNOLIA GROVE SQ 201, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 317, LEESBURG, V..., Leesburg, VA 20176

$430,000

2 beds

2 baths

1,415 sq ft

Condo

19385 CYPRESS RIDGE TER 317, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Cadence at Lansdowne

43899 SIREN SONG TER, LEESBURG, VA, 2017..., Leesburg, VA 20176

$789,000

3 beds

4 baths

2,780 sq ft

43899 SIREN SONG TER, LEESBURG, VA, 2017...

Community: Cadence at Lansdowne

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 404, LEESBURG, V..., Leesburg, VA 20176

$330,000

2 beds

2 baths

1,038 sq ft

Condo

19375 CYPRESS RIDGE TER 404, LEESBURG, V...

Community: Lansdowne Woods of Virginia

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 RDG 515, LEESBURG, VA, 201..., Leesburg, VA 20176

$490,000

3 beds

2 baths

1,475 sq ft

Condo

19385 CYPRESS RDG 515, LEESBURG, VA, 201...

Community: Lansdowne Woods of Virginia

Heritage Hunt

13484 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$669,990

2 beds

2 baths

2,128 sq ft

13484 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Dunbarton

12028 RUTHERGLEN PL, BRISTOW, VA, 20136, Bristow, VA 20136

$775,000

4 beds

3 baths

3,754 sq ft

12028 RUTHERGLEN PL, BRISTOW, VA, 20136

Community: Dunbarton

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 206, LEESBURG, V..., Leesburg, VA 20176

$550,000

3 beds

3 baths

1,720 sq ft

Condo

19355 CYPRESS RIDGE TER 206, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Birchwood at Brambleton

42851 LITTLEHALES TER, ASHBURN, VA, 2014..., Ashburn, VA 20148

$574,900

3 beds

3 baths

2,492 sq ft

Condo

42851 LITTLEHALES TER, ASHBURN, VA, 2014...

Community: Birchwood at Brambleton

The Woodlands of Urbana

3510 STARLIGHT ST 402, FREDERICK, MD, 21..., Frederick, MD 21704

$514,900

2 beds

2 baths

1,673 sq ft

Condo

3510 STARLIGHT ST 402, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Heritage Hunt

13928 REAL QUITE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$690,000

3 beds

3 baths

2,520 sq ft

13928 REAL QUITE CT, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Heritage Hunt

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

$530,000

3 beds

3 baths

2,090 sq ft

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

Community: Heritage Hunt

Trilogy® at Lake Frederick

222 GREBE DR, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$799,999

5 beds

5 baths

4,331 sq ft

222 GREBE DR, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Heritage Hunt

5968 PINEY GROVE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$750,000

2 beds

3 baths

2,873 sq ft

5968 PINEY GROVE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Emerald Pointe

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$339,900

2 beds

2 baths

1,834 sq ft

19446 SAPPHIRE 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

Willow Lawn Cottages

1845 ROSSER LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$370,000

2 beds

2 baths

1,200 sq ft

1845 ROSSER LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

Birchwood at Brambleton

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

$474,999

1 beds

2 baths

1,229 sq ft

Condo

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

Community: Birchwood at Brambleton

The Village at Foxfield

2 DERR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769

$555,000

3 beds

3 baths

2,279 sq ft

2 DERR LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

Regency at Dominion Valley

15100 HEATHER MILL LN 304, HAYMARKET, VA..., Haymarket, VA 20169

$449,000

2 beds

2 baths

1,499 sq ft

Condo

15100 HEATHER MILL LN 304, HAYMARKET, VA...

Community: Regency at Dominion Valley

Lansdowne Woods of Virginia

19370 MAGNOLIA GROVE SQ 403, LEESBURG, V..., Leesburg, VA 20176

$350,000

2 beds

2 baths

1,168 sq ft

Condo

19370 MAGNOLIA GROVE SQ 403, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Heritage Hunt

13452 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$749,900

3 beds

3 baths

2,632 sq ft

13452 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Heritage Hunt

6943 CUMBERSTONE PL, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$589,900

2 beds

2 baths

1,920 sq ft

6943 CUMBERSTONE PL, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Cadence at Lansdowne

19006 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176

$939,900

3 beds

5 baths

3,679 sq ft

19006 CORAL REEF SQ, LEESBURG, VA, 20176

Community: Cadence at Lansdowne

Trilogy® at Lake Frederick

145 COWBIRD, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$558,900

3 beds

2 baths

1,771 sq ft

145 COWBIRD, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

The Retreat at Poland Hill

43489 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152

$925,000

4 beds

4 baths

3,567 sq ft

43489 BETTYS FARM DR, CHANTILLY, VA, 201...

Community: The Retreat at Poland Hill

Trilogy® at Lake Frederick

107 WAKE ROBIN CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$410,000

3 beds

4 baths

2,487 sq ft

107 WAKE ROBIN CT, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

Heritage Hunt

6005 PINEY GROVE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$825,000

4 beds

4 baths

3,735 sq ft

6005 PINEY GROVE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Suffield Meadows

6708 STREAM VIEW LN, WARRENTON, VA, 2018..., Warrenton, VA 20187

$619,900

3 beds

3 baths

3,701 sq ft

Condo

6708 STREAM VIEW LN, WARRENTON, VA, 2018...

Community: Suffield Meadows

Regency at Dominion Valley

15508 HAGEN WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$889,900

3 beds

3 baths

3,810 sq ft

15508 HAGEN WAY, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Birchwood at Brambleton

23640 BOLTON CRESCENT TER 403, ASHBURN, ..., Ashburn, VA 20148

$745,000

3 beds

2 baths

1,908 sq ft

Condo

23640 BOLTON CRESCENT TER 403, ASHBURN, ...

Community: Birchwood at Brambleton

Regency at Belmont

43927 HURLEYS HUNT TER, ASHBURN, VA, 201..., Ashburn, VA 20147

$1,099,000

3 beds

4 baths

3,255 sq ft

43927 HURLEYS HUNT TER, ASHBURN, VA, 201...

Community: Regency at Belmont

Bloomfields 55+

2644 BLAZING STAR ST, FREDERICK, MD, 217..., Frederick, MD 21702

$665,990

2 beds

2 baths

2,915 sq ft

2644 BLAZING STAR ST, FREDERICK, MD, 217...

Community: Bloomfields 55+

Bloomfields 55+

2619 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702

$809,990

4 beds

4 baths

4,034 sq ft

2619 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

Bloomfields 55+

2617 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702

$779,990

4 beds

4 baths

3,591 sq ft

2617 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

Bloomfields 55+

2615 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702

$729,990

3 beds

3 baths

3,357 sq ft

2615 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

Bloomfields 55+

2613 BROADLEAF, FREDERICK, MD, 21702, Frederick, MD 21702

$699,990

3 beds

3 baths

2,915 sq ft

2613 BROADLEAF, FREDERICK, MD, 21702

Community: Bloomfields 55+

Montebello

21630 HAWKSBILL HIGH CIR 202, STERLING, ..., Sterling, VA 20164

$724,999

3 beds

2 baths

1,940 sq ft

Condo

21630 HAWKSBILL HIGH CIR 202, STERLING, ...

Community: Montebello

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

134 ATLANTIS LN, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$605,000

3 beds

3 baths

2,173 sq ft

134 ATLANTIS LN, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Rosehill Manor Villas

19536 COSMOS ST, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$394,900

2 beds

2 baths

1,819 sq ft

19536 COSMOS ST, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

1 2 3 4 5…6

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 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 Cottage Glen, Trilogy® at Lake Frederick, Willow Run.

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, Cottage Glen is a gated communities with 25 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 620 days. The average price of homes for sale in these communities is approximately $480,385, 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 $625,881, 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

202 homes

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: Jul 21, 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 - Page 3

51 communities near Winchester Area

202 homes near Winchester Area

3 beds

3 baths

2,358 sq ft

2 beds

2 baths

1,387 sq ft

Condo

2 beds

2 baths

1,415 sq ft

Condo

3 beds

4 baths

2,780 sq ft

2 beds

2 baths

1,038 sq ft

Condo

3 beds

2 baths

1,475 sq ft

Condo

2 beds

2 baths

2,128 sq ft

4 beds

3 baths

3,754 sq ft

3 beds

3 baths

1,720 sq ft

Condo

3 beds

3 baths

2,492 sq ft

Condo

2 beds

2 baths

1,673 sq ft

Condo

3 beds

3 baths

2,520 sq ft

3 beds

3 baths

2,090 sq ft

5 beds

5 baths

4,331 sq ft

2 beds

3 baths

2,873 sq ft

2 beds

2 baths

1,834 sq ft

2 beds

2 baths

1,200 sq ft

1 beds

2 baths

1,229 sq ft

Condo

3 beds

3 baths

2,279 sq ft

2 beds

2 baths

1,499 sq ft

Condo

2 beds

2 baths

1,168 sq ft

Condo

3 beds

3 baths

2,632 sq ft

2 beds