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

229 homes near Winchester Area

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5 rating (2 reviews)

Trilogy® at Lake Frederic...

$400ks - $900ks

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

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

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

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 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

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

Montebello

$300ks - $600ks

Montebello, Sterling, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

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

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

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

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

The Signature at Broadlan...

$300ks - $400ks

The Signature at Broadlan..., Ashburn, VA

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 45 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

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

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

The Village at Harvest Ri...

$400ks - $500ks

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

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 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 Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes

Albert Courts

$100ks - $200ks

Albert Courts, Thurmont, MD

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

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

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

Carter's Mill

$400ks - $700ks

Carter's Mill, Haymarket, VA

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

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

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

1...2

Trilogy® at Lake Frederick

107 OSPREY DR, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$519,900

3 beds

4 baths

3,007 sq ft

107 OSPREY DR, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Cindy Certified

12875 MOSAIC PARK WAY 4-B, HERNDON, VA, ..., Herndon, VA 20171

$574,990

2 beds

2 baths

1,333 sq ft

Condo

12875 MOSAIC PARK WAY 4-B, HERNDON, VA, ...

Winchester Landing

126 MAURY, WINCHESTER, VA, 22602, Winchester, VA 22602

$389,900

3 beds

3 baths

1,630 sq ft

126 MAURY, WINCHESTER, VA, 22602

Community: Winchester Landing

The Highlands at Blue Ridge Shadows

79 PUTTER CT, FRONT ROYAL, VA, 22630, Front Royal, VA 22630

$530,000

3 beds

2 baths

1,829 sq ft

79 PUTTER CT, FRONT ROYAL, VA, 22630

Community: The Highlands at Blue Ridge Shadows

Heritage Hunt

6872 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$699,999

2 beds

2 baths

2,066 sq ft

6872 SADDLE RUN WAY, 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

Trilogy® at Lake Frederick

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

$680,000

3 beds

4 baths

3,333 sq ft

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

Community: Trilogy® at Lake Frederick

Regency at Belmont

43931 NORMAN NEWS TER, ASHBURN, VA, 2014..., Ashburn, VA 20147

$1,085,000

3 beds

4 baths

3,255 sq ft

43931 NORMAN NEWS TER, ASHBURN, VA, 2014...

Community: Regency at Belmont

Cindy Certified

2324 WIND CHARM ST 306, HERNDON, VA, 201..., Herndon, VA 20171

$525,000

2 beds

2 baths

1,515 sq ft

Condo

2324 WIND CHARM ST 306, HERNDON, VA, 201...

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 107, LEESBURG, V..., Leesburg, VA 20176

$315,000

1 beds

1 baths

874 sq ft

Condo

19385 CYPRESS RIDGE TER 107, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Cindy Certified

3927 FAIR RIDGE DR 307, FAIRFAX, VA, 220..., Fairfax, VA 22033

$569,900

2 beds

2 baths

1,301 sq ft

Condo

3927 FAIR RIDGE DR 307, FAIRFAX, VA, 220...

Heritage Hunt

13039 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$700,000

3 beds

3 baths

2,474 sq ft

13039 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

Gatherings at Wellington

10275 FOUNTAIN CIR 306, MANASSAS, VA, 20..., Manassas, VA 20110

$374,900

2 beds

2 baths

1,558 sq ft

Condo

10275 FOUNTAIN CIR 306, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Birchwood at Brambleton

23669 GOLDEN EMBERS SQ 403, ASHBURN, VA,..., Ashburn, VA 20148

$729,900

3 beds

2 baths

2,148 sq ft

Condo

23669 GOLDEN EMBERS SQ 403, ASHBURN, VA,...

Community: Birchwood at Brambleton

Cindy Certified

6765 AZALEA GARDEN LN, HAYMARKET, VA, 20..., Haymarket, VA 20169

$725,000

2 beds

2 baths

1,609 sq ft

6765 AZALEA GARDEN LN, HAYMARKET, VA, 20...

Cadence at Lansdowne

43928 MARITIME SONG TER, LEESBURG, VA, 2..., Leesburg, VA 20176

$945,000

5 beds

5 baths

3,969 sq ft

43928 MARITIME SONG TER, LEESBURG, VA, 2...

Community: Cadence at Lansdowne

Heritage Hunt

13919 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$775,000

4 beds

4 baths

4,779 sq ft

13919 CHELMSFORD DR, 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

Trilogy® at Lake Frederick

106 FRINGETREE CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$667,000

4 beds

3 baths

4,047 sq ft

106 FRINGETREE CT, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

The Village at Foxfield

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

$625,000

3 beds

3 baths

2,208 sq ft

7 DERR LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

Trilogy® at Lake Frederick

142 MILKWEED DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$554,900

3 beds

2 baths

1,769 sq ft

142 MILKWEED DR, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

The Woodlands of Urbana

3231 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704

$709,000

3 beds

3 baths

2,612 sq ft

3231 THORNAPPLE DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

Regency at Dominion Valley

15110 HEATHER MILL LN 307, HAYMARKET, VA..., Haymarket, VA 20169

$425,000

2 beds

2 baths

1,538 sq ft

Condo

15110 HEATHER MILL LN 307, HAYMARKET, VA...

Community: Regency at Dominion Valley

Birchwood at Brambleton

23631 HAVELOCK WALK TER 203, ASHBURN, VA..., Ashburn, VA 20148

$440,000

2 beds

2 baths

1,012 sq ft

Condo

23631 HAVELOCK WALK TER 203, ASHBURN, VA...

Community: Birchwood at Brambleton

Trilogy® at Lake Frederick

133 SKIPPER DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$624,900

3 beds

3 baths

2,843 sq ft

133 SKIPPER DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

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

$820,000

4 beds

4 baths

4,828 sq ft

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

Community: Trilogy® at Lake Frederick

Suffield Meadows

6727 HOLLY FARM LN, WARRENTON, VA, 20187, Warrenton, VA 20187

$659,000

4 beds

3 baths

3,066 sq ft

Condo

6727 HOLLY FARM LN, WARRENTON, VA, 20187

Community: Suffield Meadows

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 408, LEESBURG, V..., Leesburg, VA 20176

$379,999

2 beds

2 baths

1,105 sq ft

Condo

19355 CYPRESS RIDGE TER 408, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Crestwood Village

5679 BARBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703

$404,900

2 beds

2 baths

1,148 sq ft

5679 BARBERRY CT, FREDERICK, MD, 21703

Community: Crestwood Village

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

Questions? Call us: (540) 452-4199

Heritage Hunt

13890 CHELMSFORD DR 305, GAINESVILLE, VA..., Gainesville, VA 20155

$425,000

2 beds

2 baths

1,388 sq ft

Condo

13890 CHELMSFORD DR 305, GAINESVILLE, VA...

Community: Heritage Hunt

Montebello

21630 HAWKSBILL HIGH CIR 406, STERLING, ..., Sterling, VA 20164

$699,999

3 beds

2 baths

1,825 sq ft

Condo

21630 HAWKSBILL HIGH CIR 406, STERLING, ...

Community: Montebello

Trilogy® at Lake Frederick

112 FRINGETREE CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$548,750

4 beds

3 baths

2,080 sq ft

112 FRINGETREE CT, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

Emerald Pointe

19418 PEARL DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

4 beds

3 baths

3,114 sq ft

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

Community: Trilogy® at Lake Frederick

JerMae Estates

5 GEOLEY CT, THURMONT, MD, 21788, Thurmont, MD 21788

$474,999

4 beds

3 baths

2,038 sq ft

5 GEOLEY CT, THURMONT, MD, 21788

Community: JerMae Estates

Ballenger Run

5312 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703

$559,900

3 beds

4 baths

3,194 sq ft

5312 CRAPE MYRTLE DR, FREDERICK, MD, 217...

Community: Ballenger Run

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

Questions? Call us: (540) 452-4199

Birchwood at Brambleton

42874 FIREFLY SONATA TER 403, ASHBURN, V..., Ashburn, VA 20148

$609,000

3 beds

2 baths

1,712 sq ft

Condo

42874 FIREFLY SONATA TER 403, ASHBURN, V...

Community: Birchwood at Brambleton

Cindy Certified

3927 FAIR RIDGE DR 303, FAIRFAX, VA, 220..., Fairfax, VA 22033

$565,000

2 beds

2 baths

1,301 sq ft

Condo

3927 FAIR RIDGE DR 303, FAIRFAX, VA, 220...

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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?

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229 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: Sep 06, 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 3

51 communities near Winchester Area

229 homes near Winchester Area

3 beds

4 baths

3,007 sq ft

2 beds

2 baths

1,333 sq ft

Condo

3 beds

3 baths

1,630 sq ft

3 beds

2 baths

1,829 sq ft

2 beds

2 baths

2,066 sq ft

3 beds

4 baths

3,333 sq ft

3 beds

4 baths

3,255 sq ft

2 beds

2 baths

1,515 sq ft

Condo

1 beds

1 baths

874 sq ft

Condo

2 beds

2 baths

1,301 sq ft

Condo

3 beds

3 baths

2,474 sq ft

2 beds

2 baths

1,558 sq ft

Condo

3 beds

2 baths

2,148 sq ft

Condo

2 beds

2 baths

1,609 sq ft

5 beds

5 baths

3,969 sq ft

4 beds

4 baths

4,779 sq ft

4 beds

3 baths

4,047 sq ft

3 beds

3 baths

2,208 sq ft

3 beds

2 baths

1,769 sq ft

3 beds

3 baths

2,612 sq ft

2 beds

2 baths

1,538 sq ft

Condo

2 beds

2 baths

1,012 sq ft

Condo

3 beds

3 baths

2,843 sq ft