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

94 communities near Winchester Area

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3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

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

Questions? Call us: (860) 238-3620

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes

The Village at Oxford Gre...

$400ks - $500ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 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.

Rivington

$300ks - $900ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

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

Questions? Call us: (860) 238-3620

Glassbury Court at Cold S...

$500ks - $700ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

1 rating (1 reviews)

Plymouth Estates at Mount...

$400ks - $500ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

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

Questions? Call us: (860) 238-3620

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

New Construction | 55+ age-restricted | Built 2025 - present | 85 homes

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

The Vineyards at Mount Si...

$800ks - $1Ms

The Vineyards at Mount Si..., Mount Sinai, NY

New Construction | 55+ age-restricted | Built 2020 - present | 91 homes

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

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

Questions? Call us: (860) 238-3620

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

The Vineyards at Miller P...

$500ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

1 2...3

New Jefferson Village

39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$379,000

2 beds

2 baths

1,000 sq ft

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598

159 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (860) 238-3620

New Oronoque Village

511 OPA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$589,900

2 beds

2 baths

1,620 sq ft

Condo

511 OPA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Jefferson Village

184 LONG HILL DR A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$489,000

2 beds

2 baths

1,200 sq ft

Condo

184 LONG HILL DR A, YORKTOWN, NY, 10598

Community: Jefferson Village

New The Vineyards at Mount Sinai

72 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$999,999

2 beds

4 baths

3,736 sq ft

Condo

72 FARM ACRE CIR, BROOKHAVEN, NY, 11766

Community: The Vineyards at Mount Sinai

New Heritage Village

105 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$230,000

2 beds

2 baths

1,432 sq ft

Condo

105 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$374,500

2 beds

2 baths

1,398 sq ft

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Autumn Fields

37 QUAIL HOLW 37, ENFIELD, CT, 06082, Enfield, CT 06082

$419,000

2 beds

3 baths

1,679 sq ft

Condo

37 QUAIL HOLW 37, ENFIELD, CT, 06082

Community: Autumn Fields

New Jefferson Village

20 HASTINGS CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$345,000

1 beds

1 baths

800 sq ft

Condo

20 HASTINGS CT A, YORKTOWN, NY, 10598

Community: Jefferson Village

New Leisure Glen

276 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$585,000

2 beds

2 baths

1,666 sq ft

Condo

276 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Glenwood Village

1661 OLD COUNTRY RD 254, RIVERHEAD, NY, ..., Riverhead, NY 11901

$185,000

2 beds

2 baths

1,036 sq ft

Manufactured Home

1661 OLD COUNTRY RD 254, RIVERHEAD, NY, ...

Community: Glenwood Village

New Rivington

215 CENTER MEADOW LN 215, DANBURY, CT, 0..., Danbury, CT 06810

$499,000

2 beds

2 baths

1,258 sq ft

Condo

215 CENTER MEADOW LN 215, DANBURY, CT, 0...

Community: Rivington

New Heritage Village

4 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$245,000

1 beds

1 baths

928 sq ft

Condo

4 HERITAGE VLG A, SOUTHBURY, CT, 06488

27 HERITAGE LN, WOODBRIDGE, CT, 06525

Community: Regency at Woodbridge

Heritage Hills

813 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$899,000

2 beds

2 baths

1,663 sq ft

Condo

813 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

The Village at Oxford Greens

1159 ST ANDREWS DR 80, OXFORD, CT, 06478, Oxford, CT 06478

$799,900

2 beds

3 baths

1,955 sq ft

Condo

Community: Regency at Fishkill

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

Questions? Call us: (860) 238-3620

Fieldstone Village

101 SUNRISE HILL CIR 101, ORANGE, CT, 06..., Orange, CT 06477

$875,000

2 beds

3 baths

2,350 sq ft

Condo

101 SUNRISE HILL CIR 101, ORANGE, CT, 06...

Community: Fieldstone Village

Sonoma Woods

52 SONOMA LN 52, MIDDLETOWN, CT, 06457, Middletown, CT 06457

$559,900

3 beds

3 baths

1,996 sq ft

Condo

52 SONOMA LN 52, MIDDLETOWN, CT, 06457

Community: Sonoma Woods

Glenwood Village

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ..., Riverhead, NY 11901

$375,000

3 beds

2 baths

1,317 sq ft

Manufactured Home

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ...

Community: Glenwood Village

Leisure Village

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$349,000

2 beds

1 baths

875 sq ft

Condo

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Woodridge Strathmore Terrace

18 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$525,000

2 beds

2 baths

1,240 sq ft

Condo

18 CHIPPENDALE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

The Retreat at Carmel

8 ATKINS CT, CARMEL, NY, 10512, Carmel, NY 10512

$690,000

2 beds

3 baths

2,148 sq ft

Condo

8 ATKINS CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

Leisure Glen

29 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,900

2 beds

2 baths

1,314 sq ft

Condo

29 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Spring Lake Village

142 TIMBER RDG 142, SOUTHINGTON, CT, 064..., Southington, CT 06489

$359,900

2 beds

3 baths

1,601 sq ft

Condo

142 TIMBER RDG 142, SOUTHINGTON, CT, 064...

Community: Spring Lake Village

Heritage Village

399 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$165,000

2 beds

2 baths

1,076 sq ft

Condo

399 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Glassbury Court at Cold Spring

5 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516

$712,000

2 beds

2 baths

1,974 sq ft

Condo

5 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516

Community: Glassbury Court at Cold Spring

Chatfield Farms

6 WOODLAND PATH 6, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$799,000

3 beds

4 baths

2,600 sq ft

Condo

6 WOODLAND PATH 6, BEACON FALLS, CT, 064...

Community: Chatfield Farms

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

Questions? Call us: (860) 238-3620

Leisure Village

179 VENTRY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$319,000

2 beds

1 baths

1,085 sq ft

Condo

179 VENTRY CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Heritage Hills

493 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$600,000

2 beds

2 baths

1,470 sq ft

Condo

493 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Home
Connecticut
Winchester Area

Frequently Asked Questions

What size 55+ communities are there in the Winchester Area?

In the Winchester Area, there are no large communities, no medium communities, and 2 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 31 homes, the largest has 38 homes, and the average communities consists of 34 homes.

Are there new 55+ homes available in the Winchester Area?

Yes, there is new 55+ home available in the Winchester Area. The most recent communities started in the Winchester Area include Oak Meadow Estates, Clockmaker's Hill. There is also 1 communities in the Winchester Area that offers new construction homes, including Oak Meadow Estates.

Are there gated 55+ communities in the Winchester Area?

No, there are no gated 55+ communities in the Winchester Area.

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 281 days. The average price of homes for sale in these communities is approximately $485,000, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $485,000.

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: (860) 238-3620

94 communities

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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: Aug 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, CT 55+ active adult communities & homes for sale

94 communities near Winchester Area

208 homes near Winchester Area

2 beds

2 baths

1,000 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds

2 baths

1,620 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

4 baths

3,736 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

1,679 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,036 sq ft

Manufactured Home

2 beds

2 baths

1,258 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

1 baths

874 sq ft

Condo

2 beds

2 baths

1,070 sq ft

Condo

2 beds

2 baths

1,172 sq ft

Condo

2 beds