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

95 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

4 rating (1 review)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

3 rating (2 reviews)

Heritage Hills

$400ks - $900ks

Heritage Hills, Somers, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

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

Questions? Call us: (860) 238-3620

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

1 rating (1 review)

Plymouth Estates at Mount...

$400ks - $500ks

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

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

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

Questions? Call us: (860) 238-3620

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

5 rating (1 review)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

5 rating (1 review)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Glassbury Court at Cold S...

$600ks - $700ks

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

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 90 homes

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

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

Questions? Call us: (860) 238-3620

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

5 rating (1 review)

The Villages at Mount Sin...

$600ks

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

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

The Village at Whispering...

$400ks

The Village at Whispering..., Rotterdam, NY

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

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

Questions? Call us: (860) 238-3620

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

36 SUSSEX DR A, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (860) 238-3620

New Heritage Hills

343 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$520,000

2 beds

2 baths

1,435 sq ft

Condo

343 HERITAGE HLS C, SOMERS, NY, 10589

261 CARRIAGE DR 261, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

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

Questions? Call us: (860) 238-3620

New Heritage Hills

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

$490,000

2 beds

2 baths

1,138 sq ft

Condo

314 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New The Powder Forest Homes

4 ASHTON CIR 4, SIMSBURY, CT, 06070, Simsbury, CT 06070

$729,000

2 beds

4 baths

2,381 sq ft

4 ASHTON CIR 4, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

New Leisure Knoll

259 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$599,000

2 beds

2 baths

1,135 sq ft

Condo

259 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Stoneleigh Woods at Riverhead

47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$599,999

2 beds

3 baths

1,942 sq ft

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

New Plymouth Estates at Mount Sinai

262 POND CIR 262, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$599,000

2 beds

2 baths

1,820 sq ft

Condo

262 POND CIR 262, BROOKHAVEN, NY, 11766

Community: Plymouth Estates at Mount Sinai

New Foxwood Village

1407 MIDDLE RD 103, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$449,000

2 beds

2 baths

1,586 sq ft

Manufactured Home

1407 MIDDLE RD 103, RIVERHEAD, NY, 11933

Community: Foxwood Village

New Foxwood Village

1407 MIDDLE RD 233, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$405,000

3 beds

2 baths

3,133 sq ft

Manufactured Home

1407 MIDDLE RD 233, RIVERHEAD, NY, 11933

Community: Foxwood Village

New Leisure Village

449 ARLINGTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$310,000

2 beds

1 baths

1,074 sq ft

Condo

449 ARLINGTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Heritage Village

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

$275,000

2 beds

2 baths

1,076 sq ft

Condo

399 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Hills

788 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$749,900

2 beds

2 baths

1,764 sq ft

Condo

788 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Woodridge Strathmore Terrace

41 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$599,000

2 beds

2 baths

1,501 sq ft

Condo

41 CHIPPENDALE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

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

Questions? Call us: (860) 238-3620

New The Vineyards at Miller Place

48 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764

$619,996

2 beds

3 baths

1,486 sq ft

Condo

48 AVERY LN, BROOKHAVEN, NY, 11764

Community: The Vineyards at Miller Place

Leisure Glen

562 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$670,000

2 beds

2 baths

1,652 sq ft

House

562 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Leisure Glen

3 BALDWIN CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,900

2 beds

2 baths

1,542 sq ft

Condo

3 BALDWIN CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Jefferson Village

116 VILLAGE RD D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$529,000

2 beds

2 baths

1,200 sq ft

Condo

116 VILLAGE RD D, YORKTOWN, NY, 10598

Community: Jefferson Village

Overlook

4052 FAIRWAYS DR 293, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

3 beds

3 baths

2,274 sq ft

Condo

4052 FAIRWAYS DR 293, CARMEL, NY, 10512

Community: Overlook

Overlook

4004 FAIRWAYS DR 296, CARMEL, NY, 10512, Carmel, NY 10512

$869,000

3 beds

3 baths

2,309 sq ft

House

4004 FAIRWAYS DR 296, CARMEL, NY, 10512

Community: Overlook

Leisure Village

470B DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$339,000

2 beds

1 baths

1,074 sq ft

Condo

470B DARWEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Village

Meadow Brook Estates

107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478

$569,900

3 beds

3 baths

1,922 sq ft

Condo

107 MEADOW BROOK RD 107, OXFORD, CT, 064...

Community: Meadow Brook Estates

Jefferson Village

172 LONG HILL DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$675,000

2 beds

2 baths

1,550 sq ft

Condo

172 LONG HILL DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

897 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$749,900

2 beds

3 baths

1,666 sq ft

Condo

897 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Overlook

4038 FAIRWAYS DR 299, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

3 beds

3 baths

2,274 sq ft

House

4038 FAIRWAYS DR 299, CARMEL, NY, 10512

Community: Overlook

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

Questions? Call us: (860) 238-3620

The Vineyards at Miller Place

40 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764

$625,000

3 beds

3 baths

1,700 sq ft

Condo

40 AVERY LN, BROOKHAVEN, NY, 11764

Community: The Vineyards at Miller Place

Leisure Glen

488 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$659,000

2 beds

2 baths

1,652 sq ft

Condo

488 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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Connecticut
Winchester Area

Frequently Asked Questions

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

Of the 2 55+ communities in the Winchester Area, 2 are for sale and none are rentals. By size, 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 397 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?

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Answers from local 55+ experts

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Want to learn more about 55+ communities in Winchester Area?

Call us: (860) 238-3620

95 communities

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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: Nov 07, 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

95 communities near Winchester Area

246 homes near Winchester Area

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,248 sq ft

Manufactured Home

2 beds

2 baths

1,212 sq ft

Condo

1 beds

1 baths

725 sq ft

Condo

2 beds

2 baths

1,435 sq ft

Condo

2 beds

2 baths

1,370 sq ft

Condo

2 beds

2 baths

1,272 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,427 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Mobile Home

2 beds

2 baths

1,240 sq ft

Condo

2 beds

2 baths

1,240 sq ft

Condo

3 beds

4 baths

2,596 sq ft

Condo

3 beds

2 baths

1,780 sq ft

Condo

2 beds

2 baths

1,207 sq ft

Condo

2 beds

2 baths

1,138 sq ft

Condo

2 beds

4 baths

2,381 sq ft

2 beds

2 baths

1,135 sq ft

Condo

2 beds

3 baths