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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

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

Questions? Call us: (860) 238-3620

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

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

Questions? Call us: (860) 238-3620

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 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 Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

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

Questions? Call us: (860) 238-3620

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

The Vineyards at Miller P...

$500ks

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

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

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

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

Questions? Call us: (860) 238-3620

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

5 rating (1 reviews)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

New The Village at Oxford Greens

443 TEE SHOT DR 443, OXFORD, CT, 06478, Oxford, CT 06478

$689,900

3 beds

3 baths

2,759 sq ft

Condo

443 TEE SHOT DR 443, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Heritage Hills

29 HERITAGE HLS 29D, SOMERS, NY, 10589, Somers, NY 10589

$495,000

2 beds

3 baths

1,340 sq ft

Condo

29 HERITAGE HLS 29D, 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 Heritage Hills

606 HERITAGE HILLS DR C, SOMERS, NY, 105..., Somers, NY 10589

$825,000

3 beds

2 baths

1,905 sq ft

Condo

606 HERITAGE HILLS DR C, SOMERS, NY, 105...

Community: Heritage Hills

New Hopmeadow Place

1 W ST 310, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,430 sq ft

Condo

1 W ST 310, SIMSBURY, CT, 06070

Community: Hopmeadow Place

New Leisure Knoll

152B LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$374,000

1 beds

1 baths

530 sq ft

Condo

152B LAURANCE LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Oronoque Village

448 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614

$525,000

1 beds

3 baths

1,438 sq ft

Condo

448 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

New The Powder Forest Homes

6 RONAN WAY 6, SIMSBURY, CT, 06070, Simsbury, CT 06070

$739,900

2 beds

3 baths

1,864 sq ft

2803 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...

567 INVERNESS CT 567, OXFORD, CT, 06478

Community: The Village at Oxford Greens

The Powder Forest Homes

15 BANTRY RD 15, SIMSBURY, CT, 06070, Simsbury, CT 06070

$949,000

4 beds

3 baths

1,878 sq ft

15 BANTRY RD 15, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Oronoque Village

283 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$625,000

2 beds

3 baths

1,415 sq ft

Condo

283 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Overlook

1001 COTTAGE DR 1, CARMEL, NY, 10512, Carmel, NY 10512

$1,250,000

2 beds

4 baths

2,900 sq ft

Condo

1001 COTTAGE DR 1, CARMEL, NY, 10512

Community: Overlook

Meadow Brook Estates

211 MEADOW BROOK RD 211, OXFORD, CT, 064..., Oxford, CT 06478

$625,000

3 beds

3 baths

2,201 sq ft

Condo

211 MEADOW BROOK RD 211, OXFORD, CT, 064...

Community: Meadow Brook Estates

Heritage Village

10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$364,000

3 beds

2 baths

1,716 sq ft

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488

Condo

293 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

Newbury Village

46 GREAT HERON LN 46, BROOKFIELD, CT, 06..., Brookfield, CT 06804

$699,000

2 beds

4 baths

2,560 sq ft

Condo

46 GREAT HERON LN 46, BROOKFIELD, CT, 06...

Community: Newbury Village

Liberty at Newtown

25 FRANKLIN CT 25, NEWTOWN, CT, 06470, Newtown, CT 06470

$545,000

2 beds

2 baths

1,413 sq ft

Condo

25 FRANKLIN CT 25, NEWTOWN, CT, 06470

Community: Liberty at Newtown

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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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: Jun 25, 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

209 homes near Winchester Area

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,145 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

3 beds

3 baths

2,759 sq ft

Condo

2 beds

3 baths

1,340 sq ft

Condo

3 beds

2 baths

1,905 sq ft

Condo

2 beds

2 baths

1,430 sq ft

Condo

1 beds

1 baths

530 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

3 baths

1,864 sq ft

2 beds

2 baths

1,631 sq ft

Condo

2 beds

2 baths

1,188 sq ft

Condo

2 beds

2 baths

1,807 sq ft

Condo

2 beds

2 baths

1,214 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

3 baths

1,350 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

4 baths