Winchester Area, CT 55+ active adult communities & homes for sale - Page 6

228 homes 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 - $900ks

Heritage Hills, Somers, NY

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

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

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

Questions? Call us: (860) 238-3620

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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.

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

5 rating (1 review)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

5 rating (1 review)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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

Questions? Call us: (860) 238-3620

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

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

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

Glassbury Court at Cold S...

$600ks - $700ks

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

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

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

Questions? Call us: (860) 238-3620

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

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

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

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

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

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

Questions? Call us: (860) 238-3620

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

1 2...3

Fairview at Oxford Greens

941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478

$674,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$674,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470

Community: Newtown Woods

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

Questions? Call us: (860) 238-3620

Glassbury Court at Cold Spring

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051..., Philipstown, NY 10516

$698,000

2 beds

2 baths

1,974 sq ft

Condo

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051...

Community: Glassbury Court at Cold Spring

Glenwood Village

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ..., Riverhead, NY 11901

$239,999

2 beds

2 baths

980 sq ft

Manufactured Home

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ...

Community: Glenwood Village

Heritage Village

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

$337,900

2 beds

2 baths

1,432 sq ft

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$559,900

1 beds

2 baths

1,375 sq ft

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

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

$625,000

3 beds

2 baths

1,689 sq ft

Condo

156 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

The Cottages at Wire Mill

16 WIRE MILL RD A, STAMFORD, CT, 06903, Stamford, CT 06903

$1,495,000

3 beds

4 baths

3,244 sq ft

16 WIRE MILL RD A, STAMFORD, CT, 06903

Community: The Cottages at Wire Mill

Jefferson Village

27 WALDEN CT J, YORKTOWN, NY, 10598, Yorktown, NY 10598

$349,900

1 beds

1 baths

800 sq ft

Condo

Community: Heritage Village

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

Questions? Call us: (860) 238-3620

Heritage Village

1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$225,000

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Liberty at Newtown

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

$499,000

2 beds

2 baths

1,413 sq ft

Condo

25 FRANKLIN CT 25, NEWTOWN, CT, 06470

Community: Liberty at Newtown

Leisure Knoll

183 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$414,500

2 beds

1 baths

960 sq ft

Condo

183 KINGSTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

The Village at Oxford Greens

527 PUTTING GREEN LN 527, OXFORD, CT, 06..., Oxford, CT 06478

$650,000

3 beds

3 baths

2,008 sq ft

Condo

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

Heritage Village

73 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$199,900

2 beds

2 baths

1,044 sq ft

Condo

73 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

1 2 3 4 5 6

Home
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

228 homes

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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: Nov 02, 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 - Page 6

95 communities near Winchester Area

228 homes near Winchester Area

2 beds

2 baths

1,682 sq ft

2 beds

2 baths

1,682 sq ft

2 beds

2 baths

1,500 sq ft

Manufactured Home

2 beds

3 baths

1,550 sq ft

Condo

2 beds

2 baths

1,747 sq ft

Condo

2 beds

2 baths

1,974 sq ft

Condo

2 beds

2 baths

980 sq ft

Manufactured Home

2 beds

2 baths

1,432 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

3 beds

4 baths

3,244 sq ft

1 beds

1 baths

800 sq ft

Condo

2 beds

3 baths

2,729 sq ft

Condo

2 beds

2 baths

1,631 sq ft

Condo

2 beds

2 baths

2,008 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,413 sq ft

Condo

2 beds

1 baths

960 sq ft

Condo

3 beds

3 baths

2,008 sq ft

Condo