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

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

682 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 238-3620

Heritage Village

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

$415,000

2 beds

2 baths

1,432 sq ft

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$319,900

2 beds

2 baths

1,000 sq ft

Condo

Community: Meadow Brook Estates

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

Questions? Call us: (860) 238-3620

Spring Lake Village

1 HICKORY HL 1, SOUTHINGTON, CT, 06489, Southington, CT 06489

$239,000

2 beds

2 baths

1,285 sq ft

Condo

1 HICKORY HL 1, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Heritage Village

226A S DURKEE HILL RD 226A, SOUTHBURY, C..., Southbury, CT 06488

$309,500

2 beds

2 baths

1,398 sq ft

Condo

226A S DURKEE HILL RD 226A, SOUTHBURY, C...

Community: Heritage Village

Leisure Knoll

257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,900

2 beds

2 baths

1,000 sq ft

Condo

257 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Beckley Farms

91 SCENIC DR 91, BERLIN, CT, 06037, Berlin, CT 06037

$679,900

3 beds

3 baths

2,068 sq ft

Condo

91 SCENIC DR 91, BERLIN, CT, 06037

Community: Beckley Farms

Foxwood Village

1407 MIDDLE RD 45, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$315,000

2 beds

2 baths

1,100 sq ft

House

1407 MIDDLE RD 45, RIVERHEAD, NY, 11933

Community: Foxwood Village

Heritage Hills

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

$750,000

2 beds

3 baths

1,531 sq ft

Condo

823 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

397 KRUEGER CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$439,700

3 beds

2 baths

1,716 sq ft

Condo

397 KRUEGER CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478

$629,900

2 beds

3 baths

2,232 sq ft

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$629,900

2 beds

3 baths

2,232 sq ft

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Oronoque Village

55 BLACKHAWK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$639,000

2 beds

3 baths

1,360 sq ft

Condo

55 BLACKHAWK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$519,000

2 beds

3 baths

1,438 sq ft

Condo

209 ACORN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (860) 238-3620

Heritage Village

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

$400,000

2 beds

2 baths

1,432 sq ft

Condo

633 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$289,000

2 beds

2 baths

1,432 sq ft

Condo

626 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

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

$975,000

3 beds

2 baths

1,905 sq ft

Condo

593 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

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

$525,000

2 beds

2 baths

1,396 sq ft

Condo

154 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

45 JEFFERSON OVAL G, YORKTOWN, NY, 10598, Yorktown, NY 10598

$429,900

2 beds

2 baths

1,100 sq ft

Condo

45 JEFFERSON OVAL G, YORKTOWN, NY, 10598

Community: Jefferson Village

Rivington

11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810

$595,000

2 beds

4 baths

1,572 sq ft

Condo

11 MERCY ST 11, DANBURY, CT, 06810

Community: Rivington

Jefferson Village

18L HASTINGS CT, YORKTOWN, NY, 10598, Yorktown, NY 10598

$340,000

2 beds

1 baths

1,000 sq ft

Condo

18L HASTINGS CT, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

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

$198,000

1 beds

1 baths

928 sq ft

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Bidwell Village

94 STONEHOUSE RD 13, COVENTRY, CT, 06238, Coventry, CT 06238

$365,000

3 beds

4 baths

1,810 sq ft

Condo

94 STONEHOUSE RD 13, COVENTRY, CT, 06238

Community: Bidwell Village

Sunken Pond Estates

3704 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$529,000

2 beds

3 baths

1,350 sq ft

Condo

3704 AMEN COR, RIVERHEAD, NY, 11901

Community: Sunken Pond Estates

Plymouth Estates at Mount Sinai

240 IRA RD, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$589,999

2 beds

2 baths

1,396 sq ft

Condo

240 IRA RD, BROOKHAVEN, NY, 11766

Community: Plymouth Estates at Mount Sinai

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

Questions? Call us: (860) 238-3620

Overlook

2055 SUMMIT LOOP 95, CARMEL, NY, 10512, Carmel, NY 10512

$899,000

2 beds

2 baths

2,102 sq ft

Condo

2055 SUMMIT LOOP 95, CARMEL, NY, 10512

Community: Overlook

Leisure Knoll

473 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,000

2 beds

2 baths

1,350 sq ft

House

473 STRATFORD LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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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?

Insights and market stats
Instant new home alerts
Answers from local 55+ experts

Thanks! A local 55+ expert will be in touch shortly.

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 3

95 communities near Winchester Area

228 homes near Winchester Area

2 beds

2 baths

1,549 sq ft

Condo

3 beds

3 baths

2,412 sq ft

Condo

2 beds

2 baths

1,420 sq ft

Condo

2 beds

2 baths

1,285 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,328 sq ft

Condo

2 beds

3 baths

1,931 sq ft

Condo

1 beds

2 baths

967 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

1 beds

2 baths

1,480 sq ft

Condo

2 beds

2 baths

1,807 sq ft

Condo

2 beds

2 baths

1,386 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

2,484 sq ft

Condo

2 beds

2 baths

1,285 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds