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

169 homes near Winchester Area

Sort by:

Relevance

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 - $1Ms

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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

Questions? Call us: (860) 238-3620

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

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

Questions? Call us: (860) 238-3620

The Vineyards at Miller P...

$500ks

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

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

5 rating (1 reviews)

Paris Square

$600ks - $900ks

Paris Square, Northvale, NJ

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

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

Questions? Call us: (860) 238-3620

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

New Construction | 55+ age-restricted | Built 2014 - present | 16 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

1 2...3

Regency at Woodbridge

5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ..., Woodbridge, CT 06525

$749,000

3 beds

3 baths

Condo

5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ...

Community: Regency at Woodbridge

Heritage Village

405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$199,900

2 beds

2 baths

1,044 sq ft

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488

182 HERITAGE HLS A, 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

Oronoque Village

151 S TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$449,000

1 beds

3 baths

1,426 sq ft

Condo

151 S TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

The Retreat at Carmel

4 FROST CT, CARMEL, NY, 10512, Carmel, NY 10512

$759,900

2 beds

3 baths

2,035 sq ft

Condo

4 FROST CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

Heritage Village

761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$339,900

2 beds

2 baths

1,063 sq ft

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Liberty at Newtown

79 SUZIE DR # 79, NEWTOWN, CT, 06470, Newtown, CT 06470

$575,000

2 beds

3 baths

2,317 sq ft

Condo

79 SUZIE DR # 79, NEWTOWN, CT, 06470

Community: Liberty at Newtown

Leisure Glen

10 OAKDALE CT, RIDGE, NY, 11961, Ridge, NY 11961

$599,900

2 beds

2 baths

1,666 sq ft

Condo

10 OAKDALE CT, RIDGE, NY, 11961

Community: Leisure Glen

Heritage Village

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

$310,000

2 beds

2 baths

1,432 sq ft

Condo

891 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Rivington

85 WINDING RIDGE WAY # 85, DANBURY, CT, ..., Danbury, CT 06810

$825,000

3 beds

4 baths

1,794 sq ft

Condo

85 WINDING RIDGE WAY # 85, DANBURY, CT, ...

Community: Rivington

Leisure Village

186 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961

$289,000

2 beds

1 baths

900 sq ft

Condo

186 VENTRY CT UNIT C, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

Leisure Village

116 EXMORE CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961

$299,000

2 beds

1 baths

875 sq ft

Condo

116 EXMORE CT UNIT B, RIDGE, NY, 11961

Community: Leisure Village

The Retreat at Carmel

2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512, Carmel, NY 10512

$459,900

2 beds

2 baths

1,323 sq ft

Condo

2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512

Community: The Retreat at Carmel

Heritage Hills

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

$600,000

2 beds

2 baths

1,470 sq ft

Condo

537 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

The Summit at Bethel

32 HUNTING RIDGE LN # 32, BETHEL, CT, 06..., Bethel, CT 06801

$689,000

3 beds

4 baths

2,090 sq ft

Condo

32 HUNTING RIDGE LN # 32, BETHEL, CT, 06...

Community: The Summit at Bethel

Leisure Village

373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$415,000

2 beds

1 baths

1,171 sq ft

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

Spring Lake Village

1 COACH DR # 1, SOUTHINGTON, CT, 06489, Southington, CT 06489

$279,900

2 beds

2 baths

1,323 sq ft

Condo

1 COACH DR # 1, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Bartlett Hill

9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064..., Portland, CT 06480

$505,000

2 beds

3 baths

1,404 sq ft

Condo

9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064...

Community: Bartlett Hill

The Retreat at Carmel

14 LANGDON GRV, CARMEL, NY, 10512, Carmel, NY 10512

$679,900

3 beds

3 baths

3,000 sq ft

Condo

14 LANGDON GRV, CARMEL, NY, 10512

Condo

123 HERITAGE VLG B, 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

Baldwin Station

7 FIRE THORN LN # 7, MILFORD, CT, 06461, Milford, CT 06461

$679,950

2 beds

3 baths

2,331 sq ft

Condo

7 FIRE THORN LN # 7, MILFORD, CT, 06461

Community: Baldwin Station

Oronoque Village

766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

1 beds

3 baths

1,438 sq ft

Condo

766 NYACK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

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

$675,000

3 beds

2 baths

1,689 sq ft

Condo

59 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Leisure Village

380 WOODBRIDGE DR D, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$439,000

2 beds

2 baths

1,147 sq ft

Condo

380 WOODBRIDGE DR D, BROOKHAVEN, NY, 119...

Community: Leisure Village

Foxwood Village

1407 MIDDLE RD 275, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$425,000

3 beds

2 baths

1,530 sq ft

House

1407 MIDDLE RD 275, RIVERHEAD, NY, 11933

Community: Foxwood Village

Overlook

2042 SUMMIT LOOP # 58, CARMEL, NY, 10512, Carmel, NY 10512

$849,000

2 beds

4 baths

1,957 sq ft

Condo

2042 SUMMIT LOOP # 58, CARMEL, NY, 10512

Community: Overlook

Overlook

2080 SUMMIT LOOP # 75, CARMEL, NY, 10512, Carmel, NY 10512

$899,000

2 beds

3 baths

2,496 sq ft

Condo

2080 SUMMIT LOOP # 75, CARMEL, NY, 10512

Community: Overlook

Heritage Village

25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$449,000

2 beds

2 baths

1,447 sq ft

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

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

$414,900

1 beds

1 baths

1,055 sq ft

Condo

129 HERITAGE HLS A, 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

Rivington

$499,900

2 beds

2 baths

1,229 sq ft

Condo

1 RIVINGTON WAY UNIT 201, DANBURY, CT, 0...

Community: Rivington

Heritage Village

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

$259,900

2 beds

2 baths

1,365 sq ft

Condo

723 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

1 2 3 4…5

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 788 days. The average price of homes for sale in these communities is approximately $389,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $389,900.

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

169 homes

Remove Boundaries ×

Map Satellite

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: Feb 28, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

93 communities near Winchester Area

169 homes near Winchester Area

3 beds

3 baths

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

1 baths

1,036 sq ft

Condo

3 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,205 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

3 baths

2,035 sq ft

Condo

2 beds

2 baths

1,063 sq ft

Condo

2 beds

3 baths

2,317 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

4 baths

1,794 sq ft

Condo

2 beds

1 baths

900 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,323 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

3 beds

4 baths

2,090 sq ft

Condo

2 beds

1 baths

1,171 sq ft

Condo

2 beds

2 baths

1,323 sq ft

Condo

2 beds

3 baths