Winchester Area, CT 55+ active adult communities & homes for sale - Page 2

153 homes near Winchester Area

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Clockmaker's Hill

$100Ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

Oak Meadow Estates

$400Ks

Oak Meadow Estates, Torrington, CT

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

3 rating (2 reviews)

Heritage Hills

$300Ks - $900Ks

Heritage Hills, Somers, NY

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

3.6 rating (7 reviews)

Heritage Village

$200Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

Leisure Village

$200Ks - $400Ks

Leisure Village, Ridge, NY

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

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

Questions? Call us: (860) 238-3620

Rivington

$400Ks - $600Ks

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$200Ks - $600Ks

Jefferson Village, Yorktown Heights, NY

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

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

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

The Village at Oxford Gre...

$500Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 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.

Leisure Knoll

$400Ks

Leisure Knoll, Ridge, NY

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

Leisure Glen

$500Ks

Leisure Glen, Ridge, NY

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

Spring Lake Village

$200Ks - $300Ks

Spring Lake Village, Southington, CT

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

Regency at Prospect

$400Ks - $500Ks

Regency at Prospect, Prospect, CT

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

The Retreat at Carmel

$400Ks - $600Ks

The Retreat at Carmel, Carmel, NY

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

Overlook

$600Ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

3.5 rating (2 reviews)

Foxwood Village

$400Ks - $500Ks

Foxwood Village, Calverton, NY

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks

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

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

Meadow Brook Estates

$500Ks

Meadow Brook Estates, Oxford, CT

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

The Summit at Bethel

$600Ks

The Summit at Bethel, Bethel, CT

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

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $600Ks

Chatfield Farms, Beacon Falls, CT

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

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

Questions? Call us: (860) 238-3620

Woodridge Strathmore Terr...

$400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Regency at Wappinger

$600Ks - $700Ks

Regency at Wappinger, Wappingers Falls, NY

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

Saddle Lakes

$400Ks

Saddle Lakes, Riverhead, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400Ks - $500Ks

Sunken Pond Estates, Riverhead, NY

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

5 rating (1 reviews)

The Villages at Mount Sin...

$500Ks - $700Ks

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

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

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

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

5 rating (1 reviews)

Newtown Woods

$400Ks - $500Ks

Newtown Woods, Newtown, CT

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

Stoneleigh Woods at River...

$600Ks

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

Beckley Farms

$300Ks - $400Ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Regency at Fishkill

$400Ks - $500Ks

Regency at Fishkill, Fishkill, NY

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

South Pond Village

$100Ks - $200Ks

South Pond Village, Bloomfield, CT

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

Setauket Meadows

$600Ks - $700Ks

Setauket Meadows, Setauket, NY

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

Fieldstone Village

$500Ks - $800Ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

North Woods of Colchester

$500Ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Windcrest East

$600Ks

Windcrest East, Calverton, NY

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

Fairview at Oxford Greens

$600Ks

Fairview at Oxford Greens, Oxford, CT

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

3.5 rating (2 reviews)

Harvest Pointe

$800Ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

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

Questions? Call us: (860) 238-3620

Newbury Village

$500Ks - $600Ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

The Gardens of Wilbraham

$500Ks

The Gardens of Wilbraham, Wilbraham, MA

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

60 HERITAGE VLG B, SOUTHBURY, CT, 06488

8 WHISPER RIDGE WAY # 43, WOODBRIDGE, CT...

Community: Regency at Woodbridge

Heritage Village

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

$264,900

1 beds

1 baths

928 sq ft

Condo

953 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

Spring Lake Village

621 OVERLOOK PATH # 621, SOUTHINGTON, CT..., Southington, CT 06489

$340,000

2 beds

3 baths

1,133 sq ft

Condo

621 OVERLOOK PATH # 621, SOUTHINGTON, CT...

Community: Spring Lake Village

Heritage Village

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

$225,000

1 beds

1 baths

928 sq ft

Condo

917 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488

$409,900

2 beds

2 baths

1,432 sq ft

Condo

568A HERITAGE VLG, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$420,000

1 beds

2 baths

1,454 sq ft

Condo

87 CREEK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$389,900

2 beds

2 baths

1,398 sq ft

Condo

902 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$395,000

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

522 IROQUOIS LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

3 beds

3 baths

1,426 sq ft

Condo

522 IROQUOIS LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$364,900

2 beds

2 baths

1,398 sq ft

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

Park Glen

1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776, New Milford, CT 06776

$545,000

2 beds

2 baths

1,880 sq ft

Condo

1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776

Community: Park Glen

Oronoque Village

133 BANNOCK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$629,900

3 beds

3 baths

1,438 sq ft

Condo

133 BANNOCK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$238,000

2 beds

2 baths

1,044 sq ft

Condo

39 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

The Woods at Dunham Pond

12 HERON VIEW RD # 12, NEW FAIRFIELD, CT..., New Fairfield, CT 06812

$409,900

1 beds

2 baths

1,550 sq ft

12 HERON VIEW RD # 12, NEW FAIRFIELD, CT...

Community: The Woods at Dunham Pond

The Village at Buckingham

8 KENINGTON RD # 8, AVON, CT, 06001, Avon, CT 06001

$599,900

3 beds

3 baths

2,430 sq ft

Condo

8 KENINGTON RD # 8, AVON, CT, 06001

Community: The Village at Buckingham

Heritage Village

7 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$449,900

2 beds

2 baths

1,447 sq ft

Condo

7 HERITAGE CRST B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$369,900

2 beds

2 baths

1,398 sq ft

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Bidwell Village

94 STONEHOUSE RD UNIT 10, COVENTRY, CT, ..., Coventry, CT 06238

$425,000

3 beds

3 baths

1,717 sq ft

94 STONEHOUSE RD UNIT 10, COVENTRY, CT, ...

Community: Bidwell Village

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

Questions? Call us: (860) 238-3620

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

Oronoque Village

35 ALGONQUIN LN D, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

1 beds

2 baths

1,300 sq ft

Condo

35 ALGONQUIN LN D, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

375 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$450,000

1 beds

3 baths

1,550 sq ft

Condo

375 PIUTE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Oak Meadow Estates

65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791

$495,000

2 beds

4 baths

2,164 sq ft

Condo

65 OAK MEADOW LN # 65, HARWINTON, CT, 06...

Community: Oak Meadow Estates

Chatfield Farms

18 FIELDSTONE LN # 18, BEACON FALLS, CT,..., Beacon Falls, CT 06403

$599,000

2 beds

3 baths

2,719 sq ft

170 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

Heritage Village

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

$499,900

3 beds

2 baths

1,716 sq ft

Condo

929 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$369,900

3 beds

2 baths

1,716 sq ft

Condo

737 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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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

153 homes

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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: Jan 11, 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 2

92 communities near Winchester Area

153 homes near Winchester Area

2 beds

4 baths

2,720 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

2,331 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,204 sq ft

Condo

3 beds

3 baths

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

3 baths

1,133 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

2 baths

1,454 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

3 baths