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

93 communities 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

$100Ks - $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

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

Questions? Call us: (860) 238-3620

Rivington

$400Ks - $800Ks

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...

$600Ks - $700Ks

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

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

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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

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 - $700Ks

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

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

Questions? Call us: (860) 238-3620

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

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

Questions? Call us: (860) 238-3620

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...

$500Ks - $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

$200Ks - $400Ks

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 - $700Ks

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

Want to learn more about 55+ rental 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

1 2...3

The Gardens of Wilbraham

32 LODGE LN # 32, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$565,000

2 beds

2 baths

1,610 sq ft

Condo

32 LODGE LN # 32, WILBRAHAM, MA, 01095

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

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

Questions? Call us: (860) 238-3620

Heritage Hills

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

$625,000

2 beds

2 baths

1,559 sq ft

Condo

443 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

The Vineyards at Miller Place

45 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$650,000

2 beds

3 baths

1,853 sq ft

Condo

45 HALLEY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

Leisure Village

418 WEYMOUTH CT B, RIDGE, NY, 11961, Ridge, NY 11961

$364,999

2 beds

1 baths

1,036 sq ft

Condo

418 WEYMOUTH CT B, RIDGE, NY, 11961

Community: Leisure Village

Foxwood Village

1407 MIDDLE RD 275, CALVERTON, NY, 11933, Calverton, NY 11933

$425,000

3 beds

2 baths

1,530 sq ft

House

1407 MIDDLE RD 275, CALVERTON, NY, 11933

Community: Foxwood 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

Plymouth Estates at Mount Sinai

166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$579,999

2 beds

2 baths

1,820 sq ft

House

166 IRA RD, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

Regency at Fishkill

423 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$499,000

1 beds

2 baths

1,450 sq ft

Condo

423 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

The Village at Whispering Pines

125 WHISPERING PINES WAY, ROTTERDAM, NY,..., Rotterdam, NY 12306

$469,895

2 beds

2 baths

1,500 sq ft

House

125 WHISPERING PINES WAY, ROTTERDAM, NY,...

Condo

278 BERWICK CT UNIT B B, RIDGE, NY, 1196...

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

Heritage Hills

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

$645,000

3 beds

2 baths

1,689 sq ft

Condo

140 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598

$329,000

1 beds

1 baths

850 sq ft

Condo

156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,...

Community: Jefferson Village

Jefferson Village

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598

$549,999

2 beds

2 baths

1,300 sq ft

Condo

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...

Community: Jefferson Village

Leisure Village

405 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961

$290,000

2 beds

1 baths

874 sq ft

Condo

405 WOODBRIDGE DR D, RIDGE, NY, 11961

Community: Leisure Village

Jefferson Village

141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$675,000

2 beds

2 baths

1,555 sq ft

Condo

141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N...

Condo

10 OAKDALE CT, RIDGE, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (860) 238-3620

Heritage Hills

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

$609,000

2 beds

2 baths

1,296 sq ft

Condo

798 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

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

$596,000

2 beds

2 baths

1,428 sq ft

Condo

348 HERITAGE HLS A, SOMERS, NY, 10589

Condo

373 WOODBRIDGE DR B, 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

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

Questions? Call us: (860) 238-3620

The Villages at Mount Sinai Park

4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$775,000

3 beds

3 baths

2,850 sq ft

House

4 OAKHURST CT, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Leisure Village

274 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961

$349,999

2 beds

1 baths

836 sq ft

Condo

274 BERWICK CT A, RIDGE, NY, 11961

Community: Leisure 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

93 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: Jan 27, 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

93 communities near Winchester Area

163 homes near Winchester Area

2 beds

2 baths

1,610 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

3 beds

3 baths

3,000 sq ft

Condo

2 beds

2 baths

1,205 sq ft

Condo

2 beds

2 baths

1,559 sq ft

Condo

2 beds

3 baths

1,853 sq ft

Condo

2 beds

1 baths

1,036 sq ft

Condo

3 beds

2 baths

1,530 sq ft

House

1 beds

1 baths

1,055 sq ft

Condo

2 beds

2 baths

1,820 sq ft

House

1 beds

2 baths

1,450 sq ft

Condo

2 beds

2 baths

1,500 sq ft

House

2 beds

2 baths

1,323 sq ft

Condo

2 beds

3 baths

2,035 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

1 beds

1 baths

850 sq ft

Condo

2 beds

2 baths

1,300 sq ft

Condo

2 beds