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

89 communities near Winchester Area

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Clockmaker's Hill

$100Ks - $100Ks

Clockmaker's Hill, Winsted, CT

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

No reviews yet

Oak Meadow Estates

$200Ks - $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

No reviews yet

Leisure Village

$200Ks - $500Ks

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

No reviews yet

Rivington

$400Ks - $500Ks

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$300Ks - $400Ks

Jefferson Village, Yorktown Heights, NY

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

No reviews yet

Oronoque Village

$300Ks - $600Ks

Oronoque Village, Stratford, CT

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

No reviews yet

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

No reviews yet

Leisure Knoll

$300Ks - $500Ks

Leisure Knoll, Ridge, NY

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

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No reviews yet

Leisure Glen

$400Ks - $600Ks

Leisure Glen, Ridge, NY

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

No reviews yet

Spring Lake Village

$200Ks - $200Ks

Spring Lake Village, Southington, CT

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

4 rating (8 reviews)

Glenwood Village

$100Ks - $400Ks

Glenwood Village, Riverhead, NY

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

No reviews yet

Regency at Prospect

$400Ks - $400Ks

Regency at Prospect, Prospect, CT

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

No reviews yet

The Retreat at Carmel

$400Ks - $600Ks

The Retreat at Carmel, Carmel, NY

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

$300Ks - $400Ks

Foxwood Village, Calverton, NY

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks - $600Ks

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

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

No reviews yet

Meadow Brook Estates

$500Ks - $500Ks

Meadow Brook Estates, Oxford, CT

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

No reviews yet

The Summit at Bethel

$600Ks - $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 - $500Ks

Chatfield Farms, Beacon Falls, CT

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

No reviews yet

Woodridge Strathmore Terr...

$400Ks - $400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

No reviews yet

Regency at Wappinger

$600Ks - $700Ks

Regency at Wappinger, Wappingers Falls, NY

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

No reviews yet

Saddle Lakes

$400Ks - $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...

$700Ks - $800Ks

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

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

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

Questions? Call us: (860) 238-3620

No reviews yet

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 - $400Ks

Newtown Woods, Newtown, CT

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

No reviews yet

Stoneleigh Woods at River...

$400Ks - $600Ks

Stoneleigh Woods at River..., Riverhead, NY

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

No reviews yet

Beckley Farms

$300Ks - $400Ks

Beckley Farms, Berlin, CT

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

No reviews yet

Regency at Fishkill

$500Ks - $500Ks

Regency at Fishkill, Fishkill, NY

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

No reviews yet

South Pond Village

$200Ks - $400Ks

South Pond Village, Bloomfield, CT

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

No reviews yet

Setauket Meadows

$600Ks - $700Ks

Setauket Meadows, Setauket, NY

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

No reviews yet

Fieldstone Village

$500Ks - $800Ks

Fieldstone Village, Orange, CT

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

No reviews yet

North Woods of Colchester

$500Ks - $500Ks

North Woods of Colchester, Colchester, CT

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

No reviews yet

Windcrest East

$600Ks - $600Ks

Windcrest East, Calverton, NY

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

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

Questions? Call us: (860) 238-3620

No reviews yet

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

No reviews yet

Newbury Village

$600Ks - $700Ks

Newbury Village, Brookfield, CT

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

No reviews yet

The Gardens of Wilbraham

$300Ks - $400Ks

The Gardens of Wilbraham, Wilbraham, MA

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

No reviews yet

O'Meara Farm

$400Ks - $500Ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes

198 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

Newtown Woods

603 BROOKSIDE CT # 603, NEWTOWN, CT, 064..., Newtown, CT 06470

$499,000

2 beds

2 baths

1,504 sq ft

Condo

603 BROOKSIDE CT # 603, NEWTOWN, CT, 064...

Community: Newtown Woods

Heritage Village

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

$225,000

2 beds

2 baths

1,365 sq ft

Condo

51 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$185,000

2 beds

2 baths

1,044 sq ft

Condo

98 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

194 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$660,000

1 beds

3 baths

1,438 sq ft

Condo

194 BAYFIELD LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$430,000

3 beds

2 baths

1,716 sq ft

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$339,900

3 beds

2 baths

1,716 sq ft

Condo

665 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$200,000

1 beds

1 baths

928 sq ft

Condo

855 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Park Glen

10 HARMONY TRL # 10, NEW MILFORD, CT, 06..., New Milford, CT 06776

$645,000

2 beds

3 baths

4,023 sq ft

Condo

10 HARMONY TRL # 10, NEW MILFORD, CT, 06...

Community: Park Glen

Heritage Village

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

$409,900

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Rivington

1022 COUNTRY VIEW RD # 1022, DANBURY, CT..., Danbury, CT 06810

$499,900

2 beds

2 baths

1,330 sq ft

Condo

1022 COUNTRY VIEW RD # 1022, DANBURY, CT...

Community: Rivington

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

Questions? Call us: (860) 238-3620

Heritage Village

9 HERITAGE CIR D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$255,000

2 beds

2 baths

1,071 sq ft

Condo

9 HERITAGE CIR D, SOUTHBURY, CT, 06488

Community: Heritage Village

Newbury Village

7 STILL WATER CIR # 7, BROOKFIELD, CT, 0..., Brookfield, CT 06804

$670,000

2 beds

4 baths

2,420 sq ft

Condo

7 STILL WATER CIR # 7, BROOKFIELD, CT, 0...

Community: Newbury Village

Heritage Village

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

$300,000

2 beds

2 baths

1,432 sq ft

Condo

264 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

280 HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488

$199,000

1 beds

1 baths

928 sq ft

Condo

280 HERITAGE VLG, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency Meadows

7 REGENCY CIR # 7, TRUMBULL, CT, 06611, Trumbull, CT 06611

$749,900

3 beds

4 baths

2,338 sq ft

Condo

7 REGENCY CIR # 7, TRUMBULL, CT, 06611

Community: Regency Meadows

Oak Meadow Estates

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

$529,900

2 beds

4 baths

2,164 sq ft

Condo

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

Community: Oak Meadow Estates

Heritage Village

399 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488

$225,000

2 beds

2 baths

1,076 sq ft

Condo

399 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$234,900

2 beds

2 baths

1,365 sq ft

Condo

793 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$229,900

1 beds

1 baths

928 sq ft

Condo

741 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$275,000

2 beds

2 baths

1,398 sq ft

Condo

127 HERITAGE VLG B, SOUTHBURY, CT, 06488

Condo

535 NARRAGANSET LN B, STRATFORD, CT, 066...

Condo

7 HERITAGE LN # 67, WOODBRIDGE, CT, 0652...

Community: Regency at Woodbridge

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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?

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Answers from local 55+ experts

Want to learn more about 55+ communities in Winchester Area?

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89 communities near Winchester Area

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

89 communities near Winchester Area

215 homes near Winchester Area

2 beds

2 baths

1,440 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

1 beds

2 baths

1,118 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

3 baths

4,023 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,330 sq ft

Condo

2 beds

2 baths

1,071 sq ft

Condo

2 beds

4 baths

2,420 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

3 beds