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

234 homes 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 - $400Ks

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

$500Ks - $900Ks

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$200Ks - $500Ks

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...

$500Ks - $700Ks

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

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

No reviews yet

Leisure Knoll

$200Ks - $400Ks

Leisure Knoll, Ridge, NY

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

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No reviews yet

Leisure Glen

$400Ks - $500Ks

Leisure Glen, Ridge, NY

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

No reviews yet

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 - $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 - $500Ks

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 - $500Ks

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

$300Ks - $400Ks

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

$500Ks - $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

1 2...3

The Villages at Mount Sinai Park

13 GRAYCREST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$815,000

2 beds

2 baths

2,016 sq ft

Condo

13 GRAYCREST CT, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Leisure Village

311 WOODBRIDGE DR 311-C, RIDGE, NY, 1196..., Ridge, NY 11961

$245,000

1 beds

1 baths

684 sq ft

Condo

311 WOODBRIDGE DR 311-C, RIDGE, NY, 1196...

Community: Leisure Village

Jefferson Village

98 MOLLY PITCHER LN I, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$250,000

1 beds

1 baths

800 sq ft

Condo

98 MOLLY PITCHER LN I, YORKTOWN HEIGHTS,...

Community: Jefferson Village

New The Retreat at Carmel

2 BLAIR HTS 3336, CARMEL, NY, 10512, Carmel, NY 10512

$425,900

2 beds

2 baths

1,320 sq ft

Condo

2 BLAIR HTS 3336, CARMEL, NY, 10512

Community: The Retreat at Carmel

Glenwood Village

1661-291 OLD COUNTRY 291, RIVERHEAD, NY,..., Riverhead, NY 11901

$269,000

2 beds

1 baths

1,000 sq ft

Mobile Home

1661-291 OLD COUNTRY 291, RIVERHEAD, NY,...

Condo

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ...

Community: Jefferson Village

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

Questions? Call us: (860) 238-3620

Heritage Hills

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

$699,000

3 beds

3 baths

1,700 sq ft

Condo

228 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Leisure Village

419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119..., Ridge, NY 11961

$260,000

1 beds

1 baths

782 sq ft

Condo

419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119...

Community: Leisure Village

Leisure Village

49 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961

$319,000

2 beds

1 baths

1,100 sq ft

Condo

49 TRENT CT B, RIDGE, NY, 11961

Community: Leisure Village

Jefferson Village

29 CAMBRIDGE CT B, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598

$369,000

2 beds

1 baths

1,000 sq ft

Condo

29 CAMBRIDGE CT B, YORKTOWN HEIGHTS, NY,...

Community: Jefferson Village

Leisure Village

166 VENTRY CT B, RIDGE, NY, 11961, Ridge, NY 11961

$259,000

1 beds

1 baths

680 sq ft

House

166 VENTRY CT B, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

186 VENTRY CT D, RIDGE, NY, 11961, Ridge, NY 11961

$339,900

2 beds

1 baths

916 sq ft

Condo

186 VENTRY CT D, RIDGE, NY, 11961

Community: Leisure Village

Glenwood Village

1661 OLD COUNTRY RD 540, RIVERHEAD, NY, ..., Riverhead, NY 11901

$425,000

2 beds

2 baths

1,700 sq ft

Manufactured Home

1661 OLD COUNTRY RD 540, RIVERHEAD, NY, ...

Community: Glenwood Village

Leisure Village

305 TORQUAY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961

$355,000

2 beds

1 baths

836 sq ft

House

305 TORQUAY CT UNIT C, RIDGE, NY, 11961

Community: Leisure Village

Leisure Knoll

304 KINGSTON CT, RIDGE, NY, 11961, Ridge, NY 11961

$449,000

2 beds

2 baths

976 sq ft

Condo

304 KINGSTON CT, RIDGE, NY, 11961

Community: Leisure Knoll

Leisure Glen

1 HUNTINGTON CT, RIDGE, NY, 11961, Ridge, NY 11961

$550,000

2 beds

2 baths

1,666 sq ft

Condo

1 HUNTINGTON CT, RIDGE, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (860) 238-3620

Foxwood Village

1407 MIDDLE RD UNIT 22, CALVERTON, NY, 1..., Calverton, NY 11933

$389,999

2 beds

2 baths

1,700 sq ft

Manufactured Home

1407 MIDDLE RD UNIT 22, CALVERTON, NY, 1...

Community: Foxwood Village

Leisure Village

264 NEWCASTLE CT D, RIDGE, NY, 11961, Ridge, NY 11961

$285,000

2 beds

1 baths

836 sq ft

Condo

264 NEWCASTLE CT D, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

298 CARDIFF CT UNIT A A, RIDGE, NY, 1196..., Ridge, NY 11961

$516,999

2 beds

2 baths

1,767 sq ft

Condo

298 CARDIFF CT UNIT A A, RIDGE, NY, 1196...

Community: Leisure Village

Leisure Village

137 EASTBOURNE CT A, RIDGE, NY, 11961, Ridge, NY 11961

$299,999

2 beds

1 baths

836 sq ft

Condo

137 EASTBOURNE CT A, RIDGE, NY, 11961

Community: Leisure Village

Jefferson Village

96 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$340,000

2 beds

2 baths

1,050 sq ft

Condo

96 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...

Community: Jefferson Village

Leisure Village

280 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961

$247,000

2 beds

1 baths

875 sq ft

Condo

280 BERWICK CT B, RIDGE, NY, 11961

Community: Leisure Village

Glenwood Village

1661 OLD COUNTRY RD UNIT 543, RIVERHEAD,..., Riverhead, NY 11901

$410,000

2 beds

2 baths

1,632 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 543, RIVERHEAD,...

Community: Glenwood Village

Leisure Village

42D TRENT CT 42D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$229,000

2 beds

1 baths

875 sq ft

Condo

42D TRENT CT 42D, BROOKHAVEN, NY, 11961

Community: Leisure Village

Leisure Village

423 WOODBRIDGE D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$239,000

1 beds

1 baths

782 sq ft

Condo

423 WOODBRIDGE D, BROOKHAVEN, NY, 11961

Community: Leisure Village

Leisure Village

411A WEYMOUTH CT # 411A, RIDGE, NY, 1196..., Ridge, NY 11961

$349,000

2 beds

1 baths

1,000 sq ft

Condo

411A WEYMOUTH CT # 411A, RIDGE, NY, 1196...

Condo

384 WOODBRIDGE DR B, 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 663 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?

Call us: (860) 238-3620

234 homes near Winchester Area

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

89 communities near Winchester Area

234 homes near Winchester Area

2 beds

2 baths

2,016 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,320 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Mobile Home

2 beds

2 baths

1,468 sq ft

Condo

2 beds

2 baths

1,350 sq ft

Condo

2 beds

2 baths

1,116 sq ft

Condo

2 beds

2 baths

1,094 sq ft

Condo

2 beds

2 baths

1,736 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

2 baths

976 sq ft

House

2 beds

2 baths

960 sq ft

Manufactured Home

1 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

3 beds

3 baths

1,700 sq ft

Condo

1 beds

1 baths

782 sq ft

Condo

2 beds

1 baths

1,100 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

1 beds