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

95 communities near Winchester Area

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Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Bartlett Hollow

$200ks - $400ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

Autumn Estates

$500ks - $600ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes

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

Questions? Call us: (860) 238-3620

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

The Woods at Dunham Pond

$200ks - $400ks

The Woods at Dunham Pond, New Fairfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes

Bidwell Village

$300ks - $400ks

Bidwell Village, Coventry, CT

New Construction | 55+ age-restricted | Built 2020 - present | 37 homes

Forest Mews

$300ks - $400ks

Forest Mews, Avon, CT

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 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 Hunt Glen

$300ks

The Village at Hunt Glen, Granby, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes

O'Meara Farm

$400ks

O'Meara Farm, Farmington, CT

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes

1 2 3

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$410,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

New Jefferson Village

27 WALDEN CT F, YORKTOWN, NY, 10598, Yorktown, NY 10598

$399,000

2 beds

1 baths

925 sq ft

Condo

27 WALDEN CT F, YORKTOWN, NY, 10598

Community: Jefferson Village

New Oronoque Village

476 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$565,000

1 beds

3 baths

1,426 sq ft

Condo

476 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Leisure Village

250A NEWCASTLE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,000

2 beds

1 baths

1,085 sq ft

Condo

250A NEWCASTLE CT, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Leisure Knoll

330 BROWNFIELD DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$429,000

2 beds

1 baths

1,020 sq ft

Condo

330 BROWNFIELD DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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Questions? Call us: (860) 238-3620

New Leisure Village

190 VENTRY CT F, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$269,000

1 beds

1 baths

684 sq ft

Condo

190 VENTRY CT F, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Heritage Village

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

$215,000

2 beds

2 baths

1,000 sq ft

Condo

751 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Leisure Village

299 CARDIFF CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$489,000

2 beds

2 baths

1,308 sq ft

Condo

299 CARDIFF CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Regency at Fishkill

621 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$499,000

1 beds

2 baths

1,499 sq ft

Condo

621 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

New Newtown Woods

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064..., Newtown, CT 06470

$495,000

2 beds

2 baths

1,483 sq ft

Condo

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064...

Community: Newtown Woods

New Leisure Glen

7 SAGAPONACK CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$599,000

2 beds

2 baths

1,867 sq ft

Condo

7 SAGAPONACK CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Regency at Prospect

112 CHERRY CIR 112, PROSPECT, CT, 06712, Prospect, CT 06712

$338,903

3 beds

2 baths

1,500 sq ft

Condo

112 CHERRY CIR 112, PROSPECT, CT, 06712

Community: Regency at Prospect

Meadow Brook Estates

107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478

$625,000

3 beds

3 baths

1,922 sq ft

Condo

107 MEADOW BROOK RD 107, OXFORD, CT, 064...

Community: Meadow Brook Estates

Heritage Hills

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

$444,900

2 beds

2 baths

1,205 sq ft

Condo

175 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

40 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488

$270,000

2 beds

2 baths

1,308 sq ft

Condo

40 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$429,900

2 beds

2 baths

1,420 sq ft

Condo

28 HERITAGE CRST 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

The Summit at Bethel

14 GREAT HILL DR 14, BETHEL, CT, 06801, Bethel, CT 06801

$719,000

3 beds

3 baths

2,744 sq ft

Condo

14 GREAT HILL DR 14, BETHEL, CT, 06801

Community: The Summit at Bethel

Oronoque Village

615 CHEROKEE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$574,900

2 beds

3 baths

1,426 sq ft

Condo

615 CHEROKEE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Jefferson Village

153 FLINTLOCK WAY A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$335,000

1 beds

1 baths

845 sq ft

Condo

153 FLINTLOCK WAY A, YORKTOWN, NY, 10598

Community: Jefferson Village

The Village at Whispering Pines

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

$459,900

3 beds

2 baths

2,020 sq ft

House

47 WHISPERING PINES WAY, ROTTERDAM, NY, ...

Community: The Village at Whispering Pines

The Village at Whispering Pines

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

$459,900

3 beds

2 baths

2,020 sq ft

House

48 WHISPERING PINES WAY, ROTTERDAM, NY, ...

Community: The Village at Whispering Pines

Jefferson Village

109 VILLAGE RD D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$365,000

1 beds

1 baths

850 sq ft

Condo

109 VILLAGE RD D, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

$600,000

2 beds

2 baths

1,483 sq ft

Condo

558 HERITAGE HILLS DR B, SOMERS, NY, 105...

Community: Heritage Hills

Founders Ridge

UNIT 2-41 WEBSTER LN 145, MIDDLETOWN, CT..., Middletown, CT 06457

$689,000

2 beds

2 baths

1,555 sq ft

UNIT 2-41 WEBSTER LN 145, MIDDLETOWN, CT...

Community: Founders Ridge

Leisure Glen

20 WAINSCOTT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$599,999

2 beds

2 baths

1,666 sq ft

Condo

20 WAINSCOTT CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Leisure Glen

9 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$619,000

2 beds

2 baths

1,882 sq ft

House

9 OAKDALE CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Regency at Wappinger

5 PALMERTON DR, WAPPINGER, NY, 12590, Wappinger, NY 12590

$829,900

2 beds

3 baths

3,156 sq ft

Condo

5 PALMERTON DR, WAPPINGER, NY, 12590

Community: Regency at Wappinger

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

Questions? Call us: (860) 238-3620

The Village at Oxford Greens

84 LINKS WAY 84, OXFORD, CT, 06478, Oxford, CT 06478

$710,000

3 beds

3 baths

2,008 sq ft

Condo

84 LINKS WAY 84, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Village

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

$310,000

2 beds

2 baths

1,432 sq ft

Condo

722 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$309,000

2 beds

2 baths

1,432 sq ft

Condo

970 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Rivington

44 WARRINGTON ROUND, DANBURY, CT, 06810, Danbury, CT 06810

$628,000

3 beds

3 baths

1,600 sq ft

Condo

44 WARRINGTON ROUND, DANBURY, CT, 06810

Community: Rivington

Leisure Glen

477 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$589,000

2 beds

2 baths

1,434 sq ft

Condo

477 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Heritage Village

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

$427,500

2 beds

2 baths

1,398 sq ft

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$319,000

2 beds

2 baths

1,432 sq ft

Condo

620 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064..., Oxford, CT 06478

$624,900

2 beds

3 baths

1,673 sq ft

Condo

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Sunken Pond Estates

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$520,000

2 beds

2 baths

1,350 sq ft

Condo

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190...

Community: Sunken Pond Estates

Saddle Lakes

157 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$595,000

2 beds

2 baths

1,386 sq ft

Condo

157 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Regency at Prospect

133 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712

$550,000

2 beds

3 baths

1,850 sq ft

Condo

133 SYCAMORE DR, PROSPECT, CT, 06712

Community: Regency at Prospect

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

Questions? Call us: (860) 238-3620

Leisure Glen

279 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$569,999

2 beds

2 baths

1,542 sq ft

Condo

279 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Newtown Woods

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470, Newtown, CT 06470

$498,900

2 beds

2 baths

1,504 sq ft

Condo

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470

Community: Newtown Woods

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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 281 days. The average price of homes for sale in these communities is approximately $485,000, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $485,000.

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

Insights and market stats
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Answers from local 55+ experts

Thanks! A local 55+ expert will be in touch shortly.

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

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95 communities

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

95 communities near Winchester Area

226 homes near Winchester Area

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

1 baths

925 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

1 baths

1,020 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

1 beds

2 baths

1,499 sq ft

Condo

2 beds

2 baths

1,483 sq ft

Condo

2 beds

2 baths

1,867 sq ft

Condo

3 beds

2 baths

1,500 sq ft

Condo

3 beds

3 baths

1,922 sq ft

Condo

2 beds

2 baths

1,205 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

2 beds

2 baths

1,420 sq ft

Condo

3 beds

3 baths

2,744 sq ft

Condo

2 beds

3 baths

1,426 sq ft

Condo

1 beds

1 baths

845 sq ft

Condo

3 beds