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

93 communities near Winchester Area

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Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Forest Mews

$300ks - $400ks

Forest Mews, Avon, CT

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

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

Questions? Call us: (860) 238-3620

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

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

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

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

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes

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

Questions? Call us: (860) 238-3620

The Coach Homes at Ridgef...

$300ks - $400ks

The Coach Homes at Ridgef..., Ridgefield, CT

New Construction | 55+ age-restricted | Built 2019 - present | 30 homes

Chimney Hill

$500ks - $700ks

Chimney Hill, Farmington, CT

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes

Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$400ks - $500ks

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

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

77 Sunset Lane

$400ks - $700ks

77 Sunset Lane, Ridgefield, CT

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 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

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

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

Whitney Glen

$500ks - $600ks

Whitney Glen, Westport, CT

Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

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

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

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

Questions? Call us: (860) 238-3620

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

Bidwell Village

$300ks - $400ks

Bidwell Village, Coventry, CT

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

1 2...3

New Newbury Village

46 GREAT HERON LN 46, BROOKFIELD, CT, 06..., Brookfield, CT 06804

$725,000

2 beds

4 baths

2,560 sq ft

Condo

46 GREAT HERON LN 46, BROOKFIELD, CT, 06...

Community: Newbury Village

New Forest Mews

6 BITTERSWEET LN 6, AVON, CT, 06001, Avon, CT 06001

$599,900

3 beds

3 baths

2,548 sq ft

Condo

6 BITTERSWEET LN 6, AVON, CT, 06001

441 ARLINGTON DR B, BROOKHAVEN, NY, 1196...

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

New Heritage Village

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

$239,900

1 beds

1 baths

928 sq ft

Condo

12 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Hills

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

$675,000

2 beds

2 baths

1,484 sq ft

Condo

342 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Foxwood Village

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$469,000

3 beds

2 baths

1,792 sq ft

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933

Community: Foxwood Village

New Heritage Hills

599 HERITAGE HILLS DR A, SOMERS, NY, 105..., Somers, NY 10589

$639,000

2 beds

2 baths

1,483 sq ft

Condo

599 HERITAGE HILLS DR A, SOMERS, NY, 105...

Community: Heritage Hills

New Rivington

524 CENTER MEADOW LN 524, DANBURY, CT, 0..., Danbury, CT 06810

$519,000

2 beds

2 baths

1,258 sq ft

Condo

524 CENTER MEADOW LN 524, DANBURY, CT, 0...

Community: Rivington

New Heritage Hills

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

$594,000

2 beds

2 baths

1,265 sq ft

Condo

958 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Leisure Glen

82 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,312 sq ft

Condo

82 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Heritage Hills

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

$875,000

3 beds

2 baths

1,905 sq ft

Condo

969 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

New Leisure Knoll

259 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$445,000

2 beds

2 baths

1,135 sq ft

Condo

259 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Heritage Hills

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

$875,000

3 beds

2 baths

1,909 sq ft

Condo

412 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Rivington

78 WARRINGTON ROUND 78, DANBURY, CT, 068..., Danbury, CT 06810

$625,000

3 beds

3 baths

1,600 sq ft

Condo

78 WARRINGTON ROUND 78, DANBURY, CT, 068...

Community: Rivington

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

Questions? Call us: (860) 238-3620

New Oronoque Village

377 PIUTE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

2,025 sq ft

Condo

377 PIUTE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Leisure Glen

12 BALDWIN CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$469,990

2 beds

2 baths

1,542 sq ft

Condo

12 BALDWIN CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New The Villages at Mount Sinai Park

16 OAKHURST CT, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$789,000

2 beds

2 baths

1,929 sq ft

House

16 OAKHURST CT, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New North Woods of Colchester

26 NORTHERN BLVD 26, COLCHESTER, CT, 064..., Colchester, CT 06415

$475,000

2 beds

3 baths

2,021 sq ft

Condo

26 NORTHERN BLVD 26, COLCHESTER, CT, 064...

Community: North Woods of Colchester

New Leisure Village

404 WOODBRIDGE RD B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$359,900

2 beds

1 baths

907 sq ft

Condo

404 WOODBRIDGE RD B, BROOKHAVEN, NY, 119...

Community: Leisure Village

New Gloria Commons

32 LUCIUS CT 32, MILFORD, CT, 06460, Milford, CT 06460

$450,000

2 beds

3 baths

2,079 sq ft

Condo

32 LUCIUS CT 32, MILFORD, CT, 06460

Community: Gloria Commons

New Paris Square

2303 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647

$575,000

2 beds

2 baths

Condo

2303 RIO VISTA LN, NORTHVALE, NJ, 07647

Community: Paris Square

New Beckley Farms

13 CONCORD DR 13, BERLIN, CT, 06037, Berlin, CT 06037

$624,900

3 beds

3 baths

2,030 sq ft

Condo

13 CONCORD DR 13, BERLIN, CT, 06037

Community: Beckley Farms

New Newtown Woods

603 BROOKSIDE CT 603, NEWTOWN, CT, 06470, Newtown, CT 06470

$473,000

2 beds

2 baths

1,504 sq ft

Condo

603 BROOKSIDE CT 603, NEWTOWN, CT, 06470

Community: Newtown Woods

New Glenwood Village

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

$499,999

2 beds

2 baths

1,624 sq ft

Manufactured Home

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

Community: Glenwood Village

New Heritage Village

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

$253,900

2 beds

2 baths

1,076 sq ft

Condo

29 HERITAGE VLG B, SOUTHBURY, CT, 06488

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...

Community: Leisure Village

The Village at Oxford Greens

114 COUNTRY CLUB DR 114, OXFORD, CT, 064..., Oxford, CT 06478

2 beds

2 baths

1,398 sq ft

Condo

930 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

Leisure Village

124 EXMORE CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$354,900

2 beds

1 baths

1,085 sq ft

Condo

124 EXMORE CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

Liberty at Newtown

66 SUZIE DR 66, NEWTOWN, CT, 06470, Newtown, CT 06470

$636,000

2 beds

3 baths

2,407 sq ft

Condo

66 SUZIE DR 66, NEWTOWN, CT, 06470

Community: Liberty at Newtown

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Connecticut
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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© 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: Apr 19, 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

93 communities near Winchester Area

216 homes near Winchester Area

2 beds

4 baths

2,560 sq ft

Condo

3 beds

3 baths

2,548 sq ft

Condo

2 beds

2 baths

1,515 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

1 baths

1,074 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,484 sq ft

Condo

3 beds

2 baths

1,792 sq ft

Manufactured Home

2 beds

2 baths

1,483 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,265 sq ft

Condo

2 beds

2 baths

1,312 sq ft

Condo

3 beds

2 baths

1,905 sq ft

Condo

2 beds

2 baths

1,135 sq ft

Condo

3 beds

2 baths

1,909 sq ft

Condo

3 beds

3 baths

1,600 sq ft

Condo

1 beds

3 baths

2,025 sq ft

Condo

2 beds

2 baths

1,542 sq ft

Condo

2 beds

2 baths

1,929 sq ft

House

2 beds