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

93 communities near Winchester Area

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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

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

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

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.

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

1 2 3

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

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

Questions? Call us: (860) 238-3620

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

Community: Heritage Village

New Meadow Brook Estates

521 HEATHERWOOD CT 521, OXFORD, CT, 0647..., Oxford, CT 06478

$599,900

2 beds

3 baths

1,866 sq ft

Condo

521 HEATHERWOOD CT 521, OXFORD, CT, 0647...

Community: Meadow Brook Estates

New Glenwood Village

1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ..., Riverhead, NY 11901

$339,000

2 beds

2 baths

1,344 sq ft

Manufactured Home

1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ...

Community: Glenwood Village

New Setauket Meadows

86 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$775,000

2 beds

3 baths

1,991 sq ft

Condo

86 BRIANNA DR, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

New The Powder Forest Homes

37 BANTRY RD 37, SIMSBURY, CT, 06070, Simsbury, CT 06070

$899,000

3 beds

5 baths

2,724 sq ft

37 BANTRY RD 37, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

New Jefferson Village

51 JEFFERSON OVAL F, YORKTOWN, NY, 10598, Yorktown, NY 10598

$448,500

2 beds

2 baths

1,100 sq ft

Condo

51 JEFFERSON OVAL F, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (860) 238-3620

New Regency at Wappinger

50 STRATFORD LN, WAPPINGER, NY, 12590, Wappinger, NY 12590

$689,000

2 beds

3 baths

1,823 sq ft

Condo

50 STRATFORD LN, WAPPINGER, NY, 12590

Community: Regency at Wappinger

New Leisure Village

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$419,990

2 beds

1 baths

Condo

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

Community: Leisure Village

New The Village at Oxford Greens

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

$575,000

2 beds

2 baths

1,590 sq ft

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

Community: The Village at Oxford Greens

New Leisure Knoll

204 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$460,000

2 beds

2 baths

849 sq ft

House

204 BELFAST LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Newtown Woods

1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064..., Newtown, CT 06470

$485,000

2 beds

2 baths

1,483 sq ft

Condo

1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064...

Community: Newtown Woods

Heritage Village

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

$489,900

2 beds

2 baths

1,398 sq ft

Condo

930 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Glassbury Court at Cold Spring

19 REVOLUTION RD, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516

$567,358

2 beds

3 baths

1,806 sq ft

Condo

19 REVOLUTION RD, PHILIPSTOWN, NY, 10516

Community: Glassbury Court at Cold Spring

Jefferson Village

173 LONG HILL DR I, YORKTOWN, NY, 10598, Yorktown, NY 10598

$330,000

1 beds

1 baths

850 sq ft

Condo

173 LONG HILL DR I, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

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

$649,000

2 beds

2 baths

1,483 sq ft

Condo

612 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

Meadow Brook Estates

194 EASTWOOD DR 194, SEYMOUR, CT, 06483, Seymour, CT 06483

$599,000

2 beds

3 baths

2,295 sq ft

Condo

194 EASTWOOD DR 194, SEYMOUR, CT, 06483

Community: Meadow Brook Estates

Heritage Village

1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$229,900

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

214 WATERS EDGE DR 214, SOUTHINGTON, CT,..., Southington, CT 06489

$317,000

2 beds

3 baths

1,564 sq ft

Condo

214 WATERS EDGE DR 214, SOUTHINGTON, CT,...

Community: Spring Lake Village

Heritage Village

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

$358,000

2 beds

2 baths

1,398 sq ft

Condo

889 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

64 ENFIELD CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$369,000

2 beds

1 baths

1,085 sq ft

Condo

64 ENFIELD CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

Woodridge Strathmore Terrace

7 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$449,000

2 beds

2 baths

840 sq ft

Condo

7 COBBLESTONE WAY, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

North Woods of Colchester

24 CENTER CT 24, COLCHESTER, CT, 06415, Colchester, CT 06415

$515,000

2 beds

2 baths

1,357 sq ft

Condo

24 CENTER CT 24, COLCHESTER, CT, 06415

Community: North Woods of Colchester

Oronoque Village

402 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$515,000

2 beds

3 baths

1,118 sq ft

Condo

402 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

248 NEWCASTLE CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$415,000

2 beds

1 baths

1,085 sq ft

Condo

248 NEWCASTLE CT A, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Leisure Village

375 WOODBRIDGE DR C, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$389,000

2 beds

1 baths

1,171 sq ft

Condo

375 WOODBRIDGE DR C, BROOKHAVEN, NY, 119...

Community: Leisure Village

Heritage Village

36 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$525,000

3 beds

2 baths

1,716 sq ft

Condo

36 HERITAGE CIR 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

South Pond Village

78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$289,900

3 beds

3 baths

1,639 sq ft

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002

Community: South Pond Village

The Powder Forest Homes

3 RONAN WAY 3, SIMSBURY, CT, 06070, Simsbury, CT 06070

$629,900

2 beds

3 baths

1,284 sq ft

Condo

3 RONAN WAY 3, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

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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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REIN updates its listings on a daily basis. Data last updated: Apr 17, 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 3

93 communities near Winchester Area

204 homes near Winchester Area

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

3 baths

2,021 sq ft

Condo

2 beds

1 baths

907 sq ft

Condo

2 beds

3 baths

2,079 sq ft

Condo

2 beds

2 baths

Condo

3 beds

3 baths

2,030 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,076 sq ft

Condo

2 beds

3 baths

1,866 sq ft

Condo

2 beds

2 baths

1,344 sq ft

Manufactured Home

2 beds

3 baths

1,991 sq ft

Condo

3 beds

5 baths

2,724 sq ft

2 beds

2 baths

1,100 sq ft

Condo

2 beds

3 baths

1,823 sq ft

Condo

2 beds

1 baths

Condo

2 beds

2 baths

1,590 sq ft

2 beds

2 baths

849 sq ft

House

2 beds