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

228 homes near Winchester Area

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3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

3 rating (2 reviews)

Heritage Hills

$400ks - $900ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

4 rating (1 review)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

The Village at Oxford Gre...

$400ks - $500ks

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

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

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

Questions? Call us: (860) 238-3620

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

5 rating (1 review)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

5 rating (1 review)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

The Vineyards at Miller P...

$500ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

1 rating (1 review)

Plymouth Estates at Mount...

$400ks - $500ks

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

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

Glassbury Court at Cold S...

$600ks - $700ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

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

Questions? Call us: (860) 238-3620

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

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

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

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

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

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

Questions? Call us: (860) 238-3620

5 rating (1 review)

The Villages at Mount Sin...

$600ks

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

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

1 2...3

Leisure Village

177 VENTRY CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$449,500

2 beds

1 baths

1,085 sq ft

Condo

177 VENTRY CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

Jefferson Village

39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$349,000

2 beds

2 baths

1,000 sq ft

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

New Overlook

4052 FAIRWAYS DR 293, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

3 beds

3 baths

2,274 sq ft

Condo

4052 FAIRWAYS DR 293, CARMEL, NY, 10512

Community: Overlook

New Overlook

4004 FAIRWAYS DR 296, CARMEL, NY, 10512, Carmel, NY 10512

$869,000

3 beds

3 baths

2,309 sq ft

House

4004 FAIRWAYS DR 296, CARMEL, NY, 10512

Community: Overlook

New Leisure Village

470B DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$339,000

2 beds

1 baths

1,074 sq ft

Condo

470B DARWEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

New Meadow Brook Estates

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

$569,900

3 beds

3 baths

1,922 sq ft

Condo

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

Community: Meadow Brook Estates

New Jefferson Village

172 LONG HILL DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$675,000

2 beds

2 baths

1,550 sq ft

Condo

172 LONG HILL DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

New Heritage Hills

897 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$749,900

2 beds

3 baths

1,666 sq ft

Condo

897 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

New Overlook

4038 FAIRWAYS DR 299, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

3 beds

3 baths

2,274 sq ft

House

4038 FAIRWAYS DR 299, CARMEL, NY, 10512

Community: Overlook

New The Vineyards at Miller Place

40 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764

$625,000

3 beds

3 baths

1,700 sq ft

Condo

40 AVERY LN, BROOKHAVEN, NY, 11764

Community: The Vineyards at Miller Place

New Leisure Glen

488 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$659,000

2 beds

2 baths

1,652 sq ft

Condo

488 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Stoneleigh Woods at Riverhead

904 BALTUSROL BLVD, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$510,000

2 beds

2 baths

1,258 sq ft

Condo

904 BALTUSROL BLVD, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

New Heritage Village

27 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$390,000

2 beds

2 baths

1,447 sq ft

Condo

27 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

New Regency at Prospect

146 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712

$550,000

2 beds

3 baths

1,850 sq ft

Condo

146 SYCAMORE DR, PROSPECT, CT, 06712

Community: Regency at Prospect

New Regency at Wappinger

20 AVONDALE LN, WAPPINGER, NY, 12590, Wappinger, NY 12590

$745,000

3 beds

3 baths

2,056 sq ft

Condo

20 AVONDALE LN, WAPPINGER, NY, 12590

Community: Regency at Wappinger

New Whitney Glen

39 WHITNEY GLN 39, WESTPORT, CT, 06880, Westport, CT 06880

$925,000

2 beds

2 baths

1,600 sq ft

Condo

39 WHITNEY GLN 39, WESTPORT, CT, 06880

Community: Whitney Glen

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

Questions? Call us: (860) 238-3620

New The Vineyards at Miller Place

6 HALLEY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764

$559,000

2 beds

2 baths

1,291 sq ft

House

6 HALLEY LN, BROOKHAVEN, NY, 11764

Community: The Vineyards at Miller Place

New Heritage Village

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

$329,900

2 beds

2 baths

1,432 sq ft

Condo

809 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Sonoma Woods

2 SONOMA LN 2, MIDDLETOWN, CT, 06457, Middletown, CT 06457

$549,900

2 beds

3 baths

1,903 sq ft

2 SONOMA LN 2, MIDDLETOWN, CT, 06457

Community: Sonoma Woods

Leisure Knoll

434 KINGSTON DR 434, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,646 sq ft

Condo

434 KINGSTON DR 434, BROOKHAVEN, NY, 119...

Community: Leisure Knoll

The Villages at Mount Sinai Park

93 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$799,000

2 beds

2 baths

2,234 sq ft

House

93 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Leisure Glen

277 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$535,900

2 beds

2 baths

1,542 sq ft

Condo

277 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Heritage Village

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

$289,900

2 beds

2 baths

1,032 sq ft

Condo

45 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$325,000

2 beds

2 baths

1,432 sq ft

Condo

198 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

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

$630,000

2 beds

2 baths

1,472 sq ft

Condo

449 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

149 FLINTLOCK WAY D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$325,000

1 beds

1 baths

835 sq ft

Condo

149 FLINTLOCK WAY D, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

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

$186,000

2 beds

2 baths

1,032 sq ft

Condo

62 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

Oronoque Village

638 ONONDAGA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

1,175 sq ft

Condo

638 ONONDAGA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Pond Spring Village

41 PONDVIEW CIR 41, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403

$485,000

2 beds

2 baths

1,501 sq ft

Condo

41 PONDVIEW CIR 41, BEACON FALLS, CT, 06...

Community: Pond Spring Village

Rivington

19 WARRINGTON ROUND 19, DANBURY, CT, 068..., Danbury, CT 06810

$749,000

3 beds

3 baths

2,196 sq ft

Condo

19 WARRINGTON ROUND 19, DANBURY, CT, 068...

Community: Rivington

Heritage Village

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

$295,000

2 beds

2 baths

1,000 sq ft

Condo

786 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Village Vistas

11 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777

$1,249,000

3 beds

4 baths

3,075 sq ft

Condo

11 THERESA LN, BROOKHAVEN, NY, 11777

Community: Village Vistas

Overlook

4103 FAIRWAYS DR 152, CARMEL, NY, 10512, Carmel, NY 10512

$649,000

3 beds

3 baths

1,914 sq ft

Condo

4103 FAIRWAYS DR 152, CARMEL, NY, 10512

Community: Overlook

Overlook

4101 FAIRWAYS DR 151, CARMEL, NY, 10512, Carmel, NY 10512

$749,000

3 beds

4 baths

2,141 sq ft

Condo

4101 FAIRWAYS DR 151, CARMEL, NY, 10512

Community: Overlook

Overlook

2012 SUMMIT LOOP 42, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

2 beds

2 baths

1,948 sq ft

Condo

2012 SUMMIT LOOP 42, CARMEL, NY, 10512

Community: Overlook

Benson Woods

203 SUGAR MAPLE WAY 203, MIDDLEBURY, CT,..., Middlebury, CT 06762

$589,900

2 beds

3 baths

2,442 sq ft

Condo

203 SUGAR MAPLE WAY 203, MIDDLEBURY, CT,...

Community: Benson Woods

Leisure Village

379C WOODBRIDGE DR C, BROOKHAVEN, NY, 11..., Brookhaven, NY 11961

$459,900

2 beds

2 baths

1,168 sq ft

Condo

379C WOODBRIDGE DR C, BROOKHAVEN, NY, 11...

Community: Leisure Village

Leisure Glen

14 FLANDERS CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$450,000

2 beds

2 baths

1,212 sq ft

House

14 FLANDERS CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (860) 238-3620

Heritage Village

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

$250,000

2 beds

2 baths

1,398 sq ft

Condo

219 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$299,900

2 beds

2 baths

1,432 sq ft

Condo

974 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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Connecticut
Winchester Area

Frequently Asked Questions

What size 55+ communities are there in the Winchester Area?

Of the 2 55+ communities in the Winchester Area, 2 are for sale and none are rentals. By size, 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 397 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?

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

Call us: (860) 238-3620

228 homes

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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 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: Nov 02, 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

95 communities near Winchester Area

228 homes near Winchester Area

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

3 baths

2,274 sq ft

Condo

3 beds

3 baths

2,309 sq ft

House

2 beds

1 baths

1,074 sq ft

Condo

3 beds

3 baths

1,922 sq ft

Condo

2 beds

2 baths

1,550 sq ft

Condo

2 beds

3 baths

1,666 sq ft

Condo

3 beds

3 baths

2,274 sq ft

House

3 beds

3 baths

1,700 sq ft

Condo

2 beds

2 baths

1,652 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,447 sq ft

Condo

2 beds

3 baths

1,850 sq ft

Condo

3 beds

3 baths

2,056 sq ft

Condo

2 beds

2 baths

1,600 sq ft

Condo

2 beds

2 baths

1,291 sq ft

House

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

1,903 sq ft

2 beds

2 baths