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

95 communities near Winchester Area

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The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

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

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

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

Bidwell Village

$300ks - $400ks

Bidwell Village, Coventry, CT

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

The Cottages at Wire Mill

$1Ms

The Cottages at Wire Mill, Stamford, CT

New Construction | 55+ age-restricted | Built 2026 - present | 9 homes

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

Questions? Call us: (860) 238-3620

The Village at Whispering...

$400ks

The Village at Whispering..., Rotterdam, NY

New Construction | 55+ age-restricted | Built 2025 - present | 85 homes

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

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

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

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

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3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

The Coach Homes at Ridgef...

$300ks - $400ks

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

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

The Residences at Butterf...

$500ks - $600ks

The Residences at Butterf..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes

The Bridges at Oxford Gre...

$600ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

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

Questions? Call us: (860) 238-3620

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

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

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

1 rating (1 review)

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

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

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Chimney Hill

$500ks - $700ks

Chimney Hill, Farmington, CT

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

Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

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

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

Questions? Call us: (860) 238-3620

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Rivington Landing

$500ks

Rivington Landing, Danbury, CT

New Construction | Age-targeted | Built 2025 - 2026 | 25 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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

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

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

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

5 rating (1 review)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 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

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

Questions? Call us: (860) 238-3620

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

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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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

95 communities

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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 - Page 2

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