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

92 communities near Winchester Area

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O'Meara Farm

$400Ks - $500Ks

O'Meara Farm, Farmington, CT

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

The Bridges at Oxford Gre...

$600Ks

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

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

Liberty at Newtown

$300Ks - $400Ks

Liberty at Newtown, Newtown, CT

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

Applegate Estates

$500Ks - $400Ks

Applegate Estates, Southington, CT

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

Pond Spring Village

$300Ks

Pond Spring Village, Beacon Falls, CT

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

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

Questions? Call us: (860) 238-3620

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

Questions? Call us: (860) 238-3620

Founders Village

$500Ks - $600Ks

Founders Village, Southold, NY

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

The Vineyards at Mount Si...

$800Ks - $1Ms

The Vineyards at Mount Si..., Mount Sinai, NY

New Construction | 55+ age-restricted | Built 2020 - present | 91 homes

Glassbury Court at Cold S...

$500Ks - $700Ks

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

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

5 rating (1 reviews)

Paris Square

$400Ks - $700Ks

Paris Square, Northvale, NJ

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

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Castle Heights of Cheshir...

$500Ks - $600Ks

Castle Heights of Cheshir..., Cheshire, CT

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

The Vineyards at Miller P...

$600Ks

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

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

Baldwin Station

$400Ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

Bartlett Hill

$500Ks

Bartlett Hill, Portland, CT

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

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

Questions? Call us: (860) 238-3620

5 rating (2 reviews)

Benson Woods

$400Ks - $600Ks

Benson Woods, Middlebury, CT

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

Shaker Heights

$400Ks - $500Ks

Shaker Heights, Enfield, CT

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

5 rating (3 reviews)

Founders Ridge

$500Ks - $600Ks

Founders Ridge, Middletown, CT

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

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

Questions? Call us: (860) 238-3620

Long Hill Village

$300Ks - $400Ks

Long Hill Village, Trumbull, CT

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

Regency at Woodbridge

$600Ks - $700Ks

Regency at Woodbridge, Woodbridge, CT

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

The Village at Hunt Glen

$300Ks

The Village at Hunt Glen, Granby, CT

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

Sonoma Woods

$300Ks

Sonoma Woods, Middletown, CT

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

Hopmeadow Place

$200Ks - $300Ks

Hopmeadow Place, Simsbury, CT

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

Glassbury Court at Hunter...

$500Ks - $700Ks

Glassbury Court at Hunter..., Cortlandt, NY

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

Whitney Glen

$500Ks - $600Ks

Whitney Glen, Westport, CT

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

RiverWalk

$500Ks - $600Ks

RiverWalk, Branford, CT

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

Woodcrest at Jacobs Hill

$300Ks

Woodcrest at Jacobs Hill, Cortlandt, NY

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

Autumn Fields

$200Ks - $300Ks

Autumn Fields, Enfield, CT

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

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

Questions? Call us: (860) 238-3620

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

The Village at Buckingham

$500Ks - $600Ks

The Village at Buckingham, Avon, CT

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

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

Questions? Call us: (860) 238-3620

77 Sunset Lane

$400Ks - $700Ks

77 Sunset Lane, Ridgefield, CT

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

Evergreen

$500Ks

Evergreen, Cromwell, CT

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

Regency Meadows

$500Ks

Regency Meadows, Trumbull, CT

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

Gloria Commons

$400Ks

Gloria Commons, Milford, CT

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

Villas at Seminary Hill

$400Ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

The Residences at Butterf...

$500Ks - $600Ks

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

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

Bramble Ridge

$400Ks - $500Ks

Bramble Ridge, Suffield, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes

Chimney Hill

$500Ks - $700Ks

Chimney Hill, Farmington, CT

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

Village Vistas

$800Ks - $1Ms

Village Vistas, Port Jefferson, NY

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

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

Questions? Call us: (860) 238-3620

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

Questions? Call us: (860) 238-3620

Forest Mews

$300Ks - $400Ks

Forest Mews, Avon, CT

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

Billingsgate

$400Ks - $600Ks

Billingsgate, Simsbury, CT

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

408 LEISURE DR, RIDGE, NY, 11961

Community: Leisure Glen

The Gardens of Wilbraham

32 LODGE LN # 32, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$565,000

2 beds

2 baths

1,610 sq ft

Condo

32 LODGE LN # 32, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

Heritage Hills

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

$699,000

3 beds

2 baths

1,689 sq ft

Condo

59 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

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

Questions? Call us: (860) 238-3620

Overlook

1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512

$879,000

2 beds

3 baths

2,496 sq ft

Condo

1037 COTTAGE DR 18, CARMEL, NY, 10512

Community: Overlook

Overlook

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512

$665,000

3 beds

3 baths

1,914 sq ft

Condo

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...

Community: Overlook

Plymouth Estates at Mount Sinai

166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$579,999

2 beds

2 baths

1,820 sq ft

House

166 IRA RD, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

Leisure Village

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961

$342,000

2 beds

1 baths

1,278 sq ft

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...

Community: Leisure Village

Leisure Knoll

190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961

$434,999

2 beds

1 baths

787 sq ft

Condo

190 CANTERBURY DR, RIDGE, NY, 11961

Community: Leisure Knoll

Heritage Hills

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

$675,000

2 beds

2 baths

1,500 sq ft

Condo

55 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Leisure Village

380 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961

$439,000

2 beds

2 baths

1,147 sq ft

Condo

380 WOODBRIDGE DR D, RIDGE, NY, 11961

Community: Leisure Village

Glenwood Village

1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ..., Riverhead, NY 11901

$219,000

2 beds

2 baths

1,144 sq ft

Mobile Home

1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ...

Condo

798 HERITAGE HLS D, SOMERS, NY, 10589

Manufactured Home

1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,...

Mobile Home

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ...

Community: Glenwood Village

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

Questions? Call us: (860) 238-3620

Leisure Village

474 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961

$400,000

2 beds

2 baths

1,200 sq ft

Condo

474 DARWEN DR B, RIDGE, NY, 11961

Community: Leisure Village

Overlook

4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512

$668,000

3 beds

3 baths

1,914 sq ft

Condo

4071 FAIRWAYS DR 136, CARMEL, NY, 10512

Community: Overlook

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

Questions? Call us: (860) 238-3620

Leisure Village

167 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961

$210,000

1 beds

1 baths

684 sq ft

Condo

167 VENTRY CT UNIT C, RIDGE, NY, 11961

Community: Leisure Village

Stoneleigh Woods at Riverhead

4 HAVERTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$660,000

2 beds

3 baths

2,175 sq ft

Condo

4 HAVERTON CT, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Leisure Knoll

145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961

$489,999

2 beds

2 baths

913 sq ft

House

145 EDINBURGH DR, RIDGE, NY, 11961

Community: Leisure Knoll

Glenwood Village

1661 OLD COUNTRY RD UNIT 539, RIVERHEAD,..., Riverhead, NY 11901

$399,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 539, RIVERHEAD,...

Community: Glenwood Village

Foxwood Village

1407 MIDDLE RD 275, CALVERTON, NY, 11933, Calverton, NY 11933

$425,000

3 beds

2 baths

1,530 sq ft

House

1407 MIDDLE RD 275, CALVERTON, NY, 11933

Community: Foxwood Village

Sunken Pond Estates

4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$519,888

2 beds

2 baths

1,587 sq ft

Condo

4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

Jefferson Village

175 LONG HILL DR B, YORKTOWN HEIGHTS, NY..., Yorktown Heights, NY 10598

$399,999

2 beds

2 baths

1,159 sq ft

Condo

175 LONG HILL DR B, YORKTOWN HEIGHTS, NY...

Community: Jefferson Village

Leisure Village

412 WEYMOUTH CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961

$415,500

2 beds

1 baths

1,100 sq ft

Condo

412 WEYMOUTH CT UNIT B, RIDGE, NY, 11961

Community: Leisure Village

The Villages at Mount Sinai Park

68 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$584,000

2 beds

2 baths

1,736 sq ft

Condo

68 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

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

Questions? Call us: (860) 238-3620

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

Questions? Call us: (860) 238-3620

Heritage Hills

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

$596,000

2 beds

2 baths

1,428 sq ft

Condo

348 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Glassbury Court at Cold Spring

43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516

$727,000

2 beds

3 baths

2,620 sq ft

Condo

43 YESTERDAY DR, COLD SPRING, NY, 10516

Community: Glassbury Court at Cold Spring

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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 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

92 communities

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© 2025 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: Dec 28, 2025.
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

92 communities near Winchester Area

160 homes near Winchester Area

2 beds

2 baths

1,663 sq ft

Condo

2 beds

4 baths

3,500 sq ft

Condo

2 beds

2 baths

1,434 sq ft

Condo

2 beds

2 baths

1,610 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

2 beds

3 baths

2,496 sq ft

Condo

3 beds

3 baths

1,914 sq ft

Condo

2 beds

2 baths

1,820 sq ft

House

2 beds

1 baths

1,278 sq ft

Condo

2 beds

1 baths

787 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds

2 baths

1,147 sq ft

Condo

2 beds

2 baths

1,144 sq ft

Mobile Home

2 beds

2 baths

1,803 sq ft

Condo

2 beds

2 baths

1,300 sq ft

Condo

2 beds

2 baths

1,296 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

3 beds

3 baths

2,850 sq ft

Condo

2 beds

2 baths

1,559 sq ft

Condo

2 beds