Simsbury, CT 55+ active adult communities & homes for sale

85 communities near Simsbury

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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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

3 rating (2 reviews)

Heritage Hills

$400ks - $1Ms

Heritage Hills, Somers, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

New Construction | 55+ age-restricted | Built 2023 - present | 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 Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

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.

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 Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

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Questions? Call us: (860) 784-7675

The Vineyards at Miller P...

$500ks

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

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

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

Questions? Call us: (860) 784-7675

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

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Questions? Call us: (860) 784-7675

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

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

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Questions? Call us: (860) 784-7675

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

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

Questions? Call us: (860) 784-7675

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

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

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

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

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

Questions? Call us: (860) 784-7675

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

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

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

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

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

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

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

Questions? Call us: (860) 784-7675

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

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

New Heritage Hills

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

$790,000

2 beds

2 baths

1,663 sq ft

Condo

772 HERITAGE HLS A, SOMERS, NY, 10589

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

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

Questions? Call us: (860) 784-7675

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

Questions? Call us: (860) 784-7675

New Woodridge Strathmore Terrace

35 CHIPPENDALE DR, MOUNT SINAI, NY, 1176..., Mount Sinai, NY 11766

$449,999

2 beds

2 baths

1,240 sq ft

Condo

35 CHIPPENDALE DR, MOUNT SINAI, NY, 1176...

Community: Woodridge Strathmore Terrace

New Glenwood Village

181 GLYNWOOD 181, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$265,000

2 beds

1 baths

1,100 sq ft

Manufactured On Land

181 GLYNWOOD 181, RIVERHEAD, NY, 11901

Community: Glenwood Village

Rivington

503 CENTER MEADOW LN # 503, DANBURY, CT,..., Danbury, CT 06810

$514,950

2 beds

2 baths

1,258 sq ft

Condo

503 CENTER MEADOW LN # 503, DANBURY, CT,...

Community: Rivington

Oronoque Village

488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$599,000

1 beds

3 baths

2,199 sq ft

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$359,900

2 beds

2 baths

1,432 sq ft

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Park Glen

4 BLOSSOM CT, NEW MILFORD, CT, 06776, New Milford, CT 06776

$629,000

2 beds

3 baths

2,573 sq ft

Condo

4 BLOSSOM CT, NEW MILFORD, CT, 06776

Community: Park Glen

Leisure Knoll

206 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961

$345,000

2 beds

1 baths

658 sq ft

Condo

206 BELFAST LN, RIDGE, NY, 11961

Community: Leisure Knoll

Glenwood Village

1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ..., Riverhead, NY 11901

$249,850

2 beds

2 baths

1,050 sq ft

Mobile Home

1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ...

Community: Glenwood Village

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

Questions? Call us: (860) 784-7675

Leisure Glen

530 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961

$595,000

2 beds

2 baths

1,434 sq ft

Condo

530 LEISURE DR, RIDGE, NY, 11961

Community: Leisure Glen

Spring Lake Village

40 HICKORY HL # 40, SOUTHINGTON, CT, 064..., Southington, CT 06489

$233,527

2 beds

2 baths

1,211 sq ft

Condo

40 HICKORY HL # 40, SOUTHINGTON, CT, 064...

Community: Spring Lake Village

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

Questions? Call us: (860) 784-7675

Woodridge Strathmore Terrace

27 HEARTHSIDE DR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$399,000

1 beds

1 baths

844 sq ft

Condo

27 HEARTHSIDE DR, MOUNT SINAI, NY, 11766

Community: Woodridge Strathmore Terrace

Leisure Village

418 WEYMOUTH CT C, RIDGE, NY, 11961, Ridge, NY 11961

$349,999

2 beds

1 baths

1,036 sq ft

Condo

418 WEYMOUTH CT C, RIDGE, NY, 11961

Community: Leisure Village

Heritage Hills

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

$633,000

2 beds

2 baths

1,139 sq ft

Condo

40 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$399,000

3 beds

2 baths

1,716 sq ft

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$260,000

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

430 FALMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961

$369,000

2 beds

2 baths

1,200 sq ft

House

430 FALMOUTH CT A, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 784-7675

Leisure Village

258 NEWCASTLE CT F, RIDGE, NY, 11961, Ridge, NY 11961

$279,000

2 beds

1 baths

875 sq ft

Condo

258 NEWCASTLE CT F, RIDGE, NY, 11961

Community: Leisure Village

Oak Meadow Estates

65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791

$495,000

2 beds

4 baths

2,164 sq ft

Condo

65 OAK MEADOW LN # 65, HARWINTON, CT, 06...

Community: Oak Meadow Estates

South Pond Village

81 SILO WAY 81, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$259,999

2 beds

2 baths

1,204 sq ft

Condo

81 SILO WAY 81, BLOOMFIELD, CT, 06002

Community: South Pond Village

Heritage Hills

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

$599,000

1 beds

2 baths

1,296 sq ft

Condo

680 HERITAGE HLS C, SOMERS, NY, 10589

Condo

914 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 784-7675

Chatfield Farms

8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$699,900

3 beds

4 baths

2,610 sq ft

Condo

8 WOODLAND PATH 8, BEACON FALLS, CT, 064...

Community: Chatfield Farms

Heritage Village

419 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488

$500,000

3 beds

2 baths

1,716 sq ft

Condo

419 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

230 BLACKPOOL CT A, RIDGE, NY, 11961, Ridge, NY 11961

$289,900

2 beds

1 baths

836 sq ft

Condo

230 BLACKPOOL CT A, RIDGE, NY, 11961

Community: Leisure Village

Meadow Brook Estates

215 MEADOW BROOK RD # 215, OXFORD, CT, 0..., Oxford, CT 06478

$589,000

3 beds

3 baths

2,207 sq ft

Condo

215 MEADOW BROOK RD # 215, OXFORD, CT, 0...

Community: Meadow Brook Estates

Leisure Village

406 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$245,000

1 beds

1 baths

704 sq ft

Condo

406 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 784-7675

Long Hill Village

71 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611

$539,900

1 beds

3 baths

1,370 sq ft

Condo

71 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

Leisure Knoll

190 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$479,999

2 beds

1 baths

913 sq ft

House

190 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Heritage Village

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

$295,000

2 beds

2 baths

1,432 sq ft

Condo

915 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 784-7675

Heritage Village

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

$325,000

2 beds

2 baths

1,432 sq ft

Condo

745 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$644,900

1 beds

3 baths

1,620 sq ft

Condo

445 NORTH TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Frequently Asked Questions

What size 55+ communities are there in Simsbury?

In Simsbury, there are no large communities, no medium communities, and 3 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Simsbury?

The smallest 55+ communities in Simsbury has 37 homes, the largest has 182 homes, and the average communities consists of 95 homes.

Are there gated 55+ communities in Simsbury?

Yes, there is gated 55+ communities in Simsbury. Approximately 33.3% of 55+ communities in the area are gated. For instance, Billingsgate is a gated communities with 37 homes.

How long do listings in 55+ communities in Simsbury typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Simsbury stay on the market for around 283 days. The average price of homes for sale in these communities is approximately $685,000, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Powder Forest Homes average around $685,000.

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85 communities

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REIN updates its listings on a daily basis. Data last updated: Feb 19, 2026.
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Simsbury, CT 55+ active adult communities & homes for sale

85 communities near Simsbury

163 homes near Simsbury

2 beds

2 baths

1,663 sq ft

Condo

3 beds

3 baths

1,572 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

1,471 sq ft

Condo

2 beds

2 baths

1,240 sq ft

Condo

2 beds

1 baths

1,100 sq ft

Manufactured On Land

2 beds

2 baths

1,258 sq ft

Condo

1 beds

3 baths

2,199 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

2,573 sq ft

Condo

2 beds

1 baths

658 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Mobile Home

2 beds

2 baths

1,434 sq ft

Condo

2 beds

2 baths

1,211 sq ft

Condo

1 beds

1 baths

844 sq ft

Condo

2 beds

1 baths

1,036 sq ft

Condo

2 beds

2 baths

1,139 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds