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

85 communities near Simsbury

Sort by:

Relevance

3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3 rating (2 reviews)

Heritage Hills

$400ks - $900ks

Heritage Hills, Somers, NY

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

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

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

New Construction | 55+ age-restricted | Built 2023 - present | 142 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 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 Simsbury? 55places can help!

Questions? Call us: (860) 784-7675

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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+ rental communities in Simsbury? 55places can help!

Questions? Call us: (860) 784-7675

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

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

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

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

Questions? Call us: (860) 784-7675

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

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

Questions? Call us: (860) 784-7675

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

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

Questions? Call us: (860) 784-7675

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

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

Questions? Call us: (860) 784-7675

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

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

Questions? Call us: (860) 784-7675

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

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

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

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

1 2...3

New The Villages at Mount Sinai Park

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$899,000

3 beds

3 baths

2,455 sq ft

House

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766

47 HURON LN A, STRATFORD, CT, 06614

Community: Oronoque 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 Leisure Village

279 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$299,999

2 beds

1 baths

875 sq ft

Condo

279 BERWICK CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

New The Villages at Mount Sinai Park

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$675,000

2 beds

3 baths

1,736 sq ft

House

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Regency at Prospect

104 CHERRY CIR 104, PROSPECT, CT, 06712, Prospect, CT 06712

$328,417

3 beds

2 baths

1,500 sq ft

Condo

104 CHERRY CIR 104, PROSPECT, CT, 06712

Community: Regency at Prospect

Rivington

131 WINDING RIDGE WAY 131, DANBURY, CT, ..., Danbury, CT 06810

$770,000

3 beds

3 baths

1,592 sq ft

Condo

131 WINDING RIDGE WAY 131, DANBURY, CT, ...

Community: Rivington

Regency at Woodbridge

27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525

$599,900

3 beds

3 baths

Condo

101 HERITAGE VLG D, 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

29 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$325,000

2 beds

2 baths

1,076 sq ft

Condo

29 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

The Summit at Bethel

20 GREAT HILL DR 20, BETHEL, CT, 06801, Bethel, CT 06801

$649,000

3 beds

3 baths

2,159 sq ft

Condo

20 GREAT HILL DR 20, BETHEL, CT, 06801

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901

Community: Sunken Pond Estates

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

Questions? Call us: (860) 784-7675

Leisure Glen

587 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$575,000

2 beds

2 baths

1,454 sq ft

Condo

587 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

South Pond Village

177 THISTLE POND DR 177, BLOOMFIELD, CT,..., Bloomfield, CT 06002

$465,000

3 beds

3 baths

2,243 sq ft

177 THISTLE POND DR 177, BLOOMFIELD, CT,...

Community: South Pond Village

The Village at Oxford Greens

523 PUTTING GREEN LN 523, OXFORD, CT, 06..., Oxford, CT 06478

$625,000

2 beds

2 baths

2,008 sq ft

Condo

523 PUTTING GREEN LN 523, OXFORD, CT, 06...

Community: The Village at Oxford Greens

Heritage Village

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$225,000

1 beds

1 baths

928 sq ft

Condo

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648...

Condo

132 BISON LN B, STRATFORD, CT, 06614

Condo

79 HERITAGE VLG A, SOUTHBURY, CT, 06488

Condo

44 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

Leisure Village

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

$289,000

2 beds

1 baths

874 sq ft

Condo

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

Community: Leisure Village

Leisure Village

427 AYLESBURY CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$380,000

2 beds

2 baths

972 sq ft

Condo

427 AYLESBURY CT A, BROOKHAVEN, NY, 1196...

Community: Leisure 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.

Want more information about active adult communities around Simsbury?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Simsbury?

Call us: (860) 784-7675

85 communities

Remove Boundaries ×

Map Satellite

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: Mar 31, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

85 communities near Simsbury

180 homes near Simsbury

3 beds

3 baths

2,455 sq ft

House

2 beds

2 baths

1,416 sq ft

Condo

2 beds

2 baths

1,532 sq ft

House

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,360 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

3 baths

1,736 sq ft

House

3 beds

2 baths

1,500 sq ft

Condo

3 beds

3 baths

1,592 sq ft

Condo

3 beds

3 baths

Condo

2 beds

4 baths

2,843 sq ft

Condo

2 beds

1 baths

720 sq ft

Manufactured Home

2 beds

2 baths

1,076 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

3 beds

3 baths

2,159 sq ft

Condo

2 beds

2 baths

1,427 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,663 sq ft

Condo

2 beds

2 baths

1,312 sq ft

Condo

2 beds

2 baths