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

142 communities near Middlebury

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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 - $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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

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

Questions? Call us: (959) 214-4386

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

Questions? Call us: (959) 214-4386

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

4 rating (1 reviews)

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

5 rating (2 reviews)

Fairfield at St. James

$300ks - $500ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 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.

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 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+ communities in Middlebury? 55places can help!

Questions? Call us: (959) 214-4386

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

The Greens at Half Hollow

$600ks - $1Ms

The Greens at Half Hollow, Melville, NY

Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes

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

Questions? Call us: (959) 214-4386

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

The Seasons at East Meado...

$400ks - $600ks

The Seasons at East Meado..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

The Manors at The Colony ...

$300ks - $400ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 homes

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

Questions? Call us: (959) 214-4386

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes

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

Questions? Call us: (959) 214-4386

HarborView

$600ks - $800ks

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

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

Questions? Call us: (959) 214-4386

Country Village Estates

$300ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 homes

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes

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

Questions? Call us: (959) 214-4386

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes

5 rating (1 reviews)

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes

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

Questions? Call us: (959) 214-4386

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

1 2 3...4

New Strathmore Gate East

42 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$425,000

2 beds

2 baths

1,112 sq ft

Condo

42 FREEMONT LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

New Leisure Glen

16 HUNTINGTON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$505,000

2 beds

2 baths

1,312 sq ft

Condo

16 HUNTINGTON CT, BROOKHAVEN, NY, 11961

587 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (959) 214-4386

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

Questions? Call us: (959) 214-4386

New 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

New 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

New Greenwood Village

2 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$192,500

2 beds

2 baths

1,064 sq ft

Condo

2 DOGWOOD LN, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New 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...

Community: Heritage Village

New The Greens at Half Hollow

928 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$615,000

2 beds

2 baths

1,262 sq ft

Condo

928 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Oronoque Village

72 DAKOTA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$539,500

1 beds

3 baths

1,118 sq ft

Condo

72 DAKOTA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Oronoque Village

71 DAKOTA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$425,000

1 beds

2 baths

1,375 sq ft

Condo

71 DAKOTA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Heritage Village

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

$520,000

3 beds

2 baths

1,716 sq ft

Condo

977 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (959) 214-4386

New Jefferson Village

130G COLUMBIA CT, YORKTOWN, NY, 10598, Yorktown, NY 10598

$399,000

2 beds

2 baths

1,129 sq ft

Condo

130G COLUMBIA CT, YORKTOWN, NY, 10598

Community: Jefferson Village

New The Village at Oxford Greens

731 CHAMPIONSHIP DR 731, OXFORD, CT, 064..., Oxford, CT 06478

$629,900

2 beds

2 baths

1,539 sq ft

Condo

731 CHAMPIONSHIP DR 731, OXFORD, CT, 064...

Condo

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

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

Questions? Call us: (959) 214-4386

New Heritage Village

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

$224,900

2 beds

2 baths

1,032 sq ft

Condo

151 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

22 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$385,000

2 beds

2 baths

1,398 sq ft

Condo

22 HERITAGE CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

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

$229,000

1 beds

1 baths

928 sq ft

Condo

79 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Village Estates

137 FRANCESCA WAY, BABYLON, NY, 11701, Babylon, NY 11701

$599,999

2 beds

1 baths

1,245 sq ft

Condo

137 FRANCESCA WAY, BABYLON, NY, 11701

Condo

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...

Condo

506 DREW DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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

Questions? Call us: (959) 214-4386

Heritage Village

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

$529,000

3 beds

2 baths

1,716 sq ft

Condo

644 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

86 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$549,900

2 beds

3 baths

2,734 sq ft

Condo

86 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

252 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$639,000

2 beds

3 baths

2,494 sq ft

Condo

252 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (959) 214-4386

Heritage Hills

366 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$675,000

2 beds

2 baths

1,470 sq ft

Condo

366 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Sunrise Village

4 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$499,000

2 beds

2 baths

1,230 sq ft

Condo

4 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

Frequently Asked Questions

What size 55+ communities are there in Middlebury?

In Middlebury, 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 Middlebury?

The smallest 55+ communities in Middlebury has 24 homes, the largest has 79 homes, and the average communities consists of 51 homes.

Are there new 55+ homes available in Middlebury?

Yes, there are new 55+ homes available in Middlebury. The most recent communities started in Middlebury include Granite Woods, Benson Woods. There are also 2 communities in Middlebury that offer new construction homes, including Granite Woods, Benson Woods.

Are there gated 55+ communities in Middlebury?

No, there are no gated 55+ communities in Middlebury.

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

On average, listings in 55+ communities in Middlebury stay on the market for around 130 days. The average price of homes for sale in these communities is approximately $534,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Benson Woods average around $534,900.

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142 communities

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

142 communities near Middlebury

257 homes near Middlebury

2 beds

2 baths

1,112 sq ft

Condo

2 beds

2 baths

1,312 sq ft

Condo

2 beds

2 baths

1,447 sq ft

Condo

2 beds

2 baths

1,587 sq ft

Condo

2 beds

2 baths

1,454 sq ft

Condo

3 beds

3 baths

2,243 sq ft

2 beds

2 baths

2,008 sq ft

Condo

2 beds

2 baths

1,064 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,262 sq ft

Condo

1 beds

3 baths

1,118 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,129 sq ft

Condo

2 beds

2 baths

1,539 sq ft

Condo

1 beds

2 baths

1,426 sq ft

Condo

2 beds

2 baths

1,483 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

3 baths

2,820 sq ft

Condo

2 beds

3 baths