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

141 communities near Middlebury

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5 rating (2 reviews)

Benson Woods

$400Ks - $600Ks

Benson Woods, Middlebury, CT

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

Granite Woods

$600Ks - $700Ks

Granite Woods, Middlebury, CT

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

3 rating (2 reviews)

Heritage Hills

$300Ks - $900Ks

Heritage Hills, Somers, NY

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

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

$200Ks - $400Ks

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

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

Rivington

$400Ks - $600Ks

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$300Ks - $600Ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

Oronoque Village

$300Ks - $600Ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 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 Village at Oxford Gre...

$500Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 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.

Meadowbrook Pointe Athlet...

$800Ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Leisure Knoll

$400Ks

Leisure Knoll, Ridge, NY

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

Country Pointe Plainview

$1Ms

Country Pointe Plainview, Plainview, NY

New Construction | 55+ age-restricted | Built 2017 - present | 660 homes

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Questions? Call us: (959) 214-4386

5 rating (2 reviews)

Fairfield at St. James

$400Ks - $500Ks

Fairfield at St. James, St. James, NY

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

Leisure Glen

$400Ks - $500Ks

Leisure Glen, Ridge, NY

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

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

Questions? Call us: (959) 214-4386

Spring Lake Village

$200Ks

Spring Lake Village, Southington, CT

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

4 rating (8 reviews)

Glenwood Village

$100Ks - $200Ks

Glenwood Village, Riverhead, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100Ks - $200Ks

Greenwood Village, Manorville, NY

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

The Seasons at East Meado...

$500Ks - $600Ks

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

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

Regency at Prospect

$400Ks - $500Ks

Regency at Prospect, Prospect, CT

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

Dutchgate

$400Ks - $500Ks

Dutchgate, Valley Stream, NY

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

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Questions? Call us: (959) 214-4386

The Waterways at Moriches

$400Ks - $500Ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes

The Retreat at Carmel

$400Ks - $600Ks

The Retreat at Carmel, Carmel, NY

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

Overlook

$600Ks - $800Ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

3.5 rating (2 reviews)

Foxwood Village

$400Ks - $500Ks

Foxwood Village, Calverton, NY

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

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Questions? Call us: (959) 214-4386

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

4.6 rating (9 reviews)

Meadowbrook Pointe Links ...

$300Ks - $700Ks

Meadowbrook Pointe Links ..., Medford, NY

New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes

4 rating (1 reviews)

Vineyards at Blue Point

$800Ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

HarborView

$900Ks - $1Ms

HarborView, Port Washington, NY

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

The Club at Melville

$500Ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

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

Questions? Call us: (959) 214-4386

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

Meadow Brook Estates

$500Ks

Meadow Brook Estates, Oxford, CT

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

5 rating (1 reviews)

Encore Atlantic Shores

$700Ks - $800Ks

Encore Atlantic Shores, Eastport, NY

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

The Summit at Bethel

$600Ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $600Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

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

Questions? Call us: (959) 214-4386

5 rating (1 reviews)

Encore at Lake Grove

$600Ks - $800Ks

Encore at Lake Grove, Lake Grove, NY

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

Woodridge Strathmore Terr...

$400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Regency at Wappinger

$600Ks - $700Ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

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

Questions? Call us: (959) 214-4386

5 rating (1 reviews)

Sunrise Village

$400Ks - $500Ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes

Saddle Lakes

$400Ks

Saddle Lakes, Riverhead, NY

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

42 TRENT CT D, RIDGE, NY, 11961

Community: Leisure Village

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

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

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

Glassbury Court at Hunterbrook

2279 DALTON DR, CORTLANDT MANOR, NY, 105..., Cortlandt Manor, NY 10567

$925,000

2 beds

4 baths

3,500 sq ft

Condo

2279 DALTON DR, CORTLANDT MANOR, NY, 105...

Community: Glassbury Court at Hunterbrook

Leisure Glen

408 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961

$569,500

2 beds

2 baths

1,434 sq ft

Condo

408 LEISURE DR, RIDGE, NY, 11961

Community: Leisure Glen

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

Village Estates

66 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701

$499,000

2 beds

2 baths

1,243 sq ft

Condo

66 SARAH CT, AMITYVILLE, NY, 11701

Community: Village Estates

New The Seasons at East Meadow

434 AUTUMN DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$680,000

2 beds

3 baths

1,030 sq ft

Condo

434 AUTUMN DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

Glenwood Village

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ..., Riverhead, NY 11901

$139,999

2 beds

1 baths

816 sq ft

Mobile Home

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

Community: Glenwood Village

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

Questions? Call us: (959) 214-4386

New Leisure Glen

10 SAGAPONACK CT # 10, RIDGE, NY, 11961, Ridge, NY 11961

$649,000

2 beds

2 baths

1,867 sq ft

Condo

10 SAGAPONACK CT # 10, RIDGE, NY, 11961

Community: Leisure Glen

Jefferson Village

45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$375,000

2 beds

2 baths

1,100 sq ft

Condo

45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

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

Questions? Call us: (959) 214-4386

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

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

The Greens at Half Hollow

259 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$1,430,000

3 beds

4 baths

3,100 sq ft

Condo

259 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

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

Snug Harbor

118 HARBOR, AMITYVILLE, NY, 11701, Amityville, NY 11701

$649,000

2 beds

2 baths

935 sq ft

Condo

118 HARBOR, AMITYVILLE, NY, 11701

Condo

104 AERIE WAY, EAST QUOGUE, NY, 11942

Condo

190 CANTERBURY DR, RIDGE, NY, 11961

Condo

704 BRETON WAY # 704, GLEN COVE, NY, 115...

Community: Breton Hills

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

Questions? Call us: (959) 214-4386

Fairfield at St. James

304 GOTHAM WAY, SAINT JAMES, NY, 11780, Saint James, NY 11780

$449,803

1 beds

2 baths

Condo

304 GOTHAM WAY, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

The Waterways at Moriches

477 WOODSCREEK CT, MORICHES, NY, 11955, Moriches, NY 11955

$565,000

3 beds

2 baths

1,839 sq ft

Condo

477 WOODSCREEK CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

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

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

Questions? Call us: (959) 214-4386

Heritage Hills

262 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$525,000

2 beds

2 baths

1,427 sq ft

Condo

262 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Saddle Lakes

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$749,990

3 beds

3 baths

1,837 sq ft

Condo

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

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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141 communities

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

141 communities near Middlebury

219 homes near Middlebury

2 beds

2 baths

1,695 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,542 sq ft

Condo

2 beds

2 baths

1,296 sq ft

Condo

2 beds

1 baths

895 sq ft

Condo

3 beds

3 baths

1,914 sq ft

Condo

2 beds

3 baths

2,175 sq ft

Condo

2 beds

4 baths

3,500 sq ft

Condo

2 beds

2 baths

1,434 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

2 beds

2 baths

1,243 sq ft

Condo

2 beds

3 baths

1,030 sq ft

Condo

2 beds

1 baths

816 sq ft

Mobile Home

2 beds

2 baths

1,867 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

3 beds

3 baths

1,914 sq ft

Condo

2 beds

3 baths

2,496 sq ft

Condo

3 beds

4 baths

3,100 sq ft

Condo

1 beds