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

302 homes 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

No reviews yet

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

$100Ks - $400Ks

Heritage Village, Southbury, CT

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

No reviews yet

Leisure Village

$200Ks - $500Ks

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

No reviews yet

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

No reviews yet

Rivington

$500Ks - $900Ks

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$200Ks - $500Ks

Jefferson Village, Yorktown Heights, NY

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

No reviews yet

Oronoque Village

$300Ks - $600Ks

Oronoque Village, Stratford, CT

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

No reviews yet

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

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.

No reviews yet

Meadowbrook Pointe Athlet...

$1Ms - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

No reviews yet

Leisure Knoll

$200Ks - $400Ks

Leisure Knoll, Ridge, NY

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

No reviews yet

Country Pointe Plainview

$1Ms - $1Ms

Country Pointe Plainview, Plainview, NY

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

5 rating (1 reviews)

Fairfield at St. James

$400Ks - $600Ks

Fairfield at St. James, St. James, NY

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

No reviews yet

Leisure Glen

$400Ks - $500Ks

Leisure Glen, Ridge, NY

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

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

Questions? Call us: (959) 214-4386

No reviews yet

Spring Lake Village

$200Ks - $300Ks

Spring Lake Village, Southington, CT

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

4 rating (8 reviews)

Glenwood Village

$100Ks - $400Ks

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

No reviews yet

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

No reviews yet

Regency at Prospect

$400Ks - $400Ks

Regency at Prospect, Prospect, CT

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

No reviews yet

Dutchgate

$400Ks - $400Ks

Dutchgate, Valley Stream, NY

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

No reviews yet

The Waterways at Moriches

$400Ks - $600Ks

The Waterways at Moriches, Moriches, NY

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

No reviews yet

The Retreat at Carmel

$400Ks - $600Ks

The Retreat at Carmel, Carmel, NY

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

3.5 rating (2 reviews)

Foxwood Village

$300Ks - $400Ks

Foxwood Village, Calverton, NY

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks - $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 Middlebury? 55places can help!

Questions? Call us: (959) 214-4386

4 rating (1 reviews)

Vineyards at Blue Point

$800Ks - $800Ks

Vineyards at Blue Point, Blue Point, NY

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

No reviews yet

HarborView

$900Ks - $1Ms

HarborView, Port Washington, NY

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

No reviews yet

The Club at Melville

$500Ks - $500Ks

The Club at Melville, Melville, NY

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

No reviews yet

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

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

No reviews yet

Meadow Brook Estates

$500Ks - $500Ks

Meadow Brook Estates, Oxford, CT

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

5 rating (1 reviews)

Encore Atlantic Shores

$600Ks - $700Ks

Encore Atlantic Shores, Eastport, NY

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

No reviews yet

The Summit at Bethel

$600Ks - $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 - $500Ks

Chatfield Farms, Beacon Falls, CT

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

5 rating (1 reviews)

Encore at Lake Grove

$500Ks - $600Ks

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

No reviews yet

Woodridge Strathmore Terr...

$400Ks - $400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

No reviews yet

Regency at Wappinger

$600Ks - $700Ks

Regency at Wappinger, Wappingers Falls, NY

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

5 rating (1 reviews)

Sunrise Village

$400Ks - $400Ks

Sunrise Village, Sayville, NY

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

No reviews yet

Saddle Lakes

$400Ks - $400Ks

Saddle Lakes, Riverhead, NY

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

No reviews yet

Country Village Estates

$400Ks - $500Ks

Country Village Estates, Coram, NY

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

1 2 3...4

Heritage Village

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

$245,000

2 beds

2 baths

1,063 sq ft

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Prospect

9 LILAC LN # 9, PROSPECT, CT, 06712, Prospect, CT 06712

$454,900

2 beds

2 baths

1,503 sq ft

Condo

9 LILAC LN # 9, PROSPECT, CT, 06712

Community: Regency at Prospect

Meadow Brook Estates

199 MEADOW BROOK RD # 199, OXFORD, CT, 0..., Oxford, CT 06478

$595,000

2 beds

3 baths

1,876 sq ft

199 MEADOW BROOK RD # 199, OXFORD, CT, 0...

Community: Meadow Brook Estates

Heritage Village

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

$324,900

2 beds

2 baths

1,432 sq ft

Condo

999 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$429,900

2 beds

2 baths

1,432 sq ft

Condo

139 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

The Village at Buckingham

23 KENINGTON RD # 23, AVON, CT, 06001, Avon, CT 06001

$590,000

3 beds

3 baths

2,430 sq ft

Condo

23 KENINGTON RD # 23, AVON, CT, 06001

Community: The Village at Buckingham

Spring Lake Village

4 HICKORY HL, SOUTHINGTON, CT, 06489, Southington, CT 06489

$239,900

2 beds

2 baths

1,285 sq ft

Condo

4 HICKORY HL, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Heritage Village

1005 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$274,900

2 beds

2 baths

1,398 sq ft

Condo

1005 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

Heritage Village

4 HERITAGE CRST A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$420,000

3 beds

2 baths

1,735 sq ft

Condo

4 HERITAGE CRST A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$325,000

2 beds

2 baths

1,398 sq ft

Condo

926 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$229,500

2 beds

2 baths

1,076 sq ft

Condo

192 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$299,000

2 beds

2 baths

1,365 sq ft

Condo

331 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$384,000

2 beds

2 baths

1,432 sq ft

Condo

122 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$339,000

2 beds

2 baths

1,398 sq ft

Condo

951 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

543 S FARMS TER # 543, SOUTHINGTON, CT, ..., Southington, CT 06489

$225,000

2 beds

3 baths

1,782 sq ft

Condo

543 S FARMS TER # 543, SOUTHINGTON, CT, ...

Community: Spring Lake Village

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

Questions? Call us: (959) 214-4386

Heritage Village

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

$389,000

2 beds

2 baths

1,432 sq ft

Condo

583 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$409,900

3 beds

2 baths

1,716 sq ft

Condo

881 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Rivington

1022 COUNTRY VIEW RD # 1022, DANBURY, CT..., Danbury, CT 06810

$499,900

2 beds

2 baths

1,330 sq ft

Condo

1022 COUNTRY VIEW RD # 1022, DANBURY, CT...

Community: Rivington

Chatfield Farms

3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ..., Beacon Falls, CT 06403

$629,900

3 beds

4 baths

2,052 sq ft

3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ...

Community: Chatfield Farms

Rivington

10 OLD PASTURE DR # 10, DANBURY, CT, 068..., Danbury, CT 06810

$1,175,000

3 beds

4 baths

2,544 sq ft

Condo

10 OLD PASTURE DR # 10, DANBURY, CT, 068...

Community: Rivington

Heritage Village

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

$269,900

2 beds

2 baths

1,076 sq ft

Condo

8 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

The Gardens of Wilbraham

45 IVY CIR # 45, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$475,000

2 beds

3 baths

1,752 sq ft

Condo

45 IVY CIR # 45, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

1 2 3 4 5 6 7 8

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 Benson Woods, Granite 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 11 days. The average price of homes for sale in these communities is approximately $569,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Benson Woods average around $569,900.

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Want to learn more about 55+ communities in Middlebury?

Call us: (959) 214-4386

302 homes near Middlebury

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

137 communities near Middlebury

302 homes near Middlebury

2 beds

2 baths

1,063 sq ft

Condo

2 beds

2 baths

1,503 sq ft

Condo

2 beds

3 baths

1,876 sq ft

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

2,430 sq ft

Condo

2 beds

2 baths

1,285 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

2 baths

1,735 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

1,782 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,330 sq ft

Condo

3 beds

4 baths

2,052 sq ft

3 beds

4 baths

2,544 sq ft