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

143 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

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 - $800ks

Heritage Hills, Somers, NY

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

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

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

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Want to learn more about 55+ 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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

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

Questions? Call us: (959) 214-4386

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

The Hollows at Blue Hill

$500ks - $700ks

The Hollows at Blue Hill, Pearl River, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 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

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 homes

1 2 3...4

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

Heritage Hills

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

$469,900

1 beds

2 baths

967 sq ft

Condo

567 HERITAGE HLS B, SOMERS, NY, 10589

879 HERITAGE HLS B, SOMERS, NY, 10589

Condo

196 HERITAGE VLG E, 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 Fairfield at St. James

703 DREW DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$429,999

1 beds

1 baths

752 sq ft

Condo

703 DREW DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Heritage Hills

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

$530,000

2 beds

2 baths

1,138 sq ft

Condo

293 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Newbury Village

46 GREAT HERON LN 46, BROOKFIELD, CT, 06..., Brookfield, CT 06804

$699,000

2 beds

4 baths

2,560 sq ft

Condo

46 GREAT HERON LN 46, BROOKFIELD, CT, 06...

Community: Newbury Village

New Liberty at Newtown

25 FRANKLIN CT 25, NEWTOWN, CT, 06470, Newtown, CT 06470

$545,000

2 beds

2 baths

1,413 sq ft

Condo

25 FRANKLIN CT 25, NEWTOWN, CT, 06470

Community: Liberty at Newtown

New Heritage Hills

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

$499,000

1 beds

2 baths

967 sq ft

Condo

451 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Hills

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

$575,000

2 beds

2 baths

1,500 sq ft

Condo

300 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Oronoque Village

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

$565,000

1 beds

3 baths

1,426 sq ft

Condo

253 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

New Leisure Knoll

183 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$415,000

2 beds

1 baths

960 sq ft

Condo

183 KINGSTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Regency at Prospect

6 LILAC LN 6, PROSPECT, CT, 06712, Prospect, CT 06712

$474,900

2 beds

3 baths

1,552 sq ft

Condo

6 LILAC LN 6, PROSPECT, CT, 06712

Community: Regency at Prospect

New Country Pointe Plainview

52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803

$1,749,000

2 beds

3 baths

1,750 sq ft

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...

Community: Country Pointe Plainview

New Stoneleigh Woods at Carmel

705 EGRETS LNDG, CARMEL, NY, 10512, Carmel, NY 10512

$460,000

2 beds

2 baths

1,382 sq ft

Condo

705 EGRETS LNDG, CARMEL, NY, 10512

Community: Stoneleigh Woods at Carmel

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

Questions? Call us: (959) 214-4386

New Leisure Village

200 NEWCASTLE CT E, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$255,000

1 beds

1 baths

684 sq ft

Condo

200 NEWCASTLE CT E, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Rivington

11 ORWICH CT 11, DANBURY, CT, 06810, Danbury, CT 06810

$649,900

3 beds

4 baths

1,572 sq ft

Condo

11 ORWICH CT 11, DANBURY, CT, 06810

Community: Rivington

Windcrest East

116 GOLDEN SPRUCE DR, RIVERHEAD, NY, 119..., Riverhead, NY 11933

$774,900

3 beds

3 baths

2,200 sq ft

House

116 GOLDEN SPRUCE DR, RIVERHEAD, NY, 119...

Community: Windcrest East

Jefferson Village

17 HASTINGS CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$225,000

1 baths

550 sq ft

Condo

17 HASTINGS CT A, YORKTOWN, NY, 10598

Community: Jefferson Village

Woodridge Strathmore Terrace

32 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

3 beds

2 baths

2,030 sq ft

Condo

758 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

The Gardens of Wilbraham

77 CHERRY DR 77, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$439,900

2 beds

2 baths

1,586 sq ft

Condo

77 CHERRY DR 77, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

The Greens at Half Hollow

698 BALFOUR PL, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,099,000

2 beds

3 baths

1,941 sq ft

Condo

698 BALFOUR PL, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

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

Questions? Call us: (959) 214-4386

The Greens at Half Hollow

1165 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$749,000

2 beds

2 baths

1,159 sq ft

Condo

1165 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Regency at Prospect

10 ASH LN 10, PROSPECT, CT, 06712, Prospect, CT 06712

$539,000

2 beds

3 baths

1,928 sq ft

Condo

10 ASH LN 10, PROSPECT, CT, 06712

Community: Regency at Prospect

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.

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143 communities

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

143 communities near Middlebury

267 homes near Middlebury

2 beds

2 baths

1,624 sq ft

Manufactured Home

1 beds

2 baths

967 sq ft

Condo

2 beds

2 baths

1,330 sq ft

Condo

2 beds

2 baths

1,131 sq ft

Condo

2 beds

2 baths

1,549 sq ft

Condo

2 beds

1 baths

912 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

3 baths

2,341 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,889 sq ft

Condo

2 beds

3 baths

2,251 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

2 beds

3 baths

2,542 sq ft

Condo

3 beds

3 baths

2,304 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

1 beds

1 baths

752 sq ft

Condo

2 beds

2 baths

1,138 sq ft

Condo

2 beds

4 baths

2,560 sq ft

Condo

2 beds