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

145 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

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

5 rating (2 reviews)

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 (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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

Questions? Call us: (959) 214-4386

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

New Construction | 55+ age-restricted | Built 2017 - present | 660 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 Manors at The Colony ...

$300ks - $400ks

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

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Four Seasons at Ridgemont

$800ks - $1Ms

Four Seasons at Ridgemont, Montvale, NJ

Resale Only | 55+ age-restricted | Built 2011 - 2014 | 108 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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 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

Eagles Walk at East Quogu...

$300ks - $400ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

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

Questions? Call us: (959) 214-4386

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

1 2 3...4

Greenwood Village

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949

$245,000

2 beds

2 baths

1,130 sq ft

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...

Community: Greenwood Village

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, ...

722 HERITAGE VLG A, 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 Country Pointe Plainview

30101 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,200,000

2 beds

2 baths

1,379 sq ft

Condo

30101 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

New HarborView

100 HARBOR VIEW DR 630, NORTH HEMPSTEAD,..., North Hempstead, NY 11050

$1,299,000

3 beds

3 baths

2,426 sq ft

Condo

100 HARBOR VIEW DR 630, NORTH HEMPSTEAD,...

Community: HarborView

New Heritage Village

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

$309,000

2 beds

2 baths

1,432 sq ft

Condo

970 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Rivington

44 WARRINGTON ROUND ST 44, DANBURY, CT, ..., Danbury, CT 06810

$628,000

3 beds

3 baths

1,600 sq ft

Condo

44 WARRINGTON ROUND ST 44, DANBURY, CT, ...

Community: Rivington

New Leisure Glen

477 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$589,000

2 beds

2 baths

1,434 sq ft

Condo

477 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Country Pointe Plainview

38204 WINTERBERRY DR, OYSTER BAY, NY, 11..., Oyster Bay, NY 11803

$1,585,000

2 beds

2 baths

1,989 sq ft

Condo

38204 WINTERBERRY DR, OYSTER BAY, NY, 11...

Community: Country Pointe Plainview

New The Manors at The Colony Preserve

41 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967

$485,000

2 beds

2 baths

1,557 sq ft

Condo

41 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

Heritage Village

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

$427,500

2 beds

2 baths

1,398 sq ft

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$319,000

2 beds

2 baths

1,432 sq ft

Condo

620 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Country Pointe Preserve

119 MIA LN 76, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$940,000

2 beds

3 baths

2,187 sq ft

Condo

119 MIA LN 76, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

The Village at Oxford Greens

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064..., Oxford, CT 06478

$624,900

2 beds

3 baths

1,673 sq ft

Condo

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064...

Community: The Village at Oxford Greens

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

Questions? Call us: (959) 214-4386

Sunken Pond Estates

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$520,000

2 beds

2 baths

1,350 sq ft

Condo

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190...

Community: Sunken Pond Estates

Saddle Lakes

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

$595,000

2 beds

2 baths

1,386 sq ft

Condo

157 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Village Estates

30 SARAH CT, BABYLON, NY, 11701, Babylon, NY 11701

$599,000

2 beds

2 baths

1,251 sq ft

Condo

30 SARAH CT, BABYLON, NY, 11701

Community: Village Estates

The Greens at Half Hollow

643 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,299,999

3 beds

3 baths

2,500 sq ft

Condo

643 VERONA DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Regency at Prospect

133 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712

$550,000

2 beds

3 baths

1,850 sq ft

Condo

133 SYCAMORE DR, PROSPECT, CT, 06712

Community: Regency at Prospect

Vineyards at Moriches

19 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$775,000

2 beds

3 baths

2,251 sq ft

Condo

19 EMILIE DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Moriches

Leisure Glen

279 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$569,999

2 beds

2 baths

1,542 sq ft

Condo

279 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Newtown Woods

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470, Newtown, CT 06470

$498,900

2 beds

2 baths

1,504 sq ft

Condo

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470

Community: Newtown Woods

Heritage Hills

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

$825,000

2 beds

2 baths

1,663 sq ft

Condo

675 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$225,000

1 beds

1 baths

928 sq ft

Condo

875 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Retreat at Carmel

88 BLAIR HEIGHTS, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

3 beds

3 baths

2,695 sq ft

Condo

88 BLAIR HEIGHTS, CARMEL, NY, 10512

Condo

281 SPRING DR, HEMPSTEAD, NY, 11554

Community: The Seasons at East Meadow

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

Questions? Call us: (959) 214-4386

Overlook

2050 SUMMIT LOOP 61, CARMEL, NY, 10512, Carmel, NY 10512

$929,000

2 beds

2 baths

2,102 sq ft

Condo

2050 SUMMIT LOOP 61, CARMEL, NY, 10512

Community: Overlook

Oronoque Village

138 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$480,000

2 beds

3 baths

1,438 sq ft

Condo

138 BISON LN B, STRATFORD, CT, 06614

Community: Oronoque 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.

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145 communities

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

145 communities near Middlebury

321 homes near Middlebury

2 beds

2 baths

1,130 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

3 beds

3 baths

2,008 sq ft

Condo

1 beds

2 baths

1,235 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,379 sq ft

Condo

3 beds

3 baths

2,426 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

1,600 sq ft

Condo

2 beds

2 baths

1,434 sq ft

Condo

2 beds

2 baths

1,989 sq ft

Condo

2 beds

2 baths

1,557 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

2,187 sq ft

Condo

2 beds

3 baths

1,673 sq ft

Condo

2 beds

2 baths

1,350 sq ft

Condo

2 beds

2 baths

1,386 sq ft

Condo

2 beds

2 baths

1,251 sq ft

Condo

3 beds