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

The Greens at Half Hollow

$500Ks - $1Ms

The Greens at Half Hollow, Melville, NY

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

Rivington

$600Ks

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$200Ks - $600Ks

Jefferson Village, Yorktown Heights, NY

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

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

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

The Village at Oxford Gre...

$500Ks - $600Ks

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.

Meadowbrook Pointe Athlet...

$800Ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Leisure Knoll

$300Ks - $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

5 rating (2 reviews)

Fairfield at St. James

$400Ks

Fairfield at St. James, St. James, NY

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

Leisure Glen

$400Ks

Leisure Glen, Ridge, NY

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

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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 - $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

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

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

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

Dutchgate

$400Ks

Dutchgate, Valley Stream, NY

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

The Waterways at Moriches

$400Ks - $700Ks

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

$300Ks - $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

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

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

$600Ks - $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+ 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

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

349 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (959) 214-4386

Leisure Village

280 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961

$359,900

2 beds

1 baths

836 sq ft

Condo

280 BERWICK CT A, RIDGE, NY, 11961

Community: Leisure Village

Fairfield at St. James

914 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780

$470,000

2 beds

2 baths

1,200 sq ft

Condo

914 FENWAY RD, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

Leisure Village

169 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961

$295,000

2 beds

1 baths

875 sq ft

Condo

169 VENTRY CT A, RIDGE, NY, 11961

Community: Leisure Village

Heritage Hills

972 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$575,000

2 beds

2 baths

1,468 sq ft

Condo

972 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Kensington Estates

46 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797

$2,299,999

6 beds

5 baths

4,333 sq ft

House

46 PLAINVIEW RD, WOODBURY, NY, 11797

Community: Kensington Estates

Leisure Village

259 NEWCASTLE CT E, RIDGE, NY, 11961, Ridge, NY 11961

$254,900

1 beds

1 baths

875 sq ft

Condo

259 NEWCASTLE CT E, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

166 VENTRY CT B, RIDGE, NY, 11961, Ridge, NY 11961

$259,000

1 beds

1 baths

680 sq ft

House

166 VENTRY CT B, RIDGE, NY, 11961

Community: Leisure Village

Heritage Hills

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

$750,000

2 beds

2 baths

1,435 sq ft

Condo

356 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

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

$825,000

3 beds

2 baths

1,909 sq ft

Condo

882 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

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

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

Questions? Call us: (959) 214-4386

Jefferson Village

98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$559,900

2 beds

2 baths

1,100 sq ft

Condo

98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,...

Community: Jefferson Village

Jefferson Village

2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10..., Yorktown Heights, NY 10598

$299,999

1 beds

1 baths

800 sq ft

Condo

2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10...

Community: Jefferson Village

The Villages at Mount Sinai Park

68 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$657,000

2 beds

2 baths

1,736 sq ft

Condo

68 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

The Seasons at East Meadow

331 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$575,000

2 beds

2 baths

1,272 sq ft

Condo

331 SPRING DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

New Encore at Lake Grove

22 SONATA CT, LAKE GROVE, NY, 11755, Lake Grove, NY 11755

$599,990

2 beds

2 baths

1,429 sq ft

Condo

22 SONATA CT, LAKE GROVE, NY, 11755

Community: Encore at Lake Grove

Glenwood Village

1661 OLD COUNTRY RD 506, RIVERHEAD, NY, ..., Riverhead, NY 11901

$329,999

2 beds

2 baths

1,232 sq ft

Manufactured Home

1661 OLD COUNTRY RD 506, RIVERHEAD, NY, ...

Community: Glenwood Village

Heritage Hills

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

$585,000

2 beds

2 baths

1,470 sq ft

Condo

593 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Encore Atlantic Shores

113 OVERTURE PL, EASTPORT, NY, 11941, Eastport, NY 11941

$895,000

2 beds

3 baths

3,037 sq ft

Condo

113 OVERTURE PL, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

Fairfield at St. James

607 CABOT CT 607, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$450,000

1 beds

2 baths

929 sq ft

Condo

607 CABOT CT 607, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Stoneleigh Woods at Riverhead

159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$680,000

2 beds

3 baths

2,172 sq ft

House

159 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

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

Questions? Call us: (959) 214-4386

New Leisure Knoll

145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961

$499,999

2 beds

2 baths

913 sq ft

House

145 EDINBURGH DR, RIDGE, NY, 11961

Community: Leisure Knoll

New Leisure Village

215 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961

$319,000

2 beds

1 baths

1,085 sq ft

Condo

215 WOODBRIDGE DR A, RIDGE, NY, 11961

Community: Leisure Village

New Greenwood Village

91 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$155,000

2 beds

2 baths

938 sq ft

Condo

91 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

The Greens at Half Hollow

652 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747

$1,199,000

3 beds

3 baths

2,400 sq ft

Condo

652 BALFOUR PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Glassbury Court at Cold Spring

11 REVOLUTION RD, COLD SPRING, NY, 10516, Cold Spring, NY 10516

$515,000

2 beds

3 baths

1,806 sq ft

Condo

11 REVOLUTION RD, COLD SPRING, NY, 10516

Community: Glassbury Court at Cold Spring

Breton Hills

209 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542

$699,888

2 beds

2 baths

1,300 sq ft

Condo

209 BRETON WAY, GLEN COVE, NY, 11542

Community: Breton Hills

The Hollows at Blue Hill

41 MICHAEL ROBERTS CT, PEARL RIVER, NY, ..., Pearl River, NY 10965

$999,000

2 beds

3 baths

2,210 sq ft

Condo

41 MICHAEL ROBERTS CT, PEARL RIVER, NY, ...

Community: The Hollows at Blue Hill

Regency at Fishkill

736 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$499,000

1 beds

2 baths

1,543 sq ft

House

736 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Heritage Hills

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

$899,000

3 beds

2 baths

1,793 sq ft

Condo

370 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Setauket Meadows

95 COVE LN, EAST SETAUKET, NY, 11733, East Setauket, NY 11733

$749,990

2 beds

3 baths

1,991 sq ft

Condo

95 COVE LN, EAST SETAUKET, NY, 11733

Community: Setauket Meadows

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

Questions? Call us: (959) 214-4386

Foxwood Village

1407 MIDDLE RD UNIT 258, CALVERTON, NY, ..., Calverton, NY 11933

$525,000

3 beds

2 baths

1,568 sq ft

Manufactured Home

1407 MIDDLE RD UNIT 258, CALVERTON, NY, ...

Community: Foxwood Village

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

Glenwood Village

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$239,999

2 beds

2 baths

924 sq ft

Manufactured Home

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...

Community: Glenwood Village

The Greens at Half Hollow

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

$1,499,000

3 beds

4 baths

3,100 sq ft

Condo

259 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

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

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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 near Middlebury

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

141 communities near Middlebury

269 homes near Middlebury

2 beds

1 baths

655 sq ft

Condo

1 beds

2 baths

900 sq ft

Condo

2 beds

2 baths

1,159 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,484 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,468 sq ft

Condo

6 beds

5 baths

4,333 sq ft

House

1 beds

1 baths

875 sq ft

Condo

1 beds

1 baths

680 sq ft

House

2 beds

2 baths

1,435 sq ft

Condo

3 beds

2 baths

1,909 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,736 sq ft

Condo

2 beds

2 baths

1,272 sq ft

Condo

2 beds