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

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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

247 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (959) 214-4386

New Setauket Meadows

131 EMILYS WAY, EAST SETAUKET, NY, 11733, East Setauket, NY 11733

$735,000

2 beds

3 baths

1,773 sq ft

Condo

131 EMILYS WAY, EAST SETAUKET, NY, 11733

Community: Setauket Meadows

New Country Village Estates

122 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727

$517,000

2 beds

2 baths

1,393 sq ft

Condo

122 THEODORE DR, CORAM, NY, 11727

Community: Country Village Estates

Meadowbrook Pointe Links & Spa

279 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763

$319,298

2 beds

2 baths

1,133 sq ft

Condo

279 AUGUSTA DR, MEDFORD, NY, 11763

Community: Meadowbrook Pointe Links & Spa

Country Village Estates

56 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727

$449,000

2 beds

2 baths

1,198 sq ft

Condo

56 THEODORE DR, CORAM, NY, 11727

Community: Country Village Estates

The Seasons at East Meadow

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

$619,000

2 beds

2 baths

1,272 sq ft

Condo

319 SPRING DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

The Greens at Half Hollow

285 MADEIRA BLVD # 285, MELVILLE, NY, 11..., Melville, NY 11747

$1,555,500

3 beds

3 baths

3,200 sq ft

Condo

285 MADEIRA BLVD # 285, MELVILLE, NY, 11...

Community: The Greens at Half Hollow

Encore Atlantic Shores

48 ENCORE BLVD, EASTPORT, NY, 11941, Eastport, NY 11941

$725,000

2 beds

2 baths

2,100 sq ft

Condo

48 ENCORE BLVD, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

Heritage Hills

852 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$1,100,000

3 beds

2 baths

2,156 sq ft

Condo

852 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

Sunrise Village

133 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782

$429,000

2 beds

1 baths

1,000 sq ft

Condo

133 REVERE DR, SAYVILLE, NY, 11782

Community: Sunrise Village

Leisure Village

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961

$349,000

2 beds

1 baths

1,278 sq ft

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...

Community: Leisure Village

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

Questions? Call us: (959) 214-4386

Leisure Knoll

28 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961

$450,000

2 beds

2 baths

1,094 sq ft

Condo

28 KINGSTON DR, RIDGE, NY, 11961

Community: Leisure Knoll

The Greens at Half Hollow

262 ALTESSA BLVD # 262, MELVILLE, NY, 11..., Melville, NY 11747

$1,349,999

3 beds

4 baths

3,200 sq ft

Condo

262 ALTESSA BLVD # 262, MELVILLE, NY, 11...

Community: The Greens at Half Hollow

Regency at Fishkill

145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$579,800

2 beds

2 baths

1,803 sq ft

Condo

145 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Strathmore Gate East

46 FREEDOM LN, CORAM, NY, 11727, Coram, NY 11727

$390,000

2 beds

2 baths

1,112 sq ft

Condo

46 FREEDOM LN, CORAM, NY, 11727

Community: Strathmore Gate East

Leisure Village

311 WOODBRIDGE DR 311-C, RIDGE, NY, 1196..., Ridge, NY 11961

$245,000

1 beds

1 baths

684 sq ft

Condo

311 WOODBRIDGE DR 311-C, RIDGE, NY, 1196...

Community: Leisure Village

Jefferson Village

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

$250,000

1 beds

1 baths

800 sq ft

Condo

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

Community: Jefferson Village

Heritage Hills

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

$590,000

2 beds

2 baths

1,468 sq ft

Condo

972 C HERITAGE HLS Y., SOMERS, NY, 10589

Community: Heritage Hills

Eagles Walk at East Quogue

1601 AERIE WAY, EAST QUOGUE, NY, 11942, East Quogue, NY 11942

$535,000

2 beds

2 baths

1,275 sq ft

Condo

1601 AERIE WAY, EAST QUOGUE, NY, 11942

Community: Eagles Walk at East Quogue

Jefferson Village

40 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$539,000

2 beds

2 baths

1,350 sq ft

Condo

40 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

Leisure Knoll

215 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961

$454,990

2 beds

2 baths

1,116 sq ft

Condo

215 KINGSTON DR, RIDGE, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (959) 214-4386

Greenwood Village

93 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$129,999

2 beds

2 baths

1,100 sq ft

Condo

93 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Knoll

503 LANCASTER CT # 503, RIDGE, NY, 11961, Ridge, NY 11961

$469,000

2 beds

2 baths

1,094 sq ft

Condo

503 LANCASTER CT # 503, RIDGE, NY, 11961

Community: Leisure Knoll

Jefferson Village

73 INDEPENDENCE CT D, YORKTOWN, NY, 1059..., Yorktown, NY 10598

$385,000

2 beds

2 baths

1,100 sq ft

Condo

73 INDEPENDENCE CT D, YORKTOWN, NY, 1059...

Community: Jefferson Village

Fairfield at St. James

1104 DREW DR, SAINT JAMES, NY, 11780, Saint James, NY 11780

$429,000

1 beds

1 baths

752 sq ft

Condo

1104 DREW DR, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

The Seasons at East Meadow

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

$649,000

2 beds

2 baths

1,358 sq ft

Condo

217 SPRING DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

Leisure Village

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

$259,900

1 beds

1 baths

875 sq ft

Condo

259 NEWCASTLE CT E, RIDGE, NY, 11961

Community: Leisure Village

Jefferson Village

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598

$469,900

2 beds

2 baths

1,200 sq ft

Condo

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ...

Community: Jefferson Village

Leisure Village

49 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961

$319,000

2 beds

1 baths

1,100 sq ft

Condo

49 TRENT CT B, RIDGE, NY, 11961

Community: Leisure Village

Vineyards at Blue Point

26 AVERY WAY, BLUE POINT, NY, 11772, Blue Point, NY 11772

$899,000

2 beds

4 baths

3,388 sq ft

Condo

26 AVERY WAY, BLUE POINT, NY, 11772

Community: Vineyards at Blue Point

Greenwood Village

132 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$199,990

2 beds

2 baths

1,375 sq ft

Condo

132 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

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

Questions? Call us: (959) 214-4386

The Greens at Half Hollow

679 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747

$1,399,999

3 beds

3 baths

2,500 sq ft

Condo

679 BALFOUR PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

1000 N MADEIRA BLVD, HUNTINGTON, NY, 117..., Huntington, NY 11797

$649,999

2 beds

2 baths

1,183 sq ft

Condo

1000 N MADEIRA BLVD, HUNTINGTON, NY, 117...

Community: The Greens at Half Hollow

Meadowbrook Pointe Links & Spa

142 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763

$729,990

2 beds

3 baths

1,691 sq ft

Condo

142 AUGUSTA DR, MEDFORD, NY, 11763

Community: Meadowbrook Pointe Links & Spa

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

Leisure Village

186 VENTRY CT D, RIDGE, NY, 11961, Ridge, NY 11961

$339,900

2 beds

1 baths

916 sq ft

Condo

186 VENTRY CT D, RIDGE, NY, 11961

Community: Leisure Village

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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 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?

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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

3 baths

2,290 sq ft

Condo

2 beds

2 baths

1,150 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

3 baths

1,378 sq ft

Condo

1 beds

1 baths

967 sq ft

Condo

2 beds

3 baths

1,773 sq ft

Condo

2 beds

2 baths

1,393 sq ft

Condo

2 beds

2 baths

1,133 sq ft

Condo

2 beds

2 baths

1,198 sq ft

Condo

2 beds

2 baths

1,272 sq ft

Condo

3 beds

3 baths

3,200 sq ft

Condo

2 beds

2 baths

2,100 sq ft

Condo

3 beds

2 baths

2,156 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

1 baths

1,278 sq ft

Condo

2 beds

2 baths

1,094 sq ft

Condo

3 beds

4 baths

3,200 sq ft

Condo

2 beds

2 baths

1,803 sq ft

Condo

2 beds

2 baths

1,112 sq ft

Condo

1 beds