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

287 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

$400Ks - $600Ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1975 - 2003 | 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 - $400Ks

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

$400Ks - $1Ms

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$300Ks - $500Ks

Jefferson Village, Yorktown Heights, NY

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

No reviews yet

Oronoque Village

$500Ks - $600Ks

Oronoque Village, Stratford, CT

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

No reviews yet

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.

No reviews yet

Meadowbrook Pointe Athlet...

$800Ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

No reviews yet

Leisure Knoll

$300Ks - $500Ks

Leisure Knoll, Ridge, NY

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

No reviews yet

Country Pointe Plainview

$800Ks - $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 - $500Ks

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 - $200Ks

Spring Lake Village, Southington, CT

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

4 rating (8 reviews)

Glenwood Village

$100Ks - $300Ks

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

$300Ks - $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

$600Ks - $900Ks

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 ...

$600Ks - $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 - $800Ks

Encore Atlantic Shores, Eastport, NY

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

No reviews yet

The Summit at Bethel

$700Ks - $800Ks

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

$600Ks - $800Ks

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...

$300Ks - $400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

No reviews yet

Regency at Wappinger

$700Ks - $800Ks

Regency at Wappinger, Wappingers Falls, NY

New and Resale | 55+ age-restricted | Built 2014 - present | 225 homes

5 rating (1 reviews)

Sunrise Village

$400Ks - $500Ks

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 - $400Ks

Country Village Estates, Coram, NY

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

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...

Community: Glenwood Village

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

Questions? Call us: (959) 214-4386

New Heritage Hills

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

$650,000

2 beds

2 baths

1,470 sq ft

Condo

963 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Meadowbrooke Pointe East Meadow

506 EMANUEL WAY # 73, EAST MEADOW, NY, 1..., East Meadow, NY 11554

$720,000

1 beds

2 baths

961 sq ft

Condo

506 EMANUEL WAY # 73, EAST MEADOW, NY, 1...

Community: Meadowbrooke Pointe East Meadow

Meadowbrooke Pointe East Meadow

514 EMANUEL WAY # 77, EAST MEADOW, NY, 1..., East Meadow, NY 11554

$790,000

1 beds

3 baths

2,061 sq ft

Condo

514 EMANUEL WAY # 77, EAST MEADOW, NY, 1...

Community: Meadowbrooke Pointe East Meadow

Jefferson Village

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

$599,900

2 beds

2 baths

1,350 sq ft

Condo

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

Community: Jefferson Village

Country Village Estates

11 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727

$479,000

2 beds

2 baths

1,386 sq ft

Condo

11 THEODORE DR, CORAM, NY, 11727

Community: Country Village Estates

The Waterways at Moriches

381 QUARRY POND CT, MORICHES, NY, 11955, Moriches, NY 11955

$649,000

2 beds

2 baths

2,200 sq ft

Condo

381 QUARRY POND CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

The Waterways at Moriches

295 W MIDLAND POND CT, MORICHES, NY, 119..., Moriches, NY 11955

$699,990

2 beds

2 baths

2,149 sq ft

Condo

295 W MIDLAND POND CT, MORICHES, NY, 119...

Community: The Waterways at Moriches

New Sunken Pond Estates

3804 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$519,000

2 beds

3 baths

1,674 sq ft

Condo

3804 AMEN COR, RIVERHEAD, NY, 11901

Community: Sunken Pond Estates

Meadowbrook Pointe Links & Spa

234 AUGUSTA DR # 234, MEDFORD, NY, 11763, Medford, NY 11763

$745,000

2 beds

3 baths

1,627 sq ft

Condo

234 AUGUSTA DR # 234, MEDFORD, NY, 11763

Community: Meadowbrook Pointe Links & Spa

Country Pointe Plainview

34203 WINTERBERRY DR, PLAINVIEW, NY, 118..., Plainview, NY 11803

$899,888

2 beds

2 baths

1,335 sq ft

Condo

34203 WINTERBERRY DR, PLAINVIEW, NY, 118...

Community: Country Pointe Plainview

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

Questions? Call us: (959) 214-4386

New Dutchgate

1512 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580

$475,000

2 beds

2 baths

941 sq ft

Condo

1512 WILLOW LN, VALLEY STREAM, NY, 11580

Community: Dutchgate

Leisure Village

232A BLACKPOOL CT 232A, BROOKHAVEN, NY, ..., Brookhaven, NY 11961

$305,000

2 beds

1 baths

836 sq ft

Condo

232A BLACKPOOL CT 232A, BROOKHAVEN, NY, ...

Community: Leisure Village

The Waterways at Moriches

106 E MIDLAND POND CT # 1, MORICHES, NY,..., Moriches, NY 11955

$499,000

2 beds

2 baths

1,982 sq ft

Condo

106 E MIDLAND POND CT # 1, MORICHES, NY,...

Community: The Waterways at Moriches

Leisure Village

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

$359,900

2 beds

1 baths

1,085 sq ft

Condo

286 BERWICK CT A, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

305 TORQUAY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961

$364,500

2 beds

1 baths

836 sq ft

House

305 TORQUAY CT UNIT C, RIDGE, NY, 11961

Community: Leisure Village

The Seasons at Plainview

75 AUTUMN DR, PLAINVIEW, NY, 11803, Plainview, NY 11803

$699,999

2 beds

2 baths

1,379 sq ft

Condo

75 AUTUMN DR, PLAINVIEW, NY, 11803

Community: The Seasons at Plainview

New Saddle Lakes

107 SCENIC LAKE DR # 107, RIVERHEAD, NY,..., Riverhead, NY 11901

$639,000

2 beds

2 baths

1,631 sq ft

Condo

107 SCENIC LAKE DR # 107, RIVERHEAD, NY,...

Community: Saddle Lakes

Fairfield at St. James

206 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$570,000

3 beds

3 baths

1,649 sq ft

Condo

206 FLAIR CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Greenwood Village

87 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$179,000

2 beds

1 baths

992 sq ft

Condo

87 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

The Polo Club at Islandia

1239 OLD NICHOLS RD # 46, ISLANDIA, NY, ..., Islandia, NY 11749

$639,000

2 beds

3 baths

1,654 sq ft

Condo

1239 OLD NICHOLS RD # 46, ISLANDIA, NY, ...

Community: The Polo Club at Islandia

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

Questions? Call us: (959) 214-4386

Country Pointe Plainview

17101 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803

$1,055,000

2 beds

2 baths

1,443 sq ft

Condo

17101 ASPENWOOD DR, PLAINVIEW, NY, 11803

Community: Country Pointe Plainview

New Leisure Knoll

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

$418,000

2 beds

2 baths

900 sq ft

Condo

145 EDINBURGH DR, RIDGE, NY, 11961

Community: Leisure Knoll

Glenwood Village

1661 OLD COUNTRY RD UNIT 200, RIVERHEAD,..., Riverhead, NY 11901

$249,900

2 beds

1 baths

753 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 200, RIVERHEAD,...

Community: Glenwood Village

Vineyards at Blue Point

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

$925,000

2 beds

4 baths

3,388 sq ft

Condo

26 AVERY WAY # 26, BLUE POINT, NY, 11772

Community: Vineyards at Blue Point

New Leisure Village

68A ENFIELD CT # 68A, RIDGE, NY, 11961, Ridge, NY 11961

$369,000

2 beds

1 baths

1,048 sq ft

Condo

68A ENFIELD CT # 68A, RIDGE, NY, 11961

Community: Leisure Village

Vineyards at Moriches

52 TONI CT # 52, CENTER MORICHES, NY, 11..., Center Moriches, NY 11934

$699,000

2 beds

3 baths

2,196 sq ft

Condo

52 TONI CT # 52, CENTER MORICHES, NY, 11...

Community: Vineyards at Moriches

Encore at Lake Grove

20 CONCERTO DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755

$699,990

2 beds

3 baths

1,413 sq ft

Condo

20 CONCERTO DR, LAKE GROVE, NY, 11755

Community: Encore at Lake Grove

New Meadowbrook Pointe Athletic Club & Spa

494 PACING WAY # 301C, WESTBURY, NY, 115..., Westbury, NY 11590

$850,000

2 beds

2 baths

1,353 sq ft

Condo

494 PACING WAY # 301C, WESTBURY, NY, 115...

Community: Meadowbrook Pointe Athletic Club & Spa

Stoneleigh Woods at Riverhead

8 LAKEVIEW CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$615,000

3 beds

3 baths

2,000 sq ft

Condo

8 LAKEVIEW CT, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Vineyards at Moriches

30 TONI CT # 30, CENTER MORICHES, NY, 11..., Center Moriches, NY 11934

$725,000

2 beds

3 baths

2,204 sq ft

Condo

30 TONI CT # 30, CENTER MORICHES, NY, 11...

Condo

142 AUGUSTA DR, MEDFORD, NY, 11763

Community: Meadowbrook Pointe Links & Spa

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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.

Want more information about active adult communities around Middlebury?

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287 homes near Middlebury

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

137 communities near Middlebury

287 homes near Middlebury

3 beds

3 baths

2,850 sq ft

Condo

2 beds

2 baths

1,428 sq ft

Condo

2 beds

2 baths

1,123 sq ft

Condo

2 beds

2 baths

1,417 sq ft

Condo

2 beds

2 baths

1,152 sq ft

Manufactured Home

2 beds

2 baths

1,470 sq ft

Condo

1 beds

2 baths

961 sq ft

Condo

1 beds

3 baths

2,061 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

2,200 sq ft

Condo

2 beds

2 baths

2,149 sq ft

Condo

2 beds

3 baths

1,674 sq ft

Condo

2 beds

3 baths

1,627 sq ft

Condo

2 beds

2 baths

1,335 sq ft

Condo

2 beds

2 baths

941 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

2 baths

1,982 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds