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

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

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

280 BERWICK CT 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

Glenwood Village

1661 OLD COUNTRY RD UNIT 543, RIVERHEAD,..., Riverhead, NY 11901

$410,000

2 beds

2 baths

1,632 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 543, RIVERHEAD,...

Community: Glenwood Village

The Waterways at Moriches

414 LINDSAY LN, MORICHES, NY, 11955, Moriches, NY 11955

$549,000

2 beds

2 baths

2,141 sq ft

Condo

414 LINDSAY LN, MORICHES, NY, 11955

Community: The Waterways at Moriches

Leisure Village

42D TRENT CT 42D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$229,000

2 beds

1 baths

875 sq ft

Condo

42D TRENT CT 42D, BROOKHAVEN, NY, 11961

Community: Leisure Village

Leisure Village

423 WOODBRIDGE D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$239,000

1 beds

1 baths

782 sq ft

Condo

423 WOODBRIDGE D, BROOKHAVEN, NY, 11961

Community: Leisure Village

Leisure Village

411A WEYMOUTH CT # 411A, RIDGE, NY, 1196..., Ridge, NY 11961

$349,000

2 beds

1 baths

1,000 sq ft

Condo

411A WEYMOUTH CT # 411A, RIDGE, NY, 1196...

Community: Leisure Village

The Bel Aire at East Meadow

50 MERRICK AVE 307, EAST MEADOW, NY, 115..., East Meadow, NY 11554

$465,000

2 beds

2 baths

1,017 sq ft

Condo

50 MERRICK AVE 307, EAST MEADOW, NY, 115...

Community: The Bel Aire at East Meadow

Leisure Village

156 FALMOUTH CT B, RIDGE, NY, 11961, Ridge, NY 11961

$399,990

2 beds

1 baths

1,085 sq ft

Condo

156 FALMOUTH CT B, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

369B WOODBRIDGE DR 55+, BROOKHAVEN, NY, ..., Brookhaven, NY 11961

$344,000

2 beds

1 baths

975 sq ft

Condo

369B WOODBRIDGE DR 55+, BROOKHAVEN, NY, ...

Community: Leisure Village

Country Village Estates

36 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727

$459,999

2 beds

2 baths

1,186 sq ft

Condo

36 THEODORE DR, CORAM, NY, 11727

Community: Country Village Estates

Leisure Village

137 EASTBOURNE CT B, RIDGE, NY, 11961, Ridge, NY 11961

$249,000

2 beds

1 baths

836 sq ft

Condo

137 EASTBOURNE CT 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

Heritage Hills

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

$645,000

2 beds

2 baths

1,296 sq ft

Condo

785 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Meadowbrook Pointe Athletic Club & Spa

481 PACING WAY, WESTBURY, NY, 11590, Westbury, NY 11590

$1,100,000

2 beds

3 baths

2,800 sq ft

Condo

481 PACING WAY, WESTBURY, NY, 11590

Community: Meadowbrook Pointe Athletic Club & Spa

Jefferson Village

84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$350,000

2 beds

2 baths

1,100 sq ft

Condo

84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...

Community: Jefferson Village

Leisure Village

384 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$365,000

2 beds

2 baths

1,405 sq ft

Condo

384 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

The Waterways at Moriches

107 E MIDLAND POND CT, MORICHES, NY, 119..., Moriches, NY 11955

$499,907

2 beds

2 baths

2,141 sq ft

Condo

107 E MIDLAND POND CT, MORICHES, NY, 119...

Community: The Waterways at Moriches

The Waterways at Moriches

497 OAK BLUFF CT, MORICHES, NY, 11955, Moriches, NY 11955

$529,999

2 beds

3 baths

1,988 sq ft

Condo

497 OAK BLUFF CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

Leisure Village

273 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961

$280,000

2 beds

1 baths

836 sq ft

Condo

273 BERWICK CT B, RIDGE, NY, 11961

Community: Leisure Village

Strathmore Gate East

9 FORGE LN, CORAM, NY, 11727, Coram, NY 11727

$334,999

2 beds

2 baths

1,300 sq ft

Condo

9 FORGE LN, CORAM, NY, 11727

Community: Strathmore Gate East

Heritage Hills

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

$949,000

3 beds

2 baths

2,030 sq ft

Condo

682 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Regency at Fishkill

326 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$565,000

1 beds

2 baths

1,543 sq ft

Condo

326 REGENCY DR, FISHKILL, NY, 12524

Manufactured Home

1661 OLD COUNTRY RD 120, RIVERHEAD, NY, ...

Condo

365 SEABREEZE CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

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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?

Call us: (959) 214-4386

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

2 baths

1,700 sq ft

Manufactured Home

2 beds

1 baths

836 sq ft

House

2 beds

2 baths

1,700 sq ft

Manufactured Home

2 beds

2 baths

1,050 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,632 sq ft

Manufactured Home

2 beds

2 baths

2,141 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

1 beds

1 baths

782 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

2 baths

1,017 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

1 baths

975 sq ft

Condo

2 beds

2 baths

1,186 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

2 baths

1,296 sq ft

Condo

2 beds

3 baths

2,800 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,405 sq ft

Condo

2 beds