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

303 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 - $500Ks

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

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

$500Ks - $1Ms

The Greens at Half Hollow, Melville, NY

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

No reviews yet

Rivington

$400Ks - $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

No reviews yet

Oronoque Village

$200Ks - $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...

$800Ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

No reviews yet

Leisure Knoll

$300Ks - $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 (2 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 - $400Ks

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 - $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

$300Ks - $500Ks

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 - $700Ks

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

No reviews yet

Overlook

$600Ks - $900Ks

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 - $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 - $800Ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 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

$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 - $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

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 - $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

36 THEODORE DR, CORAM, NY, 11727

Community: Country Village Estates

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

Questions? Call us: (959) 214-4386

Greenwood Village

161 VILLAGE CIR W # 161, MANORVILLE, NY,..., Manorville, NY 11949

$169,990

2 beds

2 baths

1,258 sq ft

Condo

161 VILLAGE CIR W # 161, MANORVILLE, NY,...

Community: Greenwood Village

Leisure Village

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

$315,000

2 beds

1 baths

875 sq ft

Condo

276 BERWICK CT A, RIDGE, NY, 11961

Community: Leisure Village

The Greens at Half Hollow

382 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$1,525,000

2 beds

2 baths

2,937 sq ft

Condo

382 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

HarborView

$875,000

2 beds

3 baths

1,420 sq ft

Condo

100 HARBOR VIEW DR 439, PORT WASHINGTON,...

Community: HarborView

The Waterways at Moriches

537 HIGHLAND CT, MORICHES, NY, 11955, Moriches, NY 11955

$565,000

2 beds

2 baths

1,839 sq ft

Condo

537 HIGHLAND CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

Glenwood Village

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ..., Riverhead, NY 11901

$164,999

2 beds

1 baths

816 sq ft

Mobile Home

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ...

Community: Glenwood Village

Glenwood Village

1661 OLD COUNTRY RD UNIT 508, RIVERHEAD,..., Riverhead, NY 11901

$399,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 508, RIVERHEAD,...

Community: Glenwood Village

Greenwood Village

164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$174,990

2 beds

2 baths

938 sq ft

Manufactured Home

164 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Village

419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119..., Ridge, NY 11961

$260,000

1 beds

1 baths

782 sq ft

Condo

419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119...

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

Condo

164 IRA RD, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

The Gardens of Wilbraham

116 CHERRY DR # 116, WILBRAHAM, MA, 0109..., Wilbraham, MA 01095

$539,000

2 beds

2 baths

1,634 sq ft

Condo

116 CHERRY DR # 116, WILBRAHAM, MA, 0109...

Community: The Gardens of Wilbraham

Four Seasons at Ridgemont

301 FOUR SEASONS LN, MONTVALE, NJ, 07645, Montvale, NJ 07645

$879,000

2 beds

2 baths

Condo

301 FOUR SEASONS LN, MONTVALE, NJ, 07645

Community: Four Seasons at Ridgemont

1 2 3 4 5 6 7 8

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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Want to learn more about 55+ communities in Middlebury?

Call us: (959) 214-4386

303 homes near Middlebury

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REIN updates its listings on a daily basis. Data last updated: Nov 03, 2025.
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Middlebury, CT 55+ active adult communities & homes for sale

141 communities near Middlebury

303 homes near Middlebury

2 beds

1 baths

1,100 sq ft

Condo

1 beds

2 baths

1,161 sq ft

Condo

1 beds

1 baths

600 sq ft

Condo

2 beds

2 baths

1,839 sq ft

Condo

2 beds

2 baths

1,186 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

2,937 sq ft

Condo

2 beds

3 baths

1,420 sq ft

Condo

2 beds

2 baths

1,839 sq ft

Condo

2 beds

1 baths

816 sq ft

Mobile Home

2 beds

2 baths

1,500 sq ft

Manufactured Home

2 beds

2 baths

938 sq ft

Manufactured Home

1 beds

1 baths

782 sq ft

Condo

1 beds

1 baths

680 sq ft

House

2 beds

3 baths

2,800 sq ft

Condo

2 beds

2 baths

2,141 sq ft

Condo

2 beds

2 baths

1,839 sq ft

Condo

2 beds

2 baths

1,480 sq ft

Condo

2 beds