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

141 communities near Middlebury

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3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

3 rating (2 reviews)

Heritage Hills

$400ks - $1Ms

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes

Leisure Village

$100ks - $300ks

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

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

Questions? Call us: (959) 214-4386

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

5 rating (2 reviews)

Fairfield at St. James

$300ks - $500ks

Fairfield at St. James, St. James, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

The Village at Oxford Gre...

$400ks - $500ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

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

Questions? Call us: (959) 214-4386

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

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

Questions? Call us: (959) 214-4386

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

The Seasons at East Meado...

$400ks - $600ks

The Seasons at East Meado..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

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

Questions? Call us: (959) 214-4386

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

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

Questions? Call us: (959) 214-4386

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

The Manors at The Colony ...

$300ks - $400ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 homes

Glassbury Court at Cold S...

$500ks - $700ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

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

Questions? Call us: (959) 214-4386

HarborView

$600ks - $800ks

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

5 rating (1 reviews)

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes

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

Questions? Call us: (959) 214-4386

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

1 2 3...4

New Oronoque Village

252 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$639,000

2 beds

3 baths

2,823 sq ft

Condo

252 AGAWAM DR A, STRATFORD, CT, 06614

78 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (959) 214-4386

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

Questions? Call us: (959) 214-4386

New The Villages at Mount Sinai Park

43 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$799,000

3 beds

3 baths

2,455 sq ft

Condo

43 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New Rivington

424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810

$510,000

2 beds

2 baths

1,258 sq ft

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...

Community: Rivington

New Bartlett Hill

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480, Portland, CT 06480

$479,900

2 beds

3 baths

1,404 sq ft

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480

Community: Bartlett Hill

New Meadowbrook Pointe Links & Spa

83 PACIFIC DUNES CT 83, BROOKHAVEN, NY, ..., Brookhaven, NY 11763

$749,990

3 beds

3 baths

2,047 sq ft

Condo

83 PACIFIC DUNES CT 83, BROOKHAVEN, NY, ...

Community: Meadowbrook Pointe Links & Spa

New HarborView

100 HARBOR VIEW DR 111, NORTH HEMPSTEAD,..., North Hempstead, NY 11050

1 beds

1 baths

750 sq ft

Condo

25 FREEMONT LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

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

Questions? Call us: (959) 214-4386

New The Greens at Half Hollow

236 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,698,000

2 beds

3 baths

2,500 sq ft

Condo

236 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Heritage Hills

358 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$622,900

2 beds

3 baths

1,550 sq ft

Condo

358 HERITAGE HLS D, SOMERS, NY, 10589

House

43 VILLAGE CIR, BROOKHAVEN, NY, 11949

26 DORSET CT A, YORKTOWN, NY, 10598

Community: Jefferson Village

New The Seasons at East Meadow

394 SPRING DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$649,000

2 beds

2 baths

1,670 sq ft

Condo

394 SPRING DR, HEMPSTEAD, NY, 11554

Community: The Seasons at East Meadow

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

Questions? Call us: (959) 214-4386

New Leisure Knoll

506 LANCASTER CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,000

2 beds

2 baths

1,394 sq ft

House

506 LANCASTER CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Heritage Hills

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

$979,000

3 beds

2 baths

1,793 sq ft

Condo

392 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Village

41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,900

2 beds

3 baths

1,479 sq ft

Condo

41 E MEADOW RD, SOUTHBURY, CT, 06488

Community: Heritage Village

New Greenwood Village

65A VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$134,900

1 beds

1 baths

672 sq ft

Condo

65A VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Paris Square

5201 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647

$735,000

2 beds

2 baths

Condo

5201 RIO VISTA LN, NORTHVALE, NJ, 07647

Community: Paris Square

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

Questions? Call us: (959) 214-4386

Overlook

3004 EASTVIEW DR 105, CARMEL, NY, 10512, Carmel, NY 10512

$722,000

2 beds

3 baths

2,040 sq ft

Condo

3004 EASTVIEW DR 105, CARMEL, NY, 10512

Community: Overlook

Overlook

2031 SUMMIT LOOP 89, CARMEL, NY, 10512, Carmel, NY 10512

$789,000

2 beds

2 baths

1,948 sq ft

Condo

2031 SUMMIT LOOP 89, CARMEL, NY, 10512

Community: Overlook

Greenwood Village

135 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$139,999

2 beds

1 baths

938 sq ft

House

135 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

The Vineyards at Mount Sinai

59 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$1,075,000

2 beds

4 baths

1,982 sq ft

Condo

59 FARM ACRE CIR, BROOKHAVEN, NY, 11766

Community: The Vineyards at Mount Sinai

Regency at Fishkill

323 REGENCY DR 323, FISHKILL, NY, 12524, Fishkill, NY 12524

$485,000

1 beds

2 baths

1,450 sq ft

House

323 REGENCY DR 323, FISHKILL, NY, 12524

Condo

421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Questions? Call us: (959) 214-4386

Leisure Village

260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$259,990

1 beds

1 baths

684 sq ft

Condo

260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Meadow Brook Estates

312 SPRUCE HILL DR 312, OXFORD, CT, 0647..., Oxford, CT 06478

$529,900

2 beds

3 baths

1,564 sq ft

Condo

312 SPRUCE HILL DR 312, OXFORD, CT, 0647...

Community: Meadow Brook Estates

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

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

141 communities near Middlebury

244 homes near Middlebury

2 beds

3 baths

2,823 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

3 beds

3 baths

2,455 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

3 baths

1,404 sq ft

3 beds

3 baths

2,047 sq ft

Condo

2 beds

3 baths

Condo

2 beds

2 baths

1,315 sq ft

Condo

3 beds

3 baths

2,107 sq ft

Condo

1 beds

1 baths

750 sq ft

Condo

2 beds

3 baths

2,500 sq ft

Condo

2 beds

3 baths

1,550 sq ft

Condo

2 beds

2 baths

1,867 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,358 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Condo

3 beds

3 baths

2,455 sq ft