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

142 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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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

3 rating (2 reviews)

Heritage Hills

- $800ks

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

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

Questions? Call us: (959) 214-4386

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

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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 Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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+ communities in Middlebury? 55places can help!

Questions? Call us: (959) 214-4386

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 homes

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 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+ communities in Middlebury? 55places can help!

Questions? Call us: (959) 214-4386

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes

Eagles Walk at East Quogu...

$300ks - $400ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

New Construction | 55+ age-restricted | Built 2017 - present | 660 homes

The Hollows at Blue Hill

$500ks - $700ks

The Hollows at Blue Hill, Pearl River, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

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

Questions? Call us: (959) 214-4386

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 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

1 2 3...4

New The Village at Oxford Greens

505 TRADITIONS CT 505, OXFORD, CT, 06478, Oxford, CT 06478

$775,000

3 beds

3 baths

2,652 sq ft

Condo

505 TRADITIONS CT 505, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Stoneleigh Woods at Riverhead

47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$699,000

2 beds

3 baths

1,942 sq ft

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

New Heritage Hills

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

$875,000

3 beds

2 baths

1,909 sq ft

Condo

415 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

New Meadowbrook Pointe Athletic Club & Spa

401 PACING WAY 4101, HEMPSTEAD, NY, 1159..., Hempstead, NY 11590

$875,000

2 beds

2 baths

1,353 sq ft

Condo

401 PACING WAY 4101, HEMPSTEAD, NY, 1159...

Community: Meadowbrook Pointe Athletic Club & Spa

New Baldwin Station

69 JASMINE CIR 69, MILFORD, CT, 06461, Milford, CT 06461

$820,000

2 beds

3 baths

2,820 sq ft

Condo

69 JASMINE CIR 69, MILFORD, CT, 06461

Community: Baldwin Station

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

Questions? Call us: (959) 214-4386

New Westhampton Pines

49 SAMANTHA CIR 49, SOUTHAMPTON, NY, 119..., Southampton, NY 11977

$999,000

2 beds

2 baths

1,944 sq ft

Condo

49 SAMANTHA CIR 49, SOUTHAMPTON, NY, 119...

Community: Westhampton Pines

New Overlook

2084 SUMMIT LOOP 77, CARMEL, NY, 10512, Carmel, NY 10512

$779,000

2 beds

3 baths

2,214 sq ft

Condo

2084 SUMMIT LOOP 77, CARMEL, NY, 10512

Community: Overlook

New Stoneleigh Woods at Riverhead

1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$515,000

2 beds

3 baths

1,350 sq ft

Condo

1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190...

Community: Stoneleigh Woods at Riverhead

New Oronoque Village

664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

1,438 sq ft

664 OSAGE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New The Greens at Half Hollow

398 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,599,999

2 beds

2 baths

2,525 sq ft

Condo

398 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Oronoque Village

543 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$585,000

1 beds

3 baths

1,426 sq ft

Condo

543 N TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New Encore at Lake Grove

176 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$609,000

2 beds

2 baths

1,429 sq ft

Condo

176 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

New Regency at Prospect

196 SYCAMORE DR 196, PROSPECT, CT, 06712, Prospect, CT 06712

$307,127

3 beds

2 baths

1,500 sq ft

Condo

196 SYCAMORE DR 196, PROSPECT, CT, 06712

Community: Regency at Prospect

New The Seasons at Elwood

244 FALL CT, HUNTINGTON, NY, 11731, Huntington, NY 11731

$1,375,000

2 beds

3 baths

2,256 sq ft

Condo

244 FALL CT, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

New Founders Ridge

11 WEBSTER LN 6, MIDDLETOWN, CT, 06457, Middletown, CT 06457

$599,900

3 beds

3 baths

1,579 sq ft

11 WEBSTER LN 6, MIDDLETOWN, CT, 06457

Community: Founders Ridge

New Heritage Village

916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$390,000

2 beds

2 baths

1,432 sq ft

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (959) 214-4386

New Oronoque Village

96 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$469,000

2 beds

3 baths

1,438 sq ft

Condo

96 SEMINOLE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Leisure Knoll

1 AVON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$489,999

2 beds

2 baths

1,070 sq ft

Condo

1 AVON CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Snug Harbor

47 HARBOR N, BABYLON, NY, 11701, Babylon, NY 11701

$549,999

1 beds

1 baths

806 sq ft

Condo

47 HARBOR N, BABYLON, NY, 11701

Community: Snug Harbor

New Leisure Village

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$349,000

2 beds

1 baths

1,085 sq ft

Condo

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Setauket Meadows

100 COVE LN 100, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$769,000

2 beds

3 baths

1,820 sq ft

Condo

100 COVE LN 100, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

New Oronoque Village

315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$549,000

2 beds

3 baths

1,434 sq ft

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Leisure Village

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ..., Brookhaven, NY 11961

$299,000

2 beds

1 baths

875 sq ft

Condo

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ...

Community: Leisure Village

New Heritage Village

14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$269,000

2 beds

2 baths

1,000 sq ft

Condo

14 HERITAGE CIR B, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Manors at The Colony Preserve

17 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967

$559,000

2 beds

2 baths

1,557 sq ft

Condo

17 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

New Leisure Knoll

541 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$529,000

3 beds

2 baths

1,412 sq ft

Condo

541 STRATFORD LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Heritage Village

847 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$309,000

3 beds

2 baths

1,716 sq ft

Condo

847 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

New Oronoque Village

132 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$470,000

1 beds

3 baths

1,426 sq ft

Condo

132 BISON LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Heritage Hills

969 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$490,000

1 beds

2 baths

967 sq ft

Condo

969 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

648 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$405,000

2 beds

2 baths

1,432 sq ft

Condo

648 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Gardens of Wilbraham

56 CHERRY DR 56, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$419,000

2 beds

2 baths

1,213 sq ft

Condo

56 CHERRY DR 56, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

The Greens at Half Hollow

163 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,599,000

2 beds

2 baths

2,500 sq ft

Condo

163 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Fairfield at St. James

309 FLAIR DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$454,000

1 beds

2 baths

983 sq ft

Condo

309 FLAIR DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

The Seasons at Seaford

107 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783

$799,000

2 beds

2 baths

1,408 sq ft

Condo

107 SPRING DR, HEMPSTEAD, NY, 11783

Community: The Seasons at Seaford

The Greens at Half Hollow

385 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,299,999

3 beds

3 baths

3,060 sq ft

House

385 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Foxwood Village

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$449,000

3 beds

2 baths

1,753 sq ft

House

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933

Community: Foxwood Village

The Seasons at Seaford

13 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783

$799,000

2 beds

2 baths

1,408 sq ft

Condo

13 SPRING DR, HEMPSTEAD, NY, 11783

Community: The Seasons at Seaford

Leisure Village

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

$335,000

2 beds

1 baths

875 sq ft

Condo

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

Community: Leisure Village

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

Questions? Call us: (959) 214-4386

The Seasons at East Meadow

106 SPRING DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$675,000

2 beds

3 baths

974 sq ft

Condo

106 SPRING DR, HEMPSTEAD, NY, 11554

Community: The Seasons at East Meadow

Fairfield at St. James

607 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$529,000

1 beds

2 baths

950 sq ft

Condo

607 CABOT CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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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142 communities

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

142 communities near Middlebury

275 homes near Middlebury

3 beds

3 baths

2,652 sq ft

Condo

2 beds

3 baths

1,942 sq ft

Condo

3 beds

2 baths

1,909 sq ft

Condo

2 beds

2 baths

1,353 sq ft

Condo

2 beds

3 baths

2,820 sq ft

Condo

2 beds

2 baths

1,944 sq ft

Condo

2 beds

3 baths

2,214 sq ft

Condo

2 beds

3 baths

1,350 sq ft

Condo

1 beds

3 baths

1,438 sq ft

2 beds

2 baths

2,525 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,429 sq ft

Condo

3 beds

2 baths

1,500 sq ft

Condo

2 beds

3 baths

2,256 sq ft

Condo

3 beds

3 baths

1,579 sq ft

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,070 sq ft

Condo

1 beds

1 baths

806 sq ft

Condo

2 beds

1 baths

1,085 sq ft