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

126 communities near Middletown

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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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

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 Middletown? 55places can help!

Questions? Call us: (860) 854-8527

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

The Manors at The Colony ...

$300ks - $400ks

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

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

New Construction | 55+ age-restricted | Built 2023 - present | 142 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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

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

Questions? Call us: (860) 854-8527

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

New Construction | 55+ age-restricted | Built 2019 - present | 146 homes

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes

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

Questions? Call us: (860) 854-8527

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 homes

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$400ks - $500ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes

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

Questions? Call us: (860) 854-8527

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

4 rating (1 reviews)

Vineyards at Blue Point

$500ks - $700ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

1 2 3...4

New Heritage Village

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

$386,000

3 beds

2 baths

1,716 sq ft

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949

$245,000

2 beds

2 baths

1,130 sq ft

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...

Community: Greenwood Village

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

New Heritage Village

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

$374,500

2 beds

2 baths

1,398 sq ft

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Autumn Fields

37 QUAIL HOLW 37, ENFIELD, CT, 06082, Enfield, CT 06082

$419,000

2 beds

3 baths

1,679 sq ft

Condo

37 QUAIL HOLW 37, ENFIELD, CT, 06082

Community: Autumn Fields

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

Questions? Call us: (860) 854-8527

New Leisure Glen

276 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$585,000

2 beds

2 baths

1,666 sq ft

Condo

276 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Glenwood Village

1661 OLD COUNTRY RD 254, RIVERHEAD, NY, ..., Riverhead, NY 11901

$185,000

2 beds

2 baths

1,036 sq ft

Manufactured Home

1661 OLD COUNTRY RD 254, RIVERHEAD, NY, ...

Community: Glenwood Village

New The Waterways at Moriches

533 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$499,000

2 beds

2 baths

1,771 sq ft

Condo

533 HIGHLAND CT, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

New Greenwood Village

28 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$149,999

2 beds

2 baths

938 sq ft

Condo

28 GREENWOOD BLVD, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Rivington

215 CENTER MEADOW LN 215, DANBURY, CT, 0..., Danbury, CT 06810

$499,000

2 beds

2 baths

1,258 sq ft

Condo

215 CENTER MEADOW LN 215, DANBURY, CT, 0...

Community: Rivington

New The Waterways at Moriches

416 LINDSAY LN, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$599,999

2 beds

2 baths

1,440 sq ft

Condo

416 LINDSAY LN, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

New Heritage Village

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

$245,000

1 beds

1 baths

928 sq ft

Condo

4 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Leisure Village

404 WOODBRIDGE DR D, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$369,000

2 beds

1 baths

874 sq ft

Condo

404 WOODBRIDGE DR D, BROOKHAVEN, NY, 119...

Community: Leisure Village

New The Seasons at Salisbury

148 FIRESIDE LN 148, HOLDEN, MA, 01520, Holden, MA 01520

$700,000

2 beds

3 baths

2,601 sq ft

Condo

148 FIRESIDE LN 148, HOLDEN, MA, 01520

Community: The Seasons at Salisbury

New Leisure Knoll

7 AVON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$479,999

2 beds

2 baths

1,070 sq ft

Condo

7 AVON CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Leisure Knoll

545 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$429,000

2 beds

2 baths

1,172 sq ft

Condo

545 STRATFORD LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (860) 854-8527

New Strathmore Gate East

15 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$299,990

1 beds

1 baths

750 sq ft

Condo

15 FORGE LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

New Leisure Knoll

254 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$450,000

2 beds

1 baths

1,020 sq ft

Condo

254 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Regency at Woodbridge

27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525

$599,900

3 beds

3 baths

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525

Community: Regency at Woodbridge

New Fairfield at St. James

708 W CABOT CT 708, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$515,000

1 beds

1 baths

886 sq ft

Condo

708 W CABOT CT 708, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Fairview at Oxford Greens

1159 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478

$799,900

2 beds

3 baths

1,955 sq ft

Condo

1159 ST ANDREWS DR 90, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New The Village at Oxford Greens

$799,900

2 beds

3 baths

1,955 sq ft

Condo

1159 ST ANDREWS DR 90, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Fairfield at St. James

1006 CABOT PATH, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$399,000

1 beds

2 baths

1,003 sq ft

Condo

1006 CABOT PATH, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Encore at Lake Grove

14 CONCERTO DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$970,000

2 beds

3 baths

1,986 sq ft

Condo

14 CONCERTO DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

New The Greens at Half Hollow

1116 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$719,999

2 beds

2 baths

1,200 sq ft

Condo

1116 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Fieldstone Village

101 SUNRISE HILL CIR 101, ORANGE, CT, 06..., Orange, CT 06477

$875,000

2 beds

3 baths

2,350 sq ft

Condo

101 SUNRISE HILL CIR 101, ORANGE, CT, 06...

Community: Fieldstone Village

New Sonoma Woods

52 SONOMA LN 52, MIDDLETOWN, CT, 06457, Middletown, CT 06457

$559,900

3 beds

3 baths

1,996 sq ft

Condo

52 SONOMA LN 52, MIDDLETOWN, CT, 06457

Community: Sonoma Woods

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

Questions? Call us: (860) 854-8527

New Glenwood Village

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ..., Riverhead, NY 11901

$375,000

3 beds

2 baths

1,317 sq ft

Manufactured Home

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ...

Community: Glenwood Village

New Harmony Place

21 FIDELITY DR 73, RUTLAND, MA, 01543, Rutland, MA 01543

$489,000

2 beds

2 baths

1,582 sq ft

Condo

21 FIDELITY DR 73, RUTLAND, MA, 01543

Community: Harmony Place

New Harmony Place

23 FIDELITY DR 74, RUTLAND, MA, 01543, Rutland, MA 01543

$489,000

2 beds

2 baths

1,582 sq ft

Condo

23 FIDELITY DR 74, RUTLAND, MA, 01543

Community: Harmony Place

New Harmony Place

19 FIDELITY DR 72, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

19 FIDELITY DR 72, RUTLAND, MA, 01543

Community: Harmony Place

New Harmony Place

17 FIDELITY DR 71, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

17 FIDELITY DR 71, RUTLAND, MA, 01543

Community: Harmony Place

Leisure Village

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$349,000

2 beds

1 baths

875 sq ft

Condo

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Vineyards at Brookfield

61 AVERY DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$695,000

2 beds

2 baths

1,557 sq ft

Condo

61 AVERY DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Brookfield

Woodridge Strathmore Terrace

18 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$525,000

2 beds

2 baths

1,240 sq ft

Condo

18 CHIPPENDALE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Leisure Glen

29 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,900

2 beds

2 baths

1,314 sq ft

Condo

29 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Spring Lake Village

142 TIMBER RDG 142, SOUTHINGTON, CT, 064..., Southington, CT 06489

$359,900

2 beds

3 baths

1,601 sq ft

Condo

142 TIMBER RDG 142, SOUTHINGTON, CT, 064...

Community: Spring Lake Village

The Greens at Half Hollow

859 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$799,000

2 beds

2 baths

1,197 sq ft

Condo

859 VERONA DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

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

Questions? Call us: (860) 854-8527

Heritage Village

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

$165,000

2 beds

2 baths

1,076 sq ft

Condo

399 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Sunrise Village

40 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$565,000

2 beds

2 baths

1,230 sq ft

Condo

40 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

Frequently Asked Questions

What size 55+ communities are there in Middletown?

In Middletown, there are no large communities, no medium communities, and 3 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Middletown?

The smallest 55+ communities in Middletown has 25 homes, the largest has 75 homes, and the average communities consists of 56 homes.

Are there new 55+ homes available in Middletown?

Yes, there are new 55+ homes available in Middletown. The most recent communities started in Middletown include Founders Ridge, Bartlett Hollow, Sonoma Woods. There are also 2 communities in Middletown that offer new construction homes, including Founders Ridge, Bartlett Hollow.

Are there gated 55+ communities in Middletown?

Yes, there is gated 55+ communities in Middletown. Approximately 33.3% of 55+ communities in the area are gated. For instance, Bartlett Hollow is a gated communities with 25 homes.

How long do listings in 55+ communities in Middletown typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Middletown stay on the market for around 539 days. The average price of homes for sale in these communities is approximately $555,135, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Sonoma Woods average around $599,900, while homes in Bartlett Hollow average around $579,900.

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126 communities

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

126 communities near Middletown

238 homes near Middletown

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,130 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

1,679 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,036 sq ft

Manufactured Home

2 beds

2 baths

1,771 sq ft

Condo

2 beds

2 baths

938 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,440 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

1 baths

874 sq ft

Condo

2 beds

3 baths

2,601 sq ft

Condo

2 beds

2 baths

1,070 sq ft

Condo

2 beds

2 baths

1,172 sq ft

Condo

1 beds

1 baths

750 sq ft

Condo

2 beds

1 baths

1,020 sq ft

Condo

3 beds

3 baths

Condo

1 beds

1 baths