Middletown, CT 55+ active adult communities & homes for sale - Page 2

249 homes 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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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

Questions? Call us: (860) 854-8527

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

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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

Questions? Call us: (860) 854-8527

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

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

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

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

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

New and Resale | 55+ age-restricted | Built 2006 - present | 125 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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

The Cottages at Wire Mill

$1Ms

The Cottages at Wire Mill, Stamford, CT

New Construction | 55+ age-restricted | Built 2026 - present | 9 homes

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

Questions? Call us: (860) 854-8527

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

89 ENFIELD CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 854-8527

Village Vistas

35 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777

$1,300,000

3 beds

4 baths

3,000 sq ft

Condo

35 THERESA LN, BROOKHAVEN, NY, 11777

Community: Village Vistas

The Village at Oxford Greens

171 COUNTRY CLUB DR 171, OXFORD, CT, 064..., Oxford, CT 06478

$775,000

3 beds

3 baths

2,750 sq ft

Condo

171 COUNTRY CLUB DR 171, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Oronoque Village

621 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

2,325 sq ft

Condo

621 ONONDAGA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Westhampton Pines

79 SAMANTHA CIR, SOUTHAMPTON, NY, 11977, Southampton, NY 11977

$1,295,000

2 beds

3 baths

2,440 sq ft

Condo

79 SAMANTHA CIR, SOUTHAMPTON, NY, 11977

Community: Westhampton Pines

Leisure Glen

19 SAYVILLE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$615,000

2 beds

2 baths

1,666 sq ft

Condo

19 SAYVILLE CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Hopmeadow Place

1 W ST 215, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,477 sq ft

Condo

1 W ST 215, SIMSBURY, CT, 06070

Community: Hopmeadow Place

Glenwood Village

1661 OLD COUNTRY RD 258, RIVERHEAD, NY, ..., Riverhead, NY 11901

$389,999

2 beds

2 baths

1,310 sq ft

House

1661 OLD COUNTRY RD 258, RIVERHEAD, NY, ...

Community: Glenwood Village

The Gardens of Wilbraham

23 CHERRY DR 23, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$399,900

1 beds

2 baths

1,218 sq ft

Condo

23 CHERRY DR 23, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

The Summit at Bethel

78 GREAT HILL DR 78, BETHEL, CT, 06801, Bethel, CT 06801

$700,000

3 beds

4 baths

Condo

78 GREAT HILL DR 78, BETHEL, CT, 06801

Community: The Summit at Bethel

Meadow Brook Estates

169 MEADOW BROOK RD 169, OXFORD, CT, 064..., Oxford, CT 06478

$625,000

2 beds

3 baths

1,821 sq ft

Condo

169 MEADOW BROOK RD 169, OXFORD, CT, 064...

Community: Meadow Brook Estates

Spring Lake Village

116 TIMBER RDG, SOUTHINGTON, CT, 06489, Southington, CT 06489

$304,900

2 beds

2 baths

1,128 sq ft

Condo

116 TIMBER RDG, SOUTHINGTON, CT, 06489

Condo

416 LINDSAY LN, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

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

Questions? Call us: (860) 854-8527

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

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

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

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

Glenwood Village

1661 OLD COUNTRY RD 476, RIVERHEAD, NY, ..., Riverhead, NY 11901

$349,000

2 beds

2 baths

960 sq ft

Manufactured Home

1661 OLD COUNTRY RD 476, RIVERHEAD, NY, ...

Community: Glenwood Village

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

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

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

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

Fairview at Oxford Greens

1159 ST ANDREWS DR 80, OXFORD, CT, 06478, Oxford, CT 06478

$799,900

2 beds

3 baths

1,955 sq ft

Condo

1159 ST ANDREWS DR 80, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$799,900

2 beds

3 baths

1,955 sq ft

Condo

1159 ST ANDREWS DR 80, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

Questions? Call us: (860) 854-8527

The Greens at Half Hollow

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

$719,999

2 beds

2 baths

1,100 sq ft

Condo

1116 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

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

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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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249 homes

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Middletown, CT 55+ active adult communities & homes for sale - Page 2

127 communities near Middletown

249 homes near Middletown

2 beds

3 baths

1,750 sq ft

Condo

2 beds

2 baths

1,152 sq ft

Manufactured Home

2 beds

2 baths

1,695 sq ft

Condo

2 beds

3 baths

2,236 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

3 beds

4 baths

3,000 sq ft

Condo

3 beds

3 baths

2,750 sq ft

Condo

1 beds

3 baths

2,325 sq ft

Condo

2 beds

3 baths

2,440 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,477 sq ft

Condo

2 beds

2 baths

1,310 sq ft

House

1 beds

2 baths

1,218 sq ft

Condo

3 beds

4 baths

Condo

2 beds

3 baths

1,821 sq ft

Condo

2 beds

2 baths

1,128 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,620 sq ft

Condo

2 beds

4 baths

3,736 sq ft

Condo

2 beds

2 baths