Middletown, CT 55+ active adult communities & homes for sale - Page 3

126 communities near Middletown

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The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

Windmill Gate

$300ks - $400ks

Windmill Gate, Oakdale, NY

Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 homes

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

The Club at Melville

$500ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 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

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

Questions? Call us: (860) 854-8527

The Bel Aire at East Mead...

$300ks - $400ks

The Bel Aire at East Mead..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 95 homes

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes

Meadowbrooke Pointe East ...

$500ks - $600ks

Meadowbrooke Pointe East ..., East Meadow, NY

New Construction | 62+ age-restricted | Built 2019 - present | 104 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.

Hidden Harbor Estates

$500ks - $600ks

Hidden Harbor Estates, Copiague, NY

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

The Pines at Bohemia

$400ks - $500ks

The Pines at Bohemia, Bohemia, NY

New Construction | 55+ age-restricted | Built 2019 - present | 20 homes

The Polo Club at Islandia

$600ks - $700ks

The Polo Club at Islandia, Islandia, NY

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

Stratford Park

$600ks - $800ks

Stratford Park, Melville, NY

Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

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

Questions? Call us: (860) 854-8527

The Bridges at Oxford Gre...

$600ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

The Seasons at East North...

$700ks

The Seasons at East North..., East Northport, NY

New Construction | 55+ age-restricted | Built 2023 - present | 190 homes

Rivington Landing

$500ks

Rivington Landing, Danbury, CT

New Construction | Age-targeted | Built 2025 - 2026 | 25 homes

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

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

Questions? Call us: (860) 854-8527

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Chimney Hill

$500ks - $700ks

Chimney Hill, Farmington, CT

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes

Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

New Construction | 55+ age-restricted | Built 2014 - present | 16 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

77 Sunset Lane

$400ks - $700ks

77 Sunset Lane, Ridgefield, CT

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes

Bartlett Hollow

$200ks - $400ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

Autumn Estates

$500ks - $600ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

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

Questions? Call us: (860) 854-8527

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

1 2 3...4

New 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 Fairfield at St. James

703 DREW DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$429,999

1 beds

1 baths

752 sq ft

Condo

703 DREW DR, SMITHTOWN, NY, 11780

253 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (860) 854-8527

New Leisure Knoll

183 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$415,000

2 beds

1 baths

960 sq ft

Condo

183 KINGSTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Regency at Prospect

6 LILAC LN 6, PROSPECT, CT, 06712, Prospect, CT 06712

$474,900

2 beds

3 baths

1,552 sq ft

Condo

6 LILAC LN 6, PROSPECT, CT, 06712

Community: Regency at Prospect

New Country Pointe Plainview

52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803

$1,749,000

2 beds

3 baths

1,750 sq ft

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...

Community: Country Pointe Plainview

New Leisure Village

200 NEWCASTLE CT E, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$255,000

1 beds

1 baths

684 sq ft

Condo

200 NEWCASTLE CT E, BROOKHAVEN, NY, 1196...

Community: Leisure Village

New Rivington

11 ORWICH CT 11, DANBURY, CT, 06810, Danbury, CT 06810

$649,900

3 beds

4 baths

1,572 sq ft

Condo

11 ORWICH CT 11, DANBURY, CT, 06810

Community: Rivington

New Windcrest East

116 GOLDEN SPRUCE DR, RIVERHEAD, NY, 119..., Riverhead, NY 11933

$774,900

3 beds

3 baths

2,200 sq ft

House

116 GOLDEN SPRUCE DR, RIVERHEAD, NY, 119...

Community: Windcrest East

New Woodridge Strathmore Terrace

32 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$549,990

2 beds

2 baths

Condo

527 PUTTING GREEN LN 527, OXFORD, CT, 06...

Community: The Village at Oxford Greens

New The Gardens of Wilbraham

77 CHERRY DR 77, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$439,900

2 beds

2 baths

1,586 sq ft

Condo

77 CHERRY DR 77, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

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

Questions? Call us: (860) 854-8527

New The Greens at Half Hollow

698 BALFOUR PL, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,099,000

2 beds

3 baths

1,941 sq ft

Condo

698 BALFOUR PL, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New The Greens at Half Hollow

1165 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$749,000

2 beds

2 baths

1,159 sq ft

Condo

1165 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Regency at Prospect

10 ASH LN 10, PROSPECT, CT, 06712, Prospect, CT 06712

$539,000

2 beds

3 baths

1,928 sq ft

Condo

10 ASH LN 10, PROSPECT, CT, 06712

Community: Regency at Prospect

New Oronoque Village

493 PAWNEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$425,000

1 beds

3 baths

1,175 sq ft

Condo

493 PAWNEE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Newtown Woods

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064..., Newtown, CT 06470

$500,000

2 beds

2 baths

1,483 sq ft

Condo

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064...

Community: Newtown Woods

New Kensington Estates

238 COACH DR 56, OYSTER BAY, NY, 11797, Oyster Bay, NY 11797

$2,100,000

3 beds

4 baths

2,662 sq ft

Condo

238 COACH DR 56, OYSTER BAY, NY, 11797

Community: Kensington Estates

Heritage Village

18 HERITAGE CRST D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$474,981

3 beds

2 baths

1,735 sq ft

Condo

18 HERITAGE CRST D, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairview at Oxford Greens

1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478

$713,775

2 beds

3 baths

2,536 sq ft

Condo

Condo

59 CHERRY CIR 59, PROSPECT, CT, 06712

Community: Regency at Prospect

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

Questions? Call us: (860) 854-8527

Harbor View Estates

206 ANCHOR CT, BABYLON, NY, 11726, Babylon, NY 11726

$599,000

2 beds

2 baths

1,200 sq ft

Condo

206 ANCHOR CT, BABYLON, NY, 11726

Community: Harbor View Estates

South Pond Village

174 THISTLE POND DR 174, BLOOMFIELD, CT,..., Bloomfield, CT 06002

$449,900

2 beds

2 baths

1,535 sq ft

Condo

174 THISTLE POND DR 174, BLOOMFIELD, CT,...

Community: South Pond 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 520 days. The average price of homes for sale in these communities is approximately $556,595, 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 - Page 3

126 communities near Middletown

216 homes near Middletown

2 beds

2 baths

1,624 sq ft

Manufactured Home

1 beds

1 baths

752 sq ft

Condo

2 beds

4 baths

2,560 sq ft

Condo

2 beds

2 baths

1,413 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

1 baths

960 sq ft

Condo

2 beds

3 baths

1,552 sq ft

Condo

2 beds

3 baths

1,750 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

3 beds

4 baths

1,572 sq ft

Condo

3 beds

3 baths

2,200 sq ft

House

2 beds

2 baths

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,652 sq ft

Condo

3 beds

3 baths

2,008 sq ft

Condo

2 beds

2 baths

1,586 sq ft

Condo

2 beds

3 baths

1,941 sq ft

Condo

2 beds

2 baths

1,159 sq ft

Condo

2 beds

3 baths

1,928 sq ft

Condo

1 beds

3 baths