Middlebury, CT 55+ active adult communities & homes for sale - Page 4

145 communities near Middlebury

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Wolfe Landing

$500ks - $600ks

Wolfe Landing, Clarkstown, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 43 homes

Eden Park

$500ks - $600ks

Eden Park, Clarkstown, NY

Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes

The Views at Pomona

$200ks - $400ks

The Views at Pomona, Pomona, NY

Resale Only | 55+ age-restricted | Built 2011 - 2011 | 56 homes

Windmill Gate

$300ks - $400ks

Windmill Gate, Oakdale, NY

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

The Vineyards at Miller P...

$500ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 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

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

Knickerbocker Bay Club

$700ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 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 Residences at Butterf...

$500ks - $600ks

The Residences at Butterf..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes

Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

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

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

Meadowbrooke Pointe East ...

$500ks - $600ks

Meadowbrooke Pointe East ..., East Meadow, NY

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

Hidden Harbor Estates

$500ks - $600ks

Hidden Harbor Estates, Copiague, NY

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

The Vineyards at Mount Si...

$800ks - $1Ms

The Vineyards at Mount Si..., Mount Sinai, NY

New Construction | 55+ age-restricted | Built 2020 - present | 91 homes

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

Questions? Call us: (959) 214-4386

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

Breton Hills

$500ks

Breton Hills, Glen Cove, 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

5 rating (1 reviews)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes

The Bridges at Oxford Gre...

$600ks

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

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

Rivington Landing

$500ks

Rivington Landing, Danbury, CT

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

Regency at Pearl River

$800ks - $1Ms

Regency at Pearl River, Pearl River, NY

New Construction | 55+ age-restricted | Built 2026 - present | 36 homes

1 2 3 4

Greenwood Village

201 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$250,000

2 beds

2 baths

1,078 sq ft

Condo

201 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Jefferson Village

39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$349,000

2 beds

2 baths

1,000 sq ft

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

New Heritage Village

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

$339,900

2 beds

2 baths

1,432 sq ft

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

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

$420,000

2 beds

2 baths

1,432 sq ft

Condo

778 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Seasons at East Meadow

142 SPRING DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$725,000

2 beds

3 baths

974 sq ft

Condo

142 SPRING DR, HEMPSTEAD, NY, 11554

Community: The Seasons at East Meadow

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

Questions? Call us: (959) 214-4386

New Heritage Village

176 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$274,900

2 beds

2 baths

1,044 sq ft

Condo

176 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Dutchgate

1128 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580

$469,888

1 beds

2 baths

941 sq ft

Condo

1128 WILLOW LN, HEMPSTEAD, NY, 11580

Community: Dutchgate

New Dutchgate

101 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580

$540,000

2 beds

2 baths

941 sq ft

Condo

101 WILLOW LN, HEMPSTEAD, NY, 11580

Community: Dutchgate

New Glassbury Court at Hunterbrook

2329 DEPEYSTER DR, YORKTOWN, NY, 10567, Yorktown, NY 10567

$975,000

2 beds

4 baths

3,500 sq ft

Condo

2329 DEPEYSTER DR, YORKTOWN, NY, 10567

Community: Glassbury Court at Hunterbrook

New Heritage Hills

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

$789,000

2 beds

3 baths

1,531 sq ft

Condo

812 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Hills

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

$650,000

3 beds

3 baths

1,700 sq ft

Condo

104 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Hills

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

$619,222

2 beds

2 baths

1,484 sq ft

Condo

364 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Leisure Village

387 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,767 sq ft

Condo

387 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...

Community: Leisure Village

New Glenwood Village

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$335,000

2 beds

2 baths

1,248 sq ft

Manufactured Home

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1...

Community: Glenwood Village

New Glenwood Village

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

$410,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

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

Community: Glenwood Village

New Meadow Brook Estates

802 SAGE HILL DR 802, OXFORD, CT, 06478, Oxford, CT 06478

$675,000

2 beds

3 baths

2,258 sq ft

Condo

802 SAGE HILL DR 802, OXFORD, CT, 06478

Community: Meadow Brook Estates

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

Questions? Call us: (959) 214-4386

New Leisure Knoll

346 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$419,000

2 beds

1 baths

1,050 sq ft

Condo

346 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Sunken Pond Estates

3102 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$525,000

2 beds

2 baths

1,587 sq ft

Condo

3102 AMEN COR, RIVERHEAD, NY, 11901

Community: Sunken Pond Estates

New Rivington

71 WARRINGTON ROUND 71, DANBURY, CT, 068..., Danbury, CT 06810

$669,900

3 beds

3 baths

1,704 sq ft

Condo

71 WARRINGTON ROUND 71, DANBURY, CT, 068...

Community: Rivington

New Rivington

3 HUMBER HILL RD 3, DANBURY, CT, 06810, Danbury, CT 06810

$774,900

3 beds

4 baths

2,120 sq ft

Condo

3 HUMBER HILL RD 3, DANBURY, CT, 06810

Community: Rivington

Heritage Hills

$839,000

3 beds

2 baths

1,793 sq ft

Condo

350 HERITAGE HILLS DR C, SOMERS, NY, 105...

Community: Heritage Hills

Leisure Knoll

177 CANTERBURY DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$379,900

2 beds

1 baths

1,116 sq ft

Condo

177 CANTERBURY DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Sunrise Village

152 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$519,990

2 beds

2 baths

1,230 sq ft

Condo

152 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

The Greens at Half Hollow

1067 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$699,000

2 beds

2 baths

1,150 sq ft

Condo

1067 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Jefferson Village

38 SUSSEX DR A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$499,000

2 beds

1 baths

935 sq ft

Condo

38 SUSSEX DR A, YORKTOWN, NY, 10598

Community: Jefferson Village

Strathmore Gate East

46 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$429,999

2 beds

2 baths

1,112 sq ft

House

46 FORGE LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

Foxwood Village

1407 MIDDLE RD 271, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$465,000

3 beds

2 baths

1,792 sq ft

Manufactured Home

1407 MIDDLE RD 271, RIVERHEAD, NY, 11933

Community: Foxwood Village

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

Questions? Call us: (959) 214-4386

The Greens at Half Hollow

581 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,199,900

2 beds

3 baths

1,941 sq ft

Condo

581 VERONA DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Granite Woods

35 NUTMEG RD B5, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$250,000

2 beds

1 baths

890 sq ft

Condo

35 NUTMEG RD B5, MIDDLEBURY, CT, 06762

Community: Granite Woods

Kensington Estates

46 PLAINVIEW RD, OYSTER BAY, NY, 11797, Oyster Bay, NY 11797

$2,049,888

6 beds

5 baths

4,333 sq ft

House

46 PLAINVIEW RD, OYSTER BAY, NY, 11797

Community: Kensington Estates

Greenwood Village

33 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$225,000

2 beds

2 baths

1,134 sq ft

House

33 DOGWOOD LN, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Regency at Fishkill

231 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$489,900

1 beds

2 baths

1,499 sq ft

Condo

231 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Windcrest East

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933

$799,000

3 beds

3 baths

2,620 sq ft

Condo

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...

Community: Windcrest East

Windcrest East

29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933

$799,990

3 beds

3 baths

2,531 sq ft

Condo

29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...

Community: Windcrest East

Leisure Glen

9 AMAGANSETT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$519,900

2 beds

2 baths

1,476 sq ft

Condo

9 AMAGANSETT CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Heritage Hills

$849,000

3 beds

2 baths

1,909 sq ft

Condo

763 HERITAGE HILLS DR C, SOMERS, NY, 105...

Community: Heritage Hills

Long Hill Village

48 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611

$499,900

2 beds

2 baths

1,070 sq ft

Condo

48 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

Meadow Brook Estates

130 MEADOW BROOK RD 130, OXFORD, CT, 064..., Oxford, CT 06478

$599,000

2 beds

3 baths

1,920 sq ft

Condo

130 MEADOW BROOK RD 130, OXFORD, CT, 064...

Community: Meadow Brook Estates

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

Questions? Call us: (959) 214-4386

Jefferson Village

160 CARRIAGE CT D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$359,000

1 beds

1 baths

953 sq ft

Condo

160 CARRIAGE CT D, YORKTOWN, NY, 10598

Community: Jefferson Village

The Club at Melville

212 CLUBHOUSE CIR 212, HUNTINGTON, NY, 1..., Huntington, NY 11747

$584,000

2 beds

2 baths

1,226 sq ft

Condo

212 CLUBHOUSE CIR 212, HUNTINGTON, NY, 1...

Community: The Club at Melville

Frequently Asked Questions

What size 55+ communities are there in Middlebury?

Of the 2 55+ communities in Middlebury, 2 are for sale and none are rentals. By size, 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 894 days. The average price of homes for sale in these communities is approximately $509,975, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Benson Woods average around $629,000, while homes in Granite Woods average around $390,950.

Want more information about active adult communities around Middlebury?

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145 communities

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Middlebury, CT 55+ active adult communities & homes for sale - Page 4

145 communities near Middlebury

325 homes near Middlebury

2 beds

2 baths

1,078 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

974 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

1 beds

2 baths

941 sq ft

Condo

2 beds

2 baths

941 sq ft

Condo

2 beds

4 baths

3,500 sq ft

Condo

2 beds

3 baths

1,531 sq ft

Condo

3 beds

3 baths

1,700 sq ft

Condo

2 beds

2 baths

1,484 sq ft

Condo

2 beds

2 baths

1,767 sq ft

Condo

2 beds

2 baths

1,248 sq ft

Manufactured Home

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

3 baths

2,258 sq ft

Condo

2 beds

1 baths

1,050 sq ft

Condo

2 beds

2 baths

1,587 sq ft

Condo

3 beds

3 baths

1,704 sq ft

Condo

3 beds