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

137 communities near Middlebury

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5 rating (1 reviews)

Sunken Pond Estates

$400Ks - $400Ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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)

The Villages at Mount Sin...

$700Ks - $800Ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

No reviews yet

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

5 rating (1 reviews)

Newtown Woods

$400Ks - $500Ks

Newtown Woods, Newtown, CT

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

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Questions? Call us: (959) 214-4386

No reviews yet

Snug Harbor

$600Ks - $700Ks

Snug Harbor, Amityville, NY

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

No reviews yet

Stoneleigh Woods at River...

$400Ks - $600Ks

Stoneleigh Woods at River..., Riverhead, NY

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

No reviews yet

The Coves at Melville

$500Ks - $500Ks

The Coves at Melville, Melville, NY

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

No reviews yet

Strathmore Gate East

$300Ks - $300Ks

Strathmore Gate East, Coram, NY

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

No reviews yet

Beckley Farms

$300Ks - $400Ks

Beckley Farms, Berlin, CT

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

No reviews yet

Regency at Fishkill

$500Ks - $500Ks

Regency at Fishkill, Fishkill, NY

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

No reviews yet

South Pond Village

$200Ks - $400Ks

South Pond Village, Bloomfield, CT

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

No reviews yet

Setauket Meadows

$600Ks - $700Ks

Setauket Meadows, Setauket, NY

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

No reviews yet

The Manors at The Colony ...

$400Ks - $500Ks

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

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

No reviews yet

Vineyards at Brookfield

$600Ks - $600Ks

Vineyards at Brookfield, Center Moriches, NY

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

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

Questions? Call us: (959) 214-4386

No reviews yet

Fieldstone Village

$500Ks - $800Ks

Fieldstone Village, Orange, CT

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

No reviews yet

North Woods of Colchester

$300Ks - $400Ks

North Woods of Colchester, Colchester, CT

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

No reviews yet

The Villas at Narraganset...

$500Ks - $500Ks

The Villas at Narraganset..., Lindenhurst, NY

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

No reviews yet

Village Estates

$500Ks - $500Ks

Village Estates, Amityville, NY

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

No reviews yet

The Seasons at Plainview

$600Ks - $700Ks

The Seasons at Plainview, Plainview, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes

No reviews yet

The Hollows at Blue Hill

$1Ms - $1Ms

The Hollows at Blue Hill, Pearl River, NY

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

No reviews yet

Windcrest East

$600Ks - $600Ks

Windcrest East, Calverton, NY

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

No reviews yet

Fairview at Oxford Greens

$500Ks - $600Ks

Fairview at Oxford Greens, Oxford, CT

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

3.5 rating (2 reviews)

Harvest Pointe

$800Ks - $3Ms

Harvest Pointe, Cutchogue, NY

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

No reviews yet

Newbury Village

$400Ks - $500Ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

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

Questions? Call us: (959) 214-4386

No reviews yet

The Seasons at Seaford

$700Ks - $700Ks

The Seasons at Seaford, Seaford, NY

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

No reviews yet

Windmill Gate

$300Ks - $400Ks

Windmill Gate, Oakdale, NY

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

No reviews yet

Four Seasons at Ridgemont

$800Ks - $1Ms

Four Seasons at Ridgemont, Montvale, NJ

Resale Only | 55+ age-restricted | Built 2011 - 2014 | 108 homes

No reviews yet

The Gardens of Wilbraham

$300Ks - $400Ks

The Gardens of Wilbraham, Wilbraham, MA

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

No reviews yet

Meadowbrooke Pointe East ...

$700Ks - $700Ks

Meadowbrooke Pointe East ..., East Meadow, NY

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

No reviews yet

O'Meara Farm

$400Ks - $400Ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes

No reviews yet

Liberty at Newtown

$300Ks - $400Ks

Liberty at Newtown, Newtown, CT

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

No reviews yet

The Bel Aire at East Mead...

$400Ks - $400Ks

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

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

No reviews yet

Pond Spring Village

$300Ks - $300Ks

Pond Spring Village, Beacon Falls, CT

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

No reviews yet

Vineyards at Moriches

$700Ks - $700Ks

Vineyards at Moriches, Center Moriches, NY

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

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

Questions? Call us: (959) 214-4386

No reviews yet

Founders Village

$500Ks - $500Ks

Founders Village, Southold, NY

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

No reviews yet

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

No reviews yet

Glassbury Court at Cold S...

$700Ks - $700Ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

5 rating (1 reviews)

Paris Square

$400Ks - $700Ks

Paris Square, Northvale, NJ

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

No reviews yet

Castle Heights of Cheshir...

$500Ks - $600Ks

Castle Heights of Cheshir..., Cheshire, CT

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

16 HEARTHSIDE DR, MOUNT SINAI, NY, 11766

Community: Woodridge Strathmore Terrace

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

Questions? Call us: (959) 214-4386

Greenwood Village

77 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$165,000

2 beds

1 baths

1,000 sq ft

Condo

77 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Greenwood Village

22 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949

$141,000

2 beds

2 baths

920 sq ft

Condo

22 LIMETREE DR, MANORVILLE, NY, 11949

Community: Greenwood Village

Dutchgate

812 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580

$480,000

2 beds

2 baths

941 sq ft

Condo

812 WILLOW LN, VALLEY STREAM, NY, 11580

Community: Dutchgate

Heritage Hills

196A HERITAGE HLS # 196A, SOMERS, NY, 10..., Somers, NY 10589

$510,000

2 beds

2 baths

1,427 sq ft

Condo

196A HERITAGE HLS # 196A, SOMERS, NY, 10...

Community: Heritage Hills

Country Pointe Plainview

34203 WINTERBERRY DR, PLAINVIEW, NY, 118..., Plainview, NY 11803

$949,000

2 beds

2 baths

1,335 sq ft

Condo

34203 WINTERBERRY DR, PLAINVIEW, NY, 118...

Community: Country Pointe Plainview

Leisure Village

419 WEYMOUTH CT F, RIDGE, NY, 11961, Ridge, NY 11961

$283,000

1 beds

1 baths

782 sq ft

Condo

419 WEYMOUTH CT F, RIDGE, NY, 11961

Community: Leisure Village

Sunrise Village

133 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782

$449,000

2 beds

1 baths

1,000 sq ft

Condo

133 REVERE DR, SAYVILLE, NY, 11782

Community: Sunrise Village

Sunrise Village

14 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782

$525,000

2 beds

2 baths

1,046 sq ft

Condo

14 REVERE DR, SAYVILLE, NY, 11782

Community: Sunrise Village

Jefferson Village

92 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$379,900

1 beds

1 baths

800 sq ft

Condo

92 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,...

Community: Jefferson Village

Jessup's Landing

$2,500,000

5 beds

5 baths

2,807 sq ft

Condo

25 JESSUPS LANDING CT UNIT E, QUOGUE, NY...

Community: Jessup's Landing

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

Questions? Call us: (959) 214-4386

Leisure Village

332 WOODBRIDGE DR UNIT C WOODBRIDGE DR, ..., Ridge, NY 11961

$369,000

2 beds

1 baths

1,000 sq ft

Condo

332 WOODBRIDGE DR UNIT C WOODBRIDGE DR, ...

Community: Leisure Village

Greenwood Village

87 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$199,000

2 beds

1 baths

992 sq ft

Condo

87 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Village

277 BERWICK CT UNIT D, RIDGE, NY, 11961, Ridge, NY 11961

$339,000

2 beds

1 baths

875 sq ft

Condo

277 BERWICK CT UNIT D, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

258 NEWCASTLE CT A, RIDGE, NY, 11961, Ridge, NY 11961

$249,000

2 beds

1 baths

875 sq ft

Condo

258 NEWCASTLE CT A, RIDGE, NY, 11961

Community: Leisure Village

Foxwood Village

1407-54 MIDDLE RD 54, RIVERHEAD, NY, 119..., Riverhead, NY 11933

$324,999

2 beds

2 baths

1,280 sq ft

House

1407-54 MIDDLE RD 54, RIVERHEAD, NY, 119...

Community: Foxwood Village

Encore Atlantic Shores

68 ENCORE, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$849,999

2 beds

3 baths

3,000 sq ft

Condo

68 ENCORE, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

Leisure Village

156 FALMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961

$349,997

2 beds

1 baths

1,085 sq ft

Condo

156 FALMOUTH CT A, RIDGE, NY, 11961

Community: Leisure Village

The Seasons at East Meadow

315 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$588,000

2 beds

2 baths

1,272 sq ft

Condo

315 SPRING DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

HarborView

$1,500,000

3 beds

3 baths

2,395 sq ft

Condo

100 HARBOR VIEW DR 230, PORT WASHINGTON,...

Community: HarborView

Heritage Hills

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

$799,000

3 beds

2 baths

1,689 sq ft

Condo

239 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (959) 214-4386

The Waterways at Moriches

107 E MIDLAND POND CT, MORICHES, NY, 119..., Moriches, NY 11955

$539,000

2 beds

2 baths

2,141 sq ft

Condo

107 E MIDLAND POND CT, MORICHES, NY, 119...

Community: The Waterways at Moriches

The Polo Club at Islandia

1239 OLD NICHOLS RD # 51, ISLANDIA, NY, ..., Islandia, NY 11749

$639,000

2 beds

3 baths

1,654 sq ft

Condo

1239 OLD NICHOLS RD # 51, ISLANDIA, NY, ...

Community: The Polo Club at Islandia

Leisure Village

425 BRIDGEWATER DR UNIT A A, RIDGE, NY, ..., Ridge, NY 11961

$335,000

2 beds

2 baths

966 sq ft

Condo

425 BRIDGEWATER DR UNIT A A, RIDGE, NY, ...

Community: Leisure Village

Glenwood Village

1661-563 OLD COUNTRY RD 563, RIVERHEAD, ..., Riverhead, NY 11901

$439,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661-563 OLD COUNTRY RD 563, RIVERHEAD, ...

Community: Glenwood Village

Country Pointe Plainview

18205 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803

$1,200,000

2 beds

2 baths

1,474 sq ft

Condo

18205 ASPENWOOD DR, PLAINVIEW, NY, 11803

Community: Country Pointe Plainview

Leisure Village

135 EASTBOURNE CT UNIT C, RIDGE, NY, 119..., Ridge, NY 11961

$299,900

2 beds

1 baths

1,118 sq ft

Condo

135 EASTBOURNE CT UNIT C, RIDGE, NY, 119...

Community: Leisure Village

Leisure Knoll

460 SUMMERWOOD CT, RIDGE, NY, 11961, Ridge, NY 11961

$439,000

2 beds

2 baths

1,172 sq ft

Condo

460 SUMMERWOOD CT, RIDGE, NY, 11961

Community: Leisure Knoll

Leisure Village

269 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961

$379,999

2 beds

1 baths

1,048 sq ft

Condo

269 BERWICK CT B, RIDGE, NY, 11961

Community: Leisure Village

The Polo Club at Islandia

1239 OLD NICHOLS RD # 46, ISLANDIA, NY, ..., Islandia, NY 11749

$639,000

2 beds

3 baths

1,654 sq ft

Condo

1239 OLD NICHOLS RD # 46, ISLANDIA, NY, ...

Community: The Polo Club at Islandia

Jefferson Village

156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598

$359,000

1 beds

1 baths

850 sq ft

Condo

156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,...

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

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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 Benson Woods, Granite 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 11 days. The average price of homes for sale in these communities is approximately $569,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Benson Woods average around $569,900.

Want more information about active adult communities around Middlebury?

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137 communities near Middlebury

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

137 communities near Middlebury

306 homes near Middlebury

2 beds

2 baths

1,350 sq ft

Condo

2 beds

3 baths

2,006 sq ft

Condo

2 beds

3 baths

1,493 sq ft

Condo

2 beds

2 baths

1,427 sq ft

Condo

1 beds

1 baths

924 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

2 baths

920 sq ft

Condo

2 beds

2 baths

941 sq ft

Condo

2 beds

2 baths

1,427 sq ft

Condo

2 beds

2 baths

1,335 sq ft

Condo

1 beds

1 baths

782 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

2 baths

1,046 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

5 beds

5 baths

2,807 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

1 baths

992 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds