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

278 homes near Middlebury

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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

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 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 Middlebury? 55places can help!

Questions? Call us: (959) 214-4386

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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 Village at Oxford Gre...

$400ks - $500ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 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.

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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

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

Questions? Call us: (959) 214-4386

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

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

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

5 rating (1 reviews)

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

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

Questions? Call us: (959) 214-4386

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

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

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

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

The Hollows at Blue Hill

$500ks - $700ks

The Hollows at Blue Hill, Pearl River, NY

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

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

Questions? Call us: (959) 214-4386

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

Knickerbocker Bay Club

$700ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

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

1 2 3...4

New The Coves at Melville

27 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$585,000

2 beds

2 baths

1,109 sq ft

Condo

27 MORLEY CIR, HUNTINGTON, NY, 11747

Community: The Coves at Melville

New Heritage Village

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

$289,000

2 beds

2 baths

1,365 sq ft

Condo

877 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Summit at Bethel

6 LOCKWOOD CIR 6, BETHEL, CT, 06801, Bethel, CT 06801

$619,000

3 beds

3 baths

1,771 sq ft

Condo

6 LOCKWOOD CIR 6, BETHEL, CT, 06801

Community: The Summit at Bethel

New Greenwood Village

11 A DOGWOOD LN 11 A, BROOKHAVEN, NY, 11..., Brookhaven, NY 11949

$199,000

2 beds

2 baths

1,032 sq ft

Condo

11 A DOGWOOD LN 11 A, BROOKHAVEN, NY, 11...

Community: Greenwood Village

New The Manors at The Colony Preserve

40 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967

$540,000

2 beds

2 baths

1,360 sq ft

Condo

40 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

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

Questions? Call us: (959) 214-4386

New The Greens at Half Hollow

1075 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$699,000

2 beds

2 baths

1,166 sq ft

Condo

1075 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Pond Spring Village

37 SEPTEMBER LN 37, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403

$450,000

2 beds

3 baths

1,328 sq ft

Condo

37 SEPTEMBER LN 37, BEACON FALLS, CT, 06...

Community: Pond Spring Village

New The Waterways at Moriches

188 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$729,000

2 beds

2 baths

2,100 sq ft

Condo

188 RIVER DR, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

New The Greens at Half Hollow

1053 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$739,900

2 beds

2 baths

1,100 sq ft

Condo

1053 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Heritage Village

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

$525,000

3 beds

3 baths

1,716 sq ft

Condo

657 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

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

$215,000

2 beds

2 baths

1,044 sq ft

Condo

343 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

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 Rivington

925 OLD PASTURE DR 925, DANBURY, CT, 068..., Danbury, CT 06810

$510,000

2 beds

2 baths

1,258 sq ft

Condo

925 OLD PASTURE DR 925, DANBURY, CT, 068...

Community: Rivington

New Leisure Knoll

379 LARCHMONT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,000

2 beds

2 baths

1,070 sq ft

Condo

379 LARCHMONT CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New The Greens at Half Hollow

562 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$949,888

2 beds

3 baths

1,941 sq ft

Condo

562 BARDINI DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Chatfield Farms

24 BAYBERRY CT 24, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$725,000

3 beds

3 baths

1,981 sq ft

Condo

24 BAYBERRY CT 24, BEACON FALLS, CT, 064...

Community: Chatfield Farms

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

Questions? Call us: (959) 214-4386

New The Seasons at Elwood

53 WINTER PL 53, HUNTINGTON, NY, 11731, Huntington, NY 11731

$979,900

2 beds

3 baths

1,500 sq ft

Condo

53 WINTER PL 53, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

New Regency at Fishkill

541 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$529,000

2 beds

2 baths

1,499 sq ft

Condo

541 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

New The Seasons at Elwood

240 FALL CT, HUNTINGTON, NY, 11731, Huntington, NY 11731

$1,299,999

2 beds

3 baths

2,329 sq ft

Condo

240 FALL CT, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

New Leisure Knoll

220 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,999

2 beds

2 baths

1,445 sq ft

Condo

220 BELFAST LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Leisure Glen

515 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$560,000

2 beds

2 baths

1,434 sq ft

House

515 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Meadowbrook Pointe Athletic Club & Spa

246 ROOSEVELT WAY 11103, HEMPSTEAD, NY, ..., Hempstead, NY 11590

$1,150,000

2 beds

3 baths

1,620 sq ft

Condo

246 ROOSEVELT WAY 11103, HEMPSTEAD, NY, ...

Community: Meadowbrook Pointe Athletic Club & Spa

New Jefferson Village

131 COLUMBIA CT D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$399,000

2 beds

2 baths

1,141 sq ft

Condo

131 COLUMBIA CT D, YORKTOWN, NY, 10598

Community: Jefferson Village

The Retreat at Carmel

2 BLAIR HEIGHTS 3323, CARMEL, NY, 10512, Carmel, NY 10512

$455,000

2 beds

2 baths

1,323 sq ft

Condo

2 BLAIR HEIGHTS 3323, CARMEL, NY, 10512

Community: The Retreat at Carmel

Regency at Wappinger

2 AVONDALE LN, WAPPINGER, NY, 12590, Wappinger, NY 12590

$799,000

2 beds

4 baths

2,941 sq ft

Condo

2 AVONDALE LN, WAPPINGER, NY, 12590

Community: Regency at Wappinger

Dutchgate

205 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580

$699,999

3 beds

2 baths

1,480 sq ft

Condo

205 WILLOW LN, HEMPSTEAD, NY, 11580

Community: Dutchgate

Heritage Hills

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

$679,999

2 beds

2 baths

1,416 sq ft

Condo

386 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (959) 214-4386

Jefferson Village

23 DORSET CT C, YORKTOWN, NY, 10598, Yorktown, NY 10598

$339,000

1 beds

1 baths

700 sq ft

Condo

23 DORSET CT C, YORKTOWN, NY, 10598

Community: Jefferson Village

Meadow Brook Estates

223 MEADOW BROOK RD 223, OXFORD, CT, 064..., Oxford, CT 06478

$589,900

2 beds

2 baths

1,480 sq ft

Condo

223 MEADOW BROOK RD 223, OXFORD, CT, 064...

Community: Meadow Brook Estates

Greenwood Village

40 WILLOW CT, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$249,999

2 beds

2 baths

1,151 sq ft

Manufactured On Land

40 WILLOW CT, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Oronoque Village

261 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$550,000

2 beds

3 baths

1,620 sq ft

Condo

261 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Woodridge Strathmore Terrace

54 STANDISH DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$549,999

2 beds

2 baths

1,335 sq ft

Condo

54 STANDISH DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Heritage Village

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

$479,000

2 beds

2 baths

1,432 sq ft

Condo

899 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$599,000

1 beds

3 baths

1,438 sq ft

Condo

209 ACORN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Vineyards at Brookfield

69 AVERY DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$709,999

2 beds

3 baths

2,254 sq ft

Condo

69 AVERY DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Brookfield

The Powder Forest Homes

9 ASHTON CIR, SIMSBURY, CT, 06070, Simsbury, CT 06070

$700,000

2 beds

2 baths

1,809 sq ft

Condo

9 ASHTON CIR, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Applegate Estates

90 APPLE GATE 190, SOUTHINGTON, CT, 0648..., Southington, CT 06489

$450,000

2 beds

2 baths

1,350 sq ft

Condo

90 APPLE GATE 190, SOUTHINGTON, CT, 0648...

Community: Applegate Estates

The Village at Oxford Greens

71 LINKS WAY 71, OXFORD, CT, 06478, Oxford, CT 06478

$598,000

2 beds

2 baths

1,590 sq ft

Condo

71 LINKS WAY 71, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

Questions? Call us: (959) 214-4386

The Greens at Half Hollow

1153 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$750,000

2 beds

2 baths

1,100 sq ft

Condo

1153 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Heritage Village

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

$264,999

2 beds

2 baths

1,432 sq ft

Condo

397 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

1 2 3 4 5 6…7

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 Granite Woods, Benson Woods.

Are there gated 55+ communities in Middlebury?

No, there are no gated 55+ communities in Middlebury.

Want more information about active adult communities around Middlebury?

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278 homes

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

142 communities near Middlebury

278 homes near Middlebury

2 beds

2 baths

1,109 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

3 beds

3 baths

1,771 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

2 baths

1,360 sq ft

Condo

2 beds

2 baths

1,166 sq ft

Condo

2 beds

3 baths

1,328 sq ft

Condo

2 beds

2 baths

2,100 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

3 beds

3 baths

1,716 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,070 sq ft

Condo

2 beds

3 baths

1,941 sq ft

Condo

3 beds

3 baths

1,981 sq ft

Condo

2 beds

3 baths

1,500 sq ft

Condo

2 beds

2 baths

1,499 sq ft

Condo

2 beds

3 baths

2,329 sq ft

Condo

2 beds