Middlebury, CT 55+ rental communities & homes for rent

2 communities near Middlebury

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The Cornerstone at Hauppa...

$3,781.06 / mo

Base rent from $3,700

The Cornerstone at Hauppa..., Hauppauge, NY

New Construction | 55+ age-restricted | Built 2019 - 2020 | 96 rental homes

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

Questions? Call us: (959) 214-4386

Sylvan Woods Westchester

$3,095.78 - $4,785.78 / mo

Base rent from $2,960

Sylvan Woods Westchester, Buchanan, NY

New Construction | 55+ age-restricted | Built 2025 - present | 148 rental homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

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

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.

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

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.

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Want to learn more about 55+ communities in Middlebury?

Call us: (959) 214-4386

2 communities

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Middlebury, CT 55+ rental communities & homes for rent

2 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