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

142 communities near Middlebury

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Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

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

The Pines at Bohemia

$400ks - $500ks

The Pines at Bohemia, Bohemia, NY

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

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes

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

Questions? Call us: (959) 214-4386

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

Questions? Call us: (959) 214-4386

The Polo Club at Islandia

$600ks - $700ks

The Polo Club at Islandia, Islandia, NY

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

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

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

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

Chimney Hill

$500ks - $700ks

Chimney Hill, Farmington, CT

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

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes

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

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

Questions? Call us: (959) 214-4386

The Views at Pomona

$200ks - $400ks

The Views at Pomona, Pomona, NY

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

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

Questions? Call us: (959) 214-4386

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

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

The Seasons at East North...

$700ks

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

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

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

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

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

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

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

Stratford Park

$600ks - $800ks

Stratford Park, Melville, NY

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

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

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

Windmill Gate

$300ks - $400ks

Windmill Gate, Oakdale, NY

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

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

Questions? Call us: (959) 214-4386

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

Four Seasons at Ridgemont

$800ks - $1Ms

Four Seasons at Ridgemont, Montvale, NJ

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

The Club at Melville

$500ks

The Club at Melville, Melville, NY

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

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

Questions? Call us: (959) 214-4386

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

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

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

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

Questions? Call us: (959) 214-4386

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

Harbor View Estates

$400ks - $600ks

Harbor View Estates, Copiague, NY

New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes

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

Questions? Call us: (959) 214-4386

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

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

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

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

1 2 3...4

New The Village at Oxford Greens

1077 AUGUSTA DR 1077, OXFORD, CT, 06478, Oxford, CT 06478

$684,900

3 beds

3 baths

2,256 sq ft

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Fairview at Oxford Greens

$684,900

3 beds

3 baths

2,256 sq ft

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New Village Estates

105 FRANCESCA WAY 105, BABYLON, NY, 1170..., Babylon, NY 11701

$559,000

2 beds

1 baths

1,229 sq ft

Condo

105 FRANCESCA WAY 105, BABYLON, NY, 1170...

Community: Village Estates

New Overlook

2079 SUMMIT LOOP 103, CARMEL, NY, 10512, Carmel, NY 10512

$899,000

2 beds

2 baths

1,948 sq ft

Condo

2079 SUMMIT LOOP 103, CARMEL, NY, 10512

Community: Overlook

New Glenwood Village

1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$449,999

3 beds

2 baths

1,680 sq ft

Manufactured Home

1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1...

Community: Glenwood Village

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

Questions? Call us: (959) 214-4386

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

Questions? Call us: (959) 214-4386

New Leisure Village

72 ENFIELD CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,900

2 beds

1 baths

1,085 sq ft

Condo

72 ENFIELD CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Pond Spring Village

17 PONDVIEW CIR 17, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403

$474,900

2 beds

2 baths

1,474 sq ft

Condo

17 PONDVIEW CIR 17, BEACON FALLS, CT, 06...

Community: Pond Spring Village

New Heritage Village

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

$189,000

2 beds

2 baths

1,044 sq ft

Condo

331 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

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

$260,000

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Country Pointe Preserve

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$865,000

2 beds

3 baths

1,998 sq ft

Condo

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

Heritage Hills

29 HERITAGE HLS 29D, SOMERS, NY, 10589, Somers, NY 10589

$495,000

2 beds

3 baths

1,340 sq ft

Condo

29 HERITAGE HLS 29D, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

99 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$485,000

1 beds

3 baths

1,426 sq ft

Condo

99 SEMINOLE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$340,000

1 beds

3 baths

1,438 sq ft

Condo

89 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (959) 214-4386

The Waterways at Moriches

290 W MIDLAND POND CT 290, BROOKHAVEN, N..., Brookhaven, NY 11955

$629,000

2 beds

2 baths

1,440 sq ft

Condo

290 W MIDLAND POND CT 290, BROOKHAVEN, N...

Community: The Waterways at Moriches

The Seasons at Seaford

56 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783

$820,000

2 beds

3 baths

1,034 sq ft

Condo

56 SPRING DR, HEMPSTEAD, NY, 11783

Condo

158 CARRIAGE CT B, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (959) 214-4386

Sunrise Village

93 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$525,000

2 beds

2 baths

1,230 sq ft

Condo

93 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

The Villages at Mount Sinai Park

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$899,000

3 beds

3 baths

2,455 sq ft

House

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Jefferson Village

10 REGENTS PL D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$240,000

1 baths

550 sq ft

Condo

10 REGENTS PL D, YORKTOWN, NY, 10598

Community: Jefferson Village

O'Meara Farm

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032, Farmington, CT 06032

$480,000

2 beds

2 baths

1,416 sq ft

Condo

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032

Condo

145 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

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

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Oronoque Village

47 HURON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$409,000

2 beds

2 baths

1,360 sq ft

Condo

47 HURON LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

279 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$299,999

2 beds

1 baths

875 sq ft

Condo

279 BERWICK CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Country Village Estates

45 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$475,000

2 beds

2 baths

1,305 sq ft

Condo

45 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

The Villages at Mount Sinai Park

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$675,000

2 beds

3 baths

1,736 sq ft

House

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Regency at Prospect

104 CHERRY CIR 104, PROSPECT, CT, 06712, Prospect, CT 06712

$328,417

3 beds

2 baths

1,500 sq ft

Condo

104 CHERRY CIR 104, PROSPECT, CT, 06712

Community: Regency at Prospect

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

Questions? Call us: (959) 214-4386

Rivington

131 WINDING RIDGE WAY 131, DANBURY, CT, ..., Danbury, CT 06810

$770,000

3 beds

3 baths

1,592 sq ft

Condo

131 WINDING RIDGE WAY 131, DANBURY, CT, ...

Community: Rivington

Regency at Woodbridge

27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525

$599,900

3 beds

3 baths

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525

Community: Regency at Woodbridge

Castle Heights of Cheshire

151 VICTORIA DR, CHESHIRE, CT, 06410, Cheshire, CT 06410

$769,900

2 beds

4 baths

2,843 sq ft

Condo

151 VICTORIA DR, CHESHIRE, CT, 06410

Community: Castle Heights of Cheshire

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

Questions? Call us: (959) 214-4386

Country Village Estates

163 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$454,500

2 beds

2 baths

1,261 sq ft

Condo

163 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

The Waterways at Moriches

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

$775,000

2 beds

2 baths

2,100 sq ft

Condo

188 RIVER DR, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

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.

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 130 days. The average price of homes for sale in these communities is approximately $534,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Benson Woods average around $534,900.

Want more information about active adult communities around Middlebury?

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142 communities

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

142 communities near Middlebury

248 homes near Middlebury

3 beds

3 baths

2,256 sq ft

Condo

3 beds

3 baths

2,256 sq ft

Condo

2 beds

1 baths

1,229 sq ft

Condo

2 beds

2 baths

1,948 sq ft

Condo

3 beds

2 baths

1,680 sq ft

Manufactured Home

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,474 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

1,998 sq ft

Condo

2 beds

3 baths

1,340 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,440 sq ft

Condo

2 beds

3 baths

1,034 sq ft

Condo

2 beds

2 baths

1,379 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

2 baths

1,175 sq ft

Condo

2 beds

2 baths

1,300 sq ft

Condo

2 beds