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

95 communities near Winchester Area

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Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

Bramble Ridge

$300ks

Bramble Ridge, Suffield, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes

Cobblestone Court

$400ks - $500ks

Cobblestone Court, Essex, CT

New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes

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

Questions? Call us: (860) 238-3620

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 homes

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

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

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

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

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

77 Sunset Lane

$400ks - $700ks

77 Sunset Lane, Ridgefield, CT

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes

1 2 3

Leisure Village

177 VENTRY CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$449,500

2 beds

1 baths

1,085 sq ft

Condo

177 VENTRY CT A, BROOKHAVEN, NY, 11961

Community: Leisure 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 Overlook

4052 FAIRWAYS DR 293, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

3 beds

3 baths

2,274 sq ft

Condo

4052 FAIRWAYS DR 293, CARMEL, NY, 10512

Community: Overlook

New Overlook

4004 FAIRWAYS DR 296, CARMEL, NY, 10512, Carmel, NY 10512

$869,000

3 beds

3 baths

2,309 sq ft

House

4004 FAIRWAYS DR 296, CARMEL, NY, 10512

Community: Overlook

New Leisure Village

470B DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$339,000

2 beds

1 baths

1,074 sq ft

Condo

470B DARWEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

New Meadow Brook Estates

107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478

$569,900

3 beds

3 baths

1,922 sq ft

Condo

107 MEADOW BROOK RD 107, OXFORD, CT, 064...

Community: Meadow Brook Estates

New Jefferson Village

172 LONG HILL DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$675,000

2 beds

2 baths

1,550 sq ft

Condo

172 LONG HILL DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

New Heritage Hills

897 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$749,900

2 beds

3 baths

1,666 sq ft

Condo

897 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

New Overlook

4038 FAIRWAYS DR 299, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

3 beds

3 baths

2,274 sq ft

House

4038 FAIRWAYS DR 299, CARMEL, NY, 10512

Community: Overlook

New The Vineyards at Miller Place

40 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764

$625,000

3 beds

3 baths

1,700 sq ft

Condo

40 AVERY LN, BROOKHAVEN, NY, 11764

Community: The Vineyards at Miller Place

New Leisure Glen

488 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$659,000

2 beds

2 baths

1,652 sq ft

Condo

488 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Stoneleigh Woods at Riverhead

904 BALTUSROL BLVD, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$510,000

2 beds

2 baths

1,258 sq ft

Condo

904 BALTUSROL BLVD, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

New Heritage Village

27 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$390,000

2 beds

2 baths

1,447 sq ft

Condo

27 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

New Regency at Prospect

146 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712

$550,000

2 beds

3 baths

1,850 sq ft

Condo

146 SYCAMORE DR, PROSPECT, CT, 06712

Community: Regency at Prospect

New Regency at Wappinger

20 AVONDALE LN, WAPPINGER, NY, 12590, Wappinger, NY 12590

$745,000

3 beds

3 baths

2,056 sq ft

Condo

20 AVONDALE LN, WAPPINGER, NY, 12590

Community: Regency at Wappinger

New Whitney Glen

39 WHITNEY GLN 39, WESTPORT, CT, 06880, Westport, CT 06880

$925,000

2 beds

2 baths

1,600 sq ft

Condo

39 WHITNEY GLN 39, WESTPORT, CT, 06880

Community: Whitney Glen

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

Questions? Call us: (860) 238-3620

New The Vineyards at Miller Place

6 HALLEY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764

$559,000

2 beds

2 baths

1,291 sq ft

House

6 HALLEY LN, BROOKHAVEN, NY, 11764

Community: The Vineyards at Miller Place

New Heritage Village

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

$329,900

2 beds

2 baths

1,432 sq ft

Condo

809 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Sonoma Woods

2 SONOMA LN 2, MIDDLETOWN, CT, 06457, Middletown, CT 06457

$549,900

2 beds

3 baths

1,903 sq ft

2 SONOMA LN 2, MIDDLETOWN, CT, 06457

Community: Sonoma Woods

Leisure Knoll

434 KINGSTON DR 434, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,646 sq ft

Condo

434 KINGSTON DR 434, BROOKHAVEN, NY, 119...

Community: Leisure Knoll

The Villages at Mount Sinai Park

93 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$799,000

2 beds

2 baths

2,234 sq ft

House

93 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Leisure Glen

277 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$535,900

2 beds

2 baths

1,542 sq ft

Condo

277 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Heritage Village

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

$289,900

2 beds

2 baths

1,032 sq ft

Condo

45 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$325,000

2 beds

2 baths

1,432 sq ft

Condo

198 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

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

$630,000

2 beds

2 baths

1,472 sq ft

Condo

449 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

149 FLINTLOCK WAY D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$325,000

1 beds

1 baths

835 sq ft

Condo

149 FLINTLOCK WAY D, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

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

$186,000

2 beds

2 baths

1,032 sq ft

Condo

62 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 238-3620

Oronoque Village

638 ONONDAGA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

1,175 sq ft

Condo

638 ONONDAGA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Pond Spring Village

41 PONDVIEW CIR 41, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403

$485,000

2 beds

2 baths

1,501 sq ft

Condo

41 PONDVIEW CIR 41, BEACON FALLS, CT, 06...

Community: Pond Spring Village

Rivington

19 WARRINGTON ROUND 19, DANBURY, CT, 068..., Danbury, CT 06810

$749,000

3 beds

3 baths

2,196 sq ft

Condo

19 WARRINGTON ROUND 19, DANBURY, CT, 068...

Community: Rivington

Heritage Village

786 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$295,000

2 beds

2 baths

1,000 sq ft

Condo

786 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Village Vistas

11 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777

$1,249,000

3 beds

4 baths

3,075 sq ft

Condo

11 THERESA LN, BROOKHAVEN, NY, 11777

Community: Village Vistas

Overlook

4103 FAIRWAYS DR 152, CARMEL, NY, 10512, Carmel, NY 10512

$649,000

3 beds

3 baths

1,914 sq ft

Condo

4103 FAIRWAYS DR 152, CARMEL, NY, 10512

Community: Overlook

Overlook

4101 FAIRWAYS DR 151, CARMEL, NY, 10512, Carmel, NY 10512

$749,000

3 beds

4 baths

2,141 sq ft

Condo

4101 FAIRWAYS DR 151, CARMEL, NY, 10512

Community: Overlook

Overlook

2012 SUMMIT LOOP 42, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

2 beds

2 baths

1,948 sq ft

Condo

2012 SUMMIT LOOP 42, CARMEL, NY, 10512

Community: Overlook

Benson Woods

203 SUGAR MAPLE WAY 203, MIDDLEBURY, CT,..., Middlebury, CT 06762

$589,900

2 beds

3 baths

2,442 sq ft

Condo

203 SUGAR MAPLE WAY 203, MIDDLEBURY, CT,...

Community: Benson Woods

Leisure Village

379C WOODBRIDGE DR C, BROOKHAVEN, NY, 11..., Brookhaven, NY 11961

$459,900

2 beds

2 baths

1,168 sq ft

Condo

379C WOODBRIDGE DR C, BROOKHAVEN, NY, 11...

Community: Leisure Village

Leisure Glen

14 FLANDERS CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$450,000

2 beds

2 baths

1,212 sq ft

House

14 FLANDERS CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (860) 238-3620

Heritage Village

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

$250,000

2 beds

2 baths

1,398 sq ft

Condo

219 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$299,900

2 beds

2 baths

1,432 sq ft

Condo

974 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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Winchester Area

Frequently Asked Questions

What size 55+ communities are there in the Winchester Area?

Of the 2 55+ communities in the Winchester Area, 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 the Winchester Area?

The smallest 55+ communities in the Winchester Area has 31 homes, the largest has 38 homes, and the average communities consists of 34 homes.

Are there new 55+ homes available in the Winchester Area?

Yes, there is new 55+ home available in the Winchester Area. The most recent communities started in the Winchester Area include Oak Meadow Estates, Clockmaker's Hill. There is also 1 communities in the Winchester Area that offers new construction homes, including Oak Meadow Estates.

Are there gated 55+ communities in the Winchester Area?

No, there are no gated 55+ communities in the Winchester Area.

How long do listings in 55+ communities in the Winchester Area typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in the Winchester Area stay on the market for around 397 days. The average price of homes for sale in these communities is approximately $485,000, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $485,000.

Want to learn more about 55+ communities in the Winchester Area?

Insights and market stats
Instant new home alerts
Answers from local 55+ experts

Thanks! A local 55+ expert will be in touch shortly.

Want to learn more about 55+ communities in Winchester Area?

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95 communities

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

95 communities near Winchester Area

228 homes near Winchester Area

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

3 baths

2,274 sq ft

Condo

3 beds

3 baths

2,309 sq ft

House

2 beds

1 baths

1,074 sq ft

Condo

3 beds

3 baths

1,922 sq ft

Condo

2 beds

2 baths

1,550 sq ft

Condo

2 beds

3 baths

1,666 sq ft

Condo

3 beds

3 baths

2,274 sq ft

House

3 beds

3 baths

1,700 sq ft

Condo

2 beds

2 baths

1,652 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,447 sq ft

Condo

2 beds

3 baths

1,850 sq ft

Condo

3 beds

3 baths

2,056 sq ft

Condo

2 beds

2 baths

1,600 sq ft

Condo

2 beds

2 baths

1,291 sq ft

House

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

1,903 sq ft

2 beds

2 baths