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

92 communities near Winchester Area

Sort by:

Relevance

No reviews yet

Billingsgate

$400Ks - $600Ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

No reviews yet

Boulder Brook

$200Ks - $200Ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

No reviews yet

The Woods at Dunham Pond

$400Ks - $500Ks

The Woods at Dunham Pond, New Fairfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes

No reviews yet

The Coach Homes at Ridgef...

$200Ks - $500Ks

The Coach Homes at Ridgef..., Ridgefield, CT

New Construction | 55+ age-restricted | Built 2019 - present | 30 homes

No reviews yet

Autumn Estates

$500Ks - $600Ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

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

Questions? Call us: (860) 238-3620

No reviews yet

Bartlett Hollow

$200Ks - $400Ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

No reviews yet

RiverBend Estates

$400Ks - $400Ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

No reviews yet

Granite Woods

$600Ks - $700Ks

Granite Woods, Middlebury, CT

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

No reviews yet

Summer Wind Estates

$300Ks - $400Ks

Summer Wind Estates, North Haven, CT

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

No reviews yet

Park Glen

$500Ks - $600Ks

Park Glen, New Milford, CT

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 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

Newington Ridge Preserve

$300Ks - $400Ks

Newington Ridge Preserve, Newington, CT

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

No reviews yet

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

1 2 3

New Stoneleigh Woods at Riverhead

4 HAVERTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$660,000

2 beds

3 baths

2,175 sq ft

Condo

4 HAVERTON CT, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

New Leisure Village

280 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961

$359,900

2 beds

1 baths

836 sq ft

Condo

280 BERWICK CT A, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

65 ENFIELD CT UNIT A A, RIDGE, NY, 11961, Ridge, NY 11961

$349,999

2 beds

1 baths

1,085 sq ft

Condo

65 ENFIELD CT UNIT A A, RIDGE, NY, 11961

Community: Leisure Village

Heritage Hills

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

$600,000

2 beds

2 baths

1,428 sq ft

Condo

348 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10..., Yorktown Heights, NY 10598

$299,999

1 beds

1 baths

800 sq ft

Condo

2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10...

Community: Jefferson Village

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

Questions? Call us: (860) 238-3620

Leisure Village

98 A EASTBOURNE, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$484,000

2 beds

2 baths

1,486 sq ft

Condo

98 A EASTBOURNE, BROOKHAVEN, NY, 11961

Community: Leisure Village

Leisure Knoll

190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961

$434,999

2 beds

1 baths

787 sq ft

Condo

190 CANTERBURY DR, RIDGE, NY, 11961

Community: Leisure Knoll

Overlook

1019 COTTAGE DR # 9, CARMEL, NY, 10512, Carmel, NY 10512

$889,000

2 beds

3 baths

2,496 sq ft

Condo

1019 COTTAGE DR # 9, CARMEL, NY, 10512

Community: Overlook

Overlook

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512

$663,000

3 beds

3 baths

1,914 sq ft

Condo

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...

Community: Overlook

Leisure Knoll

144 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961

$449,500

2 beds

2 baths

Condo

144 EDINBURGH DR, RIDGE, NY, 11961

Community: Leisure Knoll

Heritage Hills

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

$615,000

2 beds

2 baths

1,483 sq ft

Condo

504 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Hills

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

$725,000

3 beds

2 baths

1,909 sq ft

Condo

688 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Leisure Knoll

147 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961

$485,000

2 beds

2 baths

1,000 sq ft

Condo

147 EDINBURGH DR, RIDGE, NY, 11961

Community: Leisure Knoll

Overlook

1042 COTTAGE DR # 25, CARMEL, NY, 10512, Carmel, NY 10512

$839,000

2 beds

2 baths

1,961 sq ft

House

1042 COTTAGE DR # 25, CARMEL, NY, 10512

Community: Overlook

Overlook

4057 FAIRWAYS DR # 129, CARMEL, NY, 1051..., Carmel, NY 10512

$689,000

3 beds

4 baths

2,131 sq ft

Condo

4057 FAIRWAYS DR # 129, CARMEL, NY, 1051...

Community: Overlook

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

Questions? Call us: (860) 238-3620

Overlook

1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512

$949,000

2 beds

3 baths

2,496 sq ft

Condo

1037 COTTAGE DR 18, CARMEL, NY, 10512

Community: Overlook

Overlook

1040 COTTAGE DR # 26, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

2 beds

2 baths

1,948 sq ft

Condo

1040 COTTAGE DR # 26, CARMEL, NY, 10512

Community: Overlook

Overlook

4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512

$667,000

3 beds

3 baths

1,914 sq ft

Condo

4071 FAIRWAYS DR 136, CARMEL, NY, 10512

Community: Overlook

The Villages at Mount Sinai Park

109 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$729,000

2 beds

2 baths

1,736 sq ft

Condo

109 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

The Villages at Mount Sinai Park

25 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$799,000

2 beds

3 baths

2,229 sq ft

Condo

25 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

New Heritage Hills

137 HERITAGE HLS # B B, SOMERS, NY, 1058..., Somers, NY 10589

$400,000

1 beds

1 baths

955 sq ft

Condo

137 HERITAGE HLS # B B, SOMERS, NY, 1058...

Community: Heritage Hills

Glenwood Village

1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ..., Riverhead, NY 11901

$229,000

2 beds

2 baths

1,144 sq ft

Mobile Home

1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ...

Community: Glenwood Village

Heritage Hills

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

$389,900

1 beds

1 baths

955 sq ft

Condo

247 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Glassbury Court at Cold Spring

5 NORWEGIAN WOOD, COLD SPRING, NY, 10516, Cold Spring, NY 10516

$695,000

2 beds

2 baths

1,974 sq ft

Condo

5 NORWEGIAN WOOD, COLD SPRING, NY, 10516

Community: Glassbury Court at Cold Spring

Glassbury Court at Cold Spring

43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516

$729,000

2 beds

3 baths

2,620 sq ft

Condo

43 YESTERDAY DR, COLD SPRING, NY, 10516

Community: Glassbury Court at Cold Spring

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

Questions? Call us: (860) 238-3620

Heritage Hills

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

$619,000

2 beds

2 baths

1,296 sq ft

Condo

798 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

34 WARWICK PL C, YORKTOWN HEIGHTS, NY, 1..., Yorktown Heights, NY 10598

$329,900

2 beds

2 baths

1,000 sq ft

Condo

34 WARWICK PL C, YORKTOWN HEIGHTS, NY, 1...

Community: Jefferson Village

Glassbury Court at Cold Spring

11 REVOLUTION RD, COLD SPRING, NY, 10516, Cold Spring, NY 10516

$515,000

2 beds

3 baths

1,806 sq ft

Condo

11 REVOLUTION RD, COLD SPRING, NY, 10516

Community: Glassbury Court at Cold Spring

New Jefferson Village

148 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$499,000

2 beds

2 baths

1,159 sq ft

Condo

148 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

Heritage Hills

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

$550,000

2 beds

2 baths

1,427 sq ft

Condo

150 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

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

$525,000

1 beds

2 baths

1,098 sq ft

Condo

627 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

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

$595,000

2 beds

2 baths

1,470 sq ft

Condo

438 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Sunken Pond Estates

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$469,000

2 beds

3 baths

1,350 sq ft

Condo

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

Heritage Hills

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

$669,000

2 beds

2 baths

1,468 sq ft

Condo

523 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

41 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$399,000

2 beds

2 baths

1,100 sq ft

Condo

41 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

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

Questions? Call us: (860) 238-3620

Leisure Knoll

304 KINGSTON CT, RIDGE, NY, 11961, Ridge, NY 11961

$429,000

2 beds

2 baths

976 sq ft

Condo

304 KINGSTON CT, RIDGE, NY, 11961

Community: Leisure Knoll

Regency at Fishkill

423 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$499,000

1 beds

2 baths

1,450 sq ft

Condo

423 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Leisure Village

329 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961

$389,000

2 beds

2 baths

1,130 sq ft

Condo

329 WOODBRIDGE DR A, RIDGE, NY, 11961

Community: Leisure Village

Jefferson Village

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598

$464,900

2 beds

2 baths

1,200 sq ft

Condo

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ...

Community: Jefferson Village

Glenwood Village

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$250,000

2 beds

2 baths

924 sq ft

Manufactured Home

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...

Community: Glenwood Village

1 2 3 4 5 6…7

Home
Connecticut
Winchester Area

Frequently Asked Questions

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

In the Winchester Area, 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 788 days. The average price of homes for sale in these communities is approximately $389,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $389,900.

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

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

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

Call us: (860) 238-3620

92 communities near Winchester Area

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2025 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Oct 29, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

92 communities near Winchester Area

246 homes near Winchester Area

2 beds

3 baths

2,175 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,428 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,486 sq ft

Condo

2 beds

1 baths

787 sq ft

Condo

2 beds

3 baths

2,496 sq ft

Condo

3 beds

3 baths

1,914 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

1,483 sq ft

Condo

3 beds

2 baths

1,909 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,961 sq ft

House

3 beds

4 baths

2,131 sq ft

Condo

2 beds

3 baths

2,496 sq ft

Condo

2 beds

2 baths

1,948 sq ft

Condo

3 beds

3 baths

1,914 sq ft

Condo

2 beds

2 baths

1,736 sq ft

Condo

2 beds

3 baths