Call us at (860) 238-3620 to learn more about active adult communities near Winchester Area
Winchester Area, CT 55+ active adult communities & homes for sale
89 communities near Winchester Area
234 homes near Winchester Area
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![Clockmaker's Hill]()
$100Ks
- $100Ks
Clockmaker's Hill, Winsted, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2014
|
38 homes
No reviews yet
![Oak Meadow Estates]()
$200Ks
- $400Ks
Oak Meadow Estates, Torrington, CT
New and Resale
|
55+ age-restricted
|
Built 2013 - present
|
31 homes
3 rating (2 reviews)
![Heritage Hills]()
$300Ks
- $900Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$100Ks
- $400Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
No reviews yet
![Leisure Village]()
$200Ks
- $500Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
Want to learn more about 55+ communities in Winchester Area?
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(860) 238-3620
No reviews yet
![Rivington]()
$500Ks
- $900Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$200Ks
- $500Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
No reviews yet
![Oronoque Village]()
$300Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
No reviews yet
![The Village at Oxford Gre...]()
$500Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
No reviews yet
![Leisure Knoll]()
$200Ks
- $400Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 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
![Leisure Glen]()
$400Ks
- $500Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
No reviews yet
![Spring Lake Village]()
$200Ks
- $300Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
No reviews yet
![Regency at Prospect]()
$400Ks
- $400Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
No reviews yet
![The Retreat at Carmel]()
$400Ks
- $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
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Questions? Call us:
(860) 238-3620
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
- $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
No reviews yet
![Meadow Brook Estates]()
$500Ks
- $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
No reviews yet
![The Summit at Bethel]()
$600Ks
- $600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $500Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 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
![Woodridge Strathmore Terr...]()
$400Ks
- $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
No reviews yet
![Regency at Wappinger]()
$600Ks
- $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only
|
55+ age-restricted
|
Built 2014 - 2020
|
225 homes
No reviews yet
![Saddle Lakes]()
$400Ks
- $400Ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2000 - 2002
|
196 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400Ks
- $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
5 rating (1 reviews)
![The Villages at Mount Sin...]()
$700Ks
- $800Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(860) 238-3620
No reviews yet
![The Powder Forest Homes]()
$600Ks
- $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
5 rating (1 reviews)
![Newtown Woods]()
$400Ks
- $500Ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
No reviews yet
![Stoneleigh Woods at River...]()
$400Ks
- $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
No reviews yet
![Beckley Farms]()
$300Ks
- $400Ks
Beckley Farms, Berlin, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
170 homes
No reviews yet
![Regency at Fishkill]()
$500Ks
- $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 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
![South Pond Village]()
$200Ks
- $400Ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
No reviews yet
![Setauket Meadows]()
$600Ks
- $700Ks
Setauket Meadows, Setauket, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
150 homes
No reviews yet
![Fieldstone Village]()
$500Ks
- $800Ks
Fieldstone Village, Orange, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2018
|
142 homes
No reviews yet
![North Woods of Colchester]()
$300Ks
- $400Ks
North Woods of Colchester, Colchester, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
140 homes
No reviews yet
![Windcrest East]()
$600Ks
- $600Ks
Windcrest East, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
126 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
No reviews yet
![Fairview at Oxford Greens]()
$500Ks
- $700Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
3.5 rating (2 reviews)
![Harvest Pointe]()
$800Ks
- $3Ms
Harvest Pointe, Cutchogue, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
124 homes
No reviews yet
![Newbury Village]()
$600Ks
- $700Ks
Newbury Village, Brookfield, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
120 homes
No reviews yet
![The Gardens of Wilbraham]()
$300Ks
- $400Ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
108 homes
No reviews yet
![O'Meara Farm]()
$400Ks
- $500Ks
O'Meara Farm, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 1998 - 2005
|
104 homes
Heritage Village
![4 HERITAGE CRST A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,735 sq ft
|Condo
4 HERITAGE CRST A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24109465 • Venture Real Estate, Inc., Patrick...
Heritage Village
![926 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
926 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24100579 • Joseph Bette REALTORS Inc, Cynthia...
Heritage Village
![192 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,076 sq ft
|Condo
192 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24102203 • Coldwell Banker Realty, Krista Pet...
Heritage Village
![122 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
122 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24092348 • Berkshire Hathaway NE Prop., Miche...
Heritage Village
![331 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
331 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24112486 • Around Town Real Estate LLC, Andre...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Heritage Village
![951 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
951 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24091509 • RE/MAX Right Choice, Dianne Camell...
Spring Lake Village
![543 S FARMS TER # 543, SOUTHINGTON, CT, ..., Southington, CT 06489]()
2 beds
|3 baths
|1,782 sq ft
|Condo
543 S FARMS TER # 543, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24102912 • Coldwell Banker Realty, Philip Gia...
Heritage Village
![583 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
583 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24110832 • Coldwell Banker Realty, Tim Dent
Heritage Village
![881 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
881 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24098891 • Joseph Bette REALTORS Inc, Deborah...
Heritage Village
![21 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
21 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24100068 • Around Town Real Estate LLC, Andre...
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.
Rivington
![1022 COUNTRY VIEW RD # 1022, DANBURY, CT..., Danbury, CT 06810]()
2 beds
|2 baths
|1,330 sq ft
|Condo
1022 COUNTRY VIEW RD # 1022, DANBURY, CT...
Community: Rivington
MLS 24093428 • Coldwell Banker Realty, Pamela Dos...
Chatfield Farms
![3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ..., Beacon Falls, CT 06403]()
3 beds
|4 baths
|2,052 sq ft
3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ...
Community: Chatfield Farms
MLS 24101359 • Dow Della Valle, E. Tyler Della Va...
Rivington
![10 OLD PASTURE DR # 10, DANBURY, CT, 068..., Danbury, CT 06810]()
3 beds
|4 baths
|2,544 sq ft
|Condo
10 OLD PASTURE DR # 10, DANBURY, CT, 068...
Community: Rivington
MLS 24088793 • William Raveis Real Estate, Patty ...
Heritage Village
![8 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,076 sq ft
|Condo
8 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24099184 • Joseph Bette REALTORS Inc, Justin ...
The Gardens of Wilbraham
![45 IVY CIR # 45, WILBRAHAM, MA, 01095, Wilbraham, MA 01095]()
2 beds
|3 baths
|1,752 sq ft
|Condo
45 IVY CIR # 45, WILBRAHAM, MA, 01095
Community: The Gardens of Wilbraham
MLS 73397613 • Coldwell Banker Realty - Western M...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Leisure Village
![28 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 869368 • Signature Premier Properties, Jose A...
Leisure Village
![406 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961]()
1 beds
|1 baths
|679 sq ft
|Condo
406 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
MLS 883217 • American Way Real Estate Inc, Kim Gr...
Jefferson Village
![73 INDEPENDENCE CT D, YORKTOWN, NY, 1059..., Yorktown, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
73 INDEPENDENCE CT D, YORKTOWN, NY, 1059...
Community: Jefferson Village
MLS 878517 • Coldwell Banker Realty, Deanna LaBar...
Glenwood Village
![1661-290 OLD COUNTRY RD 290, RIVERHEAD, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,152 sq ft
|Mobile Home
1661-290 OLD COUNTRY RD 290, RIVERHEAD, ...
Community: Glenwood Village
MLS 893962 • Keystone Realty USA Corp, Cynthia Mc...
Leisure Village
![137 EASTBOURNE CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|836 sq ft
|Condo
137 EASTBOURNE CT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 892549 • Bon Anno Realty ERA Powered, Nichola...
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.
Heritage Hills
![785 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,296 sq ft
|Condo
785 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 897392 • Houlihan Lawrence Inc., Teresa Chang
Stoneleigh Woods at Carmel
![206 EGRETS LANDING, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|2 baths
|1,492 sq ft
|Condo
206 EGRETS LANDING, CARMEL, NY, 10512
Community: Stoneleigh Woods at Carmel
MLS 893569 • Weichert Realtors, Tremaine Selby
Heritage Hills
![359 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,800 sq ft
|Condo
359 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 888850 • RE/MAX Classic Realty, Lawrence P. Z...
Heritage Hills
![133 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,780 sq ft
|Condo
133 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 878545 • Houlihan Lawrence Inc., Annpauline C...
Leisure Village
![195 E NEWCASTLE CT, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961]()
1 beds
|1 baths
|684 sq ft
|Condo
195 E NEWCASTLE CT, BROOKHAVEN, NY, 1196...
Community: Leisure Village
MLS 888315 • Integrity Core Realty, Patroy Quarry
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Regency at Fishkill
![145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
2 beds
|2 baths
|1,803 sq ft
|Condo
145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 898170 • Realty Center Hudson Valley, Edwin D...
Leisure Glen
![12 BALDWIN CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 897659 • Homeside Realty, Frank Profeta
Jefferson Village
![34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|970 sq ft
|Townhouse
34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1...
Community: Jefferson Village
MLS 875893 • Douglas Elliman Real Estate, Margare...
New
Leisure Knoll
![379 LARCHMONT CT # 379, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|976 sq ft
|Condo
379 LARCHMONT CT # 379, RIDGE, NY, 11961
Community: Leisure Knoll
MLS 899893 • Leisure Living Realty Inc, Laura Ruh...
New
Leisure Village
![268A BERWICK CT # 268A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
268A BERWICK CT # 268A, RIDGE, NY, 11961
Community: Leisure Village
MLS 900993 • Leisure Living Realty Inc, Laura Ruh...
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 Hills
![247 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|1 baths
|967 sq ft
|Condo
247 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 900231 • eXp Realty, Mark Snyder
New
Setauket Meadows
![131 EMILYS WAY, EAST SETAUKET, NY, 11733, East Setauket, NY 11733]()
2 beds
|3 baths
|1,773 sq ft
|Condo
131 EMILYS WAY, EAST SETAUKET, NY, 11733
Community: Setauket Meadows
MLS 900578 • Keystone Realty USA Corp, Anthony J....
New
Leisure Glen
![240 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 900265 • Fiore Real Estate Sales Corp, Anna M...
New
Leisure Glen
![25 DOUGLASTON CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 900603 • RE/MAX Integrity Leaders, Peter Fogl...
Heritage Hills
![852 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|2,156 sq ft
|Condo
852 HERITAGE HLS, SOMERS, NY, 10589
Community: Heritage Hills
MLS 898024 • William Raveis-New York LLC, Hope Ro...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
New
Leisure Knoll
![187 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 898631 • Signature Premier Properties, Linda ...
Leisure Village
![310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961]()
2 beds
|1 baths
|1,278 sq ft
|Condo
310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...
Community: Leisure Village
MLS 889288 • Coldwell Banker American Homes, Kath...
Leisure Knoll
![28 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 898968 • Coldwell Banker American Homes, Mary...
New
Glenwood Village
![1661 OLD COUNTRY RD UNIT 508, RIVERHEAD,..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,500 sq ft
|Manufactured Home
1661 OLD COUNTRY RD UNIT 508, RIVERHEAD,...
Community: Glenwood Village
MLS 901006 • Signature Premier Properties, Noreen...
New
Sunken Pond Estates
![2204 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,258 sq ft
|Condo
2204 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
MLS 899132 • Douglas Elliman Real Estate, Patrici...
Frequently Asked Questions
In the Winchester Area, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in the Winchester Area has 31 homes, the largest has 38 homes, and the average communities consists of 34 homes.
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.
No, there are no gated 55+ communities in the Winchester Area.
On average, listings in 55+ communities in the Winchester Area stay on the market for around 663 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?
234
homes
near Winchester Area
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