Call us at (475) 471-1908 to learn more about active adult communities in Westport
Westport, CT 55+ active adult communities & homes for sale
172 communities near Westport
393 homes near Westport
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3.6 rating (7 reviews)
![Heritage Village]()
$200ks
- $500ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
2.8 rating (4 reviews)
![Cheesequake Village]()
$100ks
- $200ks
Cheesequake Village, Old Bridge, NJ
Resale Only
|
55+ age-restricted
|
Built 1965 - 1971
|
713 homes
4 rating (1 reviews)
![Jefferson Village]()
$100ks
- $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
2.8 rating (5 reviews)
![The Villages NJ]()
$200ks
- $300ks
The Villages NJ, Howell, NJ
Resale Only
|
55+ age-restricted
|
Built 1967 - 1975
|
670 homes
5 rating (2 reviews)
![Oronoque Village]()
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
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(475) 471-1908
3 rating (2 reviews)
![Heritage Hills]()
$400ks
- $800ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
3.7 rating (3 reviews)
![Greenwood Village]()
$100ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
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Built 1980 - 2000
|
512 homes
4 rating (8 reviews)
![Glenwood Village]()
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
5 rating (2 reviews)
![Shadow Lake Village]()
$200ks
- $500ks
Shadow Lake Village, Red Bank, NJ
Resale Only
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55+ age-restricted
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Built 1972 - 1980
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952 homes
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 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.
$300ks
- $600ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
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Built 1985 - 1999
|
343 homes
4.2 rating (12 reviews)
![Surrey Downs]()
$200ks
- $300ks
Surrey Downs, Freehold, NJ
Resale Only
|
55+ age-restricted
|
Built 1986 - 1997
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443 homes
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
$700ks
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
$600ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
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(475) 471-1908
$300ks
- $900ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
$300ks
- $400ks
The Manors at The Colony ..., Shirley, NY
New Construction
|
55+ age-restricted
|
Built 2013 - present
|
150 homes
$600ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
|
55+ age-restricted
|
Built 2002 - 2004
|
270 homes
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
Download the Ultimate 55+ Homebuying Guide
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$500ks
- $600ks
Rolling Meadows at Waysid..., Ocean Township, NJ
Resale Only
|
55+ age-restricted
|
Built 2002 - 2007
|
328 homes
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
$500ks
- $1Ms
Apple Ridge, Mahwah, NJ
Resale Only
|
Age-targeted
|
Built 1977 - 1991
|
276 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$500ks
- $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
$300ks
- $400ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 homes
$500ks
- $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
90 homes
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(475) 471-1908
5 rating (2 reviews)
![Fairfield at St. James]()
$300ks
- $500ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1989
|
653 homes
$200ks
- $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
$600ks
- $700ks
Snug Harbor, Amityville, NY
Resale Only
|
55+ age-restricted
|
Built 1970 - 1974
|
176 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.
$300ks
- $500ks
Dutchgate, Valley Stream, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
348 homes
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
$700ks
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
720 homes
5 rating (1 reviews)
![Westhampton Pines]()
$900ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
4.6 rating (9 reviews)
![Meadowbrook Pointe Links ...]()
$300ks
- $700ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
280 homes
$300ks
- $400ks
Chelsea Square, Morganville, NJ
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
225 homes
$400ks
- $600ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 homes
$500ks
- $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2014
|
92 homes
Want to learn more about 55+ communities in Westport?
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Questions? Call us:
(475) 471-1908
$500ks
- $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2013
|
76 homes
$600ks
- $900ks
Country Pointe PreserveYaphank, NY
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
152 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.
Greenwood Village
![105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949]()
2 beds
|2 baths
|1,130 sq ft
|Condo
105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...
Community: Greenwood Village
MLS 1029061 • Gateway to The Hamptons R E, Janet ... • Gateway to The Hamptons R E
The Villages NJ
![41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077..., Freehold, NJ 07728]()
2 beds
|2 baths
|1,008 sq ft
|Ranch
41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077...
Community: The Villages NJ
MLS 22621215 • Coldwell Banker Realty, Karen Alba... • Coldwell Banker Realty
Glenwood Village
![1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 1011541 • Gateway to The Hamptons R E, Vivian... • Gateway to The Hamptons R E
New
Fairfield at St. James
![704 FENWAY RD, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
2 beds
|2 baths
|1,292 sq ft
|Condo
704 FENWAY RD, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 1047751 • BH&G R E Realty Connect, Danielle C... • BH&G R E Realty Connect
New
The Villages NJ
![61C PIAZZA VITTORIA, FREEHOLD, NJ, 07728, Freehold, NJ 07728]()
2 beds
|1 baths
|1,082 sq ft
|House
61C PIAZZA VITTORIA, FREEHOLD, NJ, 07728
Community: The Villages NJ
MLS 22628201 • Real Broker, LLC- Red Bank, Ramand... • Real Broker, LLC- Red Bank
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(475) 471-1908
New
Regency at Wappinger
![5 PALMERTON DR, WAPPINGER, NY, 12590, Wappinger, NY 12590]()
2 beds
|3 baths
|3,156 sq ft
|Condo
5 PALMERTON DR, WAPPINGER, NY, 12590
Community: Regency at Wappinger
MLS 1036134 • Howard Hanna Rand Realty, Mary Ann ... • Howard Hanna Rand Realty
New
Chelsea Square
![114 BLOOMSBURY DR 114, MORGANVILLE, NJ, ..., Morganville, NJ 07751]()
2 beds
|2 baths
|1,491 sq ft
|Adult Community
114 BLOOMSBURY DR 114, MORGANVILLE, NJ, ...
Community: Chelsea Square
MLS 22628093 • Keller Williams Realty Ocean Livin... • Keller Williams Realty Ocean Living
New
The Village at Oxford Greens
![84 LINKS WAY 84, OXFORD, CT, 06478, Oxford, CT 06478]()
3 beds
|3 baths
|2,008 sq ft
|Condo
84 LINKS WAY 84, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24205048 • Berkshire Hathaway NE Prop., Patty... • Berkshire Hathaway NE Prop.
New
Autumn Fields
![24 QUAIL HOLW 24, ENFIELD, CT, 06082, Enfield, CT 06082]()
1 beds
|2 baths
|1,235 sq ft
|Condo
24 QUAIL HOLW 24, ENFIELD, CT, 06082
Community: Autumn Fields
MLS 24204618 • Coldwell Banker Realty, Emilie Cou... • Coldwell Banker Realty
Heritage Village
![722 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
722 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24193881 • Coldwell Banker Realty, Beth Canto... • Coldwell Banker Realty
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.
Country Pointe Plainview
![30101 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803]()
2 beds
|2 baths
|1,379 sq ft
|Condo
30101 SPRUCE POND CIR, OYSTER BAY, NY, 1...
Community: Country Pointe Plainview
MLS 1043738 • BH&G R E Realty Connect, Caryn D. T... • BH&G R E Realty Connect
Enclave at Shrewsbury
![114 CAMPBELL CT, SHREWSBURY BORO, NJ, 07..., Shrewsbury Boro, NJ 07702]()
3 beds
|3 baths
|2,560 sq ft
|House
114 CAMPBELL CT, SHREWSBURY BORO, NJ, 07...
Community: Enclave at Shrewsbury
MLS 22627933 • C21/ Mack Morris Iris Lurie, Miche... • C21/ Mack Morris Iris Lurie
HarborView
![100 HARBOR VIEW DR 630, NORTH HEMPSTEAD,..., North Hempstead, NY 11050]()
3 beds
|3 baths
|2,426 sq ft
|Condo
100 HARBOR VIEW DR 630, NORTH HEMPSTEAD,...
Community: HarborView
MLS 1046915 • Evelyn Richards Inc, Evelyn L. Wilk... • Evelyn Richards Inc
Heritage Village
![970 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
970 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24204589 • William Pitt Sotheby's Int'l, Liz ... • William Pitt Sotheby's Int'l
Rivington
![44 WARRINGTON ROUND ST 44, DANBURY, CT, ..., Danbury, CT 06810]()
3 beds
|3 baths
|1,600 sq ft
|Condo
44 WARRINGTON ROUND ST 44, DANBURY, CT, ...
Community: Rivington
MLS 24203305 • ERA Insite Realty Services, Donna ... • ERA Insite Realty Services
Surrey Downs
![47 DATCHET CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728]()
2 beds
|2 baths
|1,261 sq ft
|Ranch
47 DATCHET CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
MLS 22627865 • Ellen Rosenbaum Real Estate, Olga ... • Ellen Rosenbaum Real Estate
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Leisure Glen
![477 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,434 sq ft
|Condo
477 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 1046192 • Howard Hanna Coach, Melora Lane CBR... • Howard Hanna Coach
Country Pointe Plainview
![38204 WINTERBERRY DR, OYSTER BAY, NY, 11..., Oyster Bay, NY 11803]()
2 beds
|2 baths
|1,989 sq ft
|Condo
38204 WINTERBERRY DR, OYSTER BAY, NY, 11...
Community: Country Pointe Plainview
MLS 1046882 • BH&G R E Realty Connect, Caryn D. T... • BH&G R E Realty Connect
The Manors at The Colony Preserve
![41 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967]()
2 beds
|2 baths
|1,557 sq ft
|Condo
41 GREENTREE CT, BROOKHAVEN, NY, 11967
Community: The Manors at The Colony Preserve
MLS 1046853 • Exit Realty Edge, Gina Valsamos PSA • Exit Realty Edge
Heritage Village
![411 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
411 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24203559 • William Raveis Real Estate, Giusep... • William Raveis Real Estate
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 Village
![620 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
620 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24204374 • Golden Heights LLC, Li Zhang • Golden Heights LLC
Country Pointe Preserve
![119 MIA LN 76, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980]()
2 beds
|3 baths
|2,187 sq ft
|Condo
119 MIA LN 76, BROOKHAVEN, NY, 11980
Community: Country Pointe Preserve
MLS 1046690 • Premier Prop At Meadowbrook Pt, Rob... • Premier Prop At Meadowbrook Pt
Shady Oaks
![64 ARROWWOOD CT, RED BANK, NJ, 07701, Red Bank, NJ 07701]()
MLS 22627763 • Coldwell Banker Realty, Charles Ma... • Coldwell Banker Realty
The Village at Oxford Greens
![733 CHAMPIONSHIP DR 733, OXFORD, CT, 064..., Oxford, CT 06478]()
2 beds
|3 baths
|1,673 sq ft
|Condo
733 CHAMPIONSHIP DR 733, OXFORD, CT, 064...
Community: The Village at Oxford Greens
MLS 24203270 • West View Properties, LLC, Matthew... • West View Properties, LLC
Sunken Pond Estates
![403 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,350 sq ft
|Condo
403 WINGED FOOT WAY, RIVERHEAD, NY, 1190...
Community: Sunken Pond Estates
MLS 1043495 • Douglas Elliman Real Estate, Patric... • Douglas Elliman Real Estate
Saddle Lakes
![157 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|2 baths
|1,386 sq ft
|Condo
157 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
MLS 1046606 • Daniel Gale Sothebys Intl Rlty, Den... • Daniel Gale Sothebys Intl Rlty
Shadow Lake Village
![38 BERKSHIRE CT, RED BANK, NJ, 07701, Red Bank, NJ 07701]()
2 beds
|3 baths
|1,408 sq ft
|Townhouse
38 BERKSHIRE CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
MLS 22627695 • Houwzer Inc., Patricia Gesswein • Houwzer Inc.
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(475) 471-1908
Village Estates
![30 SARAH CT, BABYLON, NY, 11701, Babylon, NY 11701]()
MLS 1045244 • Century 21 AA Realty, Angela Bodizs • Century 21 AA Realty
Shadow Lake Village
![21 CONCORD CT A, RED BANK, NJ, 07701, Red Bank, NJ 07701]()
2 beds
|2 baths
|1,066 sq ft
|House
21 CONCORD CT A, RED BANK, NJ, 07701
Community: Shadow Lake Village
MLS 22627680 • Coldwell Banker Realty, Kim L Spec... • Coldwell Banker Realty
The Greens at Half Hollow
![643 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
3 beds
|3 baths
|2,500 sq ft
|Condo
643 VERONA DR, HUNTINGTON, NY, 11747
Community: The Greens at Half Hollow
MLS 1045271 • Signature Premier Properties, Janic... • Signature Premier Properties
Download the Ultimate 55+ Homebuying Guide
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Regency at Prospect
![133 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|3 baths
|1,850 sq ft
|Condo
133 SYCAMORE DR, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24204172 • William Raveis Real Estate, Luis C... • William Raveis Real Estate
Vineyards at Moriches
![19 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934]()
2 beds
|3 baths
|2,251 sq ft
|Condo
19 EMILIE DR, BROOKHAVEN, NY, 11934
Community: Vineyards at Moriches
MLS 1040830 • Hampton Estates Realty LLC, Richard... • Hampton Estates Realty LLC
Leisure Glen
![279 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
MLS 1046123 • Signature Premier Properties, Jenni... • Signature Premier Properties
Newtown Woods
![623 BROOKSIDE CT 623, NEWTOWN, CT, 06470, Newtown, CT 06470]()
2 beds
|2 baths
|1,504 sq ft
|Condo
623 BROOKSIDE CT 623, NEWTOWN, CT, 06470
Community: Newtown Woods
MLS 24203843 • Berkshire Hathaway NE Prop., Jill ... • Berkshire Hathaway NE Prop.
Heritage Hills
![675 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,663 sq ft
|Condo
675 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1045730 • William Raveis-New York LLC, Lindsa... • William Raveis-New York LLC
Heritage Village
![875 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
875 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24203544 • Greg DeFazio, Greg DeFazio • Greg DeFazio
The Retreat at Carmel
![88 BLAIR HEIGHTS, CARMEL, NY, 10512, Carmel, NY 10512]()
3 beds
|3 baths
|2,695 sq ft
|Condo
88 BLAIR HEIGHTS, CARMEL, NY, 10512
Community: The Retreat at Carmel
MLS 1045319 • Coldwell Banker Realty, Sherri Malo... • Coldwell Banker Realty
Heritage Hills
![370 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,470 sq ft
|Condo
370 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1044903 • Houlihan Lawrence Inc., Lynn Conway • Houlihan Lawrence Inc.
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The Village at Buckingham
![13 KENINGTON RD 13, AVON, CT, 06001, Avon, CT 06001]()
3 beds
|3 baths
|2,024 sq ft
|Condo
13 KENINGTON RD 13, AVON, CT, 06001
Community: The Village at Buckingham
MLS 24203661 • Coldwell Banker Realty, Victoria S... • Coldwell Banker Realty
Heritage Village
![23 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
23 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24203566 • BHGRE Gaetano Marra Homes, Stephan... • BHGRE Gaetano Marra Homes
Download the Ultimate 55+ Homebuying Guide
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Frequently Asked Questions
In Westport, there is 1 small community with less than 500 homes.
The smallest 55+ community in Westport has 62 homes, the largest has 62 homes, and the average community consists of 62 homes.
No, there are no gated 55+ communities in Westport.
On average, listings in 55+ community in Westport stay on the market for around 19 days. The average price of homes for sale in this community is approximately $459,000, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Whitney Glen average around $459,000.
Want more information about active adult communities around Westport?
Want to learn more about 55+ communities in Westport?
393
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© 2026 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: Sep 10, 2026.
This application does not include information on all of the properties available for sale at this time.
