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Portland, CT 55+ active adult communities & homes for sale
124 communities near Portland
237 homes near Portland
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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
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
$300ks
- $600ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
Want to learn more about 55+ communities in Portland?
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(860) 854-7490
3.7 rating (3 reviews)
![Greenwood Village]()
$100ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
$600ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
$300ks
- $400ks
The Manors at The Colony ..., Shirley, NY
New Construction
|
55+ age-restricted
|
Built 2013 - present
|
150 homes
4 rating (8 reviews)
![Glenwood Village]()
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 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.
$400ks
- $500ks
Harmony Place, Rutland, MA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
142 homes
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
5 rating (1 reviews)
![The Villages at Mount Sin...]()
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
5 rating (1 reviews)
![Westhampton Pines]()
$900ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
5 rating (1 reviews)
![Encore at Lake Grove]()
$500ks
- $700ks
Encore at Lake Grove, Lake Grove, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2007
|
228 homes
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
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5 rating (1 reviews)
![Encore Atlantic Shores]()
$500ks
- $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$200ks
- $400ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
$800ks
- $900ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 homes
$400ks
- $500ks
The Village at Orchard Me..., Shrewsbury, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2007
|
114 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.
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
$300ks
- $900ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
$600ks
- $900ks
Country Pointe PreserveYaphank, NY
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
152 homes
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
$300ks
- $400ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
67 homes
$300ks
- $400ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
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(860) 854-7490
$300ks
- $400ks
Village Estates, Amityville, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2008
|
138 homes
$200ks
- $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
108 homes
$500ks
The Coves at Melville, Melville, NY
Resale Only
|
62+ age-restricted
|
Built 2004 - 2005
|
175 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
- $400ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
$300ks
- $400ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
$300ks
- $400ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 homes
$600ks
The Seasons at Seaford, Seaford, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
112 homes
$700ks
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
92 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$400ks
- $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
Want to learn more about 55+ communities in Portland?
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Questions? Call us:
(860) 854-7490
$300ks
- $400ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
$500ks
- $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 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.
New
Heritage Village
![132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
132 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24179565 • Berkshire Hathaway NE Prop., Jacqu...
New
Brierly Pond Village
![2 ASHTON LN 2, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|4 baths
|1,949 sq ft
|Condo
2 ASHTON LN 2, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73526921 • Century 21 XSELL REALTY, Lora Sava...
New
Founders Village
![2555 YOUNGS AVE 1D, SOUTHOLD, NY, 11971, Southold, NY 11971]()
2 beds
|2 baths
|1,100 sq ft
|House
2555 YOUNGS AVE 1D, SOUTHOLD, NY, 11971
Community: Founders Village
MLS 1006443 • Thomas J McCarthy Real Estate, Thom...
New
Oronoque Village
![13 ALGONQUIN LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,480 sq ft
|Condo
13 ALGONQUIN LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24178944 • Houlihan Lawrence, Lindsay Violett...
New
Meadow Brook Estates
![806 SAGE HILL DR 806, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|1,850 sq ft
|Condo
806 SAGE HILL DR 806, OXFORD, CT, 06478
Community: Meadow Brook Estates
MLS 24179340 • Coldwell Banker Realty, Jennifer C...
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New
Leisure Village
![196 NEWCASTLE CT C, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961]()
2 beds
|1 baths
|836 sq ft
|Condo
196 NEWCASTLE CT C, BROOKHAVEN, NY, 1196...
Community: Leisure Village
MLS 1002428 • Howard Hanna Coach, Grace Della Cro...
New
The Coves at Melville
![27 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
2 beds
|2 baths
|1,109 sq ft
|Condo
27 MORLEY CIR, HUNTINGTON, NY, 11747
Community: The Coves at Melville
MLS 1005830 • Compass Greater NY LLC, Leslye J. S...
New
Heritage Village
![877 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
877 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24178170 • Berkshire Hathaway NE Prop., Lisa ...
New
The Village at Orchard Meadows
![70 ORCHARD MEADOW DR 70, SHREWSBURY, MA,..., Shrewsbury, MA 01545]()
2 beds
|3 baths
|1,896 sq ft
|Condo
70 ORCHARD MEADOW DR 70, SHREWSBURY, MA,...
Community: The Village at Orchard Meadows
MLS 73526186 • ERA Key Realty Services, Laura Heb...
New
The Summit at Bethel
![6 LOCKWOOD CIR 6, BETHEL, CT, 06801, Bethel, CT 06801]()
3 beds
|3 baths
|1,771 sq ft
|Condo
6 LOCKWOOD CIR 6, BETHEL, CT, 06801
Community: The Summit at Bethel
MLS 24178598 • Rockoff Realty, Kevin Rockoff
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
Greenwood Village
![11 A DOGWOOD LN 11 A, BROOKHAVEN, NY, 11..., Brookhaven, NY 11949]()
2 beds
|2 baths
|1,032 sq ft
|Condo
11 A DOGWOOD LN 11 A, BROOKHAVEN, NY, 11...
Community: Greenwood Village
MLS 1005407 • Douglas Elliman Real Estate, Annett...
New
The Manors at The Colony Preserve
![40 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967]()
2 beds
|2 baths
|1,360 sq ft
|Condo
40 GREENTREE CT, BROOKHAVEN, NY, 11967
Community: The Manors at The Colony Preserve
MLS 1004153 • Realty Connect USA LLC, Brandon M. ...
New
The Greens at Half Hollow
![1075 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
2 beds
|2 baths
|1,166 sq ft
|Condo
1075 SAVOY DR, HUNTINGTON, NY, 11747
Community: The Greens at Half Hollow
MLS 1004175 • Evolution Realty of L I, Constance ...
New
Pond Spring Village
![37 SEPTEMBER LN 37, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403]()
2 beds
|3 baths
|1,328 sq ft
|Condo
37 SEPTEMBER LN 37, BEACON FALLS, CT, 06...
Community: Pond Spring Village
MLS 24178338 • mygoodagent, Cynthia Harding
New
The Waterways at Moriches
![188 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955]()
2 beds
|2 baths
|2,100 sq ft
|Condo
188 RIVER DR, BROOKHAVEN, NY, 11955
Community: The Waterways at Moriches
MLS 1004820 • Charles Rutenberg Realty Inc, Lawre...
New
The Greens at Half Hollow
![1053 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
2 beds
|2 baths
|1,100 sq ft
|Condo
1053 SAVOY DR, HUNTINGTON, NY, 11747
Community: The Greens at Half Hollow
MLS 1004604 • Douglas Elliman Real Estate, Ronni ...
Want to learn more about 55+ communities in Portland?
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(860) 854-7490
New
Heritage Village
![657 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|3 baths
|1,716 sq ft
|Condo
657 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24178782 • William Raveis Real Estate, Ruth Z...
New
The Village at Orchard Meadows
![7 BLOSSOM TREE DR 7, SHREWSBURY, MA, 015..., Shrewsbury, MA 01545]()
2 beds
|2 baths
|1,370 sq ft
|Condo
7 BLOSSOM TREE DR 7, SHREWSBURY, MA, 015...
Community: The Village at Orchard Meadows
MLS 73525443 • Coldwell Banker Realty - Worcester...
New
Heritage Village
![343 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
343 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24178882 • Berkshire Hathaway NE Prop., Donal...
New
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 1005065 • Magic Of Great Neck Realty Inc, Vit...
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
Rivington
![925 OLD PASTURE DR 925, DANBURY, CT, 068..., Danbury, CT 06810]()
2 beds
|2 baths
|1,258 sq ft
|Condo
925 OLD PASTURE DR 925, DANBURY, CT, 068...
Community: Rivington
MLS 24177442 • Compass Connecticut, LLC, Karla Mu...
New
Leisure Knoll
![379 LARCHMONT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,070 sq ft
|Condo
379 LARCHMONT CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 1004246 • Greene Realty Group, Derek J. Green...
New
The Greens at Half Hollow
![562 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
2 beds
|3 baths
|1,941 sq ft
|Condo
562 BARDINI DR, HUNTINGTON, NY, 11747
Community: The Greens at Half Hollow
MLS 1004763 • Signature Premier Properties, Janic...
New
Chatfield Farms
![24 BAYBERRY CT 24, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403]()
3 beds
|3 baths
|1,981 sq ft
|Condo
24 BAYBERRY CT 24, BEACON FALLS, CT, 064...
Community: Chatfield Farms
MLS 24177009 • Coldwell Banker Realty, Sarah Luce...
New
The Seasons at Elwood
![53 WINTER PL 53, HUNTINGTON, NY, 11731, Huntington, NY 11731]()
2 beds
|3 baths
|1,500 sq ft
|Condo
53 WINTER PL 53, HUNTINGTON, NY, 11731
Community: The Seasons at Elwood
MLS 1004565 • Signature Premier Properties, Susan...
New
The Seasons at Elwood
![240 FALL CT, HUNTINGTON, NY, 11731, Huntington, NY 11731]()
2 beds
|3 baths
|2,329 sq ft
|Condo
240 FALL CT, HUNTINGTON, NY, 11731
Community: The Seasons at Elwood
MLS 1004363 • Real Broker NY LLC, Matthew J. Lenn...
New
Leisure Knoll
![220 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,445 sq ft
|Condo
220 BELFAST LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 1003259 • Aliano Real Estate, Dennis P. Consa...
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New
Leisure Glen
![515 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,434 sq ft
|House
515 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 1002675 • Oversouth LLC, James Ragusa
New
New England Commons
![5 LITCHFIELD LN 5A, WEBSTER, MA, 01570, Webster, MA 01570]()
2 beds
|2 baths
|1,173 sq ft
|Condo
5 LITCHFIELD LN 5A, WEBSTER, MA, 01570
Community: New England Commons
MLS 73520431 • Champa Realty, Inc., Joyce Belli
Meadow Brook Estates
![223 MEADOW BROOK RD 223, OXFORD, CT, 064..., Oxford, CT 06478]()
2 beds
|2 baths
|1,480 sq ft
|Condo
223 MEADOW BROOK RD 223, OXFORD, CT, 064...
Community: Meadow Brook Estates
MLS 24177285 • William Raveis Real Estate, Pat Bl...
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
![40 WILLOW CT, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|2 baths
|1,151 sq ft
|Manufactured On Land
40 WILLOW CT, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1002194 • MYNY Residential, Gina Marie Betten...
Oronoque Village
![261 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,620 sq ft
|Condo
261 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24176935 • Higgins Group Real Estate, Sharon ...
Woodridge Strathmore Terrace
![54 STANDISH DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|1,335 sq ft
|Condo
54 STANDISH DR, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 1003024 • Coldwell Banker American Homes, Dan...
Heritage Village
![899 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
899 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24176926 • Berkshire Hathaway NE Prop., Bonni...
Oronoque Village
![209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,438 sq ft
|Condo
209 ACORN LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24176182 • Coldwell Banker Realty, Mary Kelle...
Vineyards at Brookfield
![69 AVERY DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934]()
2 beds
|3 baths
|2,254 sq ft
|Condo
69 AVERY DR, BROOKHAVEN, NY, 11934
Community: Vineyards at Brookfield
MLS 1001606 • Howard Hanna Coach, Samantha Kojac
The Powder Forest Homes
![9 ASHTON CIR, SIMSBURY, CT, 06070, Simsbury, CT 06070]()
2 beds
|2 baths
|1,809 sq ft
|Condo
9 ASHTON CIR, SIMSBURY, CT, 06070
Community: The Powder Forest Homes
MLS 24175004 • William Pitt Sotheby's Int'l, Dian...
Applegate Estates
![90 APPLE GATE 190, SOUTHINGTON, CT, 0648..., Southington, CT 06489]()
2 beds
|2 baths
|1,350 sq ft
|Condo
90 APPLE GATE 190, SOUTHINGTON, CT, 0648...
Community: Applegate Estates
MLS 24176429 • Appletown Realty Inc., John Mastri...
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The Village at Oxford Greens
![71 LINKS WAY 71, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|2 baths
|1,590 sq ft
|Condo
71 LINKS WAY 71, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24177225 • Berkshire Hathaway NE Prop., Patty...
The Greens at Half Hollow
![1153 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
2 beds
|2 baths
|1,100 sq ft
|Condo
1153 SAVOY DR, HUNTINGTON, NY, 11747
Community: The Greens at Half Hollow
MLS 1001407 • Keller Williams Points North, Jeffr...
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.
Frequently Asked Questions
In Portland, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in Portland has 56 homes, the largest has 82 homes, and the average communities consists of 69 homes.
Yes, there is gated 55+ communities in Portland. Approximately 50.0% of 55+ communities in the area are gated. For instance, Bartlett Hill is a gated communities with 82 homes.
On average, listings in 55+ communities in Portland stay on the market for around 97 days. The average price of homes for sale in these communities is approximately $487,937, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Bartlett Hill average around $487,937.
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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: May 30, 2026.
This application does not include information on all of the properties available for sale at this time.
