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Upton, MA 55+ active adult communities & homes for sale
41 communities near Upton
42 homes near Upton
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$400ks
- $600ks
Del Webb Chauncy Lake, Westborough, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
700 homes
$400ks
- $500ks
Harmony Place, Rutland, MA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
142 homes
$500ks
- $700ks
The Trails, Hopkinton, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
170 homes
$300ks
- $600ks
Pennington Crossing, Walpole, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
172 homes
$500ks
Orchard Hill, Westborough, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2010
|
100 homes
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$700ks
- $900ks
Regency at Glen Ellen, Millis, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
324 homes
$500ks
- $600ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only
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55+ age-restricted
|
Built 2010 - 2015
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69 homes
$400ks
- $500ks
The Village at Orchard Me..., Shrewsbury, MA
Resale Only
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55+ age-restricted
|
Built 2002 - 2007
|
114 homes
$400ks
- $500ks
Forest Glen, Uxbridge, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
44 homes
$500ks
- $900ks
Wyman Farms, Shrewsbury, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
26 homes
Download the Ultimate 55+ Homebuying Guide
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$400ks
- $600ks
Woodcrest Run, Sharon, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
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25 homes
$600ks
- $700ks
The Villages at Walker Me..., Westborough, MA
Resale Only
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55+ age-restricted
|
Built 1999 - 2000
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100 homes
$500ks
Northwoods at Sudbury, Sudbury, MA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2019
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43 homes
$700ks
- $800ks
Millwood Preserve, Framingham, MA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
129 homes
$500ks
- $600ks
Bigelow Farm, Northborough, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
41 homes
$600ks
- $700ks
Rockwood Meadows, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2016 - present
|
58 homes
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$700ks
Trail Ridge at Harvard, Harvard, MA
Resale Only
|
55+ age-restricted
|
Built 2008 - 2023
|
52 homes
$300ks
- $400ks
Bella Vista, Glocester, RI
Resale Only
|
55+ age-restricted
|
Built 2015 - 2021
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70 homes
$900ks
- $1Ms
Garrison Place, Carlisle, MA
Resale Only
|
55+ age-restricted
|
Built 2018 - 2019
|
16 homes
$300ks
- $400ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 homes
Download the Ultimate 55+ Homebuying Guide
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$900ks
59 North Main, Sherborn, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
12 homes
$400ks
- $600ks
Upton Ridge, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
139 homes
$500ks
- $700ks
The Lanterns at Warren Wo..., Ashland, MA
Resale Only
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55+ age-restricted
|
Built 2016 - 2020
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93 homes
$400ks
- $600ks
Brooksmont, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
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66 homes
$700ks
Brookside Village, Walpole, MA
Resale Only
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55+ age-restricted
|
Built 2018 - 2018
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30 homes
$800ks
- $1Ms
Enclave at Hudson, Hudson, MA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
64 homes
$1Ms
- $2Ms
Village at Silver Hill, Weston, MA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
8 homes
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$600ks
- $700ks
Northside Meadows, Framingham, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2019
|
60 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
Angell Brook Village, West Boylston, MA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2012
|
132 homes
$300ks
- $400ks
Pheasant Hill, Northborough, MA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2006
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48 homes
$400ks
- $500ks
The Village at Westminste..., Holden, MA
New and Resale
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55+ age-restricted
|
Built 2006 - present
|
125 homes
$200ks
- $300ks
New England Commons, Webster, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
100 homes
$500ks
Blue Heron Pond, Lancaster, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2014
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58 homes
$700ks
- $800ks
Adams Farm, Shrewsbury, MA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
90 homes
$600ks
- $700ks
Quail Ridge, Acton, MA
Resale Only
|
55+ age-restricted
|
Built 2015 - present
|
153 homes
$500ks
- $700ks
Holliston Woods, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
66 homes
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$400ks
The Villages at Crane Mea..., Marlborough, MA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2005
|
91 homes
$400ks
- $500ks
The Seasons at Salisbury, Holden, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2006
|
91 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
Orchard Hill
![19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158..., Westborough, MA 01581]()
2 beds
|3 baths
|2,183 sq ft
|Condo
19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158...
Community: Orchard Hill
MLS 73501575 • Marilyn L. Smith R. E., Marilyn Sm...
New
Del Webb Chauncy Lake
![5 PETERS FARM WAY 7107, WESTBOROUGH, MA,..., Westborough, MA 01581]()
2 beds
|2 baths
|1,512 sq ft
|Condo
5 PETERS FARM WAY 7107, WESTBOROUGH, MA,...
Community: Del Webb Chauncy Lake
MLS 73507041 • Pulte Homes of New England, Erin S...
New
Del Webb Chauncy Lake
![5 PETERS FARM WAY 7112, WESTBOROUGH, MA,..., Westborough, MA 01581]()
1 beds
|1 baths
|1,058 sq ft
|Condo
5 PETERS FARM WAY 7112, WESTBOROUGH, MA,...
Community: Del Webb Chauncy Lake
MLS 73506372 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![6 PETERS FARM WAY 411, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,375 sq ft
|Condo
6 PETERS FARM WAY 411, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73505249 • LAER Realty Partners, Pamela Taylo...
The Trails
![7 WATERVILLE LN 7, HOPKINTON, MA, 01748, Hopkinton, MA 01748]()
2 beds
|3 baths
|2,274 sq ft
|Condo
7 WATERVILLE LN 7, HOPKINTON, MA, 01748
Community: The Trails
MLS 73503809 • Realty Executives Boston West, Kar...
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Del Webb Chauncy Lake
![4204 PETERS FARM WAY 204, WESTBOROUGH, M..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
4204 PETERS FARM WAY 204, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73503550 • ERA Key Realty Services - Distinct...
Del Webb Chauncy Lake
![5 PETERS FARM WAY 5205, WESTBOROUGH, MA,..., Westborough, MA 01581]()
2 beds
|2 baths
|1,175 sq ft
|Condo
5 PETERS FARM WAY 5205, WESTBOROUGH, MA,...
Community: Del Webb Chauncy Lake
MLS 73503449 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![5 PETERS FARM WAY 307, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,512 sq ft
|Condo
5 PETERS FARM WAY 307, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73502794 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![1207 CODMAN WAY 1207, WESTBOROUGH, MA, 0..., Westborough, MA 01581]()
2 beds
|2 baths
|1,469 sq ft
|Condo
1207 CODMAN WAY 1207, WESTBOROUGH, MA, 0...
Community: Del Webb Chauncy Lake
MLS 73502585 • Keller Williams Realty, Bill Skerr...
Pennington Crossing
![1108 PENNINGTON DR 1108, WALPOLE, MA, 02..., Walpole, MA 02081]()
1 beds
|1 baths
|1,015 sq ft
|Condo
1108 PENNINGTON DR 1108, WALPOLE, MA, 02...
Community: Pennington Crossing
MLS 73502472 • Coldwell Banker Realty - Canton, A...
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.
The Villages at Walker Meadow
![3 QUAKER WAY 40, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|2 baths
|1,876 sq ft
|Condo
3 QUAKER WAY 40, WESTBOROUGH, MA, 01581
Community: The Villages at Walker Meadow
MLS 73501795 • Berkshire Hathaway HomeServices To...
Northwoods at Sudbury
![20 NORTHWOOD DR 303, SUDBURY, MA, 01776, Sudbury, MA 01776]()
1 beds
|2 baths
|1,616 sq ft
|Condo
20 NORTHWOOD DR 303, SUDBURY, MA, 01776
Community: Northwoods at Sudbury
MLS 73499458 • Jin Chung Realty LLC, Jin H. Chung
Del Webb Chauncy Lake
![4 PETERS FARM WAY 206, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,469 sq ft
|Condo
4 PETERS FARM WAY 206, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73499155 • eXp Realty, Natasha Koryak
Millwood Preserve
![11 BAITING BROOK RD 11, FRAMINGHAM, MA, ..., Framingham, MA 01701]()
3 beds
|3 baths
|2,559 sq ft
|Condo
11 BAITING BROOK RD 11, FRAMINGHAM, MA, ...
Community: Millwood Preserve
MLS 73497980 • The Greene Realty Group, Derek Gre...
Pennington Crossing
![2301 PENNINGTON DR 2301, WALPOLE, MA, 02..., Walpole, MA 02081]()
2 beds
|2 baths
|1,490 sq ft
|Condo
2301 PENNINGTON DR 2301, WALPOLE, MA, 02...
Community: Pennington Crossing
MLS 73497829 • NextHome Signature Realty, Michele...
Wyman Farms
![935 MAIN ST 23, SHREWSBURY, MA, 01545, Shrewsbury, MA 01545]()
MLS 73497648 • Realty Executives Boston West, Pat...
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Questions? Call us:
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Del Webb Chauncy Lake
![4403 PETERS FARM WAY 4403, WESTBOROUGH, ..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
4403 PETERS FARM WAY 4403, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73495616 • Lamacchia Realty, Inc., Martha Con...
Del Webb Chauncy Lake
![12308 PETERS FARM WAY 308, WESTBOROUGH, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,326 sq ft
|Condo
12308 PETERS FARM WAY 308, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73495030 • ERA Key Realty Services - Distinct...
Orchard Hill
![9 BALDWIN CT 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
3 beds
|3 baths
|2,793 sq ft
|Condo
9 BALDWIN CT 9, WESTBOROUGH, MA, 01581
Community: Orchard Hill
MLS 73493124 • Mathieu Newton Sotheby's Internati...
Del Webb Chauncy Lake
![5 PETERS FARM WAY 309, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,375 sq ft
|Condo
5 PETERS FARM WAY 309, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73489742 • Pulte Homes of New England, Erin S...
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.
Del Webb Chauncy Lake
![5 PETERS FARM WAY 104, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
1 beds
|1 baths
|972 sq ft
|Condo
5 PETERS FARM WAY 104, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73489727 • Pulte Homes of New England, Erin S...
The Trails
![28 WATERVILLE LN 28, HOPKINTON, MA, 0174..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,510 sq ft
|Condo
28 WATERVILLE LN 28, HOPKINTON, MA, 0174...
Community: The Trails
MLS 73489252 • Realty Executives Boston West, Phi...
Del Webb Chauncy Lake
![1105 PETERS FARM WAY 105, WESTBOROUGH, M..., Westborough, MA 01581]()
1 beds
|1 baths
|945 sq ft
|Condo
1105 PETERS FARM WAY 105, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73487816 • Mathieu Newton Sotheby's Internati...
Regency at Glen Ellen
![8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|4 baths
|4,247 sq ft
|Condo
8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73487461 • William Raveis R.E. & Home Service...
Harmony Place
![20 FIDELITY DR 10, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,582 sq ft
|Condo
20 FIDELITY DR 10, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73485968 • Harbor Classic Realty, Karin Ander...
Woodcrest Run
![635 OLD POST RD 210, SHARON, MA, 02067, Sharon, MA 02067]()
2 beds
|2 baths
|1,056 sq ft
|Condo
635 OLD POST RD 210, SHARON, MA, 02067
Community: Woodcrest Run
MLS 73483721 • Coldwell Banker Realty - Westwood,...
Del Webb Chauncy Lake
![6312 PETERS FARM WAY 6312, WESTBOROUGH, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,469 sq ft
|Condo
6312 PETERS FARM WAY 6312, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73481383 • Keller Williams Pinnacle MetroWest...
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Harmony Place
![10 FIDELITY DR 5, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,582 sq ft
|Condo
10 FIDELITY DR 5, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73481173 • Harbor Classic Realty, Karin Ander...
Harmony Place
![12 FIDELITY DR 6, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,582 sq ft
|Condo
12 FIDELITY DR 6, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73481167 • Harbor Classic Realty, Karin Ander...
Del Webb Chauncy Lake
![1109 PETERS FARM WAY 1109, WESTBOROUGH, ..., Westborough, MA 01581]()
1 beds
|1 baths
|1,030 sq ft
|Condo
1109 PETERS FARM WAY 1109, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73480122 • Oak Realty, Pamela Bathen
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.
Harmony Place
![15 FIDELITY DR 70, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,447 sq ft
|Condo
15 FIDELITY DR 70, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73479872 • Harbor Classic Realty, Karin Ander...
Harmony Place
![4 FIDELITY DR 2, RUTLAND, MA, 01543, Rutland, MA 01543]()
MLS 73479871 • Harbor Classic Realty, Karin Ander...
Regency at Glen Ellen
![124 GLEN ELLEN BLVD 124, MILLIS, MA, 020..., Millis, MA 02054]()
2 beds
|2 baths
|1,797 sq ft
|Condo
124 GLEN ELLEN BLVD 124, MILLIS, MA, 020...
Community: Regency at Glen Ellen
MLS 73478697 • Coldwell Banker Realty - Needham, ...
The Village at Orchard Meadows
![47 ORCHARD MEADOW DR 47, SHREWSBURY, MA,..., Shrewsbury, MA 01545]()
2 beds
|2 baths
|1,370 sq ft
|Condo
47 ORCHARD MEADOW DR 47, SHREWSBURY, MA,...
Community: The Village at Orchard Meadows
MLS 73477228 • RE/MAX Partners, Kris Koliss
Del Webb Chauncy Lake
![2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0..., Westborough, MA 01581]()
2 beds
|2 baths
|1,469 sq ft
|Condo
2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0...
Community: Del Webb Chauncy Lake
MLS 73477125 • Lamacchia Realty, Inc., Martha Con...
Forest Glen
![61 SPRING HILL DR 61, UXBRIDGE, MA, 0156..., Uxbridge, MA 01569]()
2 beds
|2 baths
|1,525 sq ft
|Condo
61 SPRING HILL DR 61, UXBRIDGE, MA, 0156...
Community: Forest Glen
MLS 73475598 • Century 21 Custom Home Realty, Rob...
Regency at Assabet Ridge
![28 BOWOOD LN 28, MARLBOROUGH, MA, 01752, Marlborough, MA 01752]()
3 beds
|3 baths
|2,205 sq ft
|Condo
28 BOWOOD LN 28, MARLBOROUGH, MA, 01752
Community: Regency at Assabet Ridge
MLS 73469241 • Coldwell Banker Realty - Sudbury, ...
Harmony Place
![10 FIDELITY DR # 5, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,582 sq ft
|Condo
10 FIDELITY DR # 5, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73465497 • Harbor Classic Realty, Karin Ander...
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Harmony Place
![12 FIDELITY DR # 6, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,582 sq ft
|Condo
12 FIDELITY DR # 6, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73460904 • Harbor Classic Realty, Karin Ander...
The Trails
![14 WATERVILLE LN # 14, HOPKINTON, MA, 01..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,274 sq ft
|Condo
14 WATERVILLE LN # 14, HOPKINTON, MA, 01...
Community: The Trails
MLS 73460639 • Realty Executives Boston West, Kar...
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 Upton, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in Upton has 58 homes, the largest has 139 homes, and the average communities consists of 98 homes.
Yes, there are new 55+ homes available in Upton. The most recent communities started in Upton include Upton Ridge, Rockwood Meadows. There are also 2 communities in Upton that offer new construction homes, including Rockwood Meadows, Upton Ridge.
No, there are no gated 55+ communities in Upton.
On average, listings in 55+ communities in Upton stay on the market for around 36 days. The average price of homes for sale in these communities is approximately $849,450, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Rockwood Meadows average around $1,049,000, while homes in Upton Ridge average around $649,900.
Want more information about active adult communities around Upton?
Want to learn more about 55+ communities in Upton?
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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: Apr 28, 2026.
This application does not include information on all of the properties available for sale at this time.
