Call us at (984) 214-4271 to learn more about active adult communities in Pittsboro
Pittsboro, NC 55+ active adult communities & homes for sale
21 communities near Pittsboro
50 homes near Pittsboro
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$400ks
- $500ks
Encore at Chatham Park, Pittsboro, NC
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
425 homes
5 rating (1 reviews)
![Fearrington Village]()
$300ks
- $1Ms
Fearrington Village, Pittsboro, NC
New and Resale
|
Age-targeted
|
Built 1975 - present
|
1,400 homes
$400ks
- $600ks
Heritage Pines, Cary, NC
Resale Only
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55+ age-restricted
|
Built 2000 - 2006
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298 homes
$400ks
- $600ks
Encore at Briar Chapel, Chapel Hill, NC
Resale Only
|
55+ age-restricted
|
Built 2016 - 2021
|
185 homes
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$500ks
- $700ks
Buckhorn Preserve, Apex, NC
Resale Only
|
Age-targeted
|
Built 2019 - 2021
|
272 homes
5 rating (4 reviews)
![Carolina Preserve]()
$400ks
- $700ks
Carolina Preserve, Cary, NC
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
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1,360 homes
$600ks
The Courtyards at West Ca..., Cary, NC
New Construction
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55+ age-restricted
|
Built 2022 - present
|
108 homes
$500ks
- $600ks
Chapelwood, Chapel Hill, NC
Resale Only
|
55+ age-restricted
|
Built 2009 - 2013
|
69 homes
Download the Ultimate 55+ Homebuying Guide
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$400ks
- $700ks
The Villas at Culp Arbor, Chapel Hill, NC
Resale Only
|
55+ age-restricted
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Built 2009 - 2013
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64 homes
5 rating (1 reviews)
![The Orchard Villas]()
$400ks
- $500ks
The Orchard Villas, Apex, NC
Resale Only
|
Age-targeted
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Built 2008 - 2015
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86 homes
$500ks
- $900ks
Retreat at Cedar Crossing, Apex, NC
New and Resale
|
55+ age-restricted
|
Built 2021 - present
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87 homes
$500ks
The Townes at West Cary, Cary, NC
Resale Only
|
55+ age-restricted
|
Built 2022 - 2023
|
34 homes
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$500ks
- $600ks
The Courtyards at Southpo..., Durham, NC
New Construction
|
Age-targeted
|
Built 2020 - present
|
161 homes
$400ks
- $600ks
The Courtyards at Homeste..., Chapel Hill, NC
Resale Only
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55+ age-restricted
|
Built 2015 - 2021
|
63 homes
$500ks
The Courtyards at O'Kelly..., Cary, NC
Resale Only
|
55+ age-restricted
|
Built 2015 - 2020
|
149 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
Carolina Preserve
![1116 MARSALIS WAY, CARY, NC, 27519, Cary, NC 27519]()
2 beds
|2 baths
|2,173 sq ft
|House
1116 MARSALIS WAY, CARY, NC, 27519
Community: Carolina Preserve
MLS 10166363 • LPT Realty, LLC, Bill Nagel
New
Heritage Pines
![431 SAWGRASS HILL CT, CARY, NC, 27519, Cary, NC 27519]()
3 beds
|3 baths
|2,905 sq ft
|Townhouse
431 SAWGRASS HILL CT, CARY, NC, 27519
Community: Heritage Pines
MLS 10165966 • Keller Williams Legacy, Karen Coe
New
Fearrington Village
![14 CASWELL, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
4 beds
|3 baths
|3,899 sq ft
|House
14 CASWELL, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10165783 • Flex Realty, Michelle Delin
The Orchard Villas
![1497 ORCHARD VILLAS AVE, APEX, NC, 27502, Apex, NC 27502]()
3 beds
|3 baths
|2,379 sq ft
|Condo
1497 ORCHARD VILLAS AVE, APEX, NC, 27502
Community: The Orchard Villas
MLS 10165474 • Compass -- Cary, Deanna Jill Kerri...
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Fearrington Village
![564 WEATHERSFIELD, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|2,485 sq ft
|Townhouse
564 WEATHERSFIELD, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10165372 • Compass -- Chapel Hill - Durham, E...
Chapelwood
![242 HALES WOOD RD, CHAPEL HILL, NC, 2751..., Chapel Hill, NC 27517]()
3 beds
|2 baths
|2,328 sq ft
|House
242 HALES WOOD RD, CHAPEL HILL, NC, 2751...
Community: Chapelwood
MLS 10165268 • Northside Realty Inc., Tip Iuliucc...
Encore at Chatham Park
![33 IMAGINE WAY, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|2,668 sq ft
|House
33 IMAGINE WAY, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10165069 • Coldwell Banker Advantage, Barbara...
Encore at Briar Chapel
![63 MIDDLETON PL, CHAPEL HILL, NC, 27516, Chapel Hill, NC 27516]()
2 beds
|2 baths
|1,774 sq ft
|House
63 MIDDLETON PL, CHAPEL HILL, NC, 27516
Community: Encore at Briar Chapel
MLS 10165051 • RE/MAX United, Martha Lucas
Blakeley
![942 RIVER BARK PL, CARY, NC, 27519, Cary, NC 27519]()
MLS 10164654 • Compass -- Chapel Hill - Durham, 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.
Fearrington Village
![4203 HENDERSON PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
4 beds
|4 baths
|3,573 sq ft
|House
4203 HENDERSON PL, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10164458 • Berkshire Hathaway HomeService, De...
Fearrington Village
![4233 HENDERSON PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|3,210 sq ft
|House
4233 HENDERSON PL, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10163662 • LPT Realty, LLC, Alyssa Boreiko Gl...
Fearrington Village
![490 BEECHMAST, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|2,491 sq ft
|Townhouse
490 BEECHMAST, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10162327 • NorthGroup Real Estate, Inc., Bonn...
Buckhorn Preserve
![1916 KINGS KNOT CT, APEX, NC, 27502, Apex, NC 27502]()
4 beds
|3 baths
|2,807 sq ft
|House
1916 KINGS KNOT CT, APEX, NC, 27502
Community: Buckhorn Preserve
MLS 10161817 • Berkshire Hathaway HomeService, Jo...
Carolina Preserve
![206 CALLUM PL, CARY, NC, 27519, Cary, NC 27519]()
MLS 10161257 • Jordan Lee Real Estate, Jane Lee
Fearrington Village
![1312 LANGDON PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|2 baths
|2,057 sq ft
|Townhouse
1312 LANGDON PL, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10159108 • Coldwell Banker HPW, Danielle Nico...
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Encore at Chatham Park
![127 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,469 sq ft
|Ranch
127 TANTARA BND, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10159088 • Weekley Homes, LLC, Karen Doyle Bu...
Buckhorn Preserve
![2969 THIRLESTANE DR, APEX, NC, 27502, Apex, NC 27502]()
4 beds
|3 baths
|2,748 sq ft
|House
2969 THIRLESTANE DR, APEX, NC, 27502
Community: Buckhorn Preserve
MLS 10158923 • Ram Realty LLC, Sathya Prabha Koda...
Heritage Pines
![438 SAWGRASS HILL CT, CARY, NC, 27519, Cary, NC 27519]()
2 beds
|2 baths
|1,389 sq ft
|Townhouse
438 SAWGRASS HILL CT, CARY, NC, 27519
Community: Heritage Pines
MLS 10157789 • Berkshire Hathaway HomeService, Ev...
Encore at Chatham Park
![62 RASPBERRY RUN, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|4 baths
|3,090 sq ft
|House
62 RASPBERRY RUN, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10157689 • Coldwell Banker - HPW, Dana Wicker...
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 Courtyards at West Cary
![444 CRAYTON OAK DR, CARY, NC, 27519, Cary, NC 27519]()
3 beds
|3 baths
|2,972 sq ft
|House
444 CRAYTON OAK DR, CARY, NC, 27519
Community: The Courtyards at West Cary
MLS 10157560 • Chosen Real Estate Group, Nicholas...
The Courtyards at West Cary
![609 CROOKED PINE DR, CARY, NC, 27519, Cary, NC 27519]()
3 beds
|3 baths
|2,503 sq ft
|House
609 CROOKED PINE DR, CARY, NC, 27519
Community: The Courtyards at West Cary
MLS 10156411 • Pharos Real Estate, LLC, Myron Smi...
Encore at Chatham Park
![120 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,467 sq ft
|Duplex
120 TANTARA BND, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10155945 • Weekley Homes, LLC, Karen Doyle Bu...
Encore at Chatham Park
![128 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,467 sq ft
|Duplex
128 TANTARA BND, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10155933 • Weekley Homes, LLC, Karen Doyle Bu...
Buckhorn Preserve
![2930 BALBARDIE DR, APEX, NC, 27502, Apex, NC 27502]()
3 beds
|3 baths
|2,828 sq ft
|House
2930 BALBARDIE DR, APEX, NC, 27502
Community: Buckhorn Preserve
MLS 10155312 • Cary-Raleigh Realty, Inc., Hannah ...
Brookside
![1107 PALISADE BLUFF LN, APEX, NC, 27502, Apex, NC 27502]()
3 beds
|3 baths
|2,241 sq ft
|Townhouse
1107 PALISADE BLUFF LN, APEX, NC, 27502
Community: Brookside
MLS 10155071 • SM North Carolina Brokerage, Jolen...
Brookside
![1105 PALISADE BLUFF LN, APEX, NC, 27502, Apex, NC 27502]()
3 beds
|3 baths
|2,221 sq ft
|Townhouse
1105 PALISADE BLUFF LN, APEX, NC, 27502
Community: Brookside
MLS 10155070 • SM North Carolina Brokerage, Jolen...
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(984) 214-4271
Encore at Briar Chapel
![66 MIDDLETON PL, CHAPEL HILL, NC, 27516, Chapel Hill, NC 27516]()
2 beds
|2 baths
|1,885 sq ft
|House
66 MIDDLETON PL, CHAPEL HILL, NC, 27516
Community: Encore at Briar Chapel
MLS 10154169 • Long & Foster Real Estate INC, Cha...
Heritage Pines
![317 INDIAN ELM LN, CARY, NC, 27519, Cary, NC 27519]()
MLS 10153558 • EXP Realty LLC, Tina Caul
The Villas at Culp Arbor
![107 CULP HILL DR, CHAPEL HILL, NC, 27517, Chapel Hill, NC 27517]()
2 beds
|2 baths
|1,085 sq ft
|Condo
107 CULP HILL DR, CHAPEL HILL, NC, 27517
Community: The Villas at Culp Arbor
MLS 10152931 • Long & Foster Real Estate INC, Dus...
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.
Fearrington Village
![145 WINDSTONE, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
7 beds
|5 baths
|4,862 sq ft
|House
145 WINDSTONE, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10152923 • Century 21 Southern Lifestyles, Lo...
Heritage Pines
![408 KNOTTS VALLEY LN, CARY, NC, 27519, Cary, NC 27519]()
3 beds
|3 baths
|2,544 sq ft
|House
408 KNOTTS VALLEY LN, CARY, NC, 27519
Community: Heritage Pines
MLS 10152202 • RE/MAX EXECUTIVE, Adam Lindsay
Encore at Briar Chapel
![90 PULASKI TRL, CHAPEL HILL, NC, 27516, Chapel Hill, NC 27516]()
2 beds
|3 baths
|2,447 sq ft
|House
90 PULASKI TRL, CHAPEL HILL, NC, 27516
Community: Encore at Briar Chapel
MLS 10150922 • Keller Williams Elite Realty, Jen ...
Brookside
![2144 BARNSIDE LN, APEX, NC, 27502, Apex, NC 27502]()
MLS 10150717 • SM North Carolina Brokerage, Jolen...
Fearrington Village
![246 FOX RIDGE RD, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|2,248 sq ft
|House
246 FOX RIDGE RD, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10146777 • Relevate Real Estate Inc., Jed Gro...
Heritage Pines
![105 ROCKPORT RIDGE WAY, CARY, NC, 27519, Cary, NC 27519]()
2 beds
|2 baths
|1,718 sq ft
|House
105 ROCKPORT RIDGE WAY, CARY, NC, 27519
Community: Heritage Pines
MLS 10143709 • Real Broker, LLC, Joseph Wells
Fearrington Village
![309 BANEBERRY CLOSE, PITTSBORO, NC, 2731..., Pittsboro, NC 27312]()
3 beds
|2 baths
|2,091 sq ft
|Townhouse
309 BANEBERRY CLOSE, PITTSBORO, NC, 2731...
Community: Fearrington Village
MLS 10140948 • Coldwell Banker Advantage, Barbara...
Encore at Chatham Park
![356 ASPEN AVE, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|2,414 sq ft
|House
356 ASPEN AVE, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10140664 • Weekley Homes, LLC, Tracey Riordan
Want to learn more about 55+ communities in Pittsboro?
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Encore at Chatham Park
![115 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,467 sq ft
|Townhouse
115 TANTARA BND, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10140654 • Weekley Homes, LLC, Erin Messier
Encore at Chatham Park
![107 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,467 sq ft
|Townhouse
107 TANTARA BND, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10140650 • Weekley Homes, LLC, Erin Messier
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 Pittsboro, there are 1 large community with over 1000 homes, no medium communities, and 1 small community with less than 500 homes.
The smallest 55+ communities in Pittsboro has 150 homes, the largest has 1400 homes, and the average communities consists of 775 homes.
Yes, there are new 55+ homes available in Pittsboro. The most recent communities started in Pittsboro include Fearrington Village, Inspire Briar Chapel. There are also 2 communities in Pittsboro that offer new construction homes, including Fearrington Village, Inspire Briar Chapel.
No, there are no gated 55+ communities in Pittsboro.
On average, listings in 55+ communities in Pittsboro stay on the market for around 188 days. The average price of homes for sale in these communities is approximately $660,702, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Fearrington Village average around $660,702.
Raleigh Durham Area 55+ Housing Market Trends
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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 12, 2026.
This application does not include information on all of the properties available for sale at this time.
