Call us at (984) 214-4271 to learn more about active adult communities in Pittsboro
Pittsboro, NC 55+ active adult communities & homes for sale
23 communities near Pittsboro
65 homes near Pittsboro
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5 rating (1 reviews)
![Fearrington Village]()
$300ks
- $1Ms
Fearrington Village, Pittsboro, NC
New and Resale
|
Age-targeted
|
Built 1975 - present
|
1,400 homes
$400ks
- $500ks
Encore at Chatham Park, Pittsboro, NC
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
425 homes
$500ks
Brookside, Apex, NC
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
75 homes
$500ks
- $1Ms
Regency at Holly Springs, Holly Springs, NC
New Construction
|
55+ age-restricted
|
Built 2023 - 2024
|
246 homes
5 rating (4 reviews)
![Carolina Preserve]()
$400ks
- $700ks
Carolina Preserve, Cary, NC
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
1,360 homes
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$400ks
- $600ks
Heritage Pines, Cary, NC
Resale Only
|
55+ age-restricted
|
Built 2000 - 2006
|
298 homes
$400ks
- $600ks
Encore at Briar Chapel, Chapel Hill, NC
Resale Only
|
55+ age-restricted
|
Built 2016 - 2021
|
185 homes
$500ks
- $700ks
Buckhorn Preserve, Apex, NC
Resale Only
|
Age-targeted
|
Built 2019 - 2021
|
272 homes
$500ks
- $700ks
Woodbury, Apex, NC
Resale Only
|
Age-targeted
|
Built 2018 - 2021
|
65 homes
$500ks
- $900ks
Retreat at Cedar Crossing, Apex, NC
New and Resale
|
55+ age-restricted
|
Built 2021 - present
|
87 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.
$500ks
- $600ks
Chapelwood, Chapel Hill, NC
Resale Only
|
55+ age-restricted
|
Built 2009 - 2013
|
69 homes
$400ks
- $600ks
Blakeley, Cary, NC
Resale Only
|
55+ age-restricted
|
Built 2017 - 2021
|
137 homes
$500ks
- $600ks
Woodhall, Cary, NC
Resale Only
|
Age-targeted
|
Built 2016 - 2021
|
145 homes
$400ks
- $700ks
The Villas at Culp Arbor, Chapel Hill, NC
Resale Only
|
55+ age-restricted
|
Built 2009 - 2013
|
64 homes
$500ks
The Townes at West Cary, Cary, NC
Resale Only
|
55+ age-restricted
|
Built 2022 - 2023
|
34 homes
$500ks
- $600ks
The Courtyards at Southpo..., Durham, NC
New Construction
|
Age-targeted
|
Built 2020 - present
|
161 homes
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$1Ms
Chapel Oaks, Chapel Hill, NC
New Construction
|
Age-targeted
|
Built 2025 - 2026
|
31 homes
Asteriaâ„¢, Pittsboro, NC
New Construction
|
Age-targeted
|
Built 2026 - present
|
4,000 homes
$700ks
Everstead, Cary, NC
New Construction
|
Age-targeted
|
Built 2026 - present
|
99 homes
$600ks
The Courtyards at West Ca..., Cary, NC
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
108 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.
5 rating (1 reviews)
![The Orchard Villas]()
$400ks
- $500ks
The Orchard Villas, Apex, NC
Resale Only
|
Age-targeted
|
Built 2008 - 2015
|
86 homes
$500ks
The Courtyards at O'Kelly..., Cary, NC
Resale Only
|
55+ age-restricted
|
Built 2015 - 2020
|
149 homes
$400ks
- $600ks
The Courtyards at Homeste..., Chapel Hill, NC
Resale Only
|
55+ age-restricted
|
Built 2015 - 2021
|
63 homes
New
Brookside
![1104 PALISADE BLUFF LN, APEX, NC, 27502, Apex, NC 27502]()
3 beds
|3 baths
|2,221 sq ft
|Townhouse
1104 PALISADE BLUFF LN, APEX, NC, 27502
Community: Brookside
MLS 10190003 • SM North Carolina Brokerage, Aimee... • SM North Carolina Brokerage
New
Brookside
![2104 BARNSIDE LN, APEX, NC, 27502, Apex, NC 27502]()
MLS 10189995 • SM North Carolina Brokerage, Aimee... • SM North Carolina Brokerage
New
Brookside
![2108 BARNSIDE LN, APEX, NC, 27502, Apex, NC 27502]()
MLS 10189980 • SM North Carolina Brokerage, Aimee... • SM North Carolina Brokerage
New
Brookside
![2110 BARNSIDE LN, APEX, NC, 27502, Apex, NC 27502]()
MLS 10189971 • SM North Carolina Brokerage, Aimee... • SM North Carolina Brokerage
New
Brookside
![1100 PALISADE BLUFF LN, APEX, NC, 27502, Apex, NC 27502]()
3 beds
|3 baths
|2,221 sq ft
|Townhouse
1100 PALISADE BLUFF LN, APEX, NC, 27502
Community: Brookside
MLS 10189976 • SM North Carolina Brokerage, Aimee... • SM North Carolina Brokerage
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New
Encore at Chatham Park
![200 IMAGINE WAY, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,571 sq ft
|House
200 IMAGINE WAY, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10189843 • DiProfio Homes, Vicki DiProfio • DiProfio Homes
New
Encore at Briar Chapel
![559 MIDDLETON PL, CHAPEL HILL, NC, 27516, Chapel Hill, NC 27516]()
3 beds
|3 baths
|2,295 sq ft
|House
559 MIDDLETON PL, CHAPEL HILL, NC, 27516
Community: Encore at Briar Chapel
MLS 10189841 • Compass -- Chapel Hill - Durham, G... • Compass -- Chapel Hill - Durham
New
Encore at Chatham Park
![151 PROSPECT PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,467 sq ft
|Townhouse
151 PROSPECT PL, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10189623 • Weekley Homes, LLC, Tracey Riordan • Weekley Homes, LLC
New
Encore at Chatham Park
![201 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,720 sq ft
|Townhouse
201 TANTARA BND, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10189565 • Weekley Homes, LLC, Tracey Riordan • Weekley Homes, LLC
New
Fearrington Village
![595 WEATHERSFIELD E, PITTSBORO, NC, 2731..., Pittsboro, NC 27312]()
3 beds
|3 baths
|2,278 sq ft
|Townhouse
595 WEATHERSFIELD E, PITTSBORO, NC, 2731...
Community: Fearrington Village
MLS 10189406 • Coldwell Banker Advantage, Barbara... • Coldwell Banker Advantage
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
![1329 LANGDON PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|2 baths
|2,394 sq ft
|Townhouse
1329 LANGDON PL, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10188894 • Coldwell Banker - HPW, Dianne Gray • Coldwell Banker - HPW
Heritage Pines
![105 ROCKPORT RIDGE WAY, CARY, NC, 27519, Cary, NC 27519]()
2 beds
|2 baths
|1,744 sq ft
|House
105 ROCKPORT RIDGE WAY, CARY, NC, 27519
Community: Heritage Pines
MLS 10188855 • Coldwell Banker HPW, Chris Martin • Coldwell Banker HPW
Woodhall
![4065 COOL OAKS DR, APEX, NC, 27523, Apex, NC 27523]()
MLS 10188864 • Coldwell Banker HPW, Michele Hende... • Coldwell Banker HPW
Encore at Chatham Park
![18 CANDLELIT WAY, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,719 sq ft
|House
18 CANDLELIT WAY, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10188798 • Weekley Homes, LLC, Tracey Riordan • Weekley Homes, LLC
Fearrington Village
![449 CROSSVINE CLOSE, PITTSBORO, NC, 2731..., Pittsboro, NC 27312]()
3 beds
|2 baths
|1,932 sq ft
|Townhouse
449 CROSSVINE CLOSE, PITTSBORO, NC, 2731...
Community: Fearrington Village
MLS 10188737 • Compass -- Raleigh, Morgan Womble • Compass -- Raleigh
Fearrington Village
![4127 THE KNLS CL, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|2 baths
|2,087 sq ft
|House
4127 THE KNLS CL, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10188676 • English Realty Group, LLC, Sandy E... • English Realty Group, LLC
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Fearrington Village
![4235 HENDERSON PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
5 beds
|4 baths
|3,735 sq ft
|House
4235 HENDERSON PL, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10188438 • Berkshire Hathaway HomeService, Do... • Berkshire Hathaway HomeService
Fearrington Village
![552 WEATHERSFIELD, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|2,418 sq ft
|Townhouse
552 WEATHERSFIELD, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10188003 • NorthGroup Real Estate, Inc., Bonn... • NorthGroup Real Estate, Inc.
Fearrington Village
![486 BEECHMAST, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|2,461 sq ft
|Townhouse
486 BEECHMAST, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10187805 • Berkshire Hathaway HomeService, To... • Berkshire Hathaway HomeService
Heritage Pines
![405 SAWGRASS HILL CT, CARY, NC, 27519, Cary, NC 27519]()
2 beds
|2 baths
|1,401 sq ft
|Townhouse
405 SAWGRASS HILL CT, CARY, NC, 27519
Community: Heritage Pines
MLS 10187578 • Berkshire Hathaway HomeService, Ev... • Berkshire Hathaway HomeService
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.
Encore at Chatham Park
![236 ASPEN AVE, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,719 sq ft
|House
236 ASPEN AVE, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10187535 • Compass -- Cary , Maureen Anne Wil... • Compass -- Cary
Encore at Chatham Park
![39 ENGLEHART CT, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,761 sq ft
|House
39 ENGLEHART CT, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10187353 • Weekley Homes, LLC, Karen Doyle Bu... • Weekley Homes, LLC
Encore at Chatham Park
![194 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
2 beds
|2 baths
|1,469 sq ft
|Townhouse
194 TANTARA BND, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10187330 • Weekley Homes, LLC, Erin Messier • Weekley Homes, LLC
Blakeley
![2836 THOMPSON BLUFF DR, CARY, NC, 27519, Cary, NC 27519]()
MLS 10186363 • Equitable Realty Group LLC, Carson... • Equitable Realty Group LLC
Fearrington Village
![686 SPINDLEWOOD, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|2 baths
|2,632 sq ft
|House
686 SPINDLEWOOD, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10185946 • Century 21 Southern Lifestyles, Br... • Century 21 Southern Lifestyles
Fearrington Village
![672 SPINDLEWOOD, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|2,199 sq ft
|House
672 SPINDLEWOOD, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10185538 • Berkshire Hathaway HomeService, To... • Berkshire Hathaway HomeService
Fearrington Village
![246 FOX RIDGE RD, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|2 baths
|2,248 sq ft
|House
246 FOX RIDGE RD, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10185237 • Relevate Real Estate Inc., Jed Gro... • Relevate Real Estate Inc.
Want to learn more about 55+ communities in Pittsboro?
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(984) 214-4271
Carolina Preserve
![116 SABISTON CT, CARY, NC, 27519, Cary, NC 27519]()
2 beds
|2 baths
|1,370 sq ft
|Townhouse
116 SABISTON CT, CARY, NC, 27519
Community: Carolina Preserve
MLS 10184918 • Costello Real Estate & Investm, Ch... • Costello Real Estate & Investm
Encore at Chatham Park
![166 IMAGINE WAY, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|2,414 sq ft
|House
166 IMAGINE WAY, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10184833 • Chatham Homes Realty, Terri McCall • Chatham Homes Realty
Heritage Pines
![210 MUIR BROOK PL, CARY, NC, 27519, Cary, NC 27519]()
MLS 10184639 • Redfin Corporation, Stacey Delgado • Redfin Corporation
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
![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... • Coldwell Banker HPW
Regency at Holly Springs
![205 TRUNNEL ST 104, HOLLY SPRINGS, NC, 2..., Holly Springs, NC 27540]()
2 beds
|2 baths
|1,682 sq ft
|House
205 TRUNNEL ST 104, HOLLY SPRINGS, NC, 2...
Community: Regency at Holly Springs
MLS 10146176 • Toll Brothers, Inc., Ann Williams • Toll Brothers, Inc.
Fearrington Village
![1390 BRADFORD PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|2 baths
|3,640 sq ft
|House
1390 BRADFORD PL, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10168414 • All About U Real Estate, Jo Ann Ga... • All About U Real Estate
Regency at Holly Springs
![208 ANCHOR BEAM CT HOME SITE 243, HOLLY ..., Holly Springs, NC 27540]()
3 beds
|2 baths
|1,880 sq ft
|House
208 ANCHOR BEAM CT HOME SITE 243, HOLLY ...
Community: Regency at Holly Springs
MLS 10166204 • Toll Brothers, Inc., Ann Williams • Toll Brothers, Inc.
Regency at Holly Springs
![104 STONENDER WAY HOME SITE 1, HOLLY SPR..., Holly Springs, NC 27540]()
3 beds
|3 baths
|2,115 sq ft
|House
104 STONENDER WAY HOME SITE 1, HOLLY SPR...
Community: Regency at Holly Springs
MLS 10152928 • Toll Brothers, Inc., Ann Williams • Toll Brothers, Inc.
Regency at Holly Springs
![105 UTLEY CREEK CT HOME SITE 214, HOLLY ..., Holly Springs, NC 27540]()
3 beds
|3 baths
|2,395 sq ft
|House
105 UTLEY CREEK CT HOME SITE 214, HOLLY ...
Community: Regency at Holly Springs
MLS 10166179 • Toll Brothers, Inc., Ann Williams • Toll Brothers, Inc.
Regency at Holly Springs
![313 ANCHOR BEAM CT HOME SITE 170, HOLLY ..., Holly Springs, NC 27540]()
3 beds
|3 baths
|2,465 sq ft
|House
313 ANCHOR BEAM CT HOME SITE 170, HOLLY ...
Community: Regency at Holly Springs
MLS 10165633 • Toll Brothers, Inc., Ann Williams • Toll Brothers, Inc.
Fearrington Village
![458 BEECHMAST, PITTSBORO, NC, 27312, Pittsboro, NC 27312]()
3 beds
|3 baths
|2,463 sq ft
|Townhouse
458 BEECHMAST, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10183952 • Mill House Properties, Adam W Jone... • Mill House Properties
Want to learn more about 55+ communities in Pittsboro?
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Carolina Preserve
![304 DOWINGTON LN, CARY, NC, 27519, Cary, NC 27519]()
3 beds
|2 baths
|2,082 sq ft
|House
304 DOWINGTON LN, CARY, NC, 27519
Community: Carolina Preserve
MLS 10183238 • LPT Realty, LLC, Jeffrey Scott Tro... • LPT Realty, LLC
Brookside
![2127 BARRIER RDG WAY, APEX, NC, 27502, Apex, NC 27502]()
3 beds
|3 baths
|2,221 sq ft
|Townhouse
2127 BARRIER RDG WAY, APEX, NC, 27502
Community: Brookside
MLS 10182378 • SM North Carolina Brokerage, Aimee... • SM North Carolina Brokerage
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 2 large communities with over 1000 homes, 1 medium community with 500-1000 homes, and 2 small communities with less than 500 homes.
The smallest 55+ communities in Pittsboro has 150 homes, the largest has 4000 homes, and the average communities consists of 1363 homes.
Yes, there are new 55+ homes available in Pittsboro. The most recent communities started in Pittsboro include Asteriaâ„¢, Del Webb at Chatham Park, Encore at Chatham Park. There are also 5 communities in Pittsboro that offer new construction homes, including Asteriaâ„¢, Fearrington Village, Encore at Chatham Park.
No, there are no gated 55+ communities in Pittsboro.
On average, listings in 55+ communities in Pittsboro stay on the market for around 368 days. The average price of homes for sale in these communities is approximately $464,400, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Fearrington Village average around $594,790, while homes in Encore at Chatham Park average around $463,460.
Raleigh Durham Area 55+ Housing Market Trends
Trend Shown:
Number of Listings
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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 02, 2026.
This application does not include information on all of the properties available for sale at this time.
