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
68 homes near Pittsboro
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5 rating (1 review)
$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
$400ks
- $600ks
Encore at Briar Chapel, Chapel Hill, NC
Resale Only |
55+ age-restricted |
Built 2016 - 2021 |
185 homes
$400ks
- $600ks
Heritage Pines, Cary, NC
Resale Only |
55+ age-restricted |
Built 2000 - 2006 |
298 homes
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(984) 214-4271
$500ks
- $700ks
Buckhorn Preserve, Apex, NC
Resale Only |
Age-targeted |
Built 2019 - 2021 |
272 homes
$500ks
- $1Ms
Regency at Holly Springs, Holly Springs, NC
New Construction |
55+ age-restricted |
Built 2023 - 2024 |
246 homes
5 rating (4 reviews)
$400ks
- $700ks
Carolina Preserve, Cary, NC
Resale Only |
55+ age-restricted |
Built 2006 - 2013 |
1,360 homes
$500ks
- $700ks
Woodbury, Apex, NC
Resale Only |
Age-targeted |
Built 2018 - 2021 |
65 homes
$500ks
- $600ks
Woodhall, Cary, NC
Resale Only |
Age-targeted |
Built 2016 - 2021 |
145 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
The Courtyards at O'Kelly..., Cary, NC
Resale Only |
55+ age-restricted |
Built 2015 - 2020 |
149 homes
$500ks
- $900ks
Retreat at Cedar Crossing, Apex, NC
New and Resale |
55+ age-restricted |
Built 2021 - present |
87 homes
$400ks
- $600ks
Blakeley, Cary, NC
Resale Only |
55+ age-restricted |
Built 2017 - 2021 |
137 homes
$500ks
- $600ks
The Courtyards at Southpo..., Durham, NC
New Construction |
Age-targeted |
Built 2020 - present |
161 homes
$700ks
Everstead, Cary, NC
New Construction |
Age-targeted |
Built 2026 - present |
99 homes
Asteriaâ„¢, Pittsboro, NC
New Construction |
Age-targeted |
Built 2026 - present |
4,000 homes
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(984) 214-4271
5 rating (1 review)
$400ks
- $500ks
The Orchard Villas, Apex, NC
Resale Only |
Age-targeted |
Built 2008 - 2015 |
86 homes
$400ks
- $700ks
The Villas at Culp Arbor, Chapel Hill, NC
Resale Only |
55+ age-restricted |
Built 2009 - 2013 |
64 homes
$500ks
- $600ks
Chapelwood, Chapel Hill, NC
Resale Only |
55+ age-restricted |
Built 2009 - 2013 |
69 homes
$400ks
- $600ks
The Courtyards at Homeste..., Chapel Hill, NC
Resale Only |
55+ age-restricted |
Built 2015 - 2021 |
63 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.
$600ks
The Courtyards at West Ca..., Cary, NC
New Construction |
55+ age-restricted |
Built 2022 - present |
108 homes
$500ks
The Townes at West Cary, Cary, NC
Resale Only |
55+ age-restricted |
Built 2022 - 2023 |
34 homes
$1Ms
Chapel Oaks, Chapel Hill, NC
New Construction |
Age-targeted |
Built 2025 - 2026 |
31 homes
New
Fearrington Village
3 beds
|3 baths
|2,463 sq ft
|Townhouse
458 BEECHMAST, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10200417 • Coldwell Banker - HPW, Dana Wicker... • Coldwell Banker - HPW
Encore at Briar Chapel
2 beds
|2 baths
|1,617 sq ft
|House
93 ABERCORN CIR, CHAPEL HILL, NC, 27516
Community: Encore at Briar Chapel
MLS 10200079 • Keller Williams Elite Realty, Pete... • Keller Williams Elite Realty
Encore at Briar Chapel
3 beds
|3 baths
|2,283 sq ft
|House
31 CLIFRIDGE CT, CHAPEL HILL, NC, 27516
Community: Encore at Briar Chapel
MLS 10200017 • Keller Williams Elite Realty, Jen ... • Keller Williams Elite Realty
Fearrington Village
3 beds
|2 baths
|2,533 sq ft
|House
1390 BRADFORD PL, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10199970 • Berkshire Hathaway HomeService, Ch... • Berkshire Hathaway HomeService
Buckhorn Preserve
3 beds
|3 baths
|2,470 sq ft
|House
3168 MAVISBANK CIR, APEX, NC, 27502
Community: Buckhorn Preserve
MLS 10199809 • Opendoor Brokerage LLC, Thomas Lad... • Opendoor Brokerage LLC
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Encore at Briar Chapel
2 beds
|2 baths
|1,868 sq ft
|House
312 MIDDLETON PL, CHAPEL HILL, NC, 27516
Community: Encore at Briar Chapel
MLS 10199078 • Compass -- Chapel Hill - Durham, P... • Compass -- Chapel Hill - Durham
Everstead
MLS 10199036 • Toll Brothers, Inc., Monica Meinke... • Toll Brothers, Inc.
Encore at Chatham Park
2 beds
|2 baths
|1,469 sq ft
|Townhouse
125 PROSPECT PL, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10199016 • Carolina's Choice Real Estate, Dav... • Carolina's Choice Real Estate
Buckhorn Preserve
5 beds
|4 baths
|3,303 sq ft
|House
1920 KINGS KNOT CT, APEX, NC, 27502
Community: Buckhorn Preserve
MLS 10198764 • Relevate Real Estate Inc., Christi... • Relevate Real Estate Inc.
Encore at Chatham Park
2 beds
|2 baths
|1,467 sq ft
|Townhouse
189 TANTARA BND, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10198640 • Weekley Homes, LLC, Tracey Riordan • Weekley Homes, LLC
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
2 beds
|2 baths
|1,726 sq ft
|Townhouse
211 TANTARA BND, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10198629 • Weekley Homes, LLC, Tracey Riordan • Weekley Homes, LLC
Buckhorn Preserve
4 beds
|3 baths
|2,818 sq ft
|House
1976 STANLAKE DR, APEX, NC, 27502
Community: Buckhorn Preserve
MLS 10198576 • Redfin Corporation, Pam Campbell • Redfin Corporation
Fearrington Village
2 beds
|3 baths
|1,968 sq ft
|Townhouse
308 BANEBERRY CLOSE, PITTSBORO, NC, 2731...
Community: Fearrington Village
MLS 10198519 • Coldwell Banker HPW, Dina Sneed Ma... • Coldwell Banker HPW
Buckhorn Preserve
3 beds
|2 baths
|1,898 sq ft
|House
1903 ROTHESAY DR, APEX, NC, 27502
Community: Buckhorn Preserve
MLS 10198470 • Coldwell Banker HPW, Tim Mock • Coldwell Banker HPW
Fearrington Village
3 beds
|2 baths
|2,248 sq ft
|House
246 FOX RDG, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10198340 • Relevate Real Estate Inc., Jed Gro... • Relevate Real Estate Inc.
Encore at Chatham Park
2 beds
|2 baths
|1,467 sq ft
|Townhouse
217 TANTARA BEND BND, PITTSBORO, NC, 273...
Community: Encore at Chatham Park
MLS 10197958 • Weekley Homes, LLC, Erin Messier • Weekley Homes, LLC
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(984) 214-4271
Encore at Chatham Park
2 beds
|2 baths
|1,726 sq ft
|Townhouse
179 TANTARA BND, PITTSBORO, NC, 27312
Community: Encore at Chatham Park
MLS 10197876 • Weekley Homes, LLC, Erin Messier • Weekley Homes, LLC
Encore at Chatham Park
2 beds
|2 baths
|1,467 sq ft
|Duplex
200 TANTARA BEND BND, PITTSBORO, NC, 273...
Community: Encore at Chatham Park
MLS 10197867 • Weekley Homes, LLC, Karen Doyle Bu... • Weekley Homes, LLC
Retreat at Cedar Crossing
3 beds
|3 baths
|2,084 sq ft
|House
3440 OLIVE GLEN DR, APEX, NC, 27502
Community: Retreat at Cedar Crossing
MLS 10197806 • C-A-RE Realty, Don Gomez • C-A-RE Realty
Fearrington Village
4 beds
|5 baths
|3,452 sq ft
|House
4230 HENDERSON PL, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10197735 • Berkshire Hathaway HomeService, Do... • 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.
The Courtyards at O'Kelly Chapel
2 beds
|2 baths
|1,910 sq ft
|House
1428 ABBOTSFORD WAY, CARY, NC, 27519
Community: The Courtyards at O'Kelly Chapel
MLS 10197448 • Long & Foster Real Estate INC/Rale... • Long & Foster Real Estate INC/Raleigh
Fearrington Village
2 beds
|2 baths
|1,694 sq ft
|Townhouse
401 LYNDFIELD CLOSE, PITTSBORO, NC, 2731...
Community: Fearrington Village
MLS 10196738 • Coldwell Banker Advantage, Michell... • Coldwell Banker Advantage
Heritage Pines
3 beds
|3 baths
|2,370 sq ft
|House
2007 HERITAGE PINES DR, CARY, NC, 27519
Community: Heritage Pines
MLS 10196060 • Berkshire Hathaway HomeService, Ev... • Berkshire Hathaway HomeService
Fearrington Village
3 beds
|3 baths
|2,620 sq ft
|Townhouse
464 BEECHMAST, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10194897 • NewStone Realty, LLC, Steve Doyle • NewStone Realty, LLC
The Courtyards at Southpoint
2 beds
|2 baths
|1,652 sq ft
|House
1015 UNBRIDLED ST, DURHAM, NC, 27713
Community: The Courtyards at Southpoint
MLS 10194366 • Coldwell Banker Advantage, Bernade... • Coldwell Banker Advantage
Woodhall
MLS 10193328 • Keller Williams Realty Cary, Kathy... • Keller Williams Realty Cary
Heritage Pines
2 beds
|2 baths
|1,713 sq ft
|Townhouse
113 UPLANDS CREEK DR, CARY, NC, 27519
Community: Heritage Pines
MLS 10193085 • Howard Hanna Allen Tate Raleigh Gl... • Howard Hanna Allen Tate Raleigh Glenwood
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Questions? Call us:
(984) 214-4271
Encore at Briar Chapel
2 beds
|2 baths
|1,611 sq ft
|House
72 BOONE ST, CHAPEL HILL, NC, 27516
Community: Encore at Briar Chapel
MLS 10192071 • Coldwell Banker Advantage, Barbara... • Coldwell Banker Advantage
The Courtyards at O'Kelly Chapel
3 beds
|3 baths
|2,094 sq ft
|House
1407 ABBOTSFORD WAY, CARY, NC, 27519
Community: The Courtyards at O'Kelly Chapel
MLS 10191919 • Howard Hanna Allen Tate Raleigh Gl... • Howard Hanna Allen Tate Raleigh Glenwood
Encore at Briar Chapel
2 beds
|2 baths
|1,885 sq ft
|House
66 MIDDLETON PL, CHAPEL HILL, NC, 27516
Community: Encore at Briar Chapel
MLS 10191606 • Long & Foster Real Estate INC, Cha... • Long & Foster Real Estate INC
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
3 beds
|2 baths
|1,610 sq ft
|House
50 TRESTLE LEAF, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10191548 • Century 21 Southern Lifestyles, Lo... • Century 21 Southern Lifestyles
Brookside
3 beds
|3 baths
|2,221 sq ft
|Townhouse
1152 MORAINE RDG RD, APEX, NC, 27502
Community: Brookside
MLS 10191258 • SM North Carolina Brokerage, Aimee... • SM North Carolina Brokerage
Fearrington Village
2 beds
|2 baths
|1,792 sq ft
|House
4055 SAMPSON, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10191033 • Dwell Real Estate, Colleen C Jelle... • Dwell Real Estate
Woodbury
3 beds
|3 baths
|1,888 sq ft
|Townhouse
3054 HORTON RIDGE BLVD, APEX, NC, 27502
Community: Woodbury
MLS 10190867 • M/I Homes of Raleigh LLC, Monica W... • M/I Homes of Raleigh LLC
Woodbury
3 beds
|3 baths
|1,906 sq ft
|Townhouse
3056 HORTON RIDGE BLVD, APEX, NC, 27502
Community: Woodbury
MLS 10190861 • M/I Homes of Raleigh LLC, Monica W... • M/I Homes of Raleigh LLC
Woodbury
3 beds
|3 baths
|1,906 sq ft
|Townhouse
3052 HORTON RIDGE BLVD, APEX, NC, 27502
Community: Woodbury
MLS 10190847 • M/I Homes of Raleigh LLC, Monica W... • M/I Homes of Raleigh LLC
Fearrington Village
2 beds
|2 baths
|1,904 sq ft
|Condo
482 BEECHMAST, PITTSBORO, NC, 27312
Community: Fearrington Village
MLS 10190275 • Bold Real Estate, George Winters • Bold Real Estate
Fearrington Village
3 beds
|2 baths
|1,888 sq ft
|Townhouse
334 WHISPERWOOD CLOSE, PITTSBORO, NC, 27...
Community: Fearrington Village
MLS 10190084 • Compass -- Chapel Hill - Durham, T... • Compass -- Chapel Hill - Durham
Want to learn more about 55+ communities in Pittsboro?
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Questions? Call us:
(984) 214-4271
Brookside
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
Brookside
MLS 10189995 • 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
Of the 5 55+ communities in Pittsboro, 4 are for sale and 1 is a rental. By size, 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 Encore at Chatham Park, Inspire Briar Chapel, Asteriaâ„¢.
No, there are no gated 55+ communities in Pittsboro.
On average, listings in 55+ communities in Pittsboro stay on the market for around 314 days. The average price of homes for sale in these communities is approximately $500,712, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Encore at Chatham Park average around $584,545, while homes in Fearrington Village average around $582,640.
Raleigh Durham Area 55+ Housing Market Trends
Trend Shown:
Number of Listings
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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 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: Oct 28, 2026.
This application does not include information on all of the properties available for sale at this time.
