Pittsboro, NC 55+ active adult communities & homes for sale

23 communities 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

Regency at Holly Springs

$500ks - $1Ms

Regency at Holly Springs, Holly Springs, NC

New Construction | 55+ age-restricted | Built 2023 - 2024 | 246 homes

Brookside

$500ks

Brookside, Apex, NC

New Construction | 55+ age-restricted | Built 2024 - present | 75 homes

Encore at Chatham Park

$400ks - $500ks

Encore at Chatham Park, Pittsboro, NC

New Construction | 55+ age-restricted | Built 2024 - present | 425 homes

Heritage Pines

$400ks - $600ks

Heritage Pines, Cary, NC

Resale Only | 55+ age-restricted | Built 2000 - 2006 | 298 homes

Want to learn more about 55+ communities in Pittsboro? 55places can help!

Questions? Call us: (984) 214-4271

Encore at Briar Chapel

$400ks - $600ks

Encore at Briar Chapel, Chapel Hill, NC

Resale Only | 55+ age-restricted | Built 2016 - 2021 | 185 homes

5 rating (4 reviews)

Carolina Preserve

$400ks - $700ks

Carolina Preserve, Cary, NC

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 1,360 homes

The Villas at Culp Arbor

$400ks - $700ks

The Villas at Culp Arbor, Chapel Hill, NC

Resale Only | 55+ age-restricted | Built 2009 - 2013 | 64 homes

The Courtyards at O'Kelly...

$500ks

The Courtyards at O'Kelly..., Cary, NC

Resale Only | 55+ age-restricted | Built 2015 - 2020 | 149 homes

Blakeley

$400ks - $600ks

Blakeley, Cary, NC

Resale Only | 55+ age-restricted | Built 2017 - 2021 | 137 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.

Buckhorn Preserve

$500ks - $700ks

Buckhorn Preserve, Apex, NC

Resale Only | Age-targeted | Built 2019 - 2021 | 272 homes

Woodbury

$500ks - $700ks

Woodbury, Apex, NC

Resale Only | Age-targeted | Built 2018 - 2021 | 65 homes

Retreat at Cedar Crossing

$500ks - $900ks

Retreat at Cedar Crossing, Apex, NC

New and Resale | 55+ age-restricted | Built 2021 - present | 87 homes

Chapelwood

$500ks - $600ks

Chapelwood, Chapel Hill, NC

Resale Only | 55+ age-restricted | Built 2009 - 2013 | 69 homes

The Courtyards at West Ca...

$600ks

The Courtyards at West Ca..., Cary, NC

New Construction | 55+ age-restricted | Built 2022 - present | 108 homes

The Townes at West Cary

$500ks

The Townes at West Cary, Cary, NC

Resale Only | 55+ age-restricted | Built 2022 - 2023 | 34 homes

Want to learn more about 55+ communities in Pittsboro? 55places can help!

Questions? Call us: (984) 214-4271

The Courtyards at Southpo...

$500ks - $600ks

The Courtyards at Southpo..., Durham, NC

New Construction | Age-targeted | Built 2020 - present | 161 homes

The Courtyards at Homeste...

$400ks - $600ks

The Courtyards at Homeste..., Chapel Hill, NC

Resale Only | 55+ age-restricted | Built 2015 - 2021 | 63 homes

5 rating (1 reviews)

The Orchard Villas

$400ks - $500ks

The Orchard Villas, Apex, NC

Resale Only | Age-targeted | Built 2008 - 2015 | 86 homes

Woodhall

$500ks - $600ks

Woodhall, Cary, NC

Resale Only | Age-targeted | Built 2016 - 2021 | 145 homes

Chapel Oaks

$1Ms

Chapel Oaks, Chapel Hill, NC

New Construction | Age-targeted | Built 2025 - 2026 | 31 homes

Asteria™

Asteria™, Pittsboro, NC

New Construction | Age-targeted | Built 2026 - present | 4,000 homes

Everstead

$700ks

Everstead, Cary, NC

226 MUIR BROOK PL, CARY, NC, 27519

Community: Heritage Pines

Want to learn more about 55+ communities in Pittsboro? 55places can help!

Questions? Call us: (984) 214-4271

Fearrington Village

484 BEECHMAST, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$379,000

3 beds

3 baths

2,216 sq ft

Townhouse

484 BEECHMAST, PITTSBORO, NC, 27312

Community: Fearrington Village

Woodbury

3101 HORTON RIDGE BLVD 287, APEX, NC, 27..., Apex, NC 27502

$534,415

4 beds

4 baths

2,092 sq ft

Townhouse

3101 HORTON RIDGE BLVD 287, APEX, NC, 27...

Community: Woodbury

Encore at Chatham Park

160 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$469,990

2 beds

2 baths

1,467 sq ft

Townhouse

160 TANTARA BND, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Fearrington Village

1379 BRADFORD PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$750,000

4 beds

3 baths

2,225 sq ft

House

1379 BRADFORD PL, PITTSBORO, NC, 27312

Community: Fearrington Village

Carolina Preserve

235 BECKINGHAM LOOP, CARY, NC, 27519, Cary, NC 27519

$945,000

5 beds

3 baths

4,570 sq ft

House

235 BECKINGHAM LOOP, CARY, NC, 27519

Community: Carolina Preserve

The Courtyards at O'Kelly Chapel

100 CHENETTE CT, CARY, NC, 27519, Cary, NC 27519

$675,000

2 beds

2 baths

1,781 sq ft

House

100 CHENETTE CT, CARY, NC, 27519

Community: The Courtyards at O'Kelly Chapel

Encore at Chatham Park

87 ENGLEHART CT, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$578,300

2 beds

2 baths

1,837 sq ft

House

87 ENGLEHART CT, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Encore at Briar Chapel

60 MIDDLETON PL, CHAPEL HILL, NC, 27516, Chapel Hill, NC 27516

$625,000

2 beds

2 baths

2,029 sq ft

House

60 MIDDLETON PL, CHAPEL HILL, NC, 27516

Community: Encore at Briar Chapel

Encore at Briar Chapel

90 PULASKI TRL, CHAPEL HILL, NC, 27516, Chapel Hill, NC 27516

$715,000

2 beds

3 baths

2,447 sq ft

House

90 PULASKI TRL, CHAPEL HILL, NC, 27516

Community: Encore at Briar Chapel

Encore at Chatham Park

142 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$469,590

2 beds

2 baths

1,469 sq ft

Townhouse

142 TANTARA BND, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Heritage Pines

408 KNOTTS VALLEY LN, CARY, NC, 27519, Cary, NC 27519

$600,000

3 beds

3 baths

2,544 sq ft

House

408 KNOTTS VALLEY LN, CARY, NC, 27519

Community: Heritage Pines

Want to learn more about 55+ communities in Pittsboro? 55places can help!

Questions? Call us: (984) 214-4271

Brookside

2113 BARRIER RIDGE WAY, APEX, NC, 27502, Apex, NC 27502

$500,000

3 beds

3 baths

2,221 sq ft

Townhouse

2113 BARRIER RIDGE WAY, APEX, NC, 27502

Community: Brookside

Blakeley

4053 ANSLEY STREAM LN, CARY, NC, 27519, Cary, NC 27519

$615,000

2 beds

3 baths

2,453 sq ft

Townhouse

4053 ANSLEY STREAM LN, CARY, NC, 27519

Community: Blakeley

Heritage Pines

204 CRYSTAL BROOK LN, CARY, NC, 27519, Cary, NC 27519

$519,900

3 beds

2 baths

1,724 sq ft

House

204 CRYSTAL BROOK LN, CARY, NC, 27519

Community: Heritage Pines

Fearrington Village

438 CROSSVINE CLOSE, PITTSBORO, NC, 2731..., Pittsboro, NC 27312

$400,000

3 beds

2 baths

2,123 sq ft

Townhouse

438 CROSSVINE CLOSE, PITTSBORO, NC, 2731...

Community: Fearrington Village

Retreat at Cedar Crossing

3440 OLIVE GLEN DR, APEX, NC, 27502, Apex, NC 27502

$649,900

3 beds

3 baths

2,141 sq ft

House

3440 OLIVE GLEN DR, APEX, NC, 27502

Community: Retreat at Cedar Crossing

Brookside

2123 BARRIER RDG WAY, APEX, NC, 27502, Apex, NC 27502

$495,000

3 beds

3 baths

2,221 sq ft

Townhouse

2123 BARRIER RDG WAY, APEX, NC, 27502

Community: Brookside

Fearrington Village

246 FOX RIDGE RD, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$574,900

3 beds

3 baths

2,248 sq ft

House

246 FOX RIDGE RD, PITTSBORO, NC, 27312

Community: Fearrington Village

Brookside

2129 BARRIER RDG WAY, APEX, NC, 27502, Apex, NC 27502

$535,000

3 beds

3 baths

2,221 sq ft

Townhouse

2129 BARRIER RDG WAY, APEX, NC, 27502

Community: Brookside

Carolina Preserve

542 TOMKINS LOOP, CARY, NC, 27519, Cary, NC 27519

$495,000

3 beds

2 baths

1,388 sq ft

House

542 TOMKINS LOOP, CARY, NC, 27519

Community: Carolina Preserve

Fearrington Village

166 WINTERSAGE, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$400,000

3 beds

2 baths

1,756 sq ft

House

166 WINTERSAGE, PITTSBORO, NC, 27312

Community: Fearrington Village

Encore at Chatham Park

200 IMAGINE WAY, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$505,000

2 beds

2 baths

1,571 sq ft

House

200 IMAGINE WAY, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Want to learn more about 55+ communities in Pittsboro? 55places can help!

Questions? Call us: (984) 214-4271

Carolina Preserve

604 BLOOMSBURY PL, CARY, NC, 27519, Cary, NC 27519

$650,000

2 beds

2 baths

2,223 sq ft

House

604 BLOOMSBURY PL, CARY, NC, 27519

Community: Carolina Preserve

Encore at Chatham Park

134 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$469,990

2 beds

2 baths

1,467 sq ft

Townhouse

134 TANTARA BND, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Regency at Holly Springs

104 ANCHOR BEAM CT HOME SITE 236, HOLLY ..., Holly Springs, NC 27540

$728,000

3 beds

3 baths

2,015 sq ft

House

104 ANCHOR BEAM CT HOME SITE 236, HOLLY ...

Community: Regency at Holly Springs

Regency at Holly Springs

216 ANCHOR BEAM CT HOME SITE 245, HOLLY ..., Holly Springs, NC 27540

$743,000

3 beds

3 baths

2,015 sq ft

House

216 ANCHOR BEAM CT HOME SITE 245, HOLLY ...

Community: Regency at Holly Springs

Fearrington Village

44 BENCHMARK, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$489,000

3 beds

2 baths

1,450 sq ft

House

44 BENCHMARK, PITTSBORO, NC, 27312

Community: Fearrington Village

Fearrington Village

1390 BRADFORD PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$997,000

3 beds

2 baths

3,640 sq ft

House

1390 BRADFORD PL, PITTSBORO, NC, 27312

Community: Fearrington Village

Heritage Pines

$495,000

2 beds

2 baths

1,574 sq ft

House

3005 HERITAGE PINES DR, CARY, NC, 27519

Community: Heritage Pines

Regency at Holly Springs

208 ANCHOR BEAM CT HOME SITE 243, HOLLY ..., Holly Springs, NC 27540

$729,000

3 beds

2 baths

1,880 sq ft

House

208 ANCHOR BEAM CT HOME SITE 243, HOLLY ...

Community: Regency at Holly Springs

Regency at Holly Springs

105 UTLEY CREEK CT HOME SITE 214, HOLLY ..., Holly Springs, NC 27540

$939,000

3 beds

3 baths

2,395 sq ft

House

105 UTLEY CREEK CT HOME SITE 214, HOLLY ...

Community: Regency at Holly Springs

Regency at Holly Springs

313 ANCHOR BEAM CT HOME SITE 170, HOLLY ..., Holly Springs, NC 27540

$932,000

3 beds

3 baths

2,465 sq ft

House

313 ANCHOR BEAM CT HOME SITE 170, HOLLY ...

Community: Regency at Holly Springs

Encore at Chatham Park

33 IMAGINE WAY, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$839,900

3 beds

3 baths

2,668 sq ft

House

33 IMAGINE WAY, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Want to learn more about 55+ communities in Pittsboro? 55places can help!

Questions? Call us: (984) 214-4271

Regency at Holly Springs

120 ANCHOR BEAM CT HOME SITE 240, HOLLY ..., Holly Springs, NC 27540

$757,000

3 beds

3 baths

2,015 sq ft

House

120 ANCHOR BEAM CT HOME SITE 240, HOLLY ...

Community: Regency at Holly Springs

Fearrington Village

490 BEECHMAST, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$425,000

3 beds

3 baths

2,491 sq ft

Townhouse

490 BEECHMAST, PITTSBORO, NC, 27312

Community: Fearrington Village

Frequently Asked Questions

What size 55+ communities are there in Pittsboro?

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.

How many homes are there in the smallest, largest, and average 55+ communities in Pittsboro?

The smallest 55+ communities in Pittsboro has 150 homes, the largest has 4000 homes, and the average communities consists of 1363 homes.

Are there new 55+ homes available in Pittsboro?

Yes, there are new 55+ homes available in Pittsboro. The most recent communities started in Pittsboro include Asteria™, Del Webb at Chatham Park, Encore at Chatham Park. There are also 5 communities in Pittsboro that offer new construction homes, including Asteria™, Fearrington Village, Encore at Chatham Park.

Are there gated 55+ communities in Pittsboro?

No, there are no gated 55+ communities in Pittsboro.

How long do listings in 55+ communities in Pittsboro typically stay on the market, and what is the average price of homes for sale?

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

Raleigh Durham Area 55+ Housing Market Trends

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23 communities

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Pittsboro, NC 55+ active adult communities & homes for sale

23 communities near Pittsboro

53 homes near Pittsboro

3 beds

3 baths

3,210 sq ft

House

4 beds

3 baths

2,748 sq ft

House

3 beds

3 baths

2,740 sq ft

House

3 beds

2 baths

2,254 sq ft

Townhouse

3 beds

2 baths

2,520 sq ft

House

3 beds

3 baths

2,216 sq ft

Townhouse

4 beds

4 baths

2,092 sq ft

Townhouse

2 beds

2 baths

1,467 sq ft

Townhouse

4 beds

3 baths

2,225 sq ft

House

5 beds

3 baths

4,570 sq ft

House

2 beds

2 baths

1,781 sq ft

House

2 beds

2 baths

1,837 sq ft

House

2 beds

2 baths

2,029 sq ft

House

2 beds

3 baths

2,447 sq ft

House

2 beds

2 baths

1,469 sq ft

Townhouse

3 beds

3 baths

2,544 sq ft

House

3 beds

3 baths

2,221 sq ft

Townhouse

2 beds

3 baths

2,453 sq ft

Townhouse

3 beds

2 baths

1,724 sq ft

House

3 beds