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

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

Regency at Holly Springs

$500ks - $1Ms

Regency at Holly Springs, Holly Springs, NC

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

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

Questions? Call us: (984) 214-4271

Woodbury

$500ks - $700ks

Woodbury, Apex, NC

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

5 rating (4 reviews)

Carolina Preserve

$400ks - $700ks

Carolina Preserve, Cary, NC

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

Encore at Briar Chapel

$400ks - $600ks

Encore at Briar Chapel, Chapel Hill, NC

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

Woodhall

$500ks - $600ks

Woodhall, Cary, NC

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

The Courtyards at O'Kelly...

$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.

Blakeley

$400ks - $600ks

Blakeley, Cary, NC

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

Chapelwood

$500ks - $600ks

Chapelwood, Chapel Hill, NC

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

Retreat at Cedar Crossing

$500ks - $900ks

Retreat at Cedar Crossing, Apex, NC

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

The Courtyards at Southpo...

$500ks - $600ks

The Courtyards at Southpo..., Durham, NC

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

Asteria™

Asteria™, Pittsboro, NC

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

Everstead

$700ks

Everstead, Cary, NC

New Construction | Age-targeted | Built 2026 - present | 99 homes

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

Questions? Call us: (984) 214-4271

Chapel Oaks

$1Ms

Chapel Oaks, Chapel Hill, NC

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

5 rating (1 reviews)

The Orchard Villas

$400ks - $500ks

The Orchard Villas, Apex, NC

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

Buckhorn Preserve

$500ks - $700ks

Buckhorn Preserve, Apex, NC

Resale Only | Age-targeted | Built 2019 - 2021 | 272 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 Homeste...

$400ks - $600ks

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

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

50 TRESTLE LEAF, PITTSBORO, NC, 27312

Community: Fearrington Village

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

Questions? Call us: (984) 214-4271

Brookside

1152 MORAINE RDG RD, APEX, NC, 27502, Apex, NC 27502

$565,000

3 beds

3 baths

2,221 sq ft

Townhouse

1152 MORAINE RDG RD, APEX, NC, 27502

Community: Brookside

Fearrington Village

4246 HENDERSON PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$1,125,000

3 beds

3 baths

3,263 sq ft

House

4246 HENDERSON PL, PITTSBORO, NC, 27312

Community: Fearrington Village

Fearrington Village

4055 SAMPSON, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$639,500

2 beds

2 baths

1,792 sq ft

House

4055 SAMPSON, PITTSBORO, NC, 27312

Community: Fearrington Village

Woodbury

3054 HORTON RIDGE BLVD, APEX, NC, 27502, Apex, NC 27502

$419,990

3 beds

3 baths

1,888 sq ft

Townhouse

3054 HORTON RIDGE BLVD, APEX, NC, 27502

Community: Woodbury

Woodbury

3056 HORTON RIDGE BLVD, APEX, NC, 27502, Apex, NC 27502

$415,990

3 beds

3 baths

1,906 sq ft

Townhouse

3056 HORTON RIDGE BLVD, APEX, NC, 27502

Community: Woodbury

Woodbury

3052 HORTON RIDGE BLVD, APEX, NC, 27502, Apex, NC 27502

$415,990

3 beds

3 baths

1,906 sq ft

Townhouse

3052 HORTON RIDGE BLVD, APEX, NC, 27502

Community: Woodbury

Fearrington Village

482 BEECHMAST, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$399,999

2 beds

2 baths

1,904 sq ft

Condo

482 BEECHMAST, PITTSBORO, NC, 27312

Community: Fearrington Village

Heritage Pines

139 ROCKPORT RIDGE WAY, CARY, NC, 27519, Cary, NC 27519

$530,000

3 beds

2 baths

1,719 sq ft

House

139 ROCKPORT RIDGE WAY, CARY, NC, 27519

Community: Heritage Pines

Fearrington Village

334 WHISPERWOOD CLOSE, PITTSBORO, NC, 27..., Pittsboro, NC 27312

$385,000

3 beds

2 baths

1,888 sq ft

Townhouse

334 WHISPERWOOD CLOSE, PITTSBORO, NC, 27...

Community: Fearrington Village

Brookside

1104 PALISADE BLUFF LN, APEX, NC, 27502, Apex, NC 27502

$514,000

3 beds

3 baths

2,221 sq ft

Townhouse

1104 PALISADE BLUFF LN, APEX, NC, 27502

Community: Brookside

Brookside

2104 BARNSIDE LN, APEX, NC, 27502, Apex, NC 27502

$525,000

3 beds

3 baths

2,221 sq ft

Townhouse

2104 BARNSIDE LN, APEX, NC, 27502

Community: Brookside

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

Questions? Call us: (984) 214-4271

Brookside

2108 BARNSIDE LN, APEX, NC, 27502, Apex, NC 27502

$515,000

3 beds

3 baths

2,221 sq ft

Townhouse

2108 BARNSIDE LN, APEX, NC, 27502

Community: Brookside

Brookside

2110 BARNSIDE LN, APEX, NC, 27502, Apex, NC 27502

$555,000

3 beds

3 baths

2,221 sq ft

Townhouse

2110 BARNSIDE LN, APEX, NC, 27502

Community: Brookside

Brookside

1100 PALISADE BLUFF LN, APEX, NC, 27502, Apex, NC 27502

$555,000

3 beds

3 baths

2,221 sq ft

Townhouse

1100 PALISADE BLUFF LN, APEX, NC, 27502

Community: Brookside

Encore at Briar Chapel

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

$800,000

3 beds

3 baths

2,295 sq ft

House

559 MIDDLETON PL, CHAPEL HILL, NC, 27516

Community: Encore at Briar Chapel

Heritage Pines

105 ROCKPORT RIDGE WAY, CARY, NC, 27519, Cary, NC 27519

$509,900

2 beds

2 baths

1,744 sq ft

House

105 ROCKPORT RIDGE WAY, CARY, NC, 27519

Community: Heritage Pines

Woodhall

4065 COOL OAKS DR, APEX, NC, 27523, Apex, NC 27523

$765,000

4 beds

3 baths

2,616 sq ft

House

4065 COOL OAKS DR, APEX, NC, 27523

Community: Woodhall

Fearrington Village

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

$440,000

3 beds

2 baths

1,932 sq ft

Townhouse

449 CROSSVINE CLOSE, PITTSBORO, NC, 2731...

Community: Fearrington Village

Fearrington Village

4127 THE KNLS CL, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$700,000

3 beds

2 baths

2,087 sq ft

House

4127 THE KNLS CL, PITTSBORO, NC, 27312

Community: Fearrington Village

Fearrington Village

552 WEATHERSFIELD, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$467,000

3 beds

3 baths

2,418 sq ft

Townhouse

552 WEATHERSFIELD, PITTSBORO, NC, 27312

Community: Fearrington Village

Fearrington Village

486 BEECHMAST, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$395,000

3 beds

3 baths

2,461 sq ft

Townhouse

486 BEECHMAST, PITTSBORO, NC, 27312

Community: Fearrington Village

Heritage Pines

405 SAWGRASS HILL CT, CARY, NC, 27519, Cary, NC 27519

$435,000

2 beds

2 baths

1,401 sq ft

Townhouse

405 SAWGRASS HILL CT, CARY, NC, 27519

Community: Heritage Pines

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

Questions? Call us: (984) 214-4271

Encore at Chatham Park

236 ASPEN AVE, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$620,000

2 beds

2 baths

1,719 sq ft

House

236 ASPEN AVE, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Encore at Chatham Park

39 ENGLEHART CT, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$599,900

2 beds

2 baths

1,761 sq ft

House

39 ENGLEHART CT, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Encore at Chatham Park

194 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$469,730

2 beds

2 baths

1,469 sq ft

Townhouse

194 TANTARA BND, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Blakeley

2836 THOMPSON BLUFF DR, CARY, NC, 27519, Cary, NC 27519

$699,999

3 beds

3 baths

2,359 sq ft

House

2836 THOMPSON BLUFF DR, CARY, NC, 27519

Community: Blakeley

Fearrington Village

686 SPINDLEWOOD, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$735,000

3 beds

2 baths

2,632 sq ft

House

686 SPINDLEWOOD, PITTSBORO, NC, 27312

Community: Fearrington Village

Fearrington Village

672 SPINDLEWOOD, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$700,000

3 beds

3 baths

2,199 sq ft

House

672 SPINDLEWOOD, PITTSBORO, NC, 27312

Community: Fearrington Village

Carolina Preserve

116 SABISTON CT, CARY, NC, 27519, Cary, NC 27519

$465,000

2 beds

2 baths

1,370 sq ft

Townhouse

116 SABISTON CT, CARY, NC, 27519

Community: Carolina Preserve

Encore at Chatham Park

166 IMAGINE WAY, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$649,900

3 beds

3 baths

2,414 sq ft

House

166 IMAGINE WAY, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Fearrington Village

1312 LANGDON PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$499,900

3 beds

2 baths

2,057 sq ft

Townhouse

1312 LANGDON PL, PITTSBORO, NC, 27312

Community: Fearrington Village

Regency at Holly Springs

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

$689,000

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

104 STONENDER WAY HOME SITE 1, HOLLY SPR..., Holly Springs, NC 27540

$942,000

3 beds

3 baths

2,115 sq ft

House

104 STONENDER WAY HOME SITE 1, HOLLY SPR...

Community: Regency at Holly Springs

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

Questions? Call us: (984) 214-4271

Regency at Holly Springs

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

$869,000

3 beds

3 baths

2,395 sq ft

House

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

Community: Regency at Holly Springs

Fearrington Village

458 BEECHMAST, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$395,000

3 beds

3 baths

2,463 sq ft

Townhouse

458 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

63 homes near Pittsboro

2 beds

2 baths

1,873 sq ft

House

2 beds

2 baths

1,611 sq ft

House

3 beds

3 baths

2,094 sq ft

House

2 beds

2 baths

1,885 sq ft

House

3 beds

2 baths

1,610 sq ft

House

3 beds

3 baths

2,221 sq ft

Townhouse

3 beds

3 baths

3,263 sq ft

House

2 beds

2 baths

1,792 sq ft

House

3 beds

3 baths

1,888 sq ft

Townhouse

3 beds

3 baths

1,906 sq ft

Townhouse

3 beds

3 baths

1,906 sq ft

Townhouse

2 beds

2 baths

1,904 sq ft

Condo

3 beds

2 baths

1,719 sq ft

House

3 beds

2 baths

1,888 sq ft

Townhouse

3 beds

3 baths

2,221 sq ft

Townhouse

3 beds

3 baths

2,221 sq ft

Townhouse

3 beds

3 baths

2,221 sq ft

Townhouse

3 beds

3 baths

2,221 sq ft

Townhouse

3 beds

3 baths

2,221 sq ft

Townhouse

3 beds