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

Encore at Chatham Park

$400ks - $500ks

Encore at Chatham Park, Pittsboro, NC

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

Brookside

$500ks

Brookside, Apex, NC

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

Heritage Pines

$400ks - $600ks

Heritage Pines, Cary, NC

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

The Courtyards at O'Kelly...

$500ks

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

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

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

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

The Courtyards at Southpo...

$500ks - $600ks

The Courtyards at Southpo..., Durham, NC

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

Woodhall

$500ks - $600ks

Woodhall, Cary, NC

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

The Courtyards at Homeste...

$400ks - $600ks

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

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

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

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

Blakeley

$400ks - $600ks

Blakeley, Cary, NC

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

The Townes at West Cary

$500ks

The Townes at West Cary, Cary, NC

44 BENCHMARK, PITTSBORO, NC, 27312

Community: Fearrington Village

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Questions? Call us: (984) 214-4271

New Fearrington Village

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

$550,000

3 beds

2 baths

2,057 sq ft

Townhouse

1312 LANGDON PL, PITTSBORO, NC, 27312

Community: Fearrington Village

New Regency at Holly Springs

205 TRUNNEL ST 104, HOLLY SPRINGS, NC, 2..., Holly Springs, NC 27540

$649,000

2 beds

2 baths

1,682 sq ft

House

205 TRUNNEL ST 104, HOLLY SPRINGS, NC, 2...

Community: Regency at Holly Springs

New Regency at Holly Springs

121 DUNTON ST, HOLLY SPRINGS, NC, 27540, Holly Springs, NC 27540

$869,000

3 beds

3 baths

2,395 sq ft

House

121 DUNTON ST, HOLLY SPRINGS, NC, 27540

Community: Regency at Holly Springs

The Villas at Culp Arbor

107 CULP HILL DR, CHAPEL HILL, NC, 27517, Chapel Hill, NC 27517

$415,000

2 beds

2 baths

1,085 sq ft

Condo

107 CULP HILL DR, CHAPEL HILL, NC, 27517

Community: The Villas at Culp Arbor

Fearrington Village

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

$895,000

3 beds

2 baths

3,640 sq ft

House

1390 BRADFORD PL, PITTSBORO, NC, 27312

Community: Fearrington Village

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

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

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

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

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

Regency at Holly Springs

421 DUNTON ST HOME SITE 187, HOLLY SPRIN..., Holly Springs, NC 27540

$979,000

3 beds

3 baths

2,465 sq ft

House

421 DUNTON ST HOME SITE 187, HOLLY SPRIN...

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

$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

Fearrington Village

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

$415,000

3 beds

3 baths

2,463 sq ft

Townhouse

458 BEECHMAST, PITTSBORO, NC, 27312

Community: Fearrington Village

The Courtyards at O'Kelly Chapel

1618 VINEYARD MIST DR, CARY, NC, 27519, Cary, NC 27519

$769,000

3 beds

3 baths

2,452 sq ft

House

1618 VINEYARD MIST DR, CARY, NC, 27519

Community: The Courtyards at O'Kelly Chapel

Carolina Preserve

304 DOWINGTON LN, CARY, NC, 27519, Cary, NC 27519

$689,000

3 beds

2 baths

2,082 sq ft

House

304 DOWINGTON LN, CARY, NC, 27519

Community: Carolina Preserve

Brookside

2127 BARRIER RDG WAY, APEX, NC, 27502, Apex, NC 27502

$475,000

3 beds

3 baths

2,221 sq ft

Townhouse

2127 BARRIER RDG WAY, APEX, NC, 27502

Community: Brookside

Regency at Holly Springs

440 DUNTON ST, HOLLY SPRINGS, NC, 27540, Holly Springs, NC 27540

$1,225,000

4 beds

4 baths

3,136 sq ft

House

440 DUNTON ST, HOLLY SPRINGS, NC, 27540

Community: Regency at Holly Springs

Fearrington Village

4200 HENDERSON PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$1,173,000

3 beds

3 baths

3,503 sq ft

House

4200 HENDERSON PL, PITTSBORO, NC, 27312

Community: Fearrington Village

Encore at Briar Chapel

93 ABERCORN CIR, CHAPEL HILL, NC, 27516, Chapel Hill, NC 27516

$600,000

2 beds

2 baths

1,617 sq ft

House

93 ABERCORN CIR, CHAPEL HILL, NC, 27516

Community: Encore at Briar Chapel

The Orchard Villas

1467 ORCHARD VILLAS AVE, APEX, NC, 27502, Apex, NC 27502

$490,000

2 beds

2 baths

1,479 sq ft

Condo

1467 ORCHARD VILLAS AVE, APEX, NC, 27502

Community: The Orchard Villas

Fearrington Village

4 MATCHWOOD, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$450,000

3 beds

2 baths

1,612 sq ft

House

4 MATCHWOOD, PITTSBORO, NC, 27312

Community: Fearrington Village

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

Questions? Call us: (984) 214-4271

Fearrington Village

804 MILLCROFT, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$775,000

3 beds

4 baths

2,615 sq ft

House

804 MILLCROFT, PITTSBORO, NC, 27312

Community: Fearrington Village

Buckhorn Preserve

2969 THIRLESTANE DR, APEX, NC, 27502, Apex, NC 27502

$649,900

4 beds

3 baths

2,748 sq ft

House

2969 THIRLESTANE DR, APEX, NC, 27502

Community: Buckhorn Preserve

Fearrington Village

862 HATFIELD, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$875,000

3 beds

3 baths

2,740 sq ft

House

862 HATFIELD, PITTSBORO, NC, 27312

Community: Fearrington Village

Fearrington Village

396 LYNDFIELD CLOSE, PITTSBORO, NC, 2731..., Pittsboro, NC 27312

$484,900

3 beds

2 baths

2,254 sq ft

Townhouse

396 LYNDFIELD CLOSE, PITTSBORO, NC, 2731...

Community: Fearrington Village

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

3050 HORTON RIDGE BLVD 287, APEX, NC, 27..., Apex, NC 27502

$534,415

4 beds

4 baths

2,092 sq ft

Townhouse

3050 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

Encore at Chatham Park

81 ENGLEHART CT, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$591,500

2 beds

2 baths

1,873 sq ft

House

81 ENGLEHART CT, 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

1,802 sq ft

House

100 CHENETTE CT, CARY, NC, 27519

Community: The Courtyards at O'Kelly Chapel

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

Questions? Call us: (984) 214-4271

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

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

60 homes near Pittsboro

3 beds

2 baths

2,248 sq ft

House

2 beds

2 baths

1,370 sq ft

Townhouse

3 beds

3 baths

2,414 sq ft

House

3 beds

3 baths

2,117 sq ft

House

3 beds

2 baths

1,450 sq ft

House

3 beds

2 baths

2,057 sq ft

Townhouse

2 beds

2 baths

1,682 sq ft

House

3 beds

3 baths

2,395 sq ft

House

2 beds

2 baths

1,085 sq ft

Condo

3 beds

2 baths

3,640 sq ft

House

3 beds

2 baths

1,880 sq ft

House

3 beds

3 baths

2,015 sq ft

House

3 beds

3 baths

2,015 sq ft

House

3 beds

3 baths

2,015 sq ft

House

3 beds

3 baths

2,115 sq ft

House

3 beds

3 baths

2,465 sq ft

House

3 beds

3 baths

2,395 sq ft

House

3 beds

3 baths

2,465 sq ft

House

3 beds

3 baths

2,463 sq ft

Townhouse

3 beds