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

53 homes near Pittsboro

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Encore at Chatham Park

$400ks - $500ks

Encore at Chatham Park, Pittsboro, NC

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

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

Heritage Pines

$400ks - $600ks

Heritage Pines, Cary, NC

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

Encore at Briar Chapel

$400ks - $600ks

Encore at Briar Chapel, Chapel Hill, NC

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

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

Questions? Call us: (984) 214-4271

The Courtyards at West Ca...

$600ks

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

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

5 rating (4 reviews)

Carolina Preserve

$400ks - $700ks

Carolina Preserve, Cary, NC

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

Buckhorn Preserve

$500ks - $700ks

Buckhorn Preserve, Apex, NC

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

The Courtyards at O'Kelly...

$500ks

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

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

Chapelwood

$500ks - $600ks

Chapelwood, Chapel Hill, NC

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

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

5 rating (1 reviews)

The Orchard Villas

$400ks - $500ks

The Orchard Villas, Apex, NC

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

The Townes at West Cary

$500ks

The Townes at West Cary, Cary, NC

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

Woodhall

$500ks - $600ks

Woodhall, Cary, NC

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

Blakeley

$400ks - $600ks

Blakeley, Cary, NC

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

Asteria™

Asteria™, Pittsboro, NC

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

Retreat at Cedar Crossing

$500ks - $900ks

Retreat at Cedar Crossing, Apex, NC

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

Chapel Oaks

$1Ms

Chapel Oaks, Chapel Hill, NC

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

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

44 BENCHMARK, 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

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

$1,150,240

3 beds

2 baths

3,640 sq ft

House

1390 BRADFORD PL, PITTSBORO, NC, 27312

Community: Fearrington Village

Heritage Pines

$505,000

2 beds

2 baths

1,574 sq ft

House

3005 HERITAGE PINES DR, CARY, NC, 27519

Community: Heritage Pines

The Courtyards at O'Kelly Chapel

1309 BETASSO DR, CARY, NC, 27519, Cary, NC 27519

$665,000

2 beds

2 baths

2,030 sq ft

House

1309 BETASSO DR, CARY, NC, 27519

Community: The Courtyards at O'Kelly Chapel

The Townes at West Cary

810 MONEY ISLAND PL, CARY, NC, 27519, Cary, NC 27519

$640,000

3 beds

3 baths

2,401 sq ft

Townhouse

810 MONEY ISLAND PL, CARY, NC, 27519

Community: The Townes at West Cary

The Courtyards at West Cary

$640,000

3 beds

3 baths

2,401 sq ft

Townhouse

810 MONEY ISLAND PL, CARY, NC, 27519

Community: The Courtyards at West Cary

Carolina Preserve

4213 DEL WEBB AVE, CARY, NC, 27519, Cary, NC 27519

$470,000

2 beds

2 baths

1,368 sq ft

Townhouse

4213 DEL WEBB AVE, CARY, NC, 27519

Community: Carolina Preserve

Heritage Pines

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

$595,000

3 beds

3 baths

2,905 sq ft

Townhouse

431 SAWGRASS HILL CT, CARY, NC, 27519

Community: Heritage Pines

Fearrington Village

14 CASWELL, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$829,900

4 beds

3 baths

3,899 sq ft

House

14 CASWELL, PITTSBORO, NC, 27312

Community: Fearrington Village

The Orchard Villas

1497 ORCHARD VILLAS AVE, APEX, NC, 27502, Apex, NC 27502

$575,000

3 beds

3 baths

2,379 sq ft

Condo

1497 ORCHARD VILLAS AVE, APEX, NC, 27502

Community: The Orchard Villas

Chapelwood

242 HALES WOOD RD, CHAPEL HILL, NC, 2751..., Chapel Hill, NC 27517

$770,000

3 beds

2 baths

2,328 sq ft

House

242 HALES WOOD RD, CHAPEL HILL, NC, 2751...

Community: Chapelwood

Encore at Chatham Park

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

$849,900

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

Encore at Briar Chapel

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

$585,500

2 beds

2 baths

1,774 sq ft

House

63 MIDDLETON PL, CHAPEL HILL, NC, 27516

Community: Encore at Briar Chapel

Fearrington Village

4203 HENDERSON PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$1,175,000

4 beds

4 baths

3,573 sq ft

House

4203 HENDERSON PL, PITTSBORO, NC, 27312

Community: Fearrington Village

Fearrington Village

4233 HENDERSON PL, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$1,049,000

3 beds

3 baths

3,210 sq ft

House

4233 HENDERSON PL, PITTSBORO, NC, 27312

Community: Fearrington Village

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

Carolina Preserve

725 BRADHURST PL, CARY, NC, 27519, Cary, NC 27519

$510,000

3 beds

2 baths

1,418 sq ft

House

725 BRADHURST PL, CARY, NC, 27519

Community: Carolina Preserve

Fearrington Village

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

$574,900

3 beds

2 baths

2,057 sq ft

Townhouse

1312 LANGDON PL, PITTSBORO, NC, 27312

Community: Fearrington Village

Encore at Chatham Park

127 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$430,000

2 beds

2 baths

1,469 sq ft

Ranch

127 TANTARA BND, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Buckhorn Preserve

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

$664,900

4 beds

3 baths

2,748 sq ft

House

2969 THIRLESTANE DR, APEX, NC, 27502

Community: Buckhorn Preserve

Heritage Pines

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

$435,000

2 beds

2 baths

1,389 sq ft

Townhouse

438 SAWGRASS HILL CT, CARY, NC, 27519

Community: Heritage Pines

Encore at Chatham Park

62 RASPBERRY RUN, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$798,000

3 beds

4 baths

3,090 sq ft

House

62 RASPBERRY RUN, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

The Courtyards at West Cary

444 CRAYTON OAK DR, CARY, NC, 27519, Cary, NC 27519

$934,900

3 beds

3 baths

2,972 sq ft

House

444 CRAYTON OAK DR, CARY, NC, 27519

Community: The Courtyards at West Cary

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

Questions? Call us: (984) 214-4271

The Courtyards at West Cary

609 CROOKED PINE DR, CARY, NC, 27519, Cary, NC 27519

$735,000

3 beds

3 baths

2,503 sq ft

House

609 CROOKED PINE DR, CARY, NC, 27519

Community: The Courtyards at West Cary

Encore at Chatham Park

120 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$459,000

2 beds

2 baths

1,467 sq ft

Duplex

120 TANTARA BND, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Encore at Chatham Park

128 TANTARA BND, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$459,000

2 beds

2 baths

1,467 sq ft

Duplex

128 TANTARA BND, PITTSBORO, NC, 27312

Community: Encore at Chatham Park

Buckhorn Preserve

2930 BALBARDIE DR, APEX, NC, 27502, Apex, NC 27502

$743,500

3 beds

3 baths

2,828 sq ft

House

2930 BALBARDIE DR, APEX, NC, 27502

Community: Buckhorn Preserve

Brookside

1105 PALISADE BLUFF LN, APEX, NC, 27502, Apex, NC 27502

$535,000

3 beds

3 baths

2,221 sq ft

Townhouse

1105 PALISADE BLUFF LN, APEX, NC, 27502

Community: Brookside

Encore at Briar Chapel

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

$644,900

2 beds

2 baths

1,885 sq ft

House

66 MIDDLETON PL, CHAPEL HILL, NC, 27516

Community: Encore at Briar Chapel

The Villas at Culp Arbor

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

$425,000

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

145 WINDSTONE, PITTSBORO, NC, 27312, Pittsboro, NC 27312

$750,000

4 beds

3 baths

4,862 sq ft

House

145 WINDSTONE, PITTSBORO, NC, 27312

Community: Fearrington Village

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

Encore at Briar Chapel

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

$725,000

2 beds

3 baths

2,447 sq ft

House

90 PULASKI TRL, CHAPEL HILL, NC, 27516

Community: Encore at Briar Chapel

Brookside

2144 BARNSIDE LN, APEX, NC, 27502, Apex, NC 27502

$498,140

3 beds

3 baths

2,221 sq ft

Townhouse

2144 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

Heritage Pines

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

$509,900

2 beds

2 baths

1,718 sq ft

House

105 ROCKPORT RIDGE WAY, CARY, NC, 27519

Community: Heritage Pines

Fearrington Village

309 BANEBERRY CLOSE, PITTSBORO, NC, 2731..., Pittsboro, NC 27312

$360,000

3 beds

2 baths

2,091 sq ft

Townhouse

309 BANEBERRY CLOSE, PITTSBORO, NC, 2731...

Community: Fearrington Village

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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™, Del Webb at Chatham Park, Inspire Briar Chapel.

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 $462,420, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Fearrington Village average around $590,371, while homes in Encore at Chatham Park average around $461,940.

Raleigh Durham Area 55+ Housing Market Trends

Trend Shown:

Number of Listings

Raleigh Durham Area 55+ Housing Market Trends

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53 homes

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

21 communities near Pittsboro

53 homes near Pittsboro

2 beds

2 baths

1,469 sq ft

Townhouse

2 beds

2 baths

1,467 sq ft

Townhouse

2 beds

2 baths

1,469 sq ft

Townhouse

2 beds

2 baths

1,467 sq ft

Townhouse

3 beds

2 baths

1,450 sq ft

House

3 beds

2 baths

3,640 sq ft

House

2 beds

2 baths

1,574 sq ft

House

2 beds

2 baths

2,030 sq ft

House

3 beds

3 baths

2,401 sq ft

Townhouse

3 beds

3 baths

2,401 sq ft

Townhouse

2 beds

2 baths

1,368 sq ft

Townhouse

3 beds

3 baths

2,905 sq ft

Townhouse

4 beds

3 baths

3,899 sq ft

House

3 beds

3 baths

2,379 sq ft

Condo

3 beds

2 baths

2,328 sq ft

House

3 beds

3 baths

2,668 sq ft

House

2 beds

2 baths

1,774 sq ft

House

4 beds

4 baths

3,573 sq ft

House

3 beds

3 baths

3,210 sq ft

House

3 beds