Real Estate Investment Properties for Sale in Pittsboro, NC

Looking for investment property in Pittsboro, NC with high ROI ?

Explore a variety of short-term homes & houses in Pittsboro, NC. Invest wisely with VRBO & Pittsboro, NC Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Pittsboro, NC

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
50 Harrison Pond Drive Pittsboro, NC See Video Walkthrough! - One-of-a-kind custom estate, perfectly positioned on a private 1....	4 beds \| 5 baths \| 4,098 sq.ft.	$1,300,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 0.5% Airbnb Rental Income: $5665 Traditional Rental Income: $2401 Airbnb ROI: 2.27% Traditional ROI: 0.5%
15 Brandon Pines Court Pittsboro, NC This gorgeous 3838 sf four bedroom custom home is being built by award winning Prewitt-Dou...	4 beds \| 5 baths \| 4,004 sq.ft.	$1,216,954	Airbnb cash on cash: 2.77% Traditional cash on cash: 1.41% Airbnb Rental Income: $5665 Traditional Rental Income: $2994 Airbnb ROI: 2.77% Traditional ROI: 1.41%
967 Bynum Road Pittsboro, NC This charming 4-bedroom, 2 bath home beautifully blends historic allure with contemporary ...	4 beds \| 2 baths \| 2,460 sq.ft.	$725,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 2.04% Airbnb Rental Income: $5665 Traditional Rental Income: $2550 Airbnb ROI: 4.97% Traditional ROI: 2.04%
121 Chapel Ridge Drive Pittsboro, NC There's something about this home that just feels right. Maybe it's the way the sunlight p...	4 beds \| 4 baths \| 3,908 sq.ft.	$1,100,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 1.41% Airbnb Rental Income: $5665 Traditional Rental Income: $3103 Airbnb ROI: 2.81% Traditional ROI: 1.41%
251 Gentry Drive Pittsboro, NC Looking for a home that feels both luxurious and livable? Welcome to 251 Gentry Drive in P...	4 beds \| 4 baths \| 3,457 sq.ft.	$998,500	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.04% Airbnb Rental Income: $5665 Traditional Rental Income: $3424 Airbnb ROI: 3.23% Traditional ROI: 2.04%
320 Dewitt Smith Road Pittsboro, NC Set on 12.55 acres, this 3-bedroom, 3.5-bathroom home blends space, style, and comfort wit...	3 beds \| N/A baths \| 2,355 sq.ft.	$830,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 1.18% Airbnb Rental Income: $3932 Traditional Rental Income: $2091 Airbnb ROI: 2.47% Traditional ROI: 1.18%
114 Margaret Mann Way Pittsboro, NC Welcome to your turn-key dream home! Looking for a beautifully maintained, move-in ready h...	4 beds \| 3 baths \| 3,461 sq.ft.	$985,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 1.5% Airbnb Rental Income: $5665 Traditional Rental Income: $2842 Airbnb ROI: 3.35% Traditional ROI: 1.5%
380 Hatley Road Pittsboro, NC Welcome to this inviting 1.5-story home featuring 3 spacious bedrooms and 2 full bathrooms...	3 beds \| 2 baths \| 2,206 sq.ft.	$520,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 2.86% Airbnb Rental Income: $3932 Traditional Rental Income: $2227 Airbnb ROI: 4.63% Traditional ROI: 2.86%
29 E Madison Pittsboro, NC Elegant, Updated & Full of Charm! Welcome to Your Fearrington Retreat This beautifully mai...	3 beds \| N/A baths \| 2,913 sq.ft.	$750,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.45% Airbnb Rental Income: $3932 Traditional Rental Income: $2561 Airbnb ROI: 2.2% Traditional ROI: 1.45%
132 Hudson Hills Road Pittsboro, NC Looking for natural serenity? 132 Hudson Hills offers a rare opportunity to own a well-kep...	3 beds \| 3 baths \| 2,093 sq.ft.	$499,000	Airbnb cash on cash: 4.9% Traditional cash on cash: 2.71% Airbnb Rental Income: $3932 Traditional Rental Income: $2068 Airbnb ROI: 4.9% Traditional ROI: 2.71%
1210 Manco Dairy Road Pittsboro, NC This expansive custom built craftsman ranch is a stunning three bedroom, two bath home tha...	3 beds \| 2 baths \| 3,309 sq.ft.	$1,150,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 0.29% Airbnb Rental Income: $3932 Traditional Rental Income: $2014 Airbnb ROI: 1.29% Traditional ROI: 0.29%
322 Bellemont Road Pittsboro, NC Notice the new price, recently reduced by the motivated sellers of 322BellemontRoad. It is...	4 beds \| 3 baths \| 3,002 sq.ft.	$548,000	Airbnb cash on cash: 6.82% Traditional cash on cash: 3.3% Airbnb Rental Income: $5665 Traditional Rental Income: $2733 Airbnb ROI: 6.82% Traditional ROI: 3.3%
9 High Ridge Lane Pittsboro, NC J3S Plan with Golf Course Views - Foundation has started on this large private wooded home...	4 beds \| N/A baths \| 3,402 sq.ft.	$1,100,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 1.5% Airbnb Rental Income: $5665 Traditional Rental Income: $2835 Airbnb ROI: 3.16% Traditional ROI: 1.5%
25 High Ridge Lane Pittsboro, NC Welcome to this stunning and spacious home nestled in a premier golf course community, off...	4 beds \| 5 baths \| 4,154 sq.ft.	$999,900	Airbnb cash on cash: 2.96% Traditional cash on cash: 2.67% Airbnb Rental Income: $5665 Traditional Rental Income: $4266 Airbnb ROI: 2.96% Traditional ROI: 2.67%
57 Hazelwood Pittsboro, NC Discover this stunning 3000 sf custom parade home in Chapel Ridge, featuring four bedrooms...	4 beds \| N/A baths \| 3,044 sq.ft.	$925,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 1.91% Airbnb Rental Income: $5665 Traditional Rental Income: $3446 Airbnb ROI: 3.17% Traditional ROI: 1.91%
72 Hazelwood Pittsboro, NC This stunning four-bedroom, three-bathroom custom home by Prewitt-Douglas sits on a cul-de...	4 beds \| 3 baths \| 3,446 sq.ft.	$1,025,000	Airbnb cash on cash: 3.48% Traditional cash on cash: 2.13% Airbnb Rental Income: $5665 Traditional Rental Income: $3236 Airbnb ROI: 3.48% Traditional ROI: 2.13%
541 Sunset Grove Drive Pittsboro, NC Tucked into a gently rolling landscape just minutes from Jordan Lake, this former award-wi...	4 beds \| N/A baths \| 3,232 sq.ft.	$1,100,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 2.61% Airbnb Rental Income: $5665 Traditional Rental Income: $4324 Airbnb ROI: 2.82% Traditional ROI: 2.61%
749 Golfers View Pittsboro, NC This stunning property, completed June 2023, offers you the laidback luxury you've always ...	4 beds \| N/A baths \| 3,540 sq.ft.	$1,000,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 0.8% Airbnb Rental Income: $5665 Traditional Rental Income: $2500 Airbnb ROI: 2.98% Traditional ROI: 0.8%
405 Fieldstone Lane Pittsboro, NC Great opportunity to bulid your custom dream home in the desirable neighborhood of Fieldst...	4 beds \| 4 baths \| 3,542 sq.ft.	$1,200,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 1.74% Airbnb Rental Income: $5665 Traditional Rental Income: $3326 Airbnb ROI: 2.82% Traditional ROI: 1.74%
26 Shadymont Drive Pittsboro, NC Embrace the Charm of County Living! This delightful four-bedroom, three-bathroom residence...	4 beds \| 3 baths \| 4,148 sq.ft.	$795,000	Airbnb cash on cash: 4.52% Traditional cash on cash: 2.17% Airbnb Rental Income: $5665 Traditional Rental Income: $2791 Airbnb ROI: 4.52% Traditional ROI: 2.17%
23 Caldwell Pittsboro, NC Discover effortless living in this beautifully maintained 3-bedroom, 2-bath home located i...	3 beds \| 2 baths \| 1,730 sq.ft.	$529,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 1.61% Airbnb Rental Income: $3932 Traditional Rental Income: $1973 Airbnb ROI: 3.86% Traditional ROI: 1.61%
109 Henrys Ridge Road Pittsboro, NC Welcome home to your perfect, private oasis. Minutes to Jordan Lake, Apex & Pittsboro, but...	4 beds \| N/A baths \| 3,357 sq.ft.	$900,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 2.28% Airbnb Rental Income: $5665 Traditional Rental Income: $3259 Airbnb ROI: 3.8% Traditional ROI: 2.28%
387 Riverstone Drive Pittsboro, NC Discover this rare Southern Living Magazine Showcase custom home in the prestigious Rivers...	4 beds \| 6 baths \| 4,700 sq.ft.	$2,289,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 0.07% Airbnb Rental Income: $5665 Traditional Rental Income: $3112 Airbnb ROI: 0.73% Traditional ROI: 0.07%
961 Cabin Creek Pittsboro, NC Welcome to this exquisite ICG-built home, completed in 2023 and nestled within Pittsboro's...	5 beds \| 4 baths \| 3,245 sq.ft.	$914,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.6% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 1.6%
2817 Silk Hope Gum Springs Road Pittsboro, NC MOVE IN NOW for the holidays!, this stunning 4-bedroom, 3.5-bath home offers over 3,200 sq...	4 beds \| N/A baths \| 3,232 sq.ft.	$949,900	Airbnb cash on cash: 3.7% Traditional cash on cash: 2.44% Airbnb Rental Income: $5665 Traditional Rental Income: $3413 Airbnb ROI: 3.7% Traditional ROI: 2.44%
13 Blackhorn Court Pittsboro, NC Another exceptional build by PREWITT-DOUGLAS CUSTOM HOMES in the highly desirable CHAPEL R...	4 beds \| N/A baths \| 4,228 sq.ft.	$1,463,001	Airbnb cash on cash: 2.14% Traditional cash on cash: 0.76% Airbnb Rental Income: $5665 Traditional Rental Income: $2650 Airbnb ROI: 2.14% Traditional ROI: 0.76%
283 Wendover Parkway Pittsboro, NC Luxury Townhome in the Vineyards at Chatham Park ! Adorable patio townhome for relaxing on...	3 beds \| N/A baths \| 1,798 sq.ft.	$399,900	Airbnb cash on cash: 5.41% Traditional cash on cash: 2.83% Airbnb Rental Income: $3932 Traditional Rental Income: $2118 Airbnb ROI: 5.41% Traditional ROI: 2.83%
180 Bur Oak Court Pittsboro, NC Lorient Homes is pleased to introduce our luxurious S1 plan with 19ft ceilings in the fami...	4 beds \| N/A baths \| 2,906 sq.ft.	$895,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 2.43% Airbnb Rental Income: $5665 Traditional Rental Income: $3133 Airbnb ROI: 4.11% Traditional ROI: 2.43%
431 Fieldstone Lane Pittsboro, NC Build your new custom home in the established and sought after neighborhood of Fieldstone ...	4 beds \| N/A baths \| 3,439 sq.ft.	$1,200,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 1.37% Airbnb Rental Income: $5665 Traditional Rental Income: $2909 Airbnb ROI: 2.82% Traditional ROI: 1.37%
57 Merriville Road Pittsboro, NC PRICE IMPROVEMENT!! Looking for a stunning and affordable home in a 55+ community? Look no...	2 beds \| 2 baths \| 1,470 sq.ft.	$440,000	Airbnb cash on cash: -5.34% Traditional cash on cash: -6.03% Airbnb Rental Income: $3240 Traditional Rental Income: $2230 Airbnb ROI: -5.34% Traditional ROI: -6.03%
1245 Golfers View Pittsboro, NC Luxurious Walkout Basement Home in Chapel Ridge. Stunning L2 plan with an 850 sqft finishe...	4 beds \| N/A baths \| 5,166 sq.ft.	$1,345,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 1.16% Airbnb Rental Income: $5665 Traditional Rental Income: $2975 Airbnb ROI: 2.41% Traditional ROI: 1.16%
183 Lookout Ridge Pittsboro, NC Lorient Homes is pleased to introduce our luxurious J2 plan. 4 Bedroom open design with a ...	4 beds \| N/A baths \| 2,902 sq.ft.	$819,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 2.5% Airbnb Rental Income: $5665 Traditional Rental Income: $2928 Airbnb ROI: 4.61% Traditional ROI: 2.5%
45 Quail Point Pittsboro, NC Ranch with Finished Walkout Basement in Chapel Ridge. This stunning R1 Plan offers nearly ...	3 beds \| N/A baths \| 3,426 sq.ft.	$1,100,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 1.36% Airbnb Rental Income: $3932 Traditional Rental Income: $2686 Airbnb ROI: 1.75% Traditional ROI: 1.36%
684 Golfers View Pittsboro, NC Luxurious J3 Plan with Finished Walkout Basement in Chapel Ridge. The J3 Plan offers an op...	4 beds \| N/A baths \| 3,951 sq.ft.	$1,150,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 1.86% Airbnb Rental Income: $5665 Traditional Rental Income: $3330 Airbnb ROI: 2.98% Traditional ROI: 1.86%
4025 Hamlets Chapel Road Pittsboro, NC Still time to personalize as the build begins on this gorgeous 3 car modern farmhouse on 1...	4 beds \| 4 baths \| 2,770 sq.ft.	$996,500	Airbnb cash on cash: 3.74% Traditional cash on cash: 1.91% Airbnb Rental Income: $5665 Traditional Rental Income: $2835 Airbnb ROI: 3.74% Traditional ROI: 1.91%
59 Mist Wood Court Pittsboro, NC Incredible new build opportunity with Pomarico Construction. True custom build, all person...	3 beds \| 3 baths \| 2,880 sq.ft.	$799,900	Airbnb cash on cash: 2.81% Traditional cash on cash: 2.33% Airbnb Rental Income: $3932 Traditional Rental Income: $2730 Airbnb ROI: 2.81% Traditional ROI: 2.33%
3680 15-501 N Pittsboro, NC Back on market with drastic price reduction! Spectacular home on 4.047 acres in prime loca...	5 beds \| 4 baths \| 6,149 sq.ft.	$1,225,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.01% Airbnb Rental Income: $null Traditional Rental Income: $4001 Airbnb ROI: N/A Traditional ROI: 2.01%
91 Imagine Way Pittsboro, NC Easy living awaits you at 91 Imagine Way. A 55+ community of Chatham Park. This lovely hom...	3 beds \| 3 baths \| 2,220 sq.ft.	$629,500	Airbnb cash on cash: 2.65% Traditional cash on cash: 1.98% Airbnb Rental Income: $3932 Traditional Rental Income: $2697 Airbnb ROI: 2.65% Traditional ROI: 1.98%
927 Woodham Pittsboro, NC MODERN LIVING IN HARMONY WITH NATURE. This custom, Energy Star home is more than a residen...	4 beds \| 3 baths \| 3,414 sq.ft.	$1,125,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 1.28% Airbnb Rental Income: $5665 Traditional Rental Income: $3242 Airbnb ROI: 2.51% Traditional ROI: 1.28%
374 Crimson Way Pittsboro, NC NEW PRICE! MOTIVATED SELLERS! Stunning 5BR/4.5BA Estate in Gated Section of Chapel Ridge! ...	5 beds \| N/A baths \| 4,334 sq.ft.	$999,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.32% Airbnb Rental Income: $null Traditional Rental Income: $3767 Airbnb ROI: N/A Traditional ROI: 2.32%

Real Estate investment in Pittsboro, NC

There are 170 properties for sale in the city of Pittsboro . The median list price in Pittsboro is $847,500 and the average price per square foot is $281. In October 2025, the average monthly cash on cash return in Pittsboro is 2.00%. The average monthly rental income in Pittsboro is $2,701.

Pittsboro, NC Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 170 investment properties available for sale in Pittsboro.

In 2025, the best neighborhood to buy investment property is Pittsboro.

The ROI for Short-Term is higher than the Long-Term in Pittsboro with average rental income of $5,665.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsboro, NC

50 Harrison Pond Drive

Pittsboro, NC

4 beds | 5 baths | 4,098 sq.ft.

$1,300,000

Airbnb cash on cash: 2.27%

Traditional cash on cash: 0.5%

Airbnb Rental Income: $5665

Traditional Rental Income: $2401

Airbnb ROI: 2.27%

Traditional ROI: 0.5%

15 Brandon Pines Court

Pittsboro, NC

4 beds | 5 baths | 4,004 sq.ft.

$1,216,954

Airbnb cash on cash: 2.77%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $5665

Traditional Rental Income: $2994

Airbnb ROI: 2.77%

Traditional ROI: 1.41%

967 Bynum Road

Pittsboro, NC

4 beds | 2 baths | 2,460 sq.ft.

$725,000

Airbnb cash on cash: 4.97%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $5665

Traditional Rental Income: $2550

Airbnb ROI: 4.97%

Traditional ROI: 2.04%

121 Chapel Ridge Drive

Pittsboro, NC

4 beds | 4 baths | 3,908 sq.ft.

$1,100,000

Airbnb cash on cash: 2.81%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $5665

Traditional Rental Income: $3103

Airbnb ROI: 2.81%

Traditional ROI: 1.41%

251 Gentry Drive

Pittsboro, NC

4 beds | 4 baths | 3,457 sq.ft.

$998,500

Airbnb cash on cash: 3.23%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $5665

Traditional Rental Income: $3424

Airbnb ROI: 3.23%

Traditional ROI: 2.04%

320 Dewitt Smith Road

Pittsboro, NC

3 beds | N/A baths | 2,355 sq.ft.

$830,000

Airbnb cash on cash: 2.47%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $3932

Traditional Rental Income: $2091

Airbnb ROI: 2.47%

Traditional ROI: 1.18%

114 Margaret Mann Way

Pittsboro, NC

4 beds | 3 baths | 3,461 sq.ft.

$985,000

Airbnb cash on cash: 3.35%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $5665

Traditional Rental Income: $2842

Airbnb ROI: 3.35%

Traditional ROI: 1.5%

380 Hatley Road

Pittsboro, NC

3 beds | 2 baths | 2,206 sq.ft.

$520,000

Airbnb cash on cash: 4.63%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $3932

Traditional Rental Income: $2227

Airbnb ROI: 4.63%