Real Estate Investment Properties for Sale in Hilton Head Island, SC
Looking for investment property in Hilton Head Island, SC with high ROI ?
Explore a variety of short-term homes & houses in Hilton Head Island, SC. Invest wisely with VRBO & Hilton Head Island, SC 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 Hilton Head Island, SC
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
58 Spindle Lane #58Hilton Head Island, SCNestled in Windmill Harbour, Hilton Head Islandsâ premier boating community, this villa ... |
2 beds | 2 baths | 1,595 sq.ft. |
$519,000 |
Airbnb cash on cash: 0.36%
|
51 Wicklow DrHilton Head Island, SCWelcome to this exceptional estate in Wexford, blending grand design with everyday comfort... |
4 beds | 8 baths | 7,078 sq.ft. |
$2,995,000 |
Airbnb cash on cash: -0.89%
|
2 Red Maple RdHilton Head Island, SCSet on a lush ¾-acre lot overlooking the 17th tee of Heron Point, this 3,285 SqFt Sea Pin... |
3 beds | 4 baths | 3,285 sq.ft. |
$1,995,000 |
Airbnb cash on cash: -0.7%
|
10 N Forest Beach Drive #2115Hilton Head Island, SCBest priced, beautifully decorated 3 bedroom unit on first floor for easy access with no s... |
3 beds | 3 baths | 1,958 sq.ft. |
$1,221,000 |
Airbnb cash on cash: 0.33%
|
24 Ocean Point NHilton Head Island, SCWelcome to 24 Ocean Point North a modern and stunning 2nd-row beach home in Port Royal! T... |
3 beds | 4 baths | 2,533 sq.ft. |
$2,295,000 |
Airbnb cash on cash: -1.21%
|
16 Timber Marsh LaneHilton Head Island, SCWelcome to Lowcountry luxury at this 4 bd/4.5-ba builders custom model home! This masterpi... |
4 beds | 5 baths | 3,513 sq.ft. |
$1,300,000 |
Airbnb cash on cash: -0.87%
|
5 Off ShoreHilton Head Island, SCWonderful opportunity to call this impressive island oasis, home! A 3 bedroom, 2.5 bath, 2... |
3 beds | 3 baths | 3,029 sq.ft. |
$1,799,000 |
Airbnb cash on cash: -0.44%
|
6 Sea Olive RoadHilton Head Island, SCCharming 3 Bedroom 2 Bath one-level home in Point Comfort, one of Hilton Head's most covet... |
3 beds | 2 baths | 1,368 sq.ft. |
$899,000 |
Airbnb cash on cash: 0.34%
|
32 Plantation DriveHilton Head Island, SC32 Plantation Drive is a 3BD, 3.5BA coastal lowcountry home tucked inside the gates of Sea... |
3 beds | 4 baths | 2,975 sq.ft. |
$1,945,000 |
Airbnb cash on cash: -0.68%
|
35 Carnoustie Road #56Hilton Head Island, SCWelcome to 56 Fazio! This updated 3-bedroom, 3-bath end-unit Fazio Villa is a rare opportu... |
3 beds | 3 baths | 2,017 sq.ft. |
$1,125,000 |
Airbnb cash on cash: 0.17%
|
20 Queens Folly Road #1863Hilton Head Island, SCCoastal Chic at its best, in highly desired St Andrews, 2nd floor, 2BR/2BA beach villa wit... |
2 beds | 2 baths | 1,177 sq.ft. |
$563,000 |
Airbnb cash on cash: -1.38%
|
3 Shelter Cove Lane #7474Hilton Head Island, SCSpacious 3BR/3BA villa in the sought-after Anchorage Villas on Hilton Head Island. One of ... |
3 beds | 3 baths | 1,555 sq.ft. |
$675,000 |
Airbnb cash on cash: 1.37%
|
20 Queens Folly Road #1661Hilton Head Island, SCBeautifully remodeled 2BR/2BA condo in St. Andrews, located in Palmetto Dunes Resort on Hi... |
2 beds | 2 baths | 1,177 sq.ft. |
$595,000 |
Airbnb cash on cash: -0.05%
|
6 Village North Drive #59Hilton Head Island, SCBeautifully updated first floor condominium offering gorgeous water views and effortless i... |
2 beds | 2 baths | 1,183 sq.ft. |
$699,000 |
Airbnb cash on cash: -1.12%
|
96 Mathews Drive #56Hilton Head Island, SCGreat investment opportunity or move in yourself!! Current lease ends April 2025! Pet frie... |
2 beds | 2 baths | 964 sq.ft. |
$285,000 |
Airbnb cash on cash: -0.34%
|
40 Folly Field Road #A209Hilton Head Island, SCWelcome to the ultimate beachside getaway on Hilton Head Island! This beautifully renovate... |
1 beds | 1 baths | 592 sq.ft. |
$318,000 |
Airbnb cash on cash: -0.64%
|
36 Deallyon Avenue #114Hilton Head Island, SCThis beautifully renovated 2nd floor Springwood Villa is just down the street from Hilton ... |
2 beds | 3 baths | 1,250 sq.ft. |
$499,000 |
Airbnb cash on cash: 1.06%
|
141 Lamotte Drive #H1Hilton Head Island, SCDiscover this charming 2BR/2BA first-floor villa in Palmetto Commons, Hilton Head Islandâ... |
2 beds | 2 baths | 985 sq.ft. |
$265,000 |
Airbnb cash on cash: -0.08%
|
85 Folly Field Road #116Hilton Head Island, SCBeach beauty awaiting a new owner. Rare gem in Island Club, fully renovated with water an... |
1 beds | 2 baths | 881 sq.ft. |
$449,000 |
Airbnb cash on cash: -0.9%
|
70 Shipyard Drive #157Hilton Head Island, SCWelcome to your perfect island retreat! This beautiful first-floor corner villa in the sou... |
2 beds | 2 baths | 1,335 sq.ft. |
$615,000 |
Airbnb cash on cash: 0.18%
|
67 Summerfield Court #623Hilton Head Island, SCCharm, Comfort and Convenience in the Heart of Hilton Head Island! Don't miss this beautif... |
3 beds | 3 baths | 1,430 sq.ft. |
$428,000 |
Airbnb cash on cash: 1.81%
|
21 S Forest Beach Drive #137Hilton Head Island, SCPicture perfect 2 bedroom 2 bath oceanfront Shorewood Villa in the heart of South Forest B... |
2 beds | 2 baths | 1,125 sq.ft. |
$879,900 |
Airbnb cash on cash: -0.3%
|
663 William Hilton Parkway #3321Hilton Head Island, SCInvestorâs Dream on Hilton Head Island! This fully furnished & renovated 3BR/2BA villa i... |
3 beds | 2 baths | 1,186 sq.ft. |
$450,000 |
Airbnb cash on cash: 0.54%
|
1 Yacht Club DriveHilton Head Island, SCBEST VALUE in Windmill Harbour! ½ a block from the SC Yacht Clubâbeautifully updated 3 ... |
3 beds | 4 baths | 2,759 sq.ft. |
$995,000 |
Airbnb cash on cash: 0.72%
|
15 N Sea Pines DriveHilton Head Island, SCDesirable turn-key home on the beach path, just steps from the white sand beaches of Hilto... |
3 beds | 4 baths | 2,188 sq.ft. |
$2,275,000 |
Airbnb cash on cash: -0.29%
|
25 Wildwood RoadHilton Head Island, SCSea Pines beauty! Do not miss this exquisite fully furnished home in Greenwood Forest - m... |
3 beds | 2 baths | 1,598 sq.ft. |
$1,050,000 |
Airbnb cash on cash: 0.07%
|
150 Lighthouse Road #A-727Hilton Head Island, SCAbsolutely stunning 2-bedroom, 2.5-bath end-unit townhouse offering spectacular views of t... |
2 beds | 3 baths | 1,441 sq.ft. |
$1,049,000 |
Airbnb cash on cash: -0.39%
|
20 Queens Folly Road #1767Hilton Head Island, SCPet-Friendly and Steps to the Pool! Embrace island living in this rarely available first-f... |
2 beds | 2 baths | 1,342 sq.ft. |
$599,900 |
Airbnb cash on cash: -0.06%
|
40 Folly Field Road #C248Hilton Head Island, SCWelcome to this stunning villa in First Ocean Row building, just steps from beach with bre... |
1 beds | 1 baths | 592 sq.ft. |
$289,500 |
Airbnb cash on cash: -0.55%
|
15 Deer Run LaneHilton Head Island, SCYou'll be on vacation every day at 15 Deer Run Lane in Sea Pines! This 3000+ sq.ft. ranch ... |
3 beds | 3 baths | 3,014 sq.ft. |
$1,775,000 |
Airbnb cash on cash: -0.6%
|
49 Fairway Winds PlaceHilton Head Island, SCGORGEOUS lagoon to golf views from this renovated Fairway Winds home tucked inside Port Ro... |
3 beds | 4 baths | 2,157 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -1.03%
|
40 Folly Field Road #B344Hilton Head Island, SCWake to the morning sun rising out of the Atlantic. 344B Hilton Head Beach and Tennis is ... |
1 beds | 1 baths | 592 sq.ft. |
$285,000 |
Airbnb cash on cash: -0.53%
|
45 Folly Field Road #18AHilton Head Island, SCThis updated 2-bedroom, 2-bath condo in Fiddlers Cove generated over $60,000 in short-term... |
2 beds | 2 baths | 757 sq.ft. |
$364,000 |
Airbnb cash on cash: -0.6%
|
47 Ocean Lane #5107Hilton Head Island, SCOne of a kind opportunity! Not only does this stunning villa have gorgeous sunrises & phen... |
2 beds | 2 baths | 1,394 sq.ft. |
$1,799,000 |
Airbnb cash on cash: -1.06%
|
4 N Forest Beach Drive #127Hilton Head Island, SCOCEANFRONT condo with TWO separate sleeping spaces, each furnished with a comfortable quee... |
1 beds | 1 baths | 518 sq.ft. |
$510,000 |
Airbnb cash on cash: 0.25%
|
147 Lighthouse Road #667Hilton Head Island, SCEnjoy all that Harbour Town has to offer from this beautiful 2 bed/2 bath Sea Pines Resort... |
2 beds | 2 baths | 1,002 sq.ft. |
$689,000 |
Airbnb cash on cash: 0.37%
|
92 High Bluff RoadHilton Head Island, SC3 BD 3BTH home with soaring 20' cathedral ceilings, floor-to-ceiling windows and golf view... |
3 beds | 4 baths | 2,477 sq.ft. |
$970,000 |
Airbnb cash on cash: -0.44%
|
663 William Hilton Parkway #4422Hilton Head Island, SCThis little gem resides within the Four Seasons Hilton Head Oceanfront Resort. 2 BR, 2 Ba,... |
2 beds | 2 baths | 831 sq.ft. |
$279,000 |
Airbnb cash on cash: 0.75%
|
53 Delander Court #18Hilton Head Island, SCWelcome to this beautifully updated 2-bedroom, 1-bathroom flat on Hilton Headâs desirabl... |
2 beds | 1 baths | 950 sq.ft. |
$340,000 |
Airbnb cash on cash: 1.97%
|
7 Shaftsbury LaneHilton Head Island, SCIndulge in the pinnacle of refined Lowcountry luxury in the prestigious, gated community o... |
4 beds | 4 baths | 4,066 sq.ft. |
$1,470,000 |
Airbnb cash on cash: -0.56%
|
Real Estate investment in Hilton-head-island, SC
There are 586 properties for sale in the city of Hilton Head Island . The median list price in Hilton Head Island is $649,000 and the average price per square foot is $361. In September 2025, the average monthly cash on cash return in Hilton Head Island is 1.00%. The average monthly rental income in Hilton Head Island is $1,674.