5+ Days Ago
Location
27 Lone Cypress Trl, Hilton Head Island, SC 29926, USA
Tour 27 Lone Cypress Trl
Contact
4 Bedroom Home at Bailey's Cove on Hilton Head Island | Small footprint. Big island life.
Pacific Capital Management
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Amenities for 27 Lone Cypress Trl
Appliances
| Dishwasher | In-Unit Laundry |
| Oven | Range |
| Refrigerator | Washer and Dryer |
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.
Policies and fees
Applicants
Applicants
One-time.
Contact Property
REQUIRED FEES
Security Deposit
One-time. Refundable.
Contact Property
Dog Policy
Not allowed
Cat Policy
Not allowed
No pets allowed.
Questions about this property’s policies and fees?
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About 27 Lone Cypress Trl
Not every dream home needs to be the biggest on the block — it just needs to be exactly right. The Jessamine at Bailey's Cove delivers precisely that. At 1,999 square feet, this smartly designed 4-bedroom, 3.5-bath new construction packs exceptional livability into every square foot, making it one of the most versatile and welcoming homes on Hilton Head Island. What sets The Jessamine apart from the moment you arrive is flexibility. The main level features a true primary suite — bedroom, full bath, and direct access to the covered deck — so whether you're embracing single-level living or simply love the idea of waking up steps from the outdoor air, this home was built with you in mind. A half bath on the main level adds everyday convenience, while the open living and kitchen area flows naturally around the beautiful LVP flooring that ties it all together. The kitchen is every bit as thoughtful as the rest of the home. Whirlpool stainless appliances, solid countertops, a generous island, and a large pantry make cooking and gathering equally enjoyable — because on Hilton Head, every meal feels a little like a celebration. Head upstairs and discover even more to love. A second primary suite on the top floor offers its own private bath, making it ideal for multigenerational living, long-term guests, or a luxurious owner's retreat away from it all. Two additional bedrooms round out the upper level — including a cozy fourth bedroom perfectly sized for a home office, nursery, or creative space — along with another full bath and a conveniently located upstairs laundry room to keep life running smoothly. Outside, the oversized two-car garage with extra storage handles all the gear that comes with island living, from paddleboards to bicycles and everything in between. New construction. Move-in ready. Hilton Head Island. Bailey's Cove | The Jessamine Plan | 4 BD · 3.5 BA · 1,999 SF Right-sized for island life. Perfect for yours.
Address details
| Zip code | 29926 |
|---|---|
| Type | House for rent |
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Rent trends in Hilton Head Island
4-bedroom apartments at 27 Lone Cypress Trl cost about 11% less than the average rent price for 4-bedroom apartments in Hilton Head Island.
Median rents as of Apr 18 2026.
Hilton Head Island
| Month | Median Rent |
|---|---|
| May 2024 | $3,966 |
| June 2024 | $3,715 |
| July 2024 | $3,950 |
| August 2024 | $4,500 |
| September 2024 | $4,000 |
| October 2024 | $3,900 |
| November 2024 | $3,900 |
| December 2024 | $3,500 |
| January 2025 | $3,500 |
| May 2025 | $3,666 |
| July 2025 | $5,250 |
| August 2025 | $4,864 |
| September 2025 | $4,400 |
| October 2025 | $4,671 |
| November 2025 | $4,048 |
| December 2025 | $3,987 |
| January 2026 | $4,257 |
| February 2026 | $4,398 |
| March 2026 | $4,500 |
| April 2026 | $4,597 |
Affordability calculator
Can I afford to live at 27 Lone Cypress Trl?
Bedrooms
4+ bedroomsRent-to-income ratio
30%
Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income
$159,800/yr
With your selected rent-to-income ratio, you'd ideally want to make $159,800 annually to afford this 4-bedrooms monthly rent price of $3,995.
For more information on rent affordability, visit our rent calculator.
Schools near 27 Lone Cypress Trl
Beaufort Jasper EOC Head Start - Leroy Gilliard EHS Center
1410 tailbird rd
beaufort, SC, 29902
PKPublic
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Internet available near 27 Lone Cypress Trl
Getting around Hilton Head Island near 27 Lone Cypress Trl
Walking
2/10
You’ll need another mode of transportation for getting around. Scooter, anyone?
Driving
10/10
Commuting is easy with multiple accessible routes and plenty of parking.
Cycling
3/10
This is semi-bikeable, but you’ll need another way of getting around.
Points of interest for 27 Lone Cypress Trl, Hilton Head Island
Groceries
0/10
Closest supermarket further than a 30-minute walk
Shopping
3/10
Some shops within walking distance
Cafes
1/10
Few or no cafés within walking distance
Restaurants
3/10
Some restaurants within walking distance
Primary schools
0/10
Closest elementary school further than a 30-minute walk
High schools
0/10
Closest high school further than a 30-minute walk
Nightlife
1/10
Few or no bars within walking distance
Explore the area around 27 Lone Cypress Trl
Walmart Supercenter
25 Pembroke Dr
Publix
45 Pembroke Dr
Harris Teeter
301 Main St
The Fresh Market
890 William Hilton Pkwy
Kroger
42 Shelter Cove Ln
Binya Boutique LLC
556 Spanish Wells Rd
Walmart Supercenter
25 Pembroke Dr
Bie LLC
80 Paddle Boat Ln
Tradewinds International Inc
17 Harbourside Ln
Sea Bees
149 Lighthouse Road Harbour Hous
Starbucks
301 Main St
Duck Donuts
890 William Hilton Pkwy
Starbucks
42 Shelter Cove Ln
North End Coffee
95 Gardner Dr
Origin Coffee Bar
35 Main St
Up the Creek Pub at Broad Creek Marina
18 Simmons Rd
New York City Pizza
45 Pembroke Dr
Club Seats
2600 Main St
Top Dawg Tavern
13 Harbourside Ln
Frankie Bones Hilton Head
1301 Main St
Benny Hudson Seafood
175 Squire Pope Rd
Walmart Bakery
25 Pembroke Dr
7th Heaven Spices LLC
7 Shelter Cove Ln
Hilton Head Social Bakery
17 Harbourside Ln
Nutrishop Low Country
50 Burnt Church Rd
Daufuskie Crab Co
18 Simmons Rd
The Daufuskie Difference
18 Simmons Rd
Up the Creek Pub at Broad Creek Marina
18 Simmons Rd
Absolute Island Wing
380 Marshland Rd
Fishcamp on Broad Creek
11 Simmons Rd
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