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37 Cypress Marsh Drive
Hilton Head Island, SC 29926

Ryan Noble
ERA Evergreen Real Estate Company
3Bedroom(s)
2Bathroom(s)
GarageParking(s)
45Picture(s)
2,176
Visits:5
Immaculate 3BR/2BA single-story home in The Headlands, Hilton Head Plantation. Features 2,176 sq ft, new roof (2021), replumbed (2022), detached garage, and cul-de-sac location. Backs to forest preserve with open space for privacy. Enjoy the new TREX deck, vaulted ceilings, wide plank floors, updated master bath, built-ins with electric fireplace, and shiplap accents in the kitchen and bath.
$809,000

22 Headlands Drive
Hilton Head Island, SC 29926

The Reed Team
Charter One Realty
3Bedroom(s)
2Bathroom(s)
GarageParking(s)
47Picture(s)
2,016
Visits:7
Hidden gem in the coveted Headlands of Hilton Head Plantation! This well-maintained 3BR/2.5BA single-level home sits on a quiet, private lot and offers the perfect mix of comfort, privacy, and location. Features include charming built-ins, a cozy fireplace, and spacious living areas. Conveniently located near the front gate with easy access to shopping, dining, and healthcare.
$899,000

11 Windy Cove Court
Hilton Head Island, SC 29926

Edward Greene
Coastal Oaks Development & Realty LLC
4Bedroom(s)
4Bathroom(s)
GarageParking(s)
3Picture(s)
3,114
Visits:11
New Construction with Oct 2025 Completion. Located in amenity-rich HHP, this homesite offers Lagoon views from Master bedroom, Living Room and Rear guest bedroom. This home has 4 bedrooms 4 bathrooms 1 half bath and 2 Car Garage. 1st Floor Hardwood floors, carpet on the 2nd floor. Quartz kitchen tops and Stainless-steel Kitchen Aid appliances.
$1,395,000

6 Oyster Rake Lane
Hilton Head Island, SC 29926

Amy Aurelio & Associates
Keller Williams Realty
3Bedroom(s)
3Bathroom(s)
GarageParking(s)
57Picture(s)
2,810
Visits:13
This beautifully landscaped 3BR/3.5BA home with a bonus room offers ideal bedroom separation and all ensuite baths. Highlights include hardwood floors, crown moulding, tray ceilings, built-ins, a fireplace, and floor-to-ceiling windows. Enjoy a spacious eat-in kitchen, formal dining room, a 2.5-car garage with a finished floor, and numerous upgrades including a newer roof and HVAC.
$1,160,000

72 Cypress Marsh Dr
Hilton Head Island, SC 29926

Lowcountry Fine Homes
Daniel Ravenel Sotheby's International Realty
3Bedroom(s)
3Bathroom(s)
GarageParking(s)
74Picture(s)
1,800
Visits:19
Exquisitely reimagined, this three bedroom, three and a half bath residence in Hilton Head Plantation offers refined living with tranquil golf course views. Showcasing organic modern finishes throughout, the home features a light-filled open floor plan, bespoke kitchen, a dedicated office or den, and spacious mudroom with laundry.
$925,000

7 Whispering Pines Court
Hilton Head Island, SC 29926

Angela Barbic
Charter One Realty
3Bedroom(s)
3Bathroom(s)
GarageParking(s)
1Picture(s)
2,815
Visits:22
Great opportunity and ready to make your own cosmetic updates. The hard stuff has been done! Roof (2015) HVAC systems (2020 & 2022), water heaters ( 2021 & 2022) water pipes (2025) and large (heated 2024) resurfaced pool! Single story with spacious light filled rooms, open flow gathering areas, including eat in kitchen/family room.
$895,000

87 Headlands Drive
Hilton Head Island, SC 29926

Richard MacDonald and Associates
Charter One Realty
3Bedroom(s)
2Bathroom(s)
GarageParking(s)
57Picture(s)
3,194
Visits:52
Magnificent transformation in this spacious home overlooking a tranquil lagoon with distant views of Bear Creek Golf Course. The entry Foyer immediately introduces you to the many “Wow Factors” of this home. Completely updated by the present owners with every imaginable upgrade. Beautiful Living Room opening to a light-filled Sunroom/Great Room overlooking the view.
$1,195,000

33 Cypress Marsh Drive
Hilton Head Island, SC 29926

Betty Hemphill
Sea Pines Real Estate - The Cottage Group, LLC
3Bedroom(s)
3Bathroom(s)
GarageParking(s)
10Picture(s)
2,211
Visits:62
Move in ready! This 3 BR, 3 BA all one level home is light & bright with high ceilings and lots of windows! Great open floor plan. Living room with built-in's and fireplace, eat-in kitchen with stainless appliances, separate dining area, laundry room and 2-car garage. Well maintained landscaping.
$840,000

35 Winding Trail Lane
Hilton Head Island, SC 29926

Christina Forbis
Charter One Realty
3Bedroom(s)
2Bathroom(s)
GarageParking(s)
39Picture(s)
2,030
Visits:106
Stylish & sunlit lagoon-view retreat in Hilton Head Plantation! This sleek single-story home dazzles w/ 9’ smooth ceilings, chic pendant lighting, floating vanities, floor-to-ceiling tiled showers, & a modern stone fireplace. Kitchen pops w/ ceiling-height dark cabinetry, pantry & a breakfast bar perfect for casual dining.
$868,000

34 Cypress Marsh Drive
Hilton Head Island, SC 29926

May River Group
Engel & Volkers
3Bedroom(s)
3Bathroom(s)
GarageParking(s)
100Picture(s)
2,623
Visits:92
Like NEW construction without the hassles of building! This fully renovated one level home in Hilton Head Plantation boasts 3BR/3BA + office/flex space. NEW luxury finishes & updated plumbing/electrical throughout. The open-concept living space features high ceilings, hardwood floors, & expansive windows that flood the interior w/ natural light.
$1,292,900

32 Oyster Rake Lane
Hilton Head Island, SC 29926

Charles Sampson Group
Charter One Realty
4Bedroom(s)
4Bathroom(s)
Three Car GarageParking(s)
63Picture(s)
3,727
Visits:99
Panoramic Views - Lagoon, Bear Creek Golf Course 18th Green, private pool. Estate size 1/2 acre private homesite with open space on three sides. At the end of a cul-de-sac between the 10th and 18th fairways. Location and View! Split bedroom floor plan - 4 bedroom or 3 plus and office, 4.5 baths, formal living room and dining room plus open eat-in kitchen/Carolina room.
$1,275,000

3 Pine Sky Court
Hilton Head Island, SC 29926

Angela Barbic
Charter One Realty
3Bedroom(s)
3Bathroom(s)
GarageParking(s)
55Picture(s)
2,235
Visits:102
Move in ready show stopper, minutes from main gate in rear of a private cul-de-sac! Fresh exterior paint, dark framed windows and front door making a striking 1st impression. Step inside to thoughtfully curated spaces with refined finishes & design elements. Walls opened & added to create open flow and privacy where desired.
$1,075,000
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