View All Oldfield Bluffton, SC Homes with Guest House Listings

4 Beds ⋅ 5 Baths ⋅ 3,847 SqFt. ⋅ HILTONHEAD-511544 MLS

Timeless custom estate in the heart of Oldfield, masterfully built by renowned builder Yestermorrow. A circular motor court shaded by majestic live oaks creates a memorable arrival to this exceptional residence. Impeccable craftsmanship is showcased throughout with custom inset cabinetry, heart pine floors, extensive millwork, and designer finishes. A welcoming front porch leads to a grand foyer, where a soaring two-story great room is anchored by a Savannah brick fireplace and flanked by custom built-ins. The gourmet kitchen is the heart of the home, featuring a charming breakfast nook with custom built-in cupboards and serving the expansive dining room and main living area. Both spaces open seamlessly to over 1,000 square feet of screened porch, creating exceptional indoor-outdoor living and entertaining. The luxurious primary suite features a private sitting area with custom built-ins, timeless finishes, and separate his-and-her closets. Upstairs, the home offers a media loft, two ensuite bedrooms, and a dedicated study. A private guest suite above the attached two-car plus golf cart garage provides ideal accommodations for family and visitors. Thoughtfully designed for lasting beauty and peace of mind, the home features a 5V metal roof, Hardie Plank siding, hurricane-rated insulated windows, a whole-house natural gas generator, and an encapsulated crawlspace. A rare opportunity to own an impeccably crafted Lowcountry residence in one of Bluffton's most sought-after private communities, where timeless architecture and exceptional quality define luxury living.

45 Oldfield Way, Bluffton

Listing courtesy of Charter One Realty.

$2,325,000

7 Beds ⋅ 6 Baths ⋅ 4,431 SqFt. ⋅ HILTONHEAD-511350 MLS

Anchored by two magnificent live oaks & gracefully positioned along one of Oldfield's most coveted streets, this exceptional custom residence captures the timeless elegance of Lowcountry living. A welcoming front porch with an integrated accessibility ramp introduces a home where soaring 12-foot ceilings, transom windows, fresh interior paint & newly installed engineered hardwood flooring create a bright atmosphere. Designed for everyday living & entertaining, the home offers 7 bedrooms, 5.5 bathrooms, multiple gathering spaces & an elevator serving the main house. The living room features coffered ceilings, a Savannah brick fireplace, custom built-ins & a grand French sliding door opening to the expansive screened porch. The renovated chef's kitchen showcases refinished custom cabinetry, an oversized island, quartzite countertops, a Wolf eight-burner range, Sub-Zero refrigerator, & Cove dishwasher. Adjacent to the kitchen, a light-filled dining area surrounded by French doors & tall windows provides a beautiful place to gather. The first-floor primary suite features custom millwork & a renovated spa bath with a stone resin soaking tub & Kohler finishes. An additional main-level suite w/ a renovated ensuite bath offers flexibility for guests, while an updated powder room serves the first floor. Upstairs, 4 additional bedrooms include one w/ a renovated ensuite bath, while the others are served by a well-appointed hall bathroom. A spacious loft captures elevated golf course & pond views, complemented by a dedicated craft or bonus room. Above the garage features a renovated guest suite with a full bath & kitchenette. The screened porch, complete w/ a fireplace & built-in grilling station, extends the living space while overlooking the 17th & 18th fairways & pond. A fenced side yard w/ turf offers space for pets, gardening or play. Recent improvements include renovated bathrooms, kitchen, & laundry room (incl. new washer & dryer), new flooring throughout the first level, spray foam insulation, attic fresh air intake system, whole-home water filtration, tankless water heaters, exterior landscape lighting, & more. A metal roof, two-car garage with golf cart bay & mature landscaping complete the property. Oldfield offers a Greg Norman Signature Golf Course, deepwater marina, River Club, Sports Club, and an exceptional collection of amenities. Thoughtfully updated & impeccably maintained, 8 Old Oak Rd is an exceptional opportunity to experience Oldfield living.

8 Old Oak Road, Bluffton

Listing courtesy of Charter One Realty.

$1,139,000

4 Beds ⋅ 5 Baths ⋅ 2,701 SqFt. ⋅ HILTONHEAD-511017 MLS

Coastal Lowcountry charm meets antique farmhouse character in this Oldfield home with 4 bedrooms, 4.5 baths, and lagoon views. Designed for efficient, easy living, the main home features pine wood floors, custom beams, reclaimed ceiling details, antique doors, and a warm open floor plan. The updated kitchen includes an expanded island, new finishes, and great flow for entertaining.The first-floor primary suite offers an updated bath with heated marble floors, while the second level includes two ensuite guest bedrooms. A private carriage house above the garage features cathedral ceilings, a kitchenette, full bath, and flexible guest space. Enjoy peaceful Lowcountry views from the screened porch overlooking the lagoon. Meticulously cared for by the original owner, the home also includes a freshly painted exterior, metal roof, copper gutters, composite front porch decking, tankless water heater, garage, and carport. As one of the few investment-style opportunities in Oldfield, the golf cottages may be rented through the club if the owner chooses, subject to club and community guidelines. Located in one of Bluffton's most beloved private communities, Oldfield offers golf, boating, equestrian amenities, dining, fitness, tennis, pickleball, trails, and true Lowcountry living along the Okatie River.

12 Rice Mill Road, Okatie

Listing courtesy of Charter One Realty.

$3,300,000

4 Beds ⋅ 6 Baths ⋅ 5,181 SqFt. ⋅ HILTONHEAD-505346 MLS

Along the banks of the Okatie River, this remarkable Lowcountry retreat was designed to feel as though it has always belonged to the landscape. Created by renowned architect Gerry Cowart and built by Yestermorrow, the home is thoughtfully nestled beneath sprawling oaks to capture sweeping marsh and river views from nearly every angle. Savannah brick accents, gas lanterns, and natural materials create an authentic sense of place rooted in classic Lowcountry design. Inside, reclaimed hardwood floors, extensive millwork, and custom built ins reflect exceptional craftsmanship at every turn. The main living space centers around a fireplace and flows seamlessly into the dining area with a custom built in, then opens to an enclosed porch with panoramic river views. From here, you move into the chef's kitchen, appointed with Sub Zero, Wolf, and Bosch appliances, a large island, walk in pantry, and coffee station. Just beyond, a cozy keeping room with fireplace and screened porch with grilling area sit to one side, while a spacious laundry and mudroom are thoughtfully tucked to the other. The main level primary suite is a private retreat with dual closets, a spa inspired bath with soaking tub and walk in shower, and its own enclosed porch with swing. Upstairs, a library with balcony, ideal as a study or reading room, anchors two ensuite bedrooms, one with a window seat and the other with its own balcony, along with conditioned storage. It's no surprise this setting has served as creative inspiration. The home and its sweeping river views influenced the backdrop of the novel Acre of Fools, now in development for a television series. Spend a quiet evening here, and you'll understand why. Beyond the main residence, a detached guest cottage offers remarkable flexibility with built in bunks, kitchenette, full bath, and a separate office with half bath and custom built ins. Outdoor living is equally compelling with a plunge pool and spa, firepit, Ipe decking, outdoor kitchen, and outdoor shower, all set against a backdrop of marsh and river views. Additional features include a 2 car garage with golf cart bay, multiple storage sheds, whole house generator, encapsulated crawlspace, advanced smart home technology, and a metal roof. Located within Oldfield, this home offers a setting as memorable as the home itself.

18 Carrier Bluff, Bluffton

Listing courtesy of Charter One Realty.

$875,000

4 Beds ⋅ 4 Baths ⋅ 2,754 SqFt. ⋅ HILTONHEAD-505176 MLS

Now offered at an exceptional new price, 59 Great Heron Way is one of the best values in Oldfield. Located in the desirable Lakeside Village, this Charleston-inspired home is freshly painted, move-in ready, and designed for effortless Lowcountry living. Enjoy lake views from the welcoming front porch, a screened porch for year-round enjoyment, and a private fenced backyard with firepit-perfect for entertaining or relaxing under the stars. Inside, thoughtful upgrades include a gas fireplace, gas range, designer lighting, smart double oven, generous storage, and a desirable first-floor primary suite. Upstairs, a spacious loft, private guest suite, and two additional bedrooms provide flexibility for family, guests, or a home office with tranquil lake views. Additional features include a Generac whole-house generator, tankless water heater, Cat6 wiring, and a two-car garage. Select furnishings are negotiable. Residents enjoy access to Oldfield's Greg Norman-designed golf course, fitness center, deepwater river access, equestrian facilities, trails, dining, and more-offering an unmatched Lowcountry lifestyle at an exceptional value.

59 Great Heron Way, Bluffton

Listing courtesy of The Agency Hilton Head. Selling Office: Charter One Realty.

$2,200,000

4 Beds ⋅ 5 Baths ⋅ 4,023 SqFt. ⋅ HILTONHEAD-505034 MLS

Spectacular and rare Oldfield offering-this exceptional Lopez Brothers custom-built residence exemplifies the extraordinary craftsmanship and attention to detail for which the builder is known. Homes of this caliber and pedigree rarely come to market.Set on an oversized 0.68-acre homesite overlooking tranquil Upper Dam Lake, this 4,023-square-foot home offers 4 bedrooms, 4 full baths, and a powder room, with a thoughtfully designed floor plan that balances elegance and everyday comfort. The warm and inviting great room features its own fireplace and flows effortlessly into the stunning screened porch-also with a fireplace-creating a seamless indoor-outdoor living experience and capturing peaceful lake views beyond.The generously sized kitchen is ideal for gathering and entertaining, showcasing a large statement island, dedicated dining area, Thermador appliances, and top-of-the-line finishes throughout. An oversized walk-in pantry with custom shelving connects directly to an expansive laundry room that easily functions as a home office or back kitchen-an exceptional and highly functional space rarely found.The primary suite is located on the main level and offers serene views along with dual custom built-in closets. Upstairs, two private guest suites each feature ensuite baths, providing comfort and privacy for family and visitors. A finished suite above the three-car garage serves beautifully as a guest house, office, or studio.The property is large enough to accommodate a pool, includes private planting gardens, and is zoned for a third building, offering remarkable flexibility for future expansion. Ideally located near the sports club and welcomed by Oldfield's iconic white fencing and charming greeter's store, the home is also just moments from the scenic beauty of the Okatie River.With beautiful views from nearly every room, this is an extraordinary Lowcountry residence offering timeless design, privacy, and enduring quality in one of the region's most coveted communities.

18 Gregorie Neck, Okatie

Listing courtesy of Charter One Realty. Selling Office: Engel & Volkers.

$1,395,000

4 Beds ⋅ 5 Baths ⋅ 3,356 SqFt. ⋅ HILTONHEAD-502746 MLS

Welcome to 34 Oldfield Village Road, a 3,356 Sq Ft custom home built in 2018 by Marler Construction, one of the Lowcountry's premier custom home builders. The main level offers pine floors, a spacious primary suite with an attached office, a beautifully finished bath with heated floors, and a well-appointed kitchen with custom details throughout. Upstairs features a gathering area, two guest bedrooms with private baths, and generous walk-in storage. The finished space over the garage includes a bedroom or flex area with a half bath, already plumbed for a future full bath if desired. Built with comfort and efficiency in mind, the home includes spray foam insulation, a whole-house natural gas generator, and a water filtration system. And to top it off, its prime location overlooking Big Arrowhead Lake provides lake views from the screened-in porch. Don't wait on this one!

34 Oldfield Village Road, Bluffton

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty. Selling Office: Daniel Ravenel Sotheby's International Realty.

$1,100,000

5 Beds ⋅ 5 Baths ⋅ 3,282 SqFt. ⋅ HILTONHEAD-502505 MLS

$10,000 seller contribution toward the Oldfield initiation fee. Privately set on a water-view lot overlooking Little Arrowhead Lake, this Lowcountry home offers a rare sense of quiet and separation within Oldfield. Backed by layered buffers of lake, community green space, and mature woods, the property enjoys peaceful views and a level of privacy not often found in the community-without rear neighbors or surrounding homes. Sweeping two-story verandas extend the living space outdoors, creating a serene setting for morning coffee, evening breezes, and relaxed Lowcountry living. Inside, an open-concept floor plan centers around a spacious great room and gourmet kitchen designed for both everyday comfort and effortless entertaining. The main-level primary suite offers privacy and convenience with dual closets and vanities, while upstairs guest bedrooms and a generous recreation room provide flexible space for visitors, hobbies, or movie nights. A detached two-car carriage house with a finished room, full bath, and wet bar adds exceptional versatility-ideal for a private guest suite, home office, or studio-set apart from the main living areas. Located within the gated community of Oldfield, residents enjoy access to Greg Norman-designed golf, equestrian facilities, deep water access, pools, fitness, tennis, pickleball, scenic trails, and a vibrant Lowcountry social atmosphere. This home offers a distinctive blend of privacy, water views, and flexibility-an increasingly rare combination in one of Bluffton's most sought-after communities.

35 Blue Dasher Lane, Bluffton

Listing courtesy of SERHANT. Selling Office: Daniel Ravenel Sotheby's International Realty.

$1,015,000

3 Beds ⋅ 3 Baths ⋅ 2,618 SqFt. ⋅ HILTONHEAD-500351 MLS

Welcome home. Nestled on a quiet cul-de-sac, 3 Pierpoint Lane rests on a meticulously landscaped half acre lot, offering tranquil lake views and an exceptional setting within the gates of the prestigious Oldfield. This elegant 3 bed, 2.5 bath home offers timeless style with modern convenience. Upon entry you will be greeted by an abundance of natural light, soaring ceilings and an open concept layout. All bedrooms are conveniently located on the first floor and with every key update completed, this home is truly move-in-ready! Updates include roof (2022), tankless hot water heater (2024), refrigerator/dishwasher (2025), and hardwood floors (2022) in every bedroom enhancing both warmth and durability. The primary bathroom was remodeled May 2024, offering a spa-like escape, complete with elegant finishes, a spacious walk-in shower, and well considered details. Upstairs you'll find a versatile bonus space, ideal as a media room, work out area, home office, or guest suite. While upstairs be sure to explore the expansive walk-in attic, perfect for all the storage you didn't know you needed! The house was professionally foam-insulated, ensuring energy efficiency and comfort year-round (2022). This custom-built home at this price point with the perfect blend of craftsmanship and comfort of modern Lowcountry living is a rare opportunity.

3 Pierpoint Lane, Bluffton

Listing courtesy of Keller Williams Realty. Selling Office: Charter One Realty.

$1,425,000

5 Beds ⋅ 5 Baths ⋅ 4,134 SqFt. ⋅ HILTONHEAD-454420 MLS

Timeless Lowcountry charm meets effortless luxury in the heart of Oldfield. This lakefront home offers 4BR/3.5BA in the main house plus a private guest suite with half kitchen over the detached garage- perfect for visitors or multi-gen living. Main level Primary Suite & guest suite (used as office), formal Dining Room, Great Room w/gas fireplace & built-in cabinetry. Fabulous open kitchen w/center island, complete with wine storage! Upstairs boasts 2 add'l guest rooms with a Jack & Jill bathroom and 2 walk-in spray foamed attic storage spaces. Enjoy serene views from your screened porch, launch a kayak from your own backyard dock, or take in golden sunsets over the water. Situated on a spacious lot with a separate golf cart garage, this home blends relaxed Southern living with resort-style amenities including golf, equestrian trails, and riverfront dining.

26 Boyds Landing, Bluffton

Listing courtesy of The Agency Hilton Head. Selling Office: Realty One Group - Lowcountry.

$2,500,000

5 Beds ⋅ 5 Baths ⋅ 4,311 SqFt. ⋅ HILTONHEAD-453621 MLS

Experience the pinnacle of Lowcountry living in this riverfront masterpiece in Oldfield’s exclusive Carrier Bluff. Designed by Court Atkins, built by Marler Construction, this 4,311 sq ft home offers sweeping Okatie River views. Sophisticated interiors feature wide-plank wood floors, high ceilings, custom shiplap, and designer finishes. The chef’s kitchen includes Wolf, Miele, and Sub-Zero appliances. Main-level primary suite, guest room, and flex space offer comfort. Upstairs, two additional bedrooms and two walk-in storage areas. Charming carriage house and space for a pool! Smart home with whole-house generator for peace of mind.

24 Carrier Bluff, Bluffton

Listing courtesy of The Agency Hilton Head. Selling Office: Oldfield Realty, LLC.

$1,839,000

4 Beds ⋅ 5 Baths ⋅ 3,968 SqFt. ⋅ HILTONHEAD-450869 MLS

Lowcountry perfection nestled on this large homesite in Oldfield! Step inside this quintessentially southern custom 4 bedroom, 4.5 bath home built in 2022. Above the oversized 3 car garage, guests will enjoy a private carriage house suite. In the main house, the primary suite and two additional guest suites are all on the first floor as well as an office/den/library. Lovely hardwood flooring and custom millwork throughout. The screened porch with fireplace and built-in outdoor kitchen provide a tranquil space for entertaining and enjoying the golf course views.

4 Groton Circle, Okatie

Listing courtesy of Charter One Realty. Selling Office: BHHS Bay Street Realty Group (701).

$1,350,000

3 Beds ⋅ 4 Baths ⋅ 2,765 SqFt. ⋅ HILTONHEAD-450031 MLS

This H2 custom built classic southern plantation home welcomes you with gracious Lowcountry porches at the front & back. The main home has an open floor plan for entertaining, a primary suite & guest suite, & office. Hardwood floors throughout with a gas cooktop in the kitchen, Kitchen Aid appliances & a double oven. Additionally, there is a lovely carriage house guest suite over the garage. The back porch of the home overlooks a gorgeous view of the pool, spa & lake & features a chef’s grill area as well as a fireplace & large entertaining area.

28 Gregorie Neck, Okatie

Listing courtesy of Charter One Realty. Selling Office: SC Real Estate Company.

$2,975,000

5 Beds ⋅ 5 Baths ⋅ 5,242 SqFt. ⋅ HILTONHEAD-449414 MLS

Southern charm meets coastal sophistication at this iconic, one-of-a-kind, 5-bedroom, 5-bathroom waterfront Oldfield estate. Offering 5,242 SQFT of superior craftsmanship with 4 covered porches, multiple fireplaces and a classic gourmet kitchen with picturesque water views from every room. The heart of the residence flows smoothly from the dining room/bar to the kitchen and through the living room onto the screened porch. A detached Guest House awaits your extended family or visitors providing a secluded & comfortable escape. Oldfield is a private community on 860 acres along The Okatie River with a world class Greg Norman golf course.

12 Carrier Bluff, Bluffton

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: The Agency Hilton Head.

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Oldfield, Bluffton, SC · Curated MLS Search

Homes with Guest House in Oldfield, Bluffton, SC

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