Cunningham Hideaway Real Estate

Welcome to Cunningham Hideaway, an enchanting subdivision nestled in the heart of St. Johns County, Florida. This hidden gem offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and anyone looking to escape the hustle and bustle of city life.

Cunningham Hideaway is renowned for its picturesque landscapes and lush greenery, providing residents with a serene environment to unwind and connect with nature. The subdivision boasts spacious lots, allowing for ample privacy while still fostering a sense of community. With an array of beautiful homes, each with unique architectural styles, you’ll find a residence that perfectly suits your lifestyle.

One of the standout features of Cunningham Hideaway is its prime location. Just a short drive from the vibrant city of St. Augustine, residents can enjoy easy access to pristine beaches, historic landmarks, and a variety of shopping and dining options. The area is also home to top-rated schools, making it an excellent choice for families seeking a nurturing environment for their children.

Outdoor enthusiasts will appreciate the nearby parks and recreational areas, offering opportunities for hiking, biking, and enjoying Florida’s stunning natural beauty. With a welcoming community spirit, frequent neighborhood gatherings, and a safe environment, Cunningham Hideaway is more than just a place to live; it’s a place to thrive.

Experience the charm and allure of Cunningham Hideaway—where your dream home awaits in one of Florida’s most desirable locations!

Newest Listings in Cunningham Hideaway

$699,900

4 Beds ⋅ 3 Baths ⋅ 2150588 MLS

Experience refined waterfront living in this beautifully maintained full brick residence set on a tranquil spring-fed lake. 95 ft. lot. Thoughtfully enhanced with over $100,000 in recent improvements, this home blends timeless quality with modern comfort. Rich hardwood floors flow throughout, leading to an expansive layout featuring four generously sized bedrooms and three full baths. The heart of the home is the impressive family room, anchored by a striking gas fireplace with a redesigned mantle, backsplash, and hearth--creating a warm yet sophisticated gathering space. Recent upgrades provide peace of mind and style, including all new windows, exterior doors, and gutters (2022). Outdoor living shines with a resurfaced pool (2021) and a brand-new screened enclosure (2026), perfect for year-round enjoyment. Plantation shutters, updated lighting, and designer ceiling fans elevate every room. The home is offered complete with all appliances, including a new secondary refrigerator 2026 along with a lightly used generator for added convenience. A 4-point inspection (April 2026) confirms the roof has 10+ years of remaining life. Enjoy the rare advantage of deeded lake irrigation, keeping your grounds lush without additional utility expense. A true blend of elegance, efficiency, and serene lakefront beauty--this exceptional home is move-in ready. Seller says make offer!

1333 S Hideaway Drive, St. Johns

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES FLORIDA NETWORK REALTY

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES FLORIDA NETWORK REALTY.

Listing courtesy of SELMA COLLIER from BERKSHIRE HATHAWAY HOMESERVICES FLORIDA NETWORK REALTY.

$795,000

5 Beds ⋅ 4 Baths ⋅ 2149190 MLS

Exceptional living in this beautifully 5 BD, 4-BA turn key pool home in Cunningham Hideaway, a NO CDD community. The open floor plan is filled with natural light and offers seamless flow, ideal for both everyday living and entertaining. Thoughtful upgrades include hardwood floors, crown molding, a jetted tub and dual vanities in the primary suite, Jack and Jill bath, and a spacious upstairs bonus room with a full bath. The elegant kitchen features granite countertops, a farm sink, pop up ventilation, double ovens, a warming drawer, vacuum sweep, and upgraded 42'' cabinetry. The oversized laundry has folding space, a utility sink, and a dedicated storage closet. Your private oasis has a screen enclosed inground pool, outdoor kitchen, and nearly half an acre of beautifully lighted, landscaped grounds. Ample parking for a boat or RV, this property offers flexibility rarely found in similar communities. Opportunities like this are few and far between; this is one you won't want to miss. The home can be sold empty, fully furnished, or partially furnished, providing options tailored to your needs.

1140 Hideaway Drive N, St. Johns

Courtesy of EXP REALTY LLC

Listing courtesy of EXP REALTY LLC.

Listing courtesy of WILLIAM TSANG from EXP REALTY LLC.

$637,000

4 Beds ⋅ 4 Baths ⋅ 2145697 MLS

Welcome to this stately Florida home in the secluded community of Cunningham Hideaway, where large lots, mature trees, and privacy create a lifestyle that is becoming increasingly difficult to find. Situated on an oversized homesite, this impressive 4-bedroom, 3.5-bath home offers room to spread out both inside and out. From the moment you arrive, you'll appreciate the inviting curb appeal, highlighted by a beautiful front entry with decorative glass front door and sidelights, mature landscaping, a side-entry garage, and plenty of parking. A double gate provides easy access to the backyard, making it ideal for storing a boat, RV, trailer, or other recreational toys. Inside, the open-concept floor plan features soaring vaulted ceilings, neutral colors, and attractive wood-look tile flooring throughout the main living areas. The spacious family room serves as the heart of the home with a wood-burning fireplace, lighted built-in cabinetry, and plenty of room for gathering with family and and friends.The kitchen is designed for both function and entertaining, offering stainless steel appliances, 42-inch cabinets, abundant counter space, a breakfast bar, and a sunny breakfast area. Formal living and dining rooms provide additional flexibility for entertaining, a home office, or multi-purpose living space. The owner's suite is a private retreat featuring a spacious sitting area, garden tub, separate shower, and generous bathroom layout. Upstairs, you'll find a large loft, additional bedroom, and full bath, creating the perfect guest suite, teen retreat, game room, or media room. Additional features include a large laundry room with extra cabinetry, providing exceptional storage and organization. Step outside and enjoy true Florida outdoor living. The covered and screened lanai overlooks a peaceful backyard filled with mature trees and abundant wildlife. A matching storage shed provides additional space for tools and equipment while blending seamlessly with the home. With plenty of room for RV and boat parking, this property offers the flexibility and freedom many buyers are searching for. If you're looking for a home with character, privacy, room for your toys, and a setting that embraces the natural beauty of Florida, this Cunningham Hideaway property deserves a closer look.

1169 Hideaway Drive N, St. Johns

Courtesy of ASSIST2SELL FULL SERVICE REALTY LLC.

Listing courtesy of ASSIST2SELL FULL SERVICE REALTY LLC..

Listing courtesy of LORI NEIGHBORS from ASSIST2SELL FULL SERVICE REALTY LLC..

$689,000

4 Beds ⋅ 3 Baths ⋅ 2142619 MLS

Beautifully updated and move-in ready, w/ 4-bedroom, 3-bath, 2,839 square feet in sought-after St. Johns County and it's A-rated schools, 1309 Hideway Drive is ready for its next family. 0.64 Acre and shaded by multiple mature oaks, this move-in ready home blends stylish renovations, functional living space, and thoughtful upgrades throughout. Inside, the fully renovated kitchen is a chef's delight: with gas ZLINE 36'' dual-fuel range, GE Cafe wi-fi enabled convection oven, 30'' Sharp drawer microwave and an added Butler's pantry for extra storage and convenience. Downstairs, you'll find COREtec luxury vinyl plank flooring, updated lighting and ceiling fans as well as LED, dimmable lighting. A redesigned laundry room adds additional functionality. The spacious layout offers multiple living areas, including a heated and cooled sunroom for year-round enjoyment. With 4 bedrooms and 3 full baths, there is flexibility for guests or home office needs. Major system updates provide peace of mind, including a new water softener (2023), new hot water heater (2024), all new windows installed in September 2024, and a new irrigation panel. Step outside to enjoy the fenced backyard with additional electric fencing that runs the full property, ideal for pets and outdoor enjoyment. Backyard fence was added in October 2025. Conveniently located near shopping, dining, and major roadways, this exceptional home offers comfort, quality, and a prime St. Johns County location.

1309 Hideaway Drive S, St. Johns

Courtesy of WATSON REALTY CORP

Listing courtesy of WATSON REALTY CORP.

Listing courtesy of Stephanie Olsen from WATSON REALTY CORP.

$599,999

5 Beds ⋅ 4 Baths ⋅ 2139368 MLS

Welcome to 1104 N Hideaway Drive, where comfort, style, and location come together in one beautifully positioned home in the heart of St. Johns. Situated on a premium end lot, this property offers added privacy along with peaceful water views that create a serene backdrop to everyday living. Inside, you'll find brand new luxury vinyl plank flooring throughout the entire first floor, giving the home a fresh, modern feel while standing up to real life. The open-concept layout is filled with natural light and flows seamlessly to the fully fenced backyard--perfect for entertaining, pets, or simply enjoying your own private outdoor space. Beyond the home itself, the location truly shines. Nestled in a sought-after St. Johns community, residents enjoy access to top-rated schools, convenient shopping and dining, and an easy commute to both Jacksonville and historic St. Augustine. Whether it's a quick trip to the beach, a round of golf, or a night out downtown, everything you love about Northeast Florida living is just minutes away. Move-in ready and thoughtfully updated, this home offers the perfect blend of comfort, convenience, and lifestyle. 1104 N Hideaway Drive isn't just a home--it's where your next chapter begins.

1104 Hideaway Drive N, St. Johns

Courtesy of KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE

Listing courtesy of KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE.

Listing courtesy of SHELBY C HODGES from KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE.

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