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27 OAK Street
About This Property
Inside, the home welcomes you with fresh new interior paint, warm travertine tile floors, and a bright open layout designed for both everyday comfort and entertaining. The kitchen has been beautifully refreshed with refinished cabinetry, granite countertops, and brand new appliances, creating a clean and functional space that flows seamlessly into the main living areas.
Upstairs, the primary suite is perfectly positioned to take in the tranquil marsh backdrop and features its own private balcony, an ideal place to enjoy your morning coffee while watching the sunrise over the marsh or unwind in the evening as coastal breezes roll in. Two additional bedrooms provide comfortable accommodations for family or guests, while a separate flex space offers versatility for a home office, reading nook, playroom, or loft style lounge.
Outside, the spacious homesite offers sweeping marsh views and a peaceful natural setting, often visited by native birds and wildlife. The property also offers a rare level of functionality with space to discreetly store an RV or boat completely tucked away from view.
Additional highlights include a garage wired for an EV charger and thoughtful interior updates that make the home completely move in ready.
Located within an A rated school district and just moments from Uptown's beloved coffee shops, restaurants, and boutiques, this home blends lifestyle, flexibility, and location. With no HOA restrictions, owners have the freedom to enjoy the property as a primary residence, second home, or short term rental.
Marsh views, privacy, modern updates, and a prime Uptown location make 27 Oak Street a rare opportunity to experience the best of St. Augustine living.
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What does this mean?
Based on our analysis, the cap rate of this property is 1.25%. A negative cap rate indicates that the property might not be feasible as an income-producing asset. The median cap rate for a near zip code 11238 is 4.23%.
How much can I actually make?
Actual monthly rental income may vary between $4,760 and $7,140 depending on unit-specific characteristics. You can change the amount using the slider to further explore.
How is cap rate calculated?
Cap Rate = Net Operating Income (NOI) / Property Asset Value.
When calculating the cap rate, we assume 100% occupancy. Leverage (mortgage) is not considered.
Cap Rate provided by RealtyHop and RentHop, learn more about cap rate here.
Price History
| Date / Event | Date | Event | Price |
|---|---|---|---|
| Jul 20, 2026 | Sold | ||
| Sold | |||
| May 12, 2026 | Listed by MAXREV, LLC | $575,000 | |
| Listed by MAXREV, LLC | |||
| Jan 18, 2025 | No longer available | - | |
| No longer available | |||
| Jan 17, 2025 | Listed by MOMENTUM REALTY | $655,000 | |
| Listed by MOMENTUM REALTY | |||
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Welcome to 27 Oak St, a marsh-front sanctuary nestled in the desirable Hildreth Back Bay of Fullerwood Park in Uptown St. Augustine! Built in 2015, this meticulously maintained 3-bedroom, 2.5-bath home seamlessly combines modern luxury with timeless charm, offering a peaceful retreat just minutes from historic downtown and the sandy shores of Vilano Beach.
Step inside to an inviting interior featuring travertine tile floors throughout the open-concept downstairs living spaces, exuding elegance and comfort. The gourmet kitchen is a standout, boasting granite countertops, white shaker cabinets, and plenty of storage for culinary adventures. Upstairs, enjoy the warmth of wood floors and freshly painted walls, with stunning marsh views from the serene primary bedroom.
The backyard is a nature lover's paradise, where a gorgeous live oak provides shade and charm while numerous wading birds—roseate spoonbills, white egrets, great blue herons, wood storks, and tri-color herons— create a tranquil and ever-changing natural scene. Whether you're sipping your morning coffee or unwinding at the end of the day, the serenity here is unmatched.
Located on a quiet, dead-end street, 27 Oak St offers peace and privacy just 2 miles from downtown St. Augustine and the sandy shores of Vilano Beach. Even better, it's walking distance to Uptown's charming coffee shops, restaurants, luxury desserts, and unique shopping experiences, making it perfectly situated for convenience and leisure.
With no HOA, this property offers flexibility, whether you're dreaming of a full-time residence in a tight-knit neighborhood or seeking the potential of seasonal living with short-term rental income.
Homes like this are rare. Don't miss your chance to own this marsh-front treasure in an "A"-rated school district. Schedule your private showing today and experience the serenity of 27 Oak St for yourself. Schedule a showing today!
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| Apr 8, 2015 | Sold | ||
| Sold | |||
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Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017