Search St. Augustine Investment Properties For Sale, Over $1,000,000

Attention All AVID Airbnb Investors! Come and DOUBLE UP your earnings!! Currently average bookings around 50%-60% and room to hit 75%-100% bookings! Numbers below are after booking & Management Fees. -Just getting started in Sept. 2022 to Dec. 2022 earnings = $24k. -Jan. 2023 to Dec. 2023 earnings = $70k. (3 times more than what was earned in 2022.) -Jan. 2024 to Aug. 2024, earnings = $60k, with bookings through Dec. 2024 estimating an additional $23k. Putting 2024 currently at roughly $83k with more bookings happening daily. (This is 1.185 times more earned than 2023.) -Based on averages we anticipate an additional $7k-$10k of income booked through the end of this year. Putting the annual income close to $95k-$100k.(about 1.428 times more than 2023.) -Future bookings for 2025 are sitting at roughly 11k with about 39 days booked. Increase your bookings to 75% projects $149k annually, and 100% booked at $199k. (Based on averages ran) *Ask for updated numbers. This pre-1900's (1860s) fully furnished turnkey property is located in the heart of our Nation's First and Oldest cities, St. Augustine's historic district and is truly one of a kind! Spending close to half a million dollars, the owner meticulously, lovingly and carefully restored this property, while maintaining its historic charm. You can own this piece of history with peace of mind that as much attention went into the aesthetic as went into the underlying structural integrity. You aren't just getting a property with some minor updates, you are getting a true internally completed restoration & renovation. The renovation includes all new plumbing, all new electrical, all new appliances, new on demand water heaters, a total scrape, repair and exterior paint job , new interior paint, structural inspection and rejuvenation where needed, no cost was spared, owner had intended on owning for the foreseeable future. The total restoration costs for this historical gem were upwards of half a million dollars. (Check out the docs tab for arch plans and more.) The area of Cuna and Spanish Streets just underwent a lengthy beautification process where we are now just next door to the most lovely walking district in all of downtown, quiet, beautiful and still in the middle of it all. The installation not only focused on the aesthetic but greatly improved the infrastructure with new sewer and water lines, a greatly improved drainage system and beautiful streetings and red brick streets. A great area to own downtown, safe and inviting. Currently an active airbnb with prime access to all of what downtown St. Augustine has to offer! Leave it as an airbnb, perfect for large groups of up to twelve, convert to a long term rental, student housing, pad split, commercial retail business or more! With commercial zoning, your possibilities are only limited by your imagination! This property and its amazing history will live on for years to come, with the recent renovations it will stand for another 170 plus years! Owning such a beautiful relic in your portfolio is certainly something to be proud of and one piece of real estate you will NOT regret owning! Schedule your private tour now! All information pertaining to the property is deemed reliable, but not guaranteed. Information to be verified by the Buyer. Be advised that cameras may exist recording audio and video inside/outside the property, such as ring doorbells. $1,350,000 Active Under Contract

59 CUNA Street St Augustine, Florida

5 Beds 3 Baths 1,628 SqFt 0.05 Acres

This 5 bedroom, 4.5 bath gem is THE BEST opportunity in historic St Augustine to own a cash cow! 4 units with proven rental income generation (1 unit leased annually, 3 through Airbnb & VRBO). Currently non-owner occupied, can easily accommodate owner who would prefer to live on premises and enjoy all that America's oldest city has to offer! Walking distance to finest dining, shopping, boating, attractions and festivals (just a few blocks from the fairgrounds). You and your guests can enjoy the splendor of St Augustine's famous Nights of Lights from mid-November through late January every year. A short drive will bring you to St Augustine and Vilano beaches, great golf and the St Augustine outlet mall. Don't miss this opportunity to enjoy all that St Augustine has to offer and earn a steady stream of reliable income. Owner has reservations from repeat visitors stretching into 2025. Current owner willing to assist in transition so you can start earning income on DAY 1 $1,349,900 Active

16 ROHDE Avenue St Augustine, Florida

5 Beds 5 Baths 2,891 SqFt 0.14 Acres

**BACK ON THE MARKET!** This is your second chance to own a historic, fully renovated multi-family gem in St. Augustine, now featuring a **BRAND NEW METAL ROOF** on both the main house and Carrera Cottage! Priced at $1,245,000—well below its appraised value—this property offers exceptional short- and long-term rental income potential. The main house boasts 2 bedrooms, 2 baths, while the Carrera Cottage features two private-entry 1-bed, 1-bath apartments with outdoor spaces. Enjoy the tranquil Carrera Courtyard, smart home features, and ample parking. Located near Flagler College and downtown, it's perfectly positioned to benefit from St. Augustine's thriving tourism market, including popular events like Nights of Lights. Projected rental income ranges from $96,000-$120,000 for short-term and $69,600-$81,600 for long-term leases. This is an outstanding investment and a rare opportunity—schedule your showing today! house offers bright, airy interiors with luxury vinyl plank flooring, updated kitchens, and bathrooms. At the heart of the property, the Carrera Courtyard provides a serene retreat with a fire pit and seating nestled beneath mature oaks, making it perfect for entertaining or unwinding. Modern smart home features, including automated thermostats and solar outdoor lighting, add convenience and appeal, while the new limestone driveway provides ample parking for residents and guests. Located within walking distance of Flagler College and downtown St. Augustine, this property is ideally situated to capitalize on the area's thriving tourism market, especially during events like Nights of Lights. With short-term rental projections of $96,000-$120,000 annually and long-term rental potential of $69,600-$81,600 annually, this property delivers incredible value and versatility for both investors and owner-occupants. Don't miss this rare chance to own a piece of St. Augustine's history while reaping the rewards of a turnkey, income-producing property. Schedule your showing today! $1,245,000 Active

64 CARRERA Street St Augustine, Florida

5 Beds 4 Baths 2,065 SqFt 0.15 Acres

Investors Dream!! This high & dry (no flooding), completely remodeled island triplex/multi-family property is a perfect income property or live in one and have the other 2 pay the mortgage. The duplex: both are 1 bed/1 bath mirror units at roughly 570 sq ft ea. with a small storage room with laundry capabilities. The Single family 2 Bed/1 Bath unit is above a huge garage/shop. (Possible 4th unit)? New roof, pavers, A/C, New insulation/spray foam, Electrical, plumbing, Whole house Aquasana water filtration system and so much more. All units can be long-term or short-term rentals. Separate power & water as well as 2 septic tanks. Lighthouse Park is a VERY desirable neighborhood. It's the perfect location for all the things St Augustine. Walking distance to tons of restaurants, bars, downtown, Anastasia State Park, the beach, AND the Amphitheatre. $1,200,000 Active

50 MAGNOLIA Drive A St Augustine, Florida

4 Beds 3 Baths 1,990 SqFt 0.15 Acres

Located in the highly sought after community of Davis Shores sits this great investment opportunity. Within walking distance to the historic downtown area and a short bike ride to the white sand beaches of St Augustine provides the epitome of Island living. Quadruplex of 1 bed /1 bath units with modern amenities and eclectic styling offers comfort for your residents. Currently all four units have long term tenants; however, short term rental is permissible, so this would make a great AirBNB. This offering is for the quadruplex located on Lot 17 & part of Lot 18. Lot 16 is no longer part of this parcel and is for sale separately. $1,200,000 Active

85 ST AUGUSTINE Boulevard 1 St Augustine, Florida

4 Beds 4 Baths 3,206 SqFt 0.36 Acres

Dreamt of owning a Triplex mere blocks to the ocean AND the river? All the outdoor options await! Three units actively listed as Short Term Rentals, grossing approximateily $100k per year for the prior 2 years. Or, live in one and rent out 2, or rent all units as long term. Your choice! This property is unique; if someone desires, they can rent all 3 units and sleep up to 16! Building 1 features 2 units: both with 3 bedrooms and 1.5 bathrooms, plus full kitchens, appliances (including washer/dryer) furniture, decor, and everything else needed. That is 6 bedrooms, 2 full and 2 half bathrooms in each unit in building 1. Building 2 features a 2 car garage and an upstairs 1 bedroom, 1 bathroom unit. New roofs and new a/c units. Reimagined front entry and driveway space: tons of parking. Whatever your desire for an investment property is, owning this triplex is the answer! $1,000,000 Active

7018 MIDDLETON Avenue St Augustine, Florida

7 Beds 5 Baths 2,888 SqFt 0.34 Acres

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