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

Construction is nearing completion on this investment opportunity in Vilano Beach! Four side-by-side NEW single-family pool homes. Each home features 1,800 sqft living space, 4 beds, 3.5 baths, one-car garage, heated saltwater pool, LVP flooring throughout, and impact resistant windows. Perfectly designed for vacation rentals, located walking distance to the beach and minutes from historic St. Augustine's top attractions, dining, and entertainment. Whether you're looking for an incoming producing rental property or your own beachside retreat, this prime location delivers both relaxation and strong investment potential. 2-10 Builders Home Warranty included with purchase. List price is for all four homes, but can also be sold individually. $4,600,000 Active

603-609 TWENTY-SECOND Street St Augustine, Florida

16 Beds 12 Baths 7,200 SqFt 0.46 Acres

Discover a lucrative investment opportunity in St. Augustine with this four-duplex property, now available for sale. Boasting full occupancy and a desirable location, this investment promises excellent returns. With the potential to adjust lease rates to match current market trends, investors can maximize their profits. Recently renovated to feature brand new flooring, countertops, fixtures, and more, this property offers a fresh, modern appeal. Don't miss out on the chance to capitalize on this perfect investment for multi-family property enthusiasts! $2,200,000 Pending

1590 MASTERS Drive 1-8 St Augustine, Florida

16 Beds 9,064 SqFt 1.83 Acres

Welcome to 307 Arricola Ave—more than just a duplex, it's a luxurious investment opportunity ready to generate income or provide a comfortable lifestyle. This property is fully furnished, turnkey-ready for short-term rentals or immediate occupancy. Built to withstand Florida's weather, this all-steel, fireproof duplex sits safely above flood levels, offering complete peace of mind against hurricanes and flooding. Step inside to discover stunning high-end LPV and tile flooring across open, inviting spaces filled with natural light. Each kitchen is a chef's delight, equipped with modern stainless steel appliances and beautiful quartz countertops. The bathrooms feature contemporary LED mirrors, and each bedroom boasts practical built-in closets, adding convenience to daily living. Both garages impress with Marble Epoxy Floors...(continued)... (...) Comfort is key with spray foam insulation throughout the property, keeping energy costs low and your living environment consistently cozy. Enjoy mornings or evenings on the inviting outdoor spaces ideal for relaxation. Perfectly located, this duplex is golf-cart accessible to the Bridge of Lions and downtown St. Augustine, where charming restaurants, unique attractions like the Historical Fort, the Amphitheater, and the Alligator Farm await exploration. $1,599,000 Active

307 ARRICOLA Avenue UNIT A UNIT B St Augustine, Florida

8 Beds 6 Baths 4,514 SqFt 0.17 Acres

Don't miss your chance to own this fully renovated, historic multi-family gem in the heart of St. Augustine—and be sure to stop by our **Broker Open on Wednesday, April 23rd from 11AM-2PM**! Tour the property, enjoy refreshments, and enter to win a gift basket filled with local St. Augustine goodies—perfect for treating yourself or a client. Now featuring a brand new metal roof on both the main house and the Carrera Cottage, this property is turnkey and ready for your next investment move. Priced at $1,245,000—well below its appraised value—it offers incredible potential for multi-generational living, house hacking, or generating short- or long-term rental income, The main house includes 2 bedrooms and 2 baths, while the Carrera Cottage offers two private-entry 1-bedroom, 1-bath apartments with their own outdoor spaces. The Carrera Courtyard is an Instagram-worthy oasis, beautifully landscaped and designed for relaxing or entertaining. Smart home features, off-street parking, and a prime location near Flagler College and historic downtown make this a standout opportunity. Whether you're looking to invest, live in one unit and rent the others, or offer premium vacation stays, the numbers speak for themselvesprojected rental income ranges from $96,000-$120,000 for short-term and $69,600-$81,600 for long-term leases. Come experience all the charm and income potential this property has to offer! $1,245,000 Active

64 CARRERA Street St Augustine, Florida

5 Beds 4 Baths 2,065 SqFt 0.15 Acres

$100K PRICE DROP!!! Priced to Sell AS-IS. This 5 (easily 6) bedroom, 4.5 bath GEM is an AMAZING OPPORTUNITY in historic St Augustine to own a SOURCE of STEADY INCOME! Property consists of 4 units with a proven rental income history that the owner is happy to share with a qualified buyer. One unit is leased annually and the other 3 others are Airbnb/ VRBO rentals. A buyer may choose to live on site and enjoy running this profitable business in America's oldest city or keep it as it is currently a full rental property. One can walk to fine dining, shopping, boating, attractions and festivals (just a few blocks from the fairgrounds). You /your guests can enjoy the splendor of St Augustine's famous Nights of Lights from mid-November through late January every year. Seller has reservations from repeat visitors stretching into 2026. Seller happy to work with new owners for a seamless transition so you earn $$$ starting 15 minutes to St Augustine and Vilano beaches, great golf courses and the St Augustine outlet mall. Don't miss this opportunity to own your place that produces great cash flow for a reliable passive income. $1,189,000 Active

16 ROHDE Avenue St Augustine, Florida

5 Beds 5 Baths 2,891 SqFt 0.14 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. $1,180,000 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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