Luxury homes for sale & real estate in Uptown, FL

Luxury Home for sale in Uptown, FL:

Timeless Elegance Meets Modern Luxury in the Heart of St. Augustine! Welcome to 31 Cincinnati Avenue, a Rare Opportunity to Own a Piece of St. Augustine’s History. Built in 1910 and Thoughtfully Expanded in 2015, This Classic Residence Offers Nearly 2,700 Square Feet of Refined Living Space on a . 30-Acre Double Lot in Sought-After Uptown, Just a Pleasant Stroll from Historic Downtown. The Property is Also Short-Term Rental Eligible, Making It Equally Ideal as a Private Estate or Luxury Investment. Inside, Soaring Ceilings, Original Yellow Heart Pine Floors, and Artisan-Crafted Trim Celebrate the Home’s Historic Roots, While Modern Enhancements Provide Every Contemporary Comfort

Luxury Home for sale in Uptown, FL:

Two cottages. One incredible opportunity! Welcome to The Sister Cottages — two beautifully restored historic homes in St. Augustine’s sought-after Abbott Tract. Sold together as a turnkey short-term rental portfolio with a transferable LLC, this rare offering provides both flexible living and exceptional income potential in one of Florida’s most desirable destinations. Completely rebuilt from the ground up in 2019, these residences blend classic craftsmanship with modern comfort, creating a pair of timeless retreats that celebrate the city’s heritage while embracing today’s lifestyle. Big Sister Cottage, originally constructed in 1844, stands as a masterwork of

Luxury Home for sale in Uptown, FL:

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 t

Luxury Home for sale in Uptown, FL:

Welcome to your perfect retreat in the heart of downtown St. Augustine! This stunning 2021 custom-built home comes fully furnished and thoughtfully decorated, ready to embrace its new owner. Designed with care, it features soaring ceilings and an open living area that welcomes natural light, creating an inviting space for gatherings. You can walk to all the sites! The charming front porch beckons you to unwind with a cool breeze, while the expansive back porch offers additional outdoor serenity. The 1st floor master suite is a peaceful haven with a beautifully appointed bathroom. Upstairs, two guest bedrooms share a full bath plus small office area. The custom Kitchen is a show-stopper! The