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$2,400,000
7 Beds ⋅ 5 Baths ⋅ 2112505 MLS
Step into the enchanting embrace of the notable Upham Winter Cottage, a captivating Queen Anne Victorian nestled on a quarter-acre lot within the heart of St. Augustine's cherished historic preservation district and listed on the National Register ofHistoric Places. This world-class historic mansion has recently been renovated from top to bottom to perfection with soft coastal hues in mind ~ enjoy the well-designed balance of rich historic beauty and modern luxury. With 5800 sq ft of living space, 5 bedrooms and 3.5 bathrooms in the main house and a 2 bedroom, 1 bath apartment with private entrance, a full kitchen, living and dining room - this home is ideal for multigenerational living or additional income. Located on historic St.George Street, the shops, restaurants, landmarks and culture of the Nation's Oldest City are only steps away. The highly active community association provides additional opportunities to socialize and enjoy the buzz of downtown living Built in 1893 as a winter retreat for John J. Upham, a veteran of the Civil War and Plains Indian War, this remarkable home showcases the graceful blend of Queen Anne Victorian architecture with examples of Moorish Revival in the courtyard arches. With stunning original millwork, wood floors and a unique octagonal shape, this home will take you back to the splendor of the Gilded Age. From joyous Flagler Era galas to legendary Mardi Gras celebrations, The Upham Winter Cottage has been a witness to countless extraordinary events throughout the ages. Today, as you step foot within these storied walls, you become a part of the Upham Winter Cottage's narrative and assume the role of its guardian, preserving the heritage of the past while crafting a new chapter in its history. Nothing compares.

268 St George Street, St. Augustine

$1,815,000
3 Beds ⋅ 4 Baths ⋅ 2118038 MLS
Along the serene edge of Maria Sanchez Lake lies one of downtown St. Augustine's most alluring hidden treasures. Beyond a graceful brick archway, this private sanctuary reveals itself — a home so captivating that every guest departs inspired and eager to return. A study in balance and beauty, the residence blends European refinement with a soulful, worldly aesthetic. Its design nods to the understated elegance of Belgian estates, the timeless sensibility of Darryl Carter, and the calm minimalism found in Asian influence. Every surface and texture — from ancient Burmese teak and reclaimed oak to artisan brickwork — was chosen with intention, creating an enduring home rooted in craftsmanship and character. The main level was envisioned for effortless entertaining and connection. Folding glass walls blur the line between indoors and out, opening completely to the front courtyard and rear lake terrace. A masterfully built summer kitchen by a local craftsman anchors the courtyard beside a peaceful plunge pool and spa-style bath. Inside, the chef's kitchen delights with a statement Viking range, open shelving, and dramatic marble slabs that extend seamlessly up the walls. Generous dining and living areas flow naturally toward the lakefront, where gentle breezes and daily scenes of herons and egrets create a living masterpiece. Originally a 1920s cottage, the home's historic essence now mingles with bold modern lines. Just off the main living area, a refined study framed by an antique arched window captures glimmering lake reflections and sunlight by day, and candlelit warmth by night. Upstairs, the lake becomes your morning view. The primary suite and an adjoining guest suite  currently used as a sitting retreat  each open to private balconies beneath a graceful old tree. Both baths are finished in marble with curated lighting and high-end fixtures. Along the south side, a screened porch invites lingering conversation or afternoon reading and transitions beautifully to a sunlit terrace ideal for herbs or climbing roses. "The Little Nest," a third-floor hideaway, crowns the home with panoramic vistas that stretch across the historic skyline to the Intracoastal. Vaulted ceilings, reclaimed beams, and marble accents create an inspiring space for writing, resting, or simply dreaming. Across the brick courtyard, the detached garden studio offers a charming bonus retreat  with its own entrance, vaulted ceilings, reclaimed-beam details, and a small kitchenette and bath. Originally permitted as a shed and not counted in the home's total living area, this stylish escape offers flexibility for guests, creative work, or quiet reflection. Timeless, tactile, and transporting  153 Washington Street is more than a residence. It's a rare experience of historic St. Augustine living, where cobblestone streets and shimmering waterways frame a lifestyle that feels both centuries old and utterly new.

153 Washington Street, St. Augustine

$1,645,000
4 Beds ⋅ 4 Baths ⋅ 2129072 MLS
Experience historic luxury at 290 St. George St, the former personal residence of famed architect Fred Henderich. Masterfully reimagined by John Benoit of BEHST Builders, this estate seamlessly fuses 1900s ''Old World'' soul with 21st-century sophistication. Positioned on a rare 62.5x200 lot stretching from St. George to Cordova St, the property offers stunning Lake Maria Sanchez views and parking for 10+ cars. The main home radiates light, showcasing original woodwork, coffered ceilings, and a gourmet kitchen with custom cabinetry and a butler's door. The primary downstairs suite features floor to ceiling tile work, a tub and a walk-in shower, flowing into a sunlit morning room. Upstairs, find a nautical suite complete with a steam shower. Beyond a private sanctuary, this estate is a lucrative asset. The detached cottage is a designer showstopper with a vaulted living area and private lakefront verandas. Perfectly positioned as a high-end luxury rental in the heart of St. Augustine.

290 St. George Street, St. Augustine

$1,020,000
3 Beds ⋅ 3 Baths ⋅ 2089684 MLS
It's a rare pleasure to find a renovation that honors the architectural integrity of the original home while embracing the comforts and functionality of modern living. This beautifully restored residence strikes that balance - offering a seamless path between the gathering rooms, kitchen, and expansive deck, all of which enjoy tranquil views of Lake Maria Sanchez. Traditional details abound, from gleaming heart pine floors to wainscoting in the generous entry foyer and living room. A wide bay window frames the front garden, while an oversized pocket door allows you to close off the kitchen when privacy is desired. The entry foyer - spacious enough to furnish, opens into a welcoming living room, leading in turn to the sunroom, dining room, and a light-filled kitchen. No matter where you stand, the lake is a constant, sparkling presence. In the late afternoon, its surface shimmers with golden hues as the sun dips toward the horizon - an everyday reminder of nature's beauty. The gathering rooms are large and have a circular flow. A fireplace on the diagonal and the bay window alcove anchor 2 distinct spaces in the living room. Its versatility invites you to arrange the room to suit your needs and style. The kitchen was designed and outfitted by a talented woodworker who previously call 314 St George St home. Its suits the bungalow style of the house, easily blending form and function with a simple beauty. The sun room runs along the south side, featuring a casual sitting area on the east end and the dining room on the west. Under-window shelves offer a place to hold your cookbooks and display your favorite dishes. French doors between kitchen and dining open to the deck and let the sunshine in during afternoon hours. The primary bedroom is en-suite with private bath and is located on the 1st floor. With 4 windows and a vaulted ceiling, 2 of those windows overlook the water while French doors lead you to the deck. Upstairs, the front bedroom features a large alcove nestled beneath the tree canopy. The rear bedroom faces the lake and both rooms share the hall bath. Laundry and welcome storage occupy 2 rooms and offer potential for adding a private bath and walk-in closet for the front bedroom. The back deck is a favorite place for dining, birdwatching, morning coffee, evening cocktails and makes for a great outdoor office too! The backyard is landscaped with native plantings and fenced to keep your 4-legged family members close by. A covered carport on the lakeside provides convenient, sheltered parking and a place for the kayak. Every detail, whether newly added or lovingly preserved, reflects a deep pride of ownership. Words and photos can only go so far - this is a home you must experience in person. With dual frontage on both St George and Cordova Streets, this home enjoys 2 of the most desirable addresses in the city's cherished residential historic district. It's a pleasant stroll along the lake, down St George St or along the bayfront as you head to the central plaza downtown to begin your exploration of the myriad culinary, cultural, architectural and historic offerings waiting to be discovered by you. Charge or gas up the car, make the airline reservations, get on the bike and come try it on - we'll be waiting for you on the porch.

314 St George Street, St. Augustine

$1,000,000
6 Beds ⋅ 5 Baths ⋅ 2061695 MLS
Back on market due to buyer financing fell through. Beautiful large and so much history entwined in this historical home. The home needs some major TLC renovation and roof but has good bones with solid concrete foundation and most importantly history and LOCATION!! As you walk into this home, one can feel the historical feel about it. As you enter into the screened front porch you are drawn to the main entry/living room and staircase. Imagine a crackling fireplace in cold Florida winter or cool nights with a beautiful original pine flooring throughout to walk on. A formal dining area and kitchen with handcrafted cabinets since the 1900's. A former butler's pantry with room on the side for pantry. Let your imagination run to restore to once was! Upstairs consist of so much potential once renovated. The Genovar's had 2 suites in past with own kitchenettes; the plumbing still exists. 5 bathrooms upstairs with jack jill bathrooms The garage apartment has a kitchen, living room, bathroom and two spacious bedrooms. The garage apartment is on same water meter but different electric meter.

271 St George Street, St. Augustine

$800,000
3 Beds ⋅ 2 Baths ⋅ 2161602 MLS
Discover the charm and character of this historic 3-bedroom, 2-bath home, set on a generous lot in a secluded residential neighborhood with close proximity to the bayfront and town. Enjoy the appeal of a peaceful setting while still being near local dining, shopping, and waterfront attractions. The multi-family lot classification also provides added potential for future development opportunities. Completely remodeled in 2020-2021, including updates to the electrical, insulation, and mechanical systems, this home offers historic character with modern improvements. A new patio and planter were added in 2022, while the roof and AC were replaced in 2024. Window tinting was added in 2026 with 20% film to help reduce solar heat transfer and glare while supporting AC efficiency. Don't miss the opportunity to own a piece of history with modern updates and incredible potential!

249 Charlotte Street, St. Augustine

$735,000
2 Beds ⋅ 3 Baths ⋅ 2126282 MLS
Classic Elegance in the Heart of St. Augustine's Historic District. Built in 2019, this exceptional residence blends Old World architectural charm with the confidence and comfort of modern construction. Elevated 10 feet above grade this thoughtfully designed single-level home offers two bedrooms and two-and-a-half baths, with soaring 10-foot ceilings that create a bright, gallery-inspired interior ideal for displaying fine art. Oversized windows fill the home with natural light, while ceiling fans in every room enhance comfort and style. Luxury vinyl tile flooring provides a refined aesthetic with effortless maintenance. The kitchen features quality cabinetry enhanced with ShelfGenie custom shelving, custom blinds, and functional design suited for everyday living and entertaining. Generous front and rear porches--recently refreshed and equipped with two new ceiling fans--extend the living space outdoors and invite relaxed enjoyment of the surroundings. A full-length driveway provides convenient rear access and ample guest parking, complemented by reserved on-street parking for area residents. The professionally curated no-lawn garden is serene and low-maintenance, attracting abundant birdlife. From the porch, enjoy visits from cardinals, bluebirds, chickadees, woodpeckers, red-winged blackbirds, Carolina wrens, doves, finches, and titmice. Hummingbirds frequent the feeder, while the birdbath is currently visited by migrating robins--creating a peaceful, immersive outdoor experience. The home is finished with resilient cedar siding and is located just a short walk from the St. Johns County River House Recreation Center, offering classes in dance, art, music, exercise, bridge, and more. The neighborhood is prized for its peaceful atmosphere, strong sense of community, and absence of short-term rental zoning, with an active Old City South Neighborhood Association hosting year-round social events. Ideally situated within easy walking distance of Lake Maria Sanchez, the Bayfront, Flagler College, and downtown St. Augustine's renowned dining, shopping, and cultural attractions.

307 St George Street, St. Augustine

$575,000
3 Beds ⋅ 2 Baths ⋅ 2128246 MLS
Discover the perfect blend of historic character and modern living in this meticulously maintained stilted cottage. Built in 2017 with authentic Old Florida style, this move-in ready home offers premium finishes, dual street access, and exceptional walkability to downtown St. Augustine's most beloved attractions. Interior Features: Open-concept kitchen with breakfast bar and modern appliances flows seamlessly into the eat-in dining area and spacious living room with electric fireplace. The primary bedroom suite boasts an oversized walk-in closet and private en-suite bathroom. Energy-efficient construction with modern systems throughout ensures comfort and low maintenance. Outdoor Living: Covered paver patio ideal for year-round entertaining, charming front porch perfect for morning coffee, and low-maintenance landscaping. Dual street access from Moore Street and Pomar Street provides rare off-street and parking—a premium amenity in historic downtown. Prime Lincolnville Location: Walk to Flagler College, Castillo de San Marcos (5 minutes), and St. George Street's shopping and dining. Minutes to Atlantic beaches. This culturally significant neighborhood features restored Victorian homes, vibrant arts community, and authentic Florida heritage in the heart of America's oldest city. Investment Opportunity: Strong vacation rental potential with proximity to 7+ million annual visitors, modern construction meeting current codes, and turnkey condition. Ideal for second home buyers, investors, retirees, or remote workers seeking walkable downtown living with historic charm. Experience modern Florida living in a historic setting. Schedule your showing today!

125 Moore Street, St. Augustine

$550,000
10 Beds ⋅ 9 Baths ⋅ 2058996 MLS
1925 HISTORIC HOME READY FOR RESTORATION IN DOWNTOWN ST AUGUSTINE. Originally built in 1925 by 2 sisters who built identical homes next door to each other! The home on the right is being totally renovated right now & can't wait to see it's sister house brought back to it's original beauty, too! Eventually this home was known as The Grafton House, a beautiful assisted living home for seniors. Located less than a mile south of The Bridge of Lions and down the street from The River House & Council on Aging & across the street from BayView Nursing Home makes it an ideal location for a variety of uses. Zoned RL-1 allows single family, multiple family or, by exception, Bed & Breakfast, Assisted Living, etc. With 10 to 12 bedrooms, 6 bathrooms, elevator shaft, huge outdoor patios (upstairs & down) fireplace & located on a corner lot, the possibilities for this historic fixer upper are endless!

168 Marine Street, St. Augustine

$425,000
3 Beds ⋅ 2 Baths ⋅ 2138878 MLS
*Newer Home for the area with upgraded 6'' exterior walls and enhanced attic insulation for superior energy efficiency* *Thoughtfully designed ADA-accessible primary suite with 36'' wide doorways and roll-in shower with grab handle* *Durable Hardie board siding offering long-lasting curb appeal and low maintenance* *Bright, open-concept layout with kitchen flowing seamlessly into the living room* *Laminate flooring throughout for a clean, cohesive look and easy upkeep* *9-foot ceilings throughout creating an open and airy feel* *Kitchen features granite countertops, stainless steel appliances, oversized sink, and glass backsplash* *Eat-in kitchen perfect for casual dining and entertaining* *Front bedroom ideal for home office, flex space, or sewing room* *Primary suite includes walk-in closet with built-in shelving and accessible bathroom layout* *Well-maintained yard with mature shade trees and double gate access* *System updates, 2023 HVAC and 2025 water heater* - Enjoy the benefits of a modern home in a well-established area just minutes from St. Augustine--without the hassle of an HOA. Built with upgraded 6-inch exterior walls and additional attic insulation, this home offers impressive energy efficiency and year-round comfort. Inside, you'll find a thoughtfully designed open layout with 9-foot ceilings and durable laminate flooring throughout. The kitchen is both stylish and functional, featuring granite countertops, stainless steel appliances, an oversized sink, glass backsplash, and a seamless flow into the main living space--perfect for everyday living and entertaining. The split-bedroom design includes a versatile front room ideal for a home office or hobby space. The primary suite stands out with ADA-accessible features, including 36-inch wide doorways, a roll-in shower with grab bar, and a spacious walk-in closet with built-in shelving. Additional highlights include ceiling fans in every room, granite vanities, an insulated garage door with built-in shelving, and major system updates like a 2023 HVAC and 2025 water heater. The backyard is shaded, well maintained, and offers convenient double-gate access. A rare opportunity to own a move-in ready, energy-efficient home with custom upgrades in a prime location close to historic downtown.

345 Orchis Road, St. Augustine

$290,000
2122040 MLS
This lot sells a dream. Close to the historic district of the Nation’s Oldest City, St. Augustine, the discerning buyer fortunate enough to purchase this prime lot in Lincolnville. Ideal for either a vacation rental, 1st or 2nd home or a commercial property. Zoned CL-1, commercial low zoning, a multi-family home, student housing, commercial space (retail, hair salon, restaurant up to 100 seats, not drive-in or fast food, club, bed & breakfast, office & more). Located in an Opportunity Zone! Giving investors even more reasons to love it! 2 sets of construction drawings have been created for a 3-story pool home, 2-car garage, guest house + 2 more parking spaces in the back w/ a total of 4 bedrooms should be permitted by city & convey. Downtown & restaurants are a short walk or bike ride away. Quaint shops & artists’ galleries nestled among the tropical foliage along cobblestone streets; award -winning restaurants filled w/ the mixed aromas of Europe & the Caribbean Sea. The City Archaeology Program stem from local construction and development that will impact cultural resources and this property is in the Archaeological zone that a review would need to be completed before any building can take place. Construction drawings would need to be submitted to the city with an application

89 Washington Street, St. Augustine

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