JACKSONVILLES TOP 10 OLDEST HOMES

Riverfront Living on the St. Johns River! Situated on a beautiful .85-acre riverfront corner lot, this charming 3 Bed, 2 bath, plus 2 half bath home offers stunning water views and timeless character. Enter through the welcoming foyer featuring a vaulted, gorgeous pine ceiling and beautifully crafted staircase. The spacious living and dining area features a wood-burning fireplace and opens to a generously sized kitchen. The Florida room showcases large picture windows overlooking the river. Upstairs, a versatile open loft opens to a gorgeous river-view balcony—ideal for a 4th bedroom, guest suite, home office, or peaceful retreat. New roof, shower, carpet and paint. Outside, the private corner lot and mature trees create a serene setting. Additional features include a detached 2-car garage with a large workshop and half bath, plus a separate oversized storage shed. Enjoy the beauty and tranquility of St. Johns River waterfront living.

806 River Road, Orange Park

$1,195,000

3 Beds ⋅ 3 Baths ⋅ 2167088 MLS

A rare gem in St. Augustine's highly coveted Abbott Tract, this circa-1900 residence captures the timeless allure of historic downtown living with the ease of modern updates. Beautifully preserved and thoughtfully enhanced, the property offers a sparkling blue lap pool surrounded by tropical foliage, the 2-bedroom, 2-bath main home along with a detached 1-bedroom, 1-bath guest suite featuring a private entrance and kitchenette--ideal for elegant guest accommodations, multigenerational living, or premium short-term rental income. Rich hardwood flooring, historic architectural details, and an undeniable sense of character define the interiors, while the open-concept rear living area creates a seamless setting for relaxed living and entertaining. The two bedrooms are gracefully situated at the front of the home, each with en-suite bath access, with one bath also conveniently serving visitors from the main hall. The kitchen is a perfect blend of style and function, featuring stainless steel appliances, ample prep space, and a breakfast bar that invites casual dining and conversation. Glass sliders off the living room open to a screened-in porch overlooking a serene backyard retreat, complete with a private pool--ideal for unwinding under the Florida sun. The detached guest suite offers flexibility and privacy, featuring a full bedroom and bath, along with a kitchenette to accommodate long or short stays. An extended driveway allows for rare off-street parking for two or more vehicles--a highly sought-after amenity in the historic district. Perfectly situated, this residence is just blocks from St. Augustine's most iconic landmarks, including the Castillo de San Marcos and the Mission Nombre de Dios. A short walk takes you to the waterfront at the end of Locust Street, where you can launch a kayak and explore the tranquil waters of Matanzas Bay. Zoned RS-2, the property also allows for weekly short-term rentals, further enhancing its value as both a personal retreat and a savvy investment. Offering historic charm, premium location, and modern livability, this is your opportunity to own a piece of St. Augustine's enduring legacy--an exceptional lifestyle awaits.

48 Osceola Street, St. Augustine

$549,900

3 Beds ⋅ 3 Baths ⋅ 2166747 MLS

Coming Soon listing, no showings. Beautifully renovated historic home blending timeless character with contemporary finishes and modern livability. Built in 1899, this Jacksonville gem welcomes you with an inviting open floor plan, brand-new wood-look LVP flooring, and a fresh, thoughtfully updated interior. The extensive renovation includes updated plumbing and electrical, a new roof, and a new HVAC system with ductwork. The stunning kitchen features a waterfall quartz island, quartz countertops, and stainless-steel appliances, creating a stylish and functional centerpiece for entertaining and everyday living. Fresh interior and exterior paint bring a clean, bright feel while preserving the Southern charm and character of this historic property. The spacious primary suite offers a private bath and private balcony. Two additional bedrooms share a beautifully appointed full bath, while the third-floor flex space provides valuable additional living area—perfect for a home office, media room, game room, playroom, or private retreat. Outside, the backyard has been thoughtfully landscaped and offers alley access for added convenience. A rare opportunity to enjoy the character of a historic home with the comfort and functionality of a comprehensive modern renovation. Professional photos coming prior to activation on MLS.

1734 Walnut Street, Jacksonville

$570,000

2 Beds ⋅ 2 Baths ⋅ 2164989 MLS

This beautifully updated 3-bedroom, 2-bath pool home offers exceptional charm in an amazing location near downtown St. Augustine. The home has been thoughtfully updated throughout while maintaining its distinctive character, creating inviting and comfortable spaces for everyday living or entertaining. Step outside to the charming back porch overlooking a private pool, fenced backyard and patio--the perfect setting for relaxing after a day exploring the city. Tucked beneath a canopy of mature oaks in a peaceful historic neighborhood, the property is conveniently located near the Fountain of Youth and just minutes from downtown St. Augustine's renowned restaurants, shopping and attractions. Currently operating as the highly rated ''Oak Canopy Escape,'' with a 4.85-star rating across 100 Airbnb reviews, this home presents an outstanding opportunity as an established short-term rental, distinctive second home or primary residence.

17 Dufferin Street, St. Augustine

$550,000

3 Beds ⋅ 2 Baths ⋅ 2162182 MLS

RARE land + location play in the heart of St. Augustine's Historic District. Zoned HP-5 (residential or commercial per city code) on a street where sales are rare. Vacant for years, in poor/uninhabitable condition; sellers have not occupied the property and make no representations as to its full condition. Priced for land value. Rebuild, renovation, STR, or business use subject to City of St. Augustine zoning, HARB, and permitting approval -- not confirmed by seller. Sold AS-IS, WHERE-IS, all faults. Cash or renovation/rehab financing only. Buyer to independently verify zoning, HARB, STR, and permitted uses with the City prior to offer, and to conduct own due diligence. Access by appointment only.

37 Grove Avenue, St. Augustine

$899,000

3 Beds ⋅ 2 Baths ⋅ 2161241 MLS

Discover the timeless elegance of this beautifully preserved Victorian residence nestled in the heart of St. Augustine's coveted Historic Abbott Tract. Situated high and dry beneath a magnificent canopy of mature oak trees, this exceptional home blends historic charm with modern comforts in one of the city's most desirable neighborhoods. Inside, rich spilled honey hardwood floors flow throughout the home, creating a warm and inviting atmosphere. The updated kitchen features quality finishes, an inviting breakfast area, and effortless access to the living spaces, making it ideal for both everyday living and entertaining Multiple covered porches provide the perfect setting to relax with a morning coffee or unwind in the evening while enjoying the tranquil surroundings and timeless beauty of the Historic District. Outside, the expansive yard offers endless possibilities, with ample space to add a resort-style pool, create lush gardens, or design your own private outdoor oasis. A detached two-car garage provides excellent storage and parking while also offering the potential for future expansion or a guest suite. Rich in character, thoughtfully updated, and ideally located just moments from Historic Downtown St. Augustine's renowned restaurants, boutique shopping, galleries, and waterfront, this remarkable Victorian offers a rare opportunity to own a true piece of the nation's oldest city's history.

18 Locust Street, St. Augustine

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 2160596 MLS

Step into a rare opportunity to own a beautifully restored piece of St. Augustine history in the desirable Abbot Tract neighborhood. Originally built in 1900, this stunning 4-bedroom, 2.5-bath home has been completely remodeled from top to bottom while thoughtfully preserving the timeless character and architectural charm that make historic homes so special. Situated on one of the largest lots in the area, this exceptional property offers the perfect blend of historic elegance and modern peace of mind. Extensive renovations include a new metal roof, new HVAC system, new structural piers, new decking, new subflooring and flooring, new windows, fresh interior and exterior paint, new appliances, and countless additional upgrades throughout the home. Enter through the side entrance from the driveway into a welcoming landing area that sets the tone for the home's inviting atmosphere. Inside, new luxury engineered flooring flows throughout most of the home, while beautiful wainscoting adds character and sophistication to the living room. The spacious primary suite is conveniently located on the first floor and features an elegant coffered ceiling, creating a private retreat within the home. A conveniently located half bath completes the main level. Upstairs, you'll find the additional bedrooms along with a second-floor laundry area for added convenience. Step outside onto the newly rebuilt upper deck, complete with outdoor ceiling fans, creating the perfect space to enjoy coastal breezes and views of the surrounding historic neighborhood. New decking on both levels, including the expansive wraparound porch on the first floor, provides abundant opportunities for outdoor entertaining and relaxation. Located just a short distance from the Intracoastal Waterway and within walking distance of Historic Downtown St. Augustine, you'll enjoy easy access to renowned restaurants, boutique shopping, local attractions, and entertainment while still enjoying the charm and tranquility of one of the city's most treasured historic neighborhoods. This is a rare chance to own a turnkey historic home that offers the beauty of the past with the comfort and reliability of modern construction updates.

22 Joiner Street, St. Augustine

$439,900

3 Beds ⋅ 3 Baths ⋅ 2159864 MLS

Built in 1899 and beautifully maintained, this Historic Springfield home blends timeless character with thoughtful updates! Situated on a fully fenced corner lot next to a beautiful neighborhood park, the home features a classic wraparound porch, mature trees, huge brick paver driveway and garage/shed. Inside, soaring ceilings, gorgeous hardwood floors and abundant natural light create an impressive sense of space. Historic details include stained glass, French doors, custom woodwork, beautiful staircases, distinctive door hardware and custom light fixtures. The updated kitchen features tall cabinetry and granite countertops, and all 2.5 baths have been beautifully renovated. Offering 3 bedrooms (plus two additional flex rooms/bedrooms on 3rd floor), inside laundry and flexible living space across three levels. Enjoy the charm and lifestyle of Historic Springfield with parks, dining and Downtown Jacksonville just minutes away.

1405 Boulevard, Jacksonville

$114,900

3 Beds ⋅ 1 Baths ⋅ 2159537 MLS

ATTENTION INVESTORS!! Bright and spacious this 3 bedroom, 1 full bath home features laminate and tile throughout, an updated kitchen with solid surface countertops and an updated bathroom. Property is being sold As-Is with the right to inspect. Seller will make NO repairs. Seller and Listing Agent make no representations and warranties. Buyer to perform own due diligence. Seller will not pay for or provide survey. Property is tenanted.

1357 Evergreen Avenue, Jacksonville

700 Walnut Street Unit A, Green Cove Springs

$964,000

4 Beds ⋅ 3 Baths ⋅ 2159368 MLS

Step into a rare piece of North Florida history at Wilcox Manor, 700 Walnut Street in the heart of Green Cove Springs, just 20 minutes from St. Augustine. Built in 1890 by the Kirkpatrick family, this fully restored Victorian sits on a beautifully landscaped .313 lot. This 4 bedroom, 3 full bath home blends historic craftsmanship with modern upgrades, offering timeless character with the modern amenities of new construction. The wraparound porch sets the tone with original woodwork and classic Southern charm. Inside, spacious rooms feature high ceilings, natural light, heart pine floors, fireplaces, and select original fixtures. The kitchen is a masterpiece of custom cabinetry, quartz countertops, ZLINE appliances, a pot filler, and pull out storage. A walnut coffee bar, hand crank casement windows, and a one of a kind island add both function and character, anchored by the original brick chimney. The primary suite includes a spa style bath with a clawfoot tub, walk in shower and sunset views through mature trees. Outside, live oaks and Spanish moss frame brick walkways, curated landscaping, and a European inspired courtyard complete with a hand tiled Soake pool. Major upgrades include new plumbing, electrical, HVAC, ductwork, insulation, and a 50 year impact rated roof, along with security, lighting, and wireless access throughout. Zoned CBD, Commercial Business District, this property offers rare flexibility for residential, business, or mixed use opportunities. Walk to downtown shops, dining, and events like Food Truck Fridays and Riverfest. The future Springside Restaurant District is just one block away. Location has easy access to the First Coast Expressway, Jacksonville, St. Johns County, and nearby beaches. Whether used as a residence, event space, or short term rental, Wilcox Manor offers character, versatility, and location. 700 Walnut Street is more than a home, it is a legacy! This listing includes the residence on approx .313 acre lot only. The adjoining .313 parcel with detached garage and pump house is being marketed separately. See MLS# 2159366 and the entire property (residence + both parcels) is also available. See MLS # 2135746.

700 Walnut Street Unit A, Green Cove Springs