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$375,000
2 Beds 1 Baths 2157451 MLS
Built in 1916, this Craftsman-style property offers historic character and exceptional versatility in the heart of Riverside. Zoned for both commercial and residential use, it has served as a professional office for the past 43 years. Located just a few blocks from the popular shops, restaurants, and entertainment of Five Points, it is also convenient to the Riverside Arts Market, St. Vincent's Hospital, downtown Jacksonville, and EverBank Stadium--home of the Jacksonville Jaguars. Additional features include rear parking and a high-and-dry location. Whether used as an office, residence, or creative live/work space, 2223 Herschel Street presents a unique opportunity in one of Jacksonville's most sought-after historic neighborhoods.

2223 Herschel Street, Jacksonville

Listing courtesy of BETTER HOMES & GARDENS REAL ESTATE LIFESTYLES REALTY.

$775,000
6 Beds 4 Baths 2154501 MLS
Rare opportunity to own a beautifully renovated duplex in the heart of Riverside! This turnkey property features two spacious units, each offering 3 bedrooms, 2 bathrooms, large living and dining areas, and updated kitchens with oversized islands, soft-close cabinetry, stainless appliances, and stylish finishes. Renovated bathrooms, hardwood floors, tankless water heaters, in-unit laundry, private entrances, covered porches, driveway, and additional off-street parking add to the appeal. Endless opportunities for investors seeking strong rental potential or owner-occupants looking to offset their mortgage by living in one unit and renting the other. Just minutes from Five Points, Downtown Jacksonville, parks, shopping, dining, and entertainment.

2830 Park Street Unit 2832, Jacksonville

Listing courtesy of KELLER WILLIAMS ST JOHNS.

$630,000
4 Beds 4 Baths 2154128 MLS
Investor opportunity in the heart of historic Riverside! This spacious duplex features two 2BR/2BA units, each filled with the timeless charm that makes this neighborhood so desirable. Original hardwood floors, beautiful wood trim, & classic architectural details create an authentic historic feel that attracts long-term tenants. Major capital improvements have already been completed with a new roof and replumbing in 2025, providing peace of mind and reducing future maintenance expenses. A rare bonus is the five off-street parking spaces, along with a 2-story screened porch offering generous outdoor living space for both units. Located just minutes from Riverside's popular restaurants, breweries, parks & shopping, this property is ideally positioned in one of Jacksonville's strongest rental markets. Whether you're expanding your portfolio or making your first investment, this income-producing duplex offers historic character, modern updates, and outstanding long term potential.

2583 Post Street, Jacksonville

Listing courtesy of CHRISTIE'S INTERNATIONAL REAL ESTATE FIRST COAST.

$699,000
4 Beds 3 Baths 2153492 MLS
Welcome to 2230 Post St. in the heart of historic Riverside, just blocks from some of Jacksonville's best restaurants, shopping, parks, and entertainment. This beautifully remodeled 1911 home blends historic charm with modern updates and feels like new construction the moment you walk inside. Offering over 2,300 square feet, the home features 4 bedrooms, 3 full bathrooms, two balconies, a covered rear deck, an extended paved driveway with extra parking, and a large storage shed. Recent upgrades include a newer roof, two brand-new 2026 Carrier HVAC systems, gorgeous original pine wood floors, remodeled bathrooms with new Kohler fixtures, Samsung stainless steel appliances, upgraded lighting and ceiling fans, built-in bookshelves, pocket doors, generous closet space, and a charming fireplace. Don't miss this rare opportunity to own a fully updated historic home in one of Jacksonville's most desirable neighborhoods. Schedule your private tour today!

2230 Post Street, Jacksonville

Listing courtesy of ATRIUM REALTY, LLC.

$895,000
6 Beds 4 Baths 2153181 MLS
Iconic 1919 Craftsman in the heart of historic Riverside, thoughtfully restored to preserve its architectural charm while incorporating modern updates. A celebrated wraparound porch welcomes you to this exceptional 3,198 square foot home featuring 6 bedrooms, including 2 first-floor primary suites, and 3.5 beautifully renovated baths. Natural light fills the home through restored leaded-glass diamond-pane windows. Soaring coffered ceilings, original wood floors, two fireplaces and a stunning bay window with built-in seating, create warm, inviting living spaces. The custom kitchen features marble countertops, a breakfast bar, high-end appliances, abundant custom cabinetry, and generous workspace. The renovated bathrooms blend classic style with modern finishes, showcasing custom tile and quality workmanship. The flexible floor plan offers 2 primary suites on the main level, providing convenience for guests or multigenerational living. Upstairs, you'll find 4 spacious bedrooms and a ful bath, offering plenty of room for family, home offices, media or hobby spaces. Back on the main level, a large laundry and mudroom with floor to ceiling built-ins, cubbies and hooks, keep life's clutter organized. Outside, the deeply shaded porch provides the perfect place to relax, entertain, and enjoy one of Riverside's most picturesque streets, while the paver sidewalk and driveway enhance the home's classic curb appeal. All major systems have been updated. This classic Craftsman style residence offers the rare opportunity to own a true historic landmark where timeless elegance, and modern comfort come together in one remarkable home.

2301 Oak Street, Jacksonville

Listing courtesy of KELLER WILLIAMS JACKSONVILLE.

$715,999
6 Beds 5 Baths 2152196 MLS
The seller is offering up to $10,000 in buyer concessions with an acceptable offer! Timeless Riverside charm meets modern luxury in this beautifully reimagined 1926 duplex with an additional 520 sq. ft. above-garage ADU, creating a rare income-producing or multi-generational living opportunity. Thoughtfully renovated from top to bottom, this property features a new roof, updated A/C systems, tankless water heaters, fully rewired electrical with new panels, and updated plumbing, blending historic character with today's modern conveniences. The main home is currently configured as separate upstairs and downstairs residences, each offering a private primary suite, spacious light-filled living areas, fully equipped kitchens with luxurious quartz countertops, brand-new stainless-steel appliances, and designer-selected finishes throughout. Every bathroom showcases its own unique style with custom tilework and carefully chosen vanities. Generous closet space and well-designed layouts ensure both comfort and functionality. The detached ADU adds even more flexibility for rental income, guest accommodations, or a private home office. Laundry hookups are conveniently located within each unit. Whether you're an investor seeking strong income potential or an owner-occupant looking to offset expenses, this one-of-a-kind Riverside property delivers the perfect blend of history, luxury, and versatility.

2916 Post Street, Jacksonville

Listing courtesy of LPT REALTY LLC.

$235,000
3 Beds 2 Baths 2152176 MLS
Seller to install new roof prior to closing with accepted offer!! A classic Riverside bungalow, refreshed and ready for its next owners! As you enter, note the original hardwood flooring, abundant natural light, fresh interior paint, and tall ceilings throughout. Moving through the separate living and dining room spaces - you're met with a spacious kitchen with plenty of cabinetry and stainless appliances. Connected to the kitchen, a large laundry room/mud room complete with a conveniently located half bath at the back of the home. This home flows beautifully as the three bedrooms are separated from the living areas, sharing a full updated bath in the hallway. With a charming front porch, off street parking and driveway, fenced backyard, and shed for additional storage - this home is in search of new owners to enjoy all Riverside has to offer! Convenient to major roadways and minutes from great local eats, breweries, and shops!

729 King Street, Jacksonville

Listing courtesy of ROOT REALTY LLC.

$699,000
4 Beds 3 Baths 2145384 MLS
Ready for its next stewards, this beautifully remodeled 1938 home offers the perfect blend of historic character, generous living spaces, and an exceptional Riverside location. Filled with natural light and thoughtfully updated for modern living, the home provides the opportunity to enjoy one of Jacksonville's most beloved neighborhoods from a residence that is both welcoming and functional. Inside, the flexible floor plan features four bedrooms and three full bathrooms, including a downstairs bedroom and full bath that is ideal for guests, a home office, or multigenerational living. The downstairs bathroom also incorporates the laundry area, creating a practical and convenient space for everyday living. Large rooms throughout the home create an airy feel, while abundant windows fill the interior with natural light. Upstairs, the spacious owner's suite serves as a private retreat with its own ensuite bathroom and walk-in closet. Two additional bedrooms and another full bathroom complete the second floor, providing plenty of room for family, guests, or work-from-home needs. Whether gathering with friends, enjoying quiet evenings at home, or simply appreciating the character of a 1938 residence that has been thoughtfully refreshed, this home offers comfort and flexibility at every turn. Situated in a fantastic Riverside location, you'll enjoy easy access to neighborhood parks, local restaurants, boutiques, coffee shops, and the vibrant community atmosphere that continues to make Riverside one of Jacksonville's most sought-after historic neighborhoods. A rare opportunity to own a move-in-ready historic home with the space, updates, and location that today's buyers are searching for.

2143 Myra Street, Jacksonville

Listing courtesy of COMPASS FLORIDA LLC.

$609,500
8 Beds 5 Baths 2148706 MLS
Exceptional Investment Opportunity in Historic Riverside! This charming 1920s multi-family property at 2022 Dellwood Avenue (Units 1-5) is an incredible addition to any real estate portfolio. Situated in one of Jacksonville's most vibrant, walkable, and highly sought-after historic districts, this 5-unit income-generating asset captures the timeless appeal of vintage architecture in a premium location. Investors will love being just a short stroll from the popular retail and dining scene of Five Points, the picturesque Riverside Park, and the world-class collections at the Cummer Museum of Art and Gardens. With immediate proximity to major employment hubs in Downtown Jacksonville, Ascension St. Vincent's Riverside, and local colleges, this property ensures a steady, high-demand tenant pool. Whether you want to buy and hold or execute a historic value-add strategy, this Riverside multi-family gem is an absolute must-see. Schedule your private tour today!

2022 Dellwood Avenue Unit 1-5, Jacksonville

Listing courtesy of JWB REALTY LLC.

$819,000
5 Beds 4 Baths 2143726 MLS
In the heart of Riverside, this 1929 home offers the kind of scale, craftsmanship, and livability that have made the neighborhood's historic homes so enduring. Spanning three full stories, the home unfolds with generous proportions, abundant natural light, and a floorplan ideal for both everyday living and entertaining. From the moment you step inside, the home feels welcoming and substantial, with historic character carried throughout in the original wood floors, large windows, and thoughtfully preserved details that speak to its era while still living comfortably for today. Beginning with the wraparound porch, which invites slow evenings and conversation, this is the home you've been waiting to see! The first floor is anchored by a spacious foyer that opens into separate living and dining rooms, creating distinct yet connected spaces for gathering. The large kitchen offers exceptional workspace and storage, ready for everything from quiet mornings at home to hosting friends and family, while a separate laundry room and first-floor half bath add convenience to the layout. Just beyond, the home's outdoor spaces become a true extension of the interior. The backyard was clearly designed with entertaining in mind. A two-tiered deck overlooks the beautifully landscaped yard and outdoor kitchen complete with a built-in grill, refrigerator, and sink, creating an effortless setting for weekend gatherings, celebrations, and long dinners outdoors. Upstairs, the second floor includes three bedrooms, among them the spacious owner's suite with a walk-in closet and an ensuite bath featuring dual sinks, a soaking tub, and separate shower. An additional full bathroom serves the remaining bedrooms on the floor. The third floor continues to offer flexibility with two additional bedrooms, a half bath, and a private balcony overlooking the backyard, ideal for guests, home office space, creative studios, or additional living quarters depending on your needs. Located in the heart of Riverside with a Walk Score of 80, this home places you moments from some of the neighborhood's most loved restaurants, shops, parks, and gathering places while offering the space, character, and presence that are becoming increasingly difficult to find. Off-street parking completes this exceptional opportunity to become the next steward of a classic Riverside home.

2598 Herschel Street, Jacksonville

Listing courtesy of COMPASS FLORIDA LLC.

$430,000
4 Beds 2 Baths 2146334 MLS
Four bedroom home with expansive front porch, large backyard and newer 2 car garage (2020) just steps from the great shops and restaurants on Stockton! This home has all the charm you would expect from a classic Riverside beauty, with original oak flooring with walnut inlay on the bottom level and pine flooring on the second. The fireplace mantel with built-ins is dreamy and the large dining room is perfect for gatherings big and small. All bedrooms on second floor. One of the best things about this house is the backyard. Fully fenced, there is a big deck, newer 2 car garage, room for a garden on the side of the house AND plenty of room in the back for a playset, room for the doggies or just a quiet peaceful retreat. In the morning, walk around the corner to Bold Bean for a cup of joe. This is historic living at its finest!

2343 Dellwood Avenue, Jacksonville

Listing courtesy of COWFORD REALTY & DESIGN LLC.

Selling Office: .

$366,000
3 Beds 1 Baths 2145891 MLS
Tucked away in one of Jacksonville's most walkable and charming neighborhoods, this beautifully refreshed home blends timeless character with thoughtful modern updates. Just around the corner from Bold Bean Coffee Roasters, 13 Gypsies, and Foo Dog Curry Traders, and only minutes from Five Points, St. Vincents hospital, and Downtown, the location is hard to beat. Inside, you'll find original hardwood floors and a classic brick wood-burning fireplace that give the home its warm, historic charm. Recent improvements include a new roof, updated landscaping, updated bathroom, and a revitalized kitchen featuring stainless steel appliances. Step outside to enjoy the inviting front porch or unwind in the spacious backyard. Rare for the area, the property also offers a detached garage and private driveway -- a huge bonus for historic neighborhood living. This move-in ready gem delivers charm, updates, and an unbeatable walkable lifestyle all in one package.

2331 Myra Street, Jacksonville

Listing courtesy of KELLER WILLIAMS JACKSONVILLE.

Selling Office: .

$710,000
4 Beds 3 Baths 2142617 MLS
Welcome to refined Riverside living, where timeless neighborhood charm meets the ease of newer construction. Built in 2015, this thoughtfully designed 4-bedroom, 3-bath residence offers a rare opportunity in one of Jacksonville's most beloved historic districts. Inside, rich hardwood floors, crown moulding, tray ceilings, custom wood blinds, ample storage, and an open-concept layout create a warm yet elevated feel. The first-floor primary suite offers a private retreat with double vanities, soaking tub, and separate shower. The kitchen is beautifully appointed with a gas stove, walk-in pantry, generous storage, and pre-piping for a future outdoor kitchen. Enjoy covered front and side porches, a 2-car garage with alley access, plus nearby dining, coffee shops, parks, shopping - all in the heart of Riverside's signature character.

2351 College Street, Jacksonville

Listing courtesy of KELLER WILLIAMS REALTY AT THE LAKES.

Selling Office: .

$550,000
3 Beds 3 Baths 2142423 MLS
Tucked in the heart of Historic Riverside, this beautifully constructed newer home blends classic charm with modern convenience. Ideally located just minutes from Murray Hill, Avondale, and Five Points, you'll enjoy vibrant shopping, dining, and easy highway access. Inside, thoughtful upgrades include Restoration Hardware lighting, fresh interior paint, new appliances, custom closet systems, new washer & dryer, and a tankless water heater. The main level features a versatile bonus room or office and an open-concept living, dining, and kitchen area perfect for entertaining. Upstairs, the spacious primary suite offers a walk-in closet and a beautifully designed en suite bath, while two additional bedrooms share a charming hall bath. Outside, relax on the extended patio that has a large shed for storage plus green space for pets or play, all within a privacy-fenced yard and equipped with a security system! Welcome Home!

2873 Green Street, Jacksonville

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES FLORIDA NETWORK REALTY.

Selling Office: .

$1,999,000
12 Beds 12 Baths 2139502 MLS
*****PRICE REDUCED***** Introducing River Breeze Apartments situated in the sought-after Riverside Historic District in Jacksonville, FL. This exceptional 12-unit apartment community offers oversized 800+ SF one-bedroom units with in-unit washer/dryer and central HVAC. The property's prime location provides a Walk Score of 89/100, allowing residents easy access to dining, retail, and entertainment options in the surrounding area, including proximity to major employment centers like Ascension St. Vincent's Riverside hospital. Investors have a compelling value-add opportunity to renovate 11 of the 12 units with modern premium finishes, unlocking significant rental upside while benefiting from the enduring appeal of the historic district. With limited supply in this prestigious neighborhood, River Breeze Apartments offers a rare chance to acquire a well-located asset in one of Jacksonville's premier locations.

2761 St Johns Avenue, Jacksonville

Listing courtesy of MCADOO MULTIFAMILY ADVISORS LLC.

$820,000
5 Beds 4 Baths 2138712 MLS
Back on market through no fault of the seller! Step into the enchanting embrace of this historic Avondale home, where classic charm intertwines seamlessly with modern luxury. As you approach, a picturesque front porch adorned with a swing beckons you to linger a while and savor the tranquil ambiance. Crossing the threshold, you'll discover a meticulously updated interior that exudes warmth and sophistication. Original wood floors grace the living spaces, evoking a sense of timeless elegance that is further accentuated by freshly painted walls throughout. The newly updated secondary bathroom adds a touch of contemporary flair, blending seamlessly with the home's traditional aesthetic. Prepare to be captivated by the gourmet kitchen, where sleek black stainless steel appliances, quartz countertops, and ample cabinet space converge to create an epicurean's paradise.

2772 Riverside Avenue, Jacksonville

Listing courtesy of ONE SOTHEBY'S INTERNATIONAL REALTY.

$820,000
4 Beds 3 Baths 2136303 MLS
Just steps from the St. Johns River, this 1913 historic residence captures the essence of Riverside living with a presence that is both timeless and inviting. A gracious wrap-around porch sets the tone, offering the perfect place to gather with friends, enjoy the river breeze, and take in the character of the neighborhood. Inside, the home is filled with natural light, enhanced by large windows that create a bright and welcoming atmosphere throughout. Each space feels open, comfortable, and thoughtfully connected. The first floor offers a blend of formal and informal living spaces designed for both everyday living and entertaining. A formal living room and dining room provide classic gathering spaces, while an additional informal living area offers flexibility and can easily serve as a home office. A full bathroom is conveniently located just off this space. The kitchen is positioned toward the rear of the home and features a gas range, generous workspace, and easy access to the backyard. A nearby laundry room adds everyday convenience. Upstairs, the second floor features three bedrooms, including a spacious owner's suite with a private ensuite bathroom. The additional bedrooms offer flexibility for guests or additional workspace, all continuing the home's light-filled feel. The third floor provides a fourth bedroom or a flexible bonus space, ideal for a guest retreat, studio, or work-from-home setup depending on your needs. Historic details are beautifully preserved throughout, including original hardwood floors, picture railing, and a classic clawfoot bathtub that reflects the home's enduring character. Outdoors, the backyard offers a private retreat beneath a canopy of a mature oak tree. A new deck and a brick paver patio create an ideal setting for entertaining and gathering. Adding to its appeal, the property carries a desirable CRO "live-work" designation, offering versatility for those seeking a home that can support both personal and professional use. Recent improvements provide peace of mind, including foundation work, upstairs HVAC system, updated plumbing and electrical, improved ductwork, and added insulation. These updates support modern living while maintaining the integrity of the home. All of this is set just moments from Riverside's favorite dining, parks, and local shops, offering a lifestyle that is vibrant and connected to one of Jacksonville's most sought-after historic neighborhoods. (Buyer to verify square feet.)

542 Lancaster Street, Jacksonville

Listing courtesy of COMPASS FLORIDA LLC.

Selling Office: .

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