Riverside Real Estate

Welcome to Riverside, a charming neighborhood nestled in the heart of Jacksonville, Florida. Known for its vibrant community spirit and rich historical roots, Riverside effortlessly combines modern living with a touch of old-world charm. This picturesque area is characterized by its stunning tree-lined streets, beautiful parks, and an eclectic mix of architectural styles, including Craftsman bungalows and Mediterranean Revival homes.

Riverside is not just a feast for the eyes; it’s a hub of activity and culture. The neighborhood boasts a variety of boutique shops, art galleries, and trendy cafes that line its sidewalks, inviting residents and visitors alike to explore and enjoy. The Riverside Arts Market, held every Saturday, showcases local artisans, farmers, and musicians, creating a lively atmosphere that truly embodies the community's creative spirit.

Nature lovers will appreciate the proximity to the scenic St. Johns River, where you can enjoy leisurely strolls, picnics, or even kayaking. With parks like Memorial Park and Riverside Park, there are plenty of green spaces for outdoor activities, family gatherings, or simply soaking in the sun.

Education is also a priority in Riverside, with access to top-rated schools and educational institutions, making it an ideal place for families. The neighborhood's sense of community is palpable, with friendly neighbors and a calendar full of local events that foster connections and create lasting memories.

Whether you’re looking for a vibrant lifestyle, a rich cultural experience, or simply a beautiful place to call home, Riverside, FL, offers a unique blend of everything you could desire. Come and discover the charm of Riverside, where every day feels like a celebration of life!

Newest Listings in Riverside

$885,000

4 Beds ⋅ 2.5 Baths ⋅ 2026029609 MLS

MCGREGOR BLVD HOMES - Welcome to this expertly crafted 4-bedroom, 2.5-bath residence, thoughtfully designed to combine architectural distinction with everyday comfort. A dramatic formal living room with soaring 20-foot ceilings is complemented by a fabulous loft/den that overlooks the space, creating an open and inviting atmosphere. A family room that also overlooks the pool area creates a perfect play space for large family gatherings while the master suite is tucked away from the other bedrooms and is truly your own private retreat. Designed by renowned architect Bruce Gora as his personal family home, this remarkable property is being offered to the public for the first time. The modern architectural design is rich in charm and character, highlighted by a stunning courtyard-style pool setting and two outdoor balconies with peaceful river views. Designer details include wood flooring, a striking metal spiral staircase leading to an upper outdoor patio, and floor-to-ceiling windows that fills the home with natural light. The fully enclosed pool and patio area provides exceptional privacy and features multiple seating areas along with a dedicated space for outdoor grilling—ideal for both relaxation and entertaining, and there is generous storage throughout the property. The home has been carefully maintained, preserving its original character while offering important updates, including an upgraded electrical panel, three air-conditioning units all less than three years old, solar power to help reduce energy costs, and a new roof installed in 2025. Ideally located on Caloosa Drive just off the tree lined streets of McGregor Boulevard, this home sits in one of Fort Myers’ most desirable neighborhoods, only minutes from the dining, shopping, and cultural attractions of Downtown Fort Myers.

1215 Caloosa DR, Fort Myers

$999,000

5 Beds ⋅ 3.5 Baths ⋅ 2026022632 MLS

Highly motivated sellers! Welcome to this fabulous estate home located in one of the area’s most sought-after neighborhoods, just moments from the historic Edison & Ford Winter Estates. Located one block from the beautiful Caloosahatchee River. Situated outside of a designated flood zone, this property offers the added peace of mind and convenience of no required flood insurance. NO FLOOD ZONE! This expansive residence offers over 3,900 square feet of living space with five bedrooms and three-and-a-half bathrooms, designed perfectly for a large family or anyone who loves to entertain. As you enter through the elegant French glass front doors from the charming front porch, you are welcomed by a spacious and inviting layout. To the right, you’ll find a beautiful formal living room or den, while the left side features an elegant dining room perfect for gatherings and holiday dinners. The heart of the home is the stunning open-concept kitchen, showcasing glass-front cabinetry, beautiful appliances, and generous space for entertaining, all flowing seamlessly into the oversized family room. The split floor plan offers privacy and functionality. On the right side of the home, you’ll find three spacious bedrooms and two full bathrooms. On the opposite wing, the luxurious primary suite features a cozy double-sided fireplace connecting the bedroom and spa-inspired bathroom, complete with a soaking tub and separate shower. The primary suite also offers direct access to the pool area. An additional bedroom and bathroom are also located on this side of the home. Step outside to your enormous outdoor living space, featuring a sparkling pool surrounded by beautiful travertine tile, creating the perfect Florida retreat for relaxing or entertaining guests. The property also includes a detached garage with endless possibilities—ideal for a mother-in-law suite conversion, private guest retreat, antique car storage, or whatever your vision may be. An additional flex space currently serves as an impressive home gym but could easily be transformed into a studio, office, or recreational area. Additional highlights include gorgeous oak and tile flooring throughout, breathtaking mature oak trees in the front yard, and an unbeatable location just minutes from Downtown Fort Myers dining, shopping, and entertainment. Located just minutes from Downtown Fort Myers, you’ll enjoy quick access to waterfront dining, live music, shopping, breweries, art walks, and community events. Spend weekends exploring the River District, catching sunsets along the water, visiting nearby marinas, or taking a short drive to Southwest Florida’s beautiful beaches, golf courses, and nature preserves. Rarely does a home combine this much space, versatility, charm, and location in one extraordinary package. This is more than just a home—it’s a lifestyle opportunity to experience the very best of Southwest Florida living.

1357 Osceola DR, Fort Myers

$409,900

2026016167 MLS

Rare opportunity to build in one of Fort Myers' most desirable in-town locations. Situated on Avocado Dr in the highly sought-after McGregor corridor, this 13,068 sq ft (0.30-acre) lot — 80' x 164' per survey — offers an ideal homesite in an established neighborhood where custom and renovated homes routinely command well over $1 million. A full set of architectural and engineering plans was developed to permit-ready status for this site, confirming its readiness for new construction. Close to downtown Fort Myers, the river district, dining, and shopping, yet tucked into a quiet residential setting. Lots in the McGregor corridor rarely come available — builders, investors, and future homeowners: bring your vision and create something special in the heart of Fort Myers.

3427 Avocado DR, Fort Myers

$3,300,000

6 Beds ⋅ 6 Baths ⋅ 2026015440 MLS

Welcome to an extraordinary custom-built Mediterranean estate in the heart of Fort Myers, just one block from the Caloosahatchee River and ideally situated off the iconic McGregor Boulevard. This private tropical oasis offers over 6,000 square feet of air-conditioned living space—including a separate ground-level guest suite—and more than 12,600 total square feet of exceptional indoor and outdoor living. Meticulously maintained and continuously updated, this residence showcases superior craftsmanship with soaring ceiling heights from 10 to 22 feet, highlighted by custom coffered and tray ceilings throughout and enhanced by elegant indirect lighting and beautifully appointed fixtures. Travertine flooring and rich hardwood floors create a seamless blend of warmth and sophistication. The gourmet kitchen is designed to impress, featuring a Sub-Zero refrigerator, walk-in pantries, wine cooler, and a dedicated bourbon room—perfect for entertaining. A charming reading nook adds character, while expansive living spaces flow effortlessly into a media room and multiple en-suite guest accommodations. The home offers six bedrooms and six bathrooms, including two luxurious primary suites. Step outside into your own resort-style retreat. The custom heated pool is a true work of art, featuring cascading rock waterfalls, a sun ledge, and exquisite marble inlays commissioned from an Australian artist. Surrounded by lush landscaping and complete privacy, the courtyard creates a serene and secluded setting. Motorized screened lanais allow for year-round enjoyment while keeping insects at bay. Additional highlights include: • Detached 3-car garage with over 1,000 sq ft air-conditioned space • Separate ground-level guest suite for privacy and flexibility • Hurricane-impact, energy-efficient glass throughout • State-of-the-art security camera system • Outdoor kitchen and grilling area • Pergola with hammock and multiple covered patios and decks • Over 1,000 sq ft front porch living space • RV parking with hookup + Tesla charging station • Hunter Douglas shades and plantation shutters throughout • Spa-inspired primary bath with multiple shower heads and body sprayers This one-of-a-kind estate offers the perfect combination of luxury, privacy, and functionality in one of Fort Myers’ most sought-after locations. Furnishings are negotiable, providing a rare turnkey opportunity. Experience elevated coastal living in a private tropical sanctuary just moments from the river.

1229 Plumosa DR, Fort Myers

$795,000

3 Beds ⋅ 2.5 Baths ⋅ 2026007454 MLS

OLD FORT MYERS — Nestled along prestigious West Riverside Drive, this exceptional Florida-style sprawling residence beautifully blends timeless architectural charm with refined modern updates. Set on an expansive nearly half-acre corner lot, the property is enveloped by lush, mature tropical landscaping that creates a serene, private estate-like setting. Offering over 3,000 square feet of living space, the thoughtfully designed floor plan is light, bright, and ideal for both everyday living and elegant entertaining. Rich hardwood floors flow throughout, while the stunning updated kitchen showcases sleek quartz countertops, quality cabinetry, and a perfect balance of style and functionality. Designed for both comfort and versatility, the home features both a spacious family room and an elegant formal living room, providing multiple gathering spaces for relaxing or hosting. Three screened lanais seamlessly bring the outdoors in, creating peaceful settings to enjoy Florida’s beautiful climate year-round. The spacious primary suite serves as a true retreat, featuring a large walk-in closet and a luxurious spa-inspired bath designed for relaxation. Generously sized guest rooms, abundant natural light, and numerous thoughtful system updates provide comfort, convenience, and peace of mind. Located just moments from the vibrant Downtown River District, this remarkable home delivers the best of Fort Myers living — classic Old Florida character, modern sophistication, and an unbeatable location near dining, shopping, entertainment, and the riverfront lifestyle. A rare opportunity to own a distinctive property in one of the area’s most sought-after neighborhoods.

3209 W Riverside DR, Fort Myers

$2,100,000

5 Beds ⋅ 5 Baths ⋅ 226007020 MLS

MUST SEE! No HOA! Located just off historic McGregor Boulevard, this elevated, all-concrete riverfront estate offers a rare combination of scale, security, and privacy along the Caloosahatchee River. Set on a private, oversized parcel and framed by new fencing and mature landscaping, the property feels intentionally secluded, yet remains only minutes from downtown Fort Myers and the vibrant River District seamlessly combining preserved architectural character with modern conveniences and upgrades. The primary suite is a serene retreat, thoughtfully positioned to take full advantage of both garden and water views. Generous in scale, it offers space for a sitting area and features a luxurious ensuite bath with dual vanities, a soaking tub, a walk-in shower, and ample closet storage—creating a refined, spa-inspired sanctuary. The 4 secondary bedrooms are comfortably sized and well-appointed, providing flexibility for family, guests, executive office space, or private quarters. There placement within the home allows for both privacy and functionality, making the layout ideal for multigenerational living,hosting extended stays, and/or as an investment property. A standout feature is the presence of TWO FULLY EQUIPPED KITCHENS, offering remarkable versatility—perfect for entertaining on a grand scale, accommodating long-term guests, or creating a separate living suite within the home. Having two kitchens also offers the ability to RENT the bottom of the home out and live on the main level! The main living areas are spacious and warm with contemporary finishes and updated systems throughout. Outdoors, the pool, fountains, river views, tropical breezes, and stunning sunset backdrops define the experience, with boating access. Located in one of Fort Myers’ most desirable riverfront areas, this property offers a rare combination of lifestyle, privacy, and thoughtful upgrades. One of the few homes in the area where potential storm-related impact has already been proactively addressed through substantial private mitigation and ongoing city drainage improvements. Designed to provide both comfort and peace of mind, while preserving the full appeal of riverfront living. Additionally, the city of Fort Myers, is in the process of installing a new drainage system to thoughtfully mitigate any flooding concerns during inclement weather. An exceptional opportunity to own a protected, thoughtfully updated historic waterfront estate in one of Fort Myers’ most coveted riverfront settings—where character, comfort, and coastal lifestyle converge.

1205 Caloosa DR, Fort Myers

$1,354,000

6 Beds ⋅ 3 Baths ⋅ 2026006878 MLS

Step into a piece of history with this captivating 1925 Spanish Colonial home, thoughtfully updated for modern living while preserving its timeless charm. OWNER FINANCING available with a substantial down payment, providing an excellent opportunity to make this dream home yours. Situated in the heart of the historic McGregor District in Old Fort Myers, this exceptional property offers an unmatched blend of elegance and comfort. Nestled on nearly half an acre just a stone’s throw from the river, this beautiful residence boasts 4 spacious bedrooms, 2 bathrooms, a den, and a bright, inviting family room. The home is located in a quiet, highly desirable community known for its socially active lifestyle, with sidewalks and streets that are both kid and pet friendly. The expansive kitchen is a chef’s delight, featuring a center island, double sinks, recessed oven, wood cabinets with stained glass accents, and an eat-in breakfast nook. French doors open to an extensive lanai and an oversized pool, perfect for entertaining or relaxing. Enjoy formal dinners in the stately dining room or unwind in the cozy sitting room by the wood-burning fireplace. A charming private courtyard adds to the home’s unique appeal. A downstairs bedroom provides added flexibility for guests or multigenerational living. The property also offers abundant parking, ideal for a boat, RV, or additional recreational toys. The property includes a separate guest house with 2 bedrooms, 1 bath, a kitchen, and living areas above an oversized 3-car garage, ideal for visitors or in-laws. Recent updates include new roofs and plumbing in 2020, restored hardwood floors, and hurricane-rated windows, ensuring both beauty and peace of mind. The front of the property is scheduled for a full re-landscaping, designed to further enhance curb appeal and create an even more impressive, picturesque estate entrance. The location offers easy access to Fort Myers Country Club, the Edison-Ford Winter Estates, hospitals, top-rated public and private schools, diverse dining and shopping options, RSW Airport, and the pristine beaches of the Gulf of Mexico. Enjoy evening strolls in this wonderful neighborhood lined with mature trees. Don’t miss your chance to own a piece of Fort Myers history in a highly sought-after community. Schedule your private showing today. No water intrusion or storm damage from Ian.

1248 Osceola DR, Fort Myers

$1,495,000

4 Beds ⋅ 4 Baths ⋅ 2025021554 MLS

Nestled on a sprawling corner lot in Old Fort Myers, this timeless home exudes old-world elegance with grand rooms, ornate ceilings and impeccable craftsmanship. Tropical gardens complete with koi ponds, pergola and wide porches are perfect for entertaining or enjoying lazy afternoons. A sleek chef's kitchen boasts a center island, domed ceiling, Sub-Zero fridge and freezer, plus Bosch induction cooktop, oven, microwave and dishwasher. A prep sink, a warming drawer and tons of cabinetry complete this awesome kitchen. The master bedroom features his and hers oversized closets, dressing room and an adjoining office/4th bedroom. An abundance of storage and built in cabinetry is found throughout the house including a large library and lighted glass display shelving. An oversized laundry room with even more storage is found adjacent to the three car garage. Additional amenities include a 40-kilowatt generator and impact windows throughout. Easy living and low maintenance make this graceful property one of a kind. This timeless Old Fort Myers gem is ready for a new owner to make it their own. Can't be duplicated at this price! See it today!

1299 Plumosa DR, Fort Myers

$1,940,000

4 Beds ⋅ 4.5 Baths ⋅ 2025021038 MLS

This exceptional new-construction opportunity brings together elegant coastal design, modern functionality, and the best of Florida living, ideal for buyers seeking a refined residence in a highly desirable Fort Myers location. Locally known and highly prestigious builder with a proven track record in this neighborhood, including completed homes that inspire confidence along with notable projects such as The Carlton. This vacant lot is being sold as a pre-construction with the plans of the sister project. Please note that all images shown are from that sister project and do not depict the actual home. They are provided to illustrate the level of craftsmanship, design style, and quality of finishes anticipated for this residence, but can be applied to this property as well. Final floor plan details, scale, and square footage remain subject to survey and applicable building requirements. A pre-negotiated construction agreement is already in place, helping ensure a smooth path to completion.

1337 Caloosa DR, Fort Myers

$895,000

3 Beds ⋅ 3 Baths ⋅ 225056672 MLS

Stunning remodel. Designer details. Ultimate location. Enter a residence where timeless charm meets high-design living—this completely reimagined three-bedroom, three-bath beauty in Fort Myers desirable McGregor Corridor is nothing short of extraordinary. Following a complete renovation, this home is a masterclass in craftsmanship, luxury and thoughtful reconfiguration. Every inch has been meticulously upgraded—walls moved, ceilings raised and features elevated—to create a living experience that is relaxed and refined. Inside, you'll be captivated by vaulted ceilings in the great room and primary suite, featuring hand-harvested cypress beams from the local Cypress Slough and crisp white tongue-and-groove wood paneling. Natural textures meet elegant design with beadboard and chair rail wainscoting throughout, a wood-burning fireplace and custom finishes. The gourmet kitchen is a showstopper, quartz countertops with full-height backsplash, a custom banquet, ZLine refrigerator with filtered water and even a left-in reverse osmosis system. The adjacent laundry room—newly added inside for convenience—makes everyday living effortless. The luxury continues outdoors with a new pool by Coastal Custom Pools, complete with marble pavers, a sun shelf with bubblers, a water feature wall and a freestanding hot tub for evening relaxation. Entertain with ease or unwind in style within your fenced-in backyard and dedicated dog run. A replaced front porch with pavers sets the tone before you even step through the door. No detail was overlooked, solid core interior doors, new impact windows, new roof, gutters, trim, tile flooring, upgraded door hardware and whole-home ADT security. There’s even a 50-amp RV plug, generator hookup, irrigation system and whole-house water softener for seamless living. The primary suite is an elegant sanctuary with navy shaker cabinets, quartz counters, Kohler Purist fixtures, custom closets, natural wood shelving and a walk-in shower with dual sinks. Each guest suite is a design lover’s dream featuring custom wallpaper, board and batten accents, built-ins and spa-inspired baths. In one of Fort Myers charming, family-friendly communities, you're a short distance from Triangle Park, the Caloosahatchee River, and all the culture, cuisine and entertainment of downtown. This is not just a remodel, it’s a home of heart and soul, curated for the way you want to live.

1219 Osceola DR, Fort Myers

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.