Riverside Real Estate

Riverside Real Estate

Welcome to Riverside, a picturesque subdivision nestled in the heart of Florida, where serene living meets vibrant community spirit. This charming neighborhood offers a perfect blend of natural beauty and modern convenience, making it an ideal place for families, retirees, and anyone looking to embrace the Florida lifestyle.

Riverside is characterized by its lush landscapes, tree-lined streets, and stunning waterfront views that provide a tranquil backdrop to everyday life. Residents can enjoy leisurely strolls along the scenic pathways, or spend sunny afternoons by the river, engaging in activities like kayaking, fishing, or simply soaking up the sun. The community is designed to foster a sense of belonging, with friendly neighbors and regular events that bring everyone together.

Convenience is at your fingertips in Riverside, with easy access to shopping centers, dining options, and recreational facilities. Whether you’re in the mood for a cozy café or a bustling restaurant, you’ll find an array of choices just minutes away. Families will appreciate the proximity to top-rated schools, ensuring that children receive a quality education in a nurturing environment.

For those who love the outdoors, Riverside is a gateway to Florida’s stunning natural attractions. With nearby parks, nature reserves, and beautiful beaches, adventure awaits just a short drive away.

In Riverside, you don’t just find a home; you discover a lifestyle. Experience the warmth of community living and the beauty of Florida’s landscapes in this exceptional subdivision. Come and explore all that Riverside has to offer—your dream home is waiting!

Newest Listings in Riverside

$1,940,000
Riverside SubDv.
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 Drive, Fort Myers
$1,295,000
5 Beds ⋅ 5 Baths ⋅ Riverside SubDv.
Where Luxury Meets Lifestyle Some homes are simply beautiful. There are houses… and then there are gathering places. An exceptional executive estate tucked away on more than two private acres in one of Tarpon Springs’ most sought-after custom home communities. Completely transformed since 2023, this home blends timeless architecture with sophisticated modern design. From the moment you walk through the front door, soaring ceilings, abundant natural light, and an expansive open floor plan create an immediate sense of warmth and elegance. At the heart of the home is a spectacular chef’s kitchen designed to be both functional and unforgettable. Marble countertops, custom cabinetry reaching 10½-foot ceilings with illuminated display lighting, premium stainless steel appliances, an 8-burner gas range, chef’s double ovens, built-in beverage refrigerator, oversized prep island, and an expansive gathering island create a space where family and friends naturally come together. Walls were thoughtfully removed to create seamless flow between the kitchen, dining, and living spaces. Pocket sliding glass doors disappear into the walls, connecting the interior to the screened lanai and creating true Florida indoor-outdoor living. Whether entertaining a crowd or enjoying a quiet evening at home, every space has been intentionally designed to bring people together. The flexible floor plan offers six bedrooms and five bathrooms, including an expansive owner’s retreat, a private guest suite on the opposite side of the home, and three additional bedrooms with two full bathrooms upstairs. A spacious game room provides endless possibilities as a media room, billiards room, playroom, or home gym. Step outside and discover your own private retreat. Relax beside the pool and spa, gather around the custom fire pit beneath the stars, or simply enjoy peaceful mornings overlooking protected conservation. Extensive professional landscaping surrounds the home, while banana, avocado, orange, tangerine, and pineapple plants offer the charm of your own Florida orchard. Luxury extends beyond what you can see. Since 2023, the home has been thoughtfully upgraded with new luxury flooring throughout the main level, new upstairs carpeting, fresh interior and exterior paint, designer lighting, a new electric fireplace, custom roller shades, new lanai screening, updated irrigation, permanent programmable architectural LED exterior lighting, new main level AC in 2026, new water heater, new pool pump, new irrigation pump, an updated security system with new alarm panel, Google Nest doorbell, and exterior cameras providing comprehensive coverage of every entrance. An oversized circular driveway welcomes guests with ease while the spacious three-car garage provides ample room for vehicles, storage, and hobbies. Set within an exclusive executive neighborhood where every residence is unique, this exceptional property offers privacy, luxury, and convenience just minutes from Gulf beaches, marinas, golf, dining, shopping, and the historic charm of Tarpon Springs. Some homes impress you. This one invites you to stay.

1079 Riverside Ridge Road, Tarpon Springs
$885,000
4 Beds ⋅ 3 Baths ⋅ Riverside SubDv.
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 Drive, Fort Myers
$999,000
5 Beds ⋅ 4 Baths ⋅ Riverside SubDv.
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 Drive, Fort Myers
$409,900
Riverside SubDv.
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 Drive, Fort Myers
$214,750
2 Beds ⋅ 2 Baths ⋅ Riverside SubDv.
Move in ready! DIRECT RIVERFRONT! Bright & Sunny 6th floor CORNER END UNIT! 2 Bedrooms & 2 full updated baths! Riverfront living is a ''Permanent Getaway'' offering you a front row seat to the sweeping landscape of the beautiful, abundant nature! Relax on your balcony & enjoy daily ''Hand Painted'' SUNSETS & the calming sights & sounds of the boats cruising by splashing ever so gently & Playful Dolphin visit often! Brand new 2026 HVAC, newer impact windows, Recently updated baths & beautifully remodeled kitchen with gleaming granite countertops. The Riverside Condo is a fabulous Beachside Condo complex with tons of Amenities! 3 pools (two are heated), 2 Fishing Docks, 4 separate laundry rooms, Shuffleboard Courts, Clubhouse & Recreation Room, Impeccably groomed landscape with DIRECT riverfront walkway for morning or evening walks! Nice for exercise! Water, Cable, Internet, Sewer, and Trash are included in your dues. Onsite Management. No pets allowed, only service animals. Just 4 blocks from ''The World's Most Famous Beach!'' & walking distance to Publix supermarket, shopping, fun to do's, restaurants & more

2711 N Halifax Avenue Unit 695, Daytona Beach
$2,100,000
5 Beds ⋅ 5 Baths ⋅ Riverside SubDv.
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 Drive, Fort Myers
$1,354,000
6 Beds ⋅ 3 Baths ⋅ Riverside SubDv.
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 Drive, Fort Myers
$1,495,000
4 Beds ⋅ 4 Baths ⋅ Riverside SubDv.
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 Drive, Fort Myers
$881,000
3 Beds ⋅ 4 Baths ⋅ Riverside SubDv.
Two houses for the price of one. Old homes are unique, full of charm and history. This historic home checks all the boxes, and one the best locations as well as close to downtown, schools, hospitals, kept mostly original to its original build, with updated electrical and plumbing, roof is only 3 years old. Never any flooding from any hurricanes in 22 years of ownership. In a neighborhood known for its close-knit neighbors, kid friendly sidewalks, pet friendly sidewalks, almost Norman Rockwell like neighborhood. With a multi-family designation, the super cute guest house has many possibilities or a rental? 3-bedroom main house, and a 1-bedroom guest house. Two car garage with plenty of room to store a boat or RV. Remember this is a 100-year-old home, antique homes are known for lack of closet space, kitchen is outdated as well, all bedrooms are upstairs. Tremendous possibilities or keep as is. If you like historic old homes, this is the one. Home is featured in Pam Miners book 'River & Road' Fort Myers Architecture from Craftsman to Modern. Chapter One. This is a unique home for that unique buyer. Location, location

1249 Osceola Drive, Fort Myers
$895,000
3 Beds ⋅ 3 Baths ⋅ Riverside SubDv.
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 Drive, Fort Myers
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