Riverside Homes with Resale Property Status Type

Welcome to Riverside, Florida—a vibrant neighborhood that perfectly blends historic charm with modern convenience. Nestled along the banks of the St. Johns River, Riverside is renowned for its picturesque tree-lined streets, beautiful parks, and a rich tapestry of culture and community spirit. This area is a haven for those who appreciate both the allure of nature and the excitement of urban living.

Riverside boasts an eclectic mix of architectural styles, from stunning Victorian homes to contemporary townhouses, making it a delightful place for anyone seeking a unique residence. The homes available here with resale property status reflect the neighborhood's character, often featuring spacious layouts, inviting outdoor spaces, and modern amenities. Whether you’re a first-time homebuyer or looking for a place to settle down, Riverside offers a variety of options to suit your lifestyle.

The community is alive with activity, hosting numerous local events, art shows, and farmers' markets that foster a strong sense of belonging. Residents enjoy easy access to a plethora of dining, shopping, and entertainment options, all within walking distance. Riverside is also home to several highly-rated schools and healthcare facilities, ensuring that families have everything they need right at their fingertips.

If you’re looking for a place that combines historical elegance with a lively community atmosphere, Riverside, FL, is the perfect destination. Explore the charm of this neighborhood and discover why so many are proud to call Riverside home!

Newest Riverside Homes with Resale Property Status Type

$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

$2,080,000

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

$881,000

3 Beds ⋅ 4 Baths ⋅ 2025016791 MLS

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 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

Start Your Search

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.