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Riverside Houses For Sale

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Results 9 of 9
Riverside, 1249 Osceola Dr, Fort Myers, Florida 33901, image 1
$839,000
  • 3 Beds
  • 4 Baths
  • 3,467 SqFt
  • $242/SqFt
House for sale in Riverside
1249 Osceola Dr, Fort Myers, FL 33901
Location, location, location, historic charm, built in 1924, a unique preserved historic home that is part of fort myers florida history, ready for a new caretaker, owner is downsizing and ready to move, well maintained as close to original build as possible with upgraded plumbing and electrical. Never any flooding from any of the recent storms like hurricane ian, zero flooding. They knew where to build in 1924. Complete new roof is three years new. Many consider between gasparilla and caloosa drive on the riverside of mcgregor the best location in fort myers. Active community, kid friendly and pet friendly sidewalks and streets. This is a unique home for that unique buyer that appreciates old historic warmth and charm. Room for a pool or maybe a pickleball court, quest house is one of the cutest self-contained guest houses with all new plumbing. Guest house has one bedroom, living room, dining area and small kitchen with a bathroom. With a multi-family designation, can be legally rented. Main house and guest house, you are getting two beautiful historic homes for the price of one. Two car garage and room to store rv or boat. Preserving the historical charm is something that has been admired by many. All bedrooms are upstairs. Home is featured in pam miners book 'river & road' fort myers architecture from craftsman to modern. Chapter one. Location, location, location
Riverside, 1299 Plumosa Dr, Fort Myers, Florida 33901, image 1
$1,495,000
  • 4 Beds
  • 4 Baths
  • 5,492 SqFt
  • $272/SqFt
House for sale in Riverside
1299 Plumosa Dr, Fort Myers, FL 33901
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!
Riverside, 3235 Avocado Dr, Fort Myers, Florida 33901, image 1
$975,000 $20K
  • 5 Beds
  • 21/2 Baths
  • 3,572 SqFt
  • $273/SqFt
House for sale in Riverside
3235 Avocado Dr, Fort Myers, FL 33901
Imagine owning a true piece of fort myers history — a landmark estate built in 1922, from the same storied era that gave us the legendary edison home. This isn’t just a house; it’s a legacy — the third grand residence ever built along the prestigious mcgregor boulevard. Lovingly maintained and deeply cherished, it offers that rare blend of historic character and modern peace of mind. Set on nearly a full acre of lush, never-flooded grounds, this property whispers the stories of a bygone era while offering ample space and endless potential for contemporary living. Step inside the main residence and feel the timeless charm that lingers in every detail — from the warm glow of the original heart pine floors to the graceful flow of rooms designed for both comfort and connection. With five generous bedrooms, two full baths, and a guest half bath, this home provides plenty of space for family and friends. A new roof (2023) ensures years of worry-free living, preserving the beauty and integrity of this historic treasure. And the charm doesn’t stop there — an inviting efficiency unit with a full bath adds versatility, perfect for guests, extended family, or potential rental income. This isn’t just a home; it’s a living piece of fort myers heritage. Picture yourself wandering the expansive grounds, feeling the echoes of generations past, and adding your own chapter to its remarkable story. Opportunities like this come once in a lifetime. Claim your place in history and become the next proud steward of this extraordinary mcgregor boulevard estate — a home where timeless elegance meets modern grace.
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Riverside, 1215 Caloosa Dr, Fort Myers, Florida 33901, image 1
$1,050,000 $45K
  • 4 Beds
  • 21/2 Baths
  • 3,259 SqFt
  • $322/SqFt
House for sale in Riverside
1215 Caloosa Dr, Fort Myers, FL 33901
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.
Riverside, 1248 Osceola Dr, Fort Myers, Florida 33901, image 1
$1,350,000
  • 6 Beds
  • 3 Baths
  • 3,582 SqFt
  • $377/SqFt
House for sale in Riverside
1248 Osceola Dr, Fort Myers, FL 33901
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 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. The property also 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 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 with sidewalks 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.
Riverside, 1219 Osceola Dr, Fort Myers, Florida 33901, image 1
$895,000 $100K
  • 3 Beds
  • 3 Baths
  • 2,222 SqFt
  • $403/SqFt
House for sale in Riverside
1219 Osceola Dr, Fort Myers, FL 33901
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.
Riverside, 1205 Caloosa Dr, Fort Myers, Florida 33901, image 1
$2,900,000
  • 5 Beds
  • 5 Baths
  • 5,680 SqFt
  • $511/SqFt
House for sale in Riverside
1205 Caloosa Dr, Fort Myers, FL 33901
All offers welcome! Must see! 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, thoughtfully enhanced 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 upgrades and advanced flood protection. This rare offering delivers both legacy appeal and contemporary peace of mind. 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. Their placement within the home allows for both privacy and functionality, making the layout ideal for multigenerational living or hosting extended stays. 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. The main living areas are spacious, warm, and inviting, blending historic details with contemporary finishes and updated systems throughout. The residence is further enhanced by a state-of-the-art flood barrier system, a significant and valuable improvement for waterfront ownership. Outdoors, the pool, fountains, river views, tropical breezes, and stunning sunset backdrops define the experience, with boating access. 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.
Riverside, 3402 W Riverside Dr, Fort Myers, Florida 33901, image 1
$4,750,000
  • 5 Beds
  • 52/2 Baths
  • 8,173 SqFt
  • $581/SqFt
House for sale in Riverside
3402 W Riverside Dr, Fort Myers, FL 33901
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, thoughtfully enhanced landscaping, the property feels intentionally secluded, yet remains only minutes from downtown fort myers and the vibrant river district. Spanning nearly 8, 700 square feet of living space, the home has been extensively upgraded and thoughtfully maintained. Highlights include a newer roof, upgraded mechanical systems and appliances, new flooring, impact-rated windows and doors throughout, soaring ceilings, and expansive living areas that feel both impressive and highly livable. Abundant natural light fills the interior, enhanced by skylights that reinforce the home’s open, forward-thinking design. Outdoor living is exceptional, with multiple balconies and lanai spaces perfectly positioned to capture breathtaking river views and unforgettable sunsets. A standout feature is the rare covered boathouse basin, an ideal solution for protected boat storage. Storage throughout the home is equally impressive, featuring extensive custom closet systems and a substantial four-car garage designed for both daily use and serious vehicle storage, ideal for car enthusiasts. The waterfront setting truly defines the estate. The pool and lanai are oriented directly toward the river, delivering unobstructed water views with no visual distractions. Approximately 150 feet of river frontage, a brand-new seawall, and a new dock create a fully turnkey waterfront experience. Elevated, substantial, and ahead of its time, this fortress-like riverfront estate is positioned within one of the area’s most established waterfront corridors, just moments from historic downtown fort myers, the edison & ford winter estates, exceptional dining, nearby schools, and everyday conveniences. This is a lifestyle and location that continues to stand the test of time.
Riverside, 1337 Caloosa Dr, Fort Myers, Florida 33901, image 1
$1,950,000
  • 4 Beds
  • 41/2 Baths
  • 2,936 SqFt
  • $664/SqFt
House for sale in Riverside
1337 Caloosa Dr, Fort Myers, FL 33901
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.
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Frequently Asked Questions

The single_family_home dues at Riverside cover: None, Street Lights, , Security, Trash Removal, Water.

Riverside Riverside is a pet-friendly “Dogs and Cats OK” subdivision for both owners and tenants. Please note that pet policies may change at the discretion of management and/or the Homeowners' Association (HOA) and may not apply to renters. Restrictions may apply to certain breeds, and size and weight limits may be in place.

Riverside Interior features include: Fireplace, French Doors, Bar, Built-In Cabinets, Closet Cabinets, Custom Mirrors, Foyer, Pantry, Smoke Detectors, Wired for Sound, Volume Ceiling, Walk-In Closet(s), Wet Bar, Window Coverings, Built-In Cabinets, Fireplace, Laundry Tub, Pull Down Stairs, Vaulted Ceiling(s), Closet Cabinets, Foyer, Tray Ceiling(s), Other

Riverside unit views: Landscaped Area, Partial River, River, Water, Water Feature, River, Pool/Club, , Trees/Woods

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Scores
Walk Score®
Car-Dependent. Almost all errands require a car.
11

100
Transit Score®
Minimal Transit. It is possible to get on a bus.
0

100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure.
31

100
Sound Score®
Bearable noise.
80

100
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