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Riverside Houses For Sale

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Riverside, 1249 Osceola Dr, Fort Myers, Florida 33901, image 1
$853,000
  • 3 Beds
  • 4 Baths
  • 3,467 SqFt
  • $246/SqFt
House for sale in Riverside
1249 Osceola Dr, Fort Myers, FL 33901
Historic charm, built in 1924, well maintained as close to original build as possible with upgraded plumbing and electrical. Complete new roof is two years old with transferable warranty. 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. 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
$995,000
  • 5 Beds
  • 21/2 Baths
  • 3,572 SqFt
  • $279/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, 1350 Hanton Ave, Fort Myers, Florida 33901, image 1
$420,000
  • 2 Beds
  • 11/2 Baths
  • 1,480 SqFt
  • $284/SqFt
House for sale in Riverside
1350 Hanton Ave, Fort Myers, FL 33901
This is your opportunity to live in old fort myers most desirable neighborhood! Situated on a corner lot and surrounded by beautiful homes, each unique and interesting. Priced to make your own with its original mid century details or rebuild into your custom dream home. The neighborhood streets are lined with sidewalks and gorgeous landscape. With its old fort myers address and mcgregor to river location, this historic and charming neighborhood is like no other! A short distance via walking, bike ride or car to all of the beauty that old fort myers has to offer including the fort myers country club, edison ford winter estates and downtown river district dining, shopping, shows and festivities. Home is not in a flood zone and received no damage or flooding during hurricane ian.
Riverside, 1230 Caloosa Dr, Fort Myers, Florida 33901, image 1
$1,145,000 $230K
  • 4 Beds
  • 4 Baths
  • 3,190 SqFt
  • $359/SqFt
House for sale in Riverside
1230 Caloosa Dr, Fort Myers, FL 33901
No insurance claims-new roof- timeless elegance with modern sophistication- welcome to this breathtaking four-bedroom, four-bathroom residence nestled on coveted caloosa drive, where history and modern design harmoniously blend. This architectural gem boasts an expansive front porch perfect for capturing magnificent florida sunsets while enjoying gentle river breezes. Privacy abounds throughout the property with its rich, native landscaping and palm tree-lined setting. The thoughtfully designed interior showcases sophisticated details that honor the area's historic aesthetic while embracing contemporary comforts. The primary bedroom offers a tranquil sanctuary, complemented by three additional bedrooms and bathrooms that provides ample space for family and guests. Every corner of this home reflects meticulous attention to detail and craftsmanship. This exceptional fully remodeled property represents a rare opportunity to embrace the fort myers lifestyle at its finest. The seamless integration of indoor and outdoor living spaces creates an environment where memories will be made for years to come. Experience the magic of living in one of fort myers most desirable neighborhoods—where native beauty, architectural distinction, and modern comfort come together in perfect harmony.
Riverside, 1257 Caloosa Dr, Fort Myers, Florida 33901, image 1
$1,399,000 $50K
  • 4 Beds
  • 4 Baths
  • 3,409 SqFt
  • $410/SqFt
House for sale in Riverside
1257 Caloosa Dr, Fort Myers, FL 33901
Mcgregor 2016 built pool home in historic location! This house is a carlton naumann custom built home on the riverside of mcgregor with four spacious bedrooms, four bathrooms, a game room/den, nice screened-in lanai that looks on to a beautiful landscaped backyard and swimming pool. The pool bath has a custom steam room! Tankless water heater and water softener system! The propane tank is buried in the front lawn that runs to the pool, fireplace with custom mantle, and kitchen stove! A well was also installed for the irrigation system! Professional landscaping by sal montalvo landscape! New brick pavers and expanded driveway!
Riverside, 1219 Osceola Dr, Fort Myers, Florida 33901, image 1
$1,095,000 $100K
  • 3 Beds
  • 3 Baths
  • 2,222 SqFt
  • $493/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 $100K
  • 5 Beds
  • 5 Baths
  • 5,680 SqFt
  • $511/SqFt
House for sale in Riverside
1205 Caloosa Dr, Fort Myers, FL 33901
A masterpiece of global design where european sophistication meets eastern tranquility tucked away along the prestigious riverside mcgregor corridor, moments from the iconic edison & ford estates and the charm of historic downtown fort myers, lies an estate that redefines luxury: 1205 caloosa dr. This private riverfront residence is more than just a home, it’s a refined sanctuary, inspired by timeless european artistry and the serene grace of asian design philosophy. Every detail has been carefully curated to create an environment of elegance, wellness, and enduring quality. 5 bedrooms | 5 full baths | 3 lavish master suites crafted for both privacy and togetherness, the home features three spacious master suites, each a luxurious retreat with spa-style baths and premium finishes. The primary suite includes a deep soaking tub, walk-in shower with body sprays, and a heated bidet — combining modern indulgence with eastern inspiration. Two designer kitchens for culinary excellence two full kitchens — one on each floor — provide the perfect setting for both everyday living and lavish entertaining. Outfitted with double ovens, high-end appliances, and custom cabinetry, the main kitchen opens to the lanai, creating a seamless indoor-outdoor flow ideal for gathering and celebration. Outdoor living at its finest the solar/electric-heated saltwater pool and travertine-and-marble-clad terrace overlook the caloosahatchee river, framed by mature bamboo and tropical gardens. Soft music flows through integrated speakers, and ceiling fans cool the lanai, setting the stage for unforgettable evenings under the stars. Architectural artistry throughout custom metalwork by renowned artist james digeorgio impact-resistant windows, new roof, and concrete block construction 4-zone a/c, tankless water heater, and whole-home surround sound custom flood barrier system for peace of mind and elevated protection gated entry with a paver circular drive and centerpiece fountain that exudes elegance a spiraling statement of beauty the lanai’s spiral staircase invites you to move between spaces with the grace of eastern garden design — a touch of form and function that ties the home's beauty together from every angle. A storybook setting. A global vision. A rare offering. 1205 caloosa dr. Is a place where history, culture, and craftsmanship converge. Whether you're hosting candlelit dinners on the terrace or seeking a peaceful escape by the river, this estate offers an unmatched lifestyle of refined luxury and meaningful design. Please call today to schedule your very own personalized showing of this amazing estate home. “pickleball court in photo is virtually staged for illustration purposes only and is not part of the existing property"
Riverside, 1318 Bougainvillea St, Fort Myers, Florida 33901, image 1
$1,750,000 $145K
  • 3 Beds
  • 3 Baths
  • 3,104 SqFt
  • $564/SqFt
House for sale in Riverside
1318 Bougainvillea St, Fort Myers, FL 33901
In the prestigious historic district of fort myers, adjacent to the iconic palm tree lined mcgregor boulevard, this exquisitely constructed custom built luxury residence is a testament to modern elegance and refined living. Situated on a large spacious lot, with well over 3, 000 square ft under air, the property features 3 bedrooms, a versatile den/flex room, 3 baths, and a massive garage with room for up to 6 vehicles. At the heart of this home lies an expansive great room, drenched in natural light, which unfolds seamlessly into a state-of-the-art chef's kitchen. Here, dual full-sized ovens and a beautiful wet bar invite culinary adventures and effortless entertaining. Feel secure that this home features hurricane rated pgt impact glass throughout, a whole home backup generator, and a full security and camera system. The pool with custom upgrades and a massive pool deck, along with a lavishly equipped outdoor kitchen, further offer an idyllic setting for hosting and relaxation. Set against the backdrop of triangle park, a community-owned green space guaranteed to remain undeveloped, this property enjoys a feeling of openness and freedom rare for being so close to the liveliness of downtown. Embrace a lifestyle where luxury meets heritage, in this distinguished home that stands as a beacon of sophistication in fort myers.
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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Subdivision Amenities

Fitness Center
Guest Room
Internet Access
Sauna
See Remarks
Shopping
Sidewalk
Streetlight
Barbecue
Bike And Jog Path
Cabana
Electric Vehicle Charging
Fitness Center
Guest Room
Internet Access
None
Park
See Remarks
Shopping
Sidewalk
Streetlight

Frequently Asked Questions

The single_family_home dues at Riverside cover: None, , Street Lights, Street Maintenance, Security, Street Lights, 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: Built-In Cabinets, Closet Cabinets, Fireplace, Foyer, French Doors, Laundry Tub, Pull Down Stairs, Smoke Detectors, Vaulted Ceiling(s), Window Coverings, Fireplace, Cathedral Ceiling(s), Pantry, Walk-In Closet(s), Bar, Built-In Cabinets, Custom Mirrors, Multi Phone Lines, Wired for Sound, Volume Ceiling, Wet Bar, Closet Cabinets, Disability Equipped, Other, Foyer, Tray Ceiling(s), Custom Mirrors, Pantry, Coffered Ceiling(s)

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

Scores

Walk Score®

Car-Dependent. Almost all errands require a car.

11

100

Transit Score®

No data.

N/A

Bike Score®

Somewhat Bikeable. Minimal bike infrastructure.

31

100

Sound Score®

Bearable noise.

80

100

Fort Myers
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