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Fort Myers, FL 33901

Riverside Houses For Sale

Q: What is included in the Riverside monthly association dues?

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

Q: What are Riverside Pet Policies & Restrictions?

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.

Q: What are the interior features of the residences?

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, Other, Tray Ceiling(s), Coffered Ceiling(s), Cathedral Ceiling(s)

Q: What are the available unit views from Riverside?

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

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Results 7 of 7

Riverside, 1249 Osceola Dr, Fort Myers, Florida 33901, image 1

Riverside, 1249 Osceola Dr, Fort Myers, Florida 33901, image 2

Riverside, 1249 Osceola Dr, Fort Myers, Florida 33901, image 3

$881,000

3 Beds
4 Baths
3,467 SqFt
$254/SqFt

House for sale in Riverside1249 Osceola Dr, Fort Myers, FL 33901

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 Remember this is a 100-year-old home, antique homes are known for lack of closet space, kitchen is outdated as well, all bedrooms are upstairs.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

Riverside, 1357 Osceola Dr, Fort Myers, Florida 33901, image 1

Riverside, 1357 Osceola Dr, Fort Myers, Florida 33901, image 2

Riverside, 1357 Osceola Dr, Fort Myers, Florida 33901, image 3

$999,000 $75K

5 Beds
3¹/₂ Baths
3,928 SqFt
$254/SqFt

House for sale in Riverside1357 Osceola Dr, Fort Myers, FL 33901

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.

Riverside, 1215 Caloosa Dr, Fort Myers, Florida 33901, image 1

Riverside, 1215 Caloosa Dr, Fort Myers, Florida 33901, image 2

Riverside, 1215 Caloosa Dr, Fort Myers, Florida 33901, image 3

$885,000

4 Beds
2¹/₂ Baths
3,259 SqFt
$272/SqFt

House for sale in Riverside1215 Caloosa Dr, Fort Myers, FL 33901

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.

Riverside, 1299 Plumosa Dr, Fort Myers, Florida 33901, image 1

Riverside, 1299 Plumosa Dr, Fort Myers, Florida 33901, image 2

$1,495,000

4 Beds
4 Baths
5,492 SqFt
$272/SqFt

House for sale in Riverside1299 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, 1205 Caloosa Dr, Fort Myers, Florida 33901, image 1

Riverside, 1205 Caloosa Dr, Fort Myers, Florida 33901, image 2

Riverside, 1205 Caloosa Dr, Fort Myers, Florida 33901, image 3

$2,080,000 $305K

5 Beds
5 Baths
5,680 SqFt
$366/SqFt

House for sale in Riverside1205 Caloosa Dr, Fort Myers, FL 33901

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.

Riverside, 1248 Osceola Dr, Fort Myers, Florida 33901, image 1

Riverside, 1248 Osceola Dr, Fort Myers, Florida 33901, image 2

$1,354,000

6 Beds
3 Baths
3,582 SqFt
$378/SqFt

House for sale in Riverside1248 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 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.

Riverside, 1219 Osceola Dr, Fort Myers, Florida 33901, image 1

Riverside, 1219 Osceola Dr, Fort Myers, Florida 33901, image 2

Riverside, 1219 Osceola Dr, Fort Myers, Florida 33901, image 3

$895,000 $100K

3 Beds
3 Baths
2,222 SqFt
$403/SqFt

House for sale in Riverside1219 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.

3 to 6 BR

Bedrooms

$881K to $3.3M

Price Tier

1,379 - 8,677

SqFt Range

1953

Year Build

Total Floors

Subdivision Amenities

Fitness Center

Guest Room

Internet Access

See Remarks

Shopping

Sidewalk

Streetlight

Bike And Jog Path

Fitness Center

Internet Access

None

Park

Sidewalk

Streetlight

Frequently Asked Questions

What is included in the Riverside monthly association dues?

What are Riverside Pet Policies & Restrictions?

What are the interior features of the residences?

What are the available unit views from Riverside?

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Ekos On Evans

Condos in Fort Myers, FL 33901

Units
144
Stories
3

Experience the perfect combination of style, comfort, and convenience at our new pet-friendly affordable housing community in Fort Myers, FL. Offering modern one, two, and three-bedroom apartment homes with sleek finishes and exceptional amenities—including a pool, covered porch, grill area, playground, and dog park—our community is designed to fit your lifestyle in the heart of where you want to be. EKOS on Evans is an affordable housing community subject to income limitations.

Details

Monarch Luxury Apartments

Condos in Fort Myers, FL 33916

Units
472
Stories
3

Welcome to Monarch Luxury Apartments, a new community in Fort Myers, Florida, designed for those who value style, comfort, and elevated everyday living. With thoughtfully designed residences and high-end amenities, Monarch offers a refined apartment lifestyle in a private, gated setting.

Our luxury apartments in Fort Myers feature open-concept floor plans with 9-foot ceilings, large windows, and modern finishes throughout. Chef-inspired kitchens include quartz countertops, custom cabinetry, tiled backsplashes, center islands, and premium stainless steel appliances. Full-size washers and dryers, smart thermostats, luxury vinyl plank flooring, and designer lighting bring convenience and sophistication home.

Beyond your front door, Monarch delivers resort-style amenities designed to fit your lifestyle. Stay active in the expansive fitness center, unwind at the zero-entry saltwater pool with cabanas, or enjoy social spaces including coworking lounges, a golf and multi-sport simulator, and a resident clubhouse. A dog park, pet spa, EV charging stations, private garages, and elevator access add ease to daily living.

Discover Monarch Luxury Apartments—where modern design, upscale amenities, and luxury apartments in Fort Myers come together.

Details

ONE Fort Myers

Condos in Fort Myers, FL 33901

Starts at
$1.3M
Units
34
Stories
21

Throughout Fort Myers, our waterfront condominiums redefine what is possible for everyday life. With upscale amenities comparable to some of the world’s top resorts, ONE raises the bar as the only true boutique high‐rise in Fort Myers.

Community Amenities

With everything you need all in our brilliantly designed Fort Myers high‐rise, the only difficulty about life at ONE is leaving. All the while, the exclusivity of ONE means that sharing amenities is exceedingly rare. Here are the resort‐caliber amenities you can expect:

Concierge services
Heated infinity edge pool with a cascading waterfall
Rejuvenating Whirlpool spa
Riverside Beach area with Cabanas
Expansive pool deck with shaded lounge chairs and cabanas
Cozy and inviting fire pits
Chef‐inspired cabana BBQ
State‐of‐the‐art fitness center and virtual on‐demand classes
Riverfront wellness center
High‐speed Wi‐Fi in all common areas
Convenient mail room and parcel receiving station
Private riverfront kayak launch area and secure kayak storage
Oversized, air‐conditioned storage space on the same floor
Professional pet grooming center and pet spa
Spacious private owners lounge and Owner’s Club Room
Newly built to the latest codes and safety standards
All within the renowned Downtown River District

Interior Features

Each luxury condo at ONE is designed with a modern yet inviting aura that instills calmness into each day. Coupled with the riverfront views, these exquisite interiors provide a ONE‐in‐a‐million lifestyle unlike traditional Southwest Florida luxury condominiums.

Only 34 exclusive condominiums available
Private entrance elevator to the unit foyer
Premium Viking appliance package with gas cooktop in a chef‐inspired kitchen
High ceilings with expansive windows facing the riverfront for breathtaking views
Designer finishes and lighting
Quartz solid surface backsplash
European‐style cabinetry and under‐cabinet lighting
Quartz waterfall kitchen island
Smart technology integration
Glass walk‐in showers with free‐standing designer tubs in primary bathrooms
His and her vanities per floor plan/ layout in primary suites
Expansive private balconies with glass railing for uninterrupted vistas
Large format tile floors and wet walls
Central hot water boiler for a nearly instant continuous hot water supply
2 assigned garage parking spots with 24‐hour controlled access
Individual Electric Vehicle Charging capability at your assigned parking spots
And beyond

Details

The Riley Apartments

Condos in Fort Myers, FL 33908

Units
275
Stories
4

Live the good life at The Riley

The Riley is more than just a residence, it’s a destination. Located near Estero, we embrace a serene way of thinking which makes each day feel special. Welcome in relaxation while you dip your toes in our resort-style pool. Appreciate the local gems around you with convenient access to renowned beaches, a variety of shops, one-of-a-kind restaurants, and entertainment. Invite tranquility to your home in our 1, 2, 3 bedroom apartments and let easy living be a way of life. Make yourself at home when you live at The Riley.

Life at The Riley is tailored with you in mind. Our emphasis on a carefree and luxurious lifestyle leaves you feeling at ease. We go beyond the expected standard by focusing on details woven throughout our space to elevate your sanctuary. We keep quality top of mind so you can enjoy making the most of the place you call home. From our contemporary finishes to our elegant kitchens and unmatched amenities, see why life at The Riley means an open door to laid back living.

Details