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Fort Myers, FL 33901
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Riverside Houses Sold

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Sold - Oct 20, 2026
Riverside, 1357 Osceola Dr, Fort Myers, Florida 33901, image 1
$915,000$235K
  • 5 Beds
  • 31/2 Baths
  • 3,928 SqFt
  • $233/SqFt
Entry-Level
House sold in Riverside
1357 Osceola Dr, Fort Myers, FL 33901
Listing Courtesy Of: RE/MAX Trend
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.
Sold - Oct 1, 2026
Riverside, 1215 Caloosa Dr, Fort Myers, Florida 33901, image 1
$835,000$50K
  • 4 Beds
  • 21/2 Baths
  • 3,259 SqFt
  • $256/SqFt
Entry-Level
House sold in Riverside
1215 Caloosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Riverside Realty Group, LLC
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.
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Sold - Sep 30, 2026
Riverside, 3235 Avocado Dr, Fort Myers, Florida 33901, image 1
$875,000$50K
  • 5 Beds
  • 31/2 Baths
  • 3,572 SqFt
  • $245/SqFt
Entry-Level
House sold in Riverside
3235 Avocado Dr, Fort Myers, FL 33901
Listing Courtesy Of: Kingfisher Real Estate, Inc.
Imagine owning a true piece of fort myers history. Built in 1922 during the same storied era as the iconic edison estate, this remarkable mcgregor boulevard residence is believed to be the third grand home built along one of fort myers’ most recognized corridors. Set on nearly a full acre of beautifully established grounds, this one-of-a-kind property offers a rare combination of historic character, generous space, and modern updates. The main residence showcases the warmth and craftsmanship of another era, including original heart pine floors and a gracious layout designed for both everyday living and entertaining. With five spacious bedrooms, two full bathrooms, and a guest half bath, the home provides plenty of room for family, guests, a home office, or flexible living spaces. A new roof installed in 2023 adds an important update while preserving the integrity and charm of this historic residence. Adding even more versatility is a separate efficiency unit with a full bathroom, ideal for overnight guests, extended family, a private workspace, or potential rental income. Outside, the expansive property offers room to enjoy the florida lifestyle while maintaining a sense of privacy rarely found this close to the heart of fort myers. The grounds have also remained high and dry, adding another valuable feature to this exceptional property. More than a home, this is an opportunity to own and preserve a piece of fort myers heritage. With its distinctive history, original architectural character, spacious homesite, and flexible living options, this mcgregor boulevard estate is ready for its next chapter.
Sold - Sep 24, 2026
Riverside, 1299 Plumosa Dr, Fort Myers, Florida 33901, image 1
$1,270,000$225K
  • 4 Beds
  • 4 Baths
  • 5,492 SqFt
  • $231/SqFt
Entry-Level
House sold in Riverside
1299 Plumosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Cornerstone Coastal Properties
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!
Sold - Jul 30, 2026
Riverside, 3402 Riverside Dr, Fort Myers, Florida 33901, image 1
$4,100,000$650K
  • 5 Beds
  • 52/2 Baths
  • 8,173 SqFt
  • $502/SqFt
Entry-Level
House sold in Riverside
3402 Riverside Dr, Fort Myers, FL 33901
Listing Courtesy Of: Royal Shell Real Estate, Inc.
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.
Sold - Mar 9, 2026
Riverside, 1230 Caloosa Dr, Fort Myers, Florida 33901, image 1
$1,050,000$475K
  • 4 Beds
  • 4 Baths
  • 3,190 SqFt
  • $329/SqFt
Entry-Level
House sold in Riverside
1230 Caloosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: LSI Companies Inc.
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.
Sold - Oct 9, 2025
Riverside, 1263 Caloosa Dr, Fort Myers, Florida 33901, image 1
$735,000$110K
  • 4 Beds
  • 4 Baths
  • 3,042 SqFt
  • $242/SqFt
Entry-Level
House for sale in Riverside
1263 Caloosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Royal Shell Real Estate, Inc.
Timeless elegance in the heart of olde mcgregor nestled between mcgregor boulevard and the caloosahatchee river, this residence offers over 3, 000 square feet of living area in one of fort myers’ most coveted neighborhoods. Located on an oversized 0.31-acre lot, this home blends space, comfort, and timeless charm just minutes from the historic downtown district. With 4 bedrooms and 4 full bathrooms—including master suites on both levels—this thoughtfully designed home is ideal for multi-generational living or hosting guests with ease and privacy. The split floor plan offers a seamless flow through open living areas, formal and informal dining spaces, and a well-appointed kitchen with granite countertops and a built-in pantry. Roof replaced in 2021. Well and sprinkler system too. Step outside to your own private retreat: a large, screened-in pool area perfect for entertaining, relaxing, or soaking up the florida sunshine. The expansive yard invites quiet moments or lively gatherings. The neighborhood offers the comfort of a vibrant, sidewalk-lined community with streetlights and a true neighborhood feel. Interior highlights include elegant crown molding, a cozy fireplace, impact-resistant windows, doors, and sliders (with the exception of the florida room’s glass panels), and a welcoming front porch sitting area. The convenience of an indoor laundry room and thoughtful details throughout add to the home’s appeal. Enjoy morning strolls or golf cart rides to local favorites, with top restaurants, shops, and cultural attractions just minutes away. Golfers will love the proximity to fort myers country club, while downtown’s vibrant arts and dining scene is within easy reach. Mcgregor boulevard isn't just an address—it’s a lifestyle. Don't miss the chance to experience it for yourself. Be sure to tour this one-of-a-kind home before making your buying decision.
Sold - Aug 29, 2025
Riverside, 1235 Osceola Dr, Fort Myers, Florida 33901, image 1
$635,000$85K
  • 3 Beds
  • 3 Baths
  • 2,006 SqFt
  • $317/SqFt
Entry-Level
House for sale in Riverside
1235 Osceola Dr, Fort Myers, FL 33901
Listing Courtesy Of: Sellstate Achievers Realty
Welcome to 1235 osceola drive, a beautifully renovated 3-bedroom, 3-bathroom home nestled in the highly sought-after and historic old mcgregor neighborhood of fort myers. Just minutes from the fort myers golf course and vibrant downtown, this home blends timeless charm with modern updates. This home has never flooded and comes with transferable below-market flood insurance policy—a standout feature in this region. Renovated in 2021, the home features a smart and functional layout with two separate living areas, and a centrally located kitchen and dining space, ideal for both everyday living and entertaining. Each of the three bedrooms includes its own en-suite bathroom, providing ultimate privacy and comfort. Relax in the main living room by the gas fireplace, and enjoy year-round peace of mind with impact-resistant windows and doors, a new roof (2022), and a water heater replaced in 2023. The detached bonus room with electricity offers flexible potential as a home office, storage space, or pool house. Outside, a barrier-fenced pool ensures safety for families with small children, and a lovely mango tree adds natural charm to the front yard. For ev drivers, the attached single-car garage includes a pre-installed electric car wall charger, making it fully move-in ready for electric or hybrid vehicles. Don’t miss this rare opportunity to own a renovated, move-in-ready home in one of fort myers’ most cherished neighborhoods—schedule your private showing today!
Sold - Oct 23, 2024
Riverside, 1350 Hanton Ave, Fort Myers, Florida 33901, image 1
$375,000
  • 2 Beds
  • 11/2 Baths
  • 1,480 SqFt
  • $253/SqFt
Entry-Level
House for sale in Riverside
1350 Hanton Ave, Fort Myers, FL 33901
Listing Courtesy Of: Cornerstone Coastal Properties
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, 1281 Caloosa Dr, Fort Myers, Florida 33901, image 1
$635,000$40K
  • 3 Beds
  • 2 Baths
  • 2,298 SqFt
  • $276/SqFt
Entry-Level
House for sale in Riverside
1281 Caloosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Realty Rents and Sales, LLC
Location, location, location! This home boasts 2298 sqft on an oversized lot with almost 0.43 acres on one of the most desirable streets in old fort myers! As you drive down the palm tree lined street towards the caloosahatchee river, you can feel the beauty of this neighborhood. As you enter the home, the open living area has a stunning wood burning fireplace which is the perfect place to sit and enjoy a book. The updated kitchen has white shaker cabinetry, 48" built in pantry, limestone countertops and stainless steel appliances with a wet bar that can be used as a separate prep area. The rear den allows for a separate living space and the huge family room would be a perfect game room with large windows overlooking the expansive fenced in back yard. Here you will find an open patio, fire pit, large mature trees and plenty of space for a pool and a detached garage and guest house. The possibilities are endless! The carport on the side of the 1 car garage has a large gate to allow access to the backyard for trailer or boat storage. The bedrooms have original oak flooring adding to the charm of this mid-century home. Fresh interior and exterior paint in june of 2024, roofs were replaced in 2013, ac replaced in 2019, bathrooms and kitchen were updated in 2018, new blown in insulation in 2019, new garage door in 2024 and chimney serviced in 2019. Flood zone x, no hoa, no cdd! Don't wait and schedule your private showing today! Houses here don't last long!
Sold - Jul 26, 2024
Riverside, 1257 Caloosa Dr, Fort Myers, Florida 33901, image 1
$1,200,000$100K
  • 4 Beds
  • 4 Baths
  • 3,409 SqFt
  • $352/SqFt
Entry-Level
House for sale in Riverside
1257 Caloosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Bay Vision Realty
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!
Sold - Jun 14, 2024
Riverside, 1318 Bougainvillea St, Fort Myers, Florida 33901, image 1
$1,550,000$145K
  • 3 Beds
  • 3 Baths
  • 3,104 SqFt
  • $499/SqFt
Entry-Level
House for sale in Riverside
1318 Bougainvillea St, Fort Myers, FL 33901
Listing Courtesy Of: John R Wood Properties
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.
Sold - Apr 5, 2024
Riverside, 3427 Avocado Dr, Fort Myers, Florida 33901, image 1
$345,000
  • 0.3 Acres
  • $1,150,000/Acre
Entry-Level
Land for sale in Riverside
3427 Avocado Dr, Fort Myers, FL 33901
Listing Courtesy Of: Coldwell Banker Realty
Situated in the highly desirable mcgregor corridor of fort myers, this cleared lot is 0.30 acres and offers tremendous potential. Lined with royal palms and running alongside the caloosahatchee river, mcgregor blvd offers history, charm and convenience. Whether you're having lunch with friends in the downtown historic river district, visiting the edison and ford winter estates, or playing 18 holes at the fort myers country club, avocado drive is at the heart of some of fort myers' most sought-after destinations. This residential lot is ready for your vision - see it today! Survey and architectural drawings available.
Sold - Nov 30, 2023
Riverside, 3421 Riverside Dr, Fort Myers, Florida 33901, image 1
$730,000
  • 3 Beds
  • 2 Baths
  • 2,159 SqFt
  • $338/SqFt
Entry-Level
House for sale in Riverside
3421 Riverside Dr, Fort Myers, FL 33901
Listing Courtesy Of: DomainRealty.com LLC
This charming home is located on the river side of mcgregor blvd in the highly coveted riverside park neighborhood of ft myers. You will immediately appreciate the open floor plan and the abundance of natural light that illuminates the spacious main living areas. The cozy fireplace adds to the home's charm. The kitchen is fully equipped with beautiful granite countertops and plenty of cabinet space for all your storage needs. The newly remodeled owner's suite is a luxurious retreat with a large en-suite bathroom and a walk-in closet. The split floor plan with 2 additional bedrooms & a bath is perfect for children & guests. The abundant outdoor living space features a pool with tanning ledge, a spacious covered lanai and extended pavers, the fully fenced backyard is a private oasis surrounded by mature native plants and fruit trees. Residents of the charming neighborhood enjoy walking to places like ft myers country club, mcgregor cafe, edison and ford winter estates. This home offers many upgrades, including a new roof, ac, water heater, pool heater, washer, dryer, outdoor screens, new fencing, fresh paint inside and outside, flooring, pool resurfacing & underground utilities.
Sold - Jun 23, 2023
Riverside, 3232 Mcgregor Blvd, Fort Myers, Florida 33901, image 1
$1,200,000
  • 4 Beds
  • 31/2 Baths
  • 4,134 SqFt
  • $290/SqFt
Entry-Level
House for sale in Riverside
3232 Mcgregor Blvd, Fort Myers, FL 33901
Listing Courtesy Of: Caloosa Realty Group LLC
Restoration done the right way in this 1925 mcgregor boulevard beauty. 3232 mcgregor has so much charm and character yet still offers the most updated and modern features that todays homeowners seek. Fantastic location as 3232 mcgregor sits in one of the most desirable neighborhoods off mcgregor. Features of the main home include partial impact glass windows, a subzero refrigerator in a very spacious and open kitchen, screened in heated pool and spa, beautiful hard wood floors, fireplace, third floor bonus room, large front porch, and outdoor fireplace. The guest house features its own temperature controlled wine room, huge kitchen with island, bathroom that could double as a pool bath, and living area.
Sold - May 31, 2023
Riverside, 1225 Osceola Dr, Fort Myers, Florida 33901, image 1
$1,350,000
  • 5 Beds
  • 4 Baths
  • 3,546 SqFt
  • $381/SqFt
Entry-Level
House for sale in Riverside
1225 Osceola Dr, Fort Myers, FL 33901
Listing Courtesy Of: Cornerstone Coastal Properties
This beautiful 2 story family home is located in the highly desirable neighborhood of riverside in old fort myers. Showcasing 5 full bedrooms, 4 baths, an impressive great room with 20' ceilings, living room, upstairs family room, 2 dining areas, breakfast bar plus an office/guest room! The great room ties the kitchen & family room together while overlooking an exterior covered patio & pool. A generous master suite offset from the rest of the house for privacy has pool access & includes a sitting area, 2 walk in closets, tub, shower & double vanity. The second level with a double landing staircase resides 4 bedrooms, 2 baths and a very special cozy & functional family/tv area which overlooks the great room. Natural light flows throughout this home from every point. Special features of the home include an "abundance of storage", wood floors thru-out including gorgeous new hickory wood floors upstairs, built-ins in all closets, keyless entries from exterior, 2 new a/c units, 1 a little less new, heated pool, new pvc fencing, metal roof 2018, gorgeous leaded glass front door, 80 gal. Hw heater, dbl garage with overhead storage racks, & last but not least, all new zen-like & calming landscaping.
Sold - Apr 3, 2023
Riverside, 3402 Riverside Dr, Fort Myers, Florida 33901, image 1
$3,695,000
  • 4 Beds
  • 52/2 Baths
  • 8,677 SqFt
  • $426/SqFt
Entry-Level
House for sale in Riverside
3402 Riverside Dr, Fort Myers, FL 33901
Listing Courtesy Of: Royal Shell Real Estate, Inc.
Riverfront! Over 140 feet of river frontage. This magnificent 8, 677 sq.Ft. Riverfront estate home offers the pinnacle of waterfront living on the banks of the caloosahatchee river. Light and bright open floor plan with soaring ceilings features formal living & dining rooms, 4 bedroom suites, 2 half baths, family room with fireplace, den, spacious state of the art kitchen with walk in pantry. There is a dedicated sound proof room to enjoy playing your favorite music. An expansive lanai with pool, two boat docks, and spectacular river views. Exceptional features, upgrades and finishes through out including hurricane resistant windows and doors, newer roof, granite countertops, security system. 4 car garage with plenty of room for storage. Luxury living at it's finest. Family privacy yet spacious rooms for entertaining. All designed to take full advantage of florida's enjoyable year round climate sure to provide years of enjoyment and memories for your family and friends. Located in the historic fort myers river district and minutes to downtown area with restaurants and shops.
Sold - Jan 6, 2023
Riverside, 1222 Caloosa Dr, Fort Myers, Florida 33901, image 1
$1,355,000
  • 4 Beds
  • 3 Baths
  • 2,419 SqFt
  • $560/SqFt
Entry-Level
House for sale in Riverside
1222 Caloosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Cornerstone Coastal Properties
In old fort myers riverside neighborhood, you'll find this moroccan inspired residence that pays tribute to classical spanish architecture while evoking modern lifestyle. This beautiful landmark home and separate fully equipped guest house with bedroom, bath, kitchen and studio is perfect for guests. This architecturally stunning home and magnificent grounds with period designed heated pool will captivate your senses. From the moment you step on the grounds you will know that every update and restoration was executed to perfection. Some of this home's many attributes include impact doors and windows, original moldings and millwork, original hardwood floors, fireplace, private outdoor heated shower, underground utilities, cost saving solar energy panels and more. This perfectly restored vintage home captures resort style living in an enchanting setting. A complete list of features, upgrades and restorations available upon request. Must see to fully appreciate!
Riverside, 1356 Bougainvillea St, Fort Myers, Florida 33901, image 1
$1,790,000
  • 4 Beds
  • 3 Baths
  • 3,251 SqFt
  • $551/SqFt
Entry-Level
House for sale in Riverside
1356 Bougainvillea St, Fort Myers, FL 33901
Listing Courtesy Of: Caloosa Realty Group LLC
Photos are post storm photos. Newer home on a wonderful street off of mcgregor. 1356 bougainville sits in the middle of one of the most desirable neighborhoods off of mcgregor. Features of this home include a wonderful and spacious floorplan with a large covered lanai, heated pool and spa, private fenced backyard, whole house generator, impact glass windows, side entry 3 car garage, gas range, large study/den, temperature controlled wine cellar located off the garage. This home did not sustain any known damage or had any water intrusion.
Riverside, 1337 Caloosa Dr, Fort Myers, Florida 33901, image 1
$400,000
  • 3 Beds
  • 2 Baths
  • 1,848 SqFt
  • $216/SqFt
Entry-Level
House for sale in Riverside
1337 Caloosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Royal Shell Real Estate, Inc.
Location, location -heart of ole fort myers between mcgregor blvd and the river. A golf cart ride to downtown fort myers or a round of golf at fort myers country club. A park like setting is directly across the street and the neighborhood boasts sidewalks. This custom built home is a true original and has several interesting feature - beam ceilings and a fireplace. Tile floors and parquet flooring underneath carpet in the living room. Please take a look at this home before making a buying decision.
Riverside, 1368 Hanton Ave, Fort Myers, Florida 33901, image 1
$375,000
  • 2 Beds
  • 1 Baths
  • 1,379 SqFt
  • $272/SqFt
Entry-Level
House for sale in Riverside
1368 Hanton Ave, Fort Myers, FL 33901
Listing Courtesy Of: Coldwell Banker Realty
Here is a great opportunity to build your own dream home on an oversized corner lot in the historic mcgregor corridor. This house and lot is situated 1.5 miles from the edison ford estates and is a short two block walk to the caloosahatchee river. Walking distance to fort myers country club. Excellent public and private schools in this family orientated, walkable neighborhood. Also close to trendy downtown fort myers restaurants, events, marinas and more. Build your own home in this desirable neighborhood with historic home(s) across the street and newly built multi million dollar homes around the corner. Not often do lots this size become available in this neighborhood as families don't want to leave! Enjoy all of the splendor of this neighborhood just a half block off of palm tree lined mcgregor blvd. This won't last long! Drive the neighborhood and see what it's all about. You will want to call this home! This home is being sold for lot value only. Home has not been lived in for years and is in disrepair.
Riverside, 3284 Avocado Dr, Fort Myers, Florida 33901, image 1
$475,000
  • 3 Beds
  • 3 Baths
  • 2,584 SqFt
  • $184/SqFt
Entry-Level
House for sale in Riverside
3284 Avocado Dr, Fort Myers, FL 33901
Listing Courtesy Of: Keller Williams Elite Realty
Price reduced! You'll love the river district of fine homes and estates! This is a historical home by age, but not a registered historical home so the new buyers is not locked into historical home building codes! The old florida lifestyle of the past * 2540 sq ft historical home * built in 1925 * brick, stone , wood construction * 3 bedroom *3 full baths * huge front porch * living room with fireplace * family room * original built in cabinets * lots of windows * hardwood floors * lots of fruit trees * original red brick driveway * out building / work shop *corner lot * newer roof * structural engineering improvements * expanded front porch * fort myers river district of fine homes & estates . Call today to schedule your very own personalized tour.
Riverside, 1299 Plumosa Dr, Fort Myers, Florida 33901, image 1
$1,750,000
  • 4 Beds
  • 4 Baths
  • 5,492 SqFt
  • $319/SqFt
Entry-Level
House for sale in Riverside
1299 Plumosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Cornerstone Coastal Properties
Old fort myers - exquisite landmark estate designed by renowned architect bruce gora. This stunning property situated on an oversize .67 acre corner lot that features a very spacious floor plan with 4br/4ba. An impressive entry welcomes you to a grand living room, well appointed kitchen, informal dining and family room and a gracious formal dining room as well. The bedrooms are all large and feature luxuriously appointed baths. The kitchen has been tastefully updated with new cabinetry and high-end appliances. The outdoor spaces are stunning. Whether looking out the front at the gorgeous meticulously maintained front with impressive mature landscaping or in the rear of the home you will find an inviting veranda perfect for entertaining with a beautiful gazebo and tranquil koi pond. All of the systems of this home have been thoughtfully planned and update as needed including: 40kw generator, impact windows and doors, 3-zone ac, and much more! Located on a sought after old fort myers street between mcgregor and the river this showplace offers everything one would desire!
Riverside, 1249 Osceola Dr, Fort Myers, Florida 33901, image 1
$887,500$8K
  • 3 Beds
  • 3 Baths
  • 3,467 SqFt
  • $256/SqFt
Entry-Level
House for sale in Riverside
1249 Osceola Dr, Fort Myers, FL 33901
Listing Courtesy Of: LISTWITHFREEDOM.COM
This home has stood proudly for 100 years on osceola drive. Quality build craftsman, never any water intrusion from the storms. You will love this location! Great neighborhood, sidewalks! Close to downtown. Many consider between gasparilla & caloosa drive on the riverside of mcgregor to be one of the best locations in fort myers. Well, preserved to its original 1924 build, with updated plumbing and electrical. Brand new roof! A beautiful canvas of originality. The home is located in one of the best locations in fort myers. Priced to leave plenty of room for the astute buyer to put their personal touches and signature on this home or keep it as is. For those that love the beauty of originality, 100-year-old homes that have been maintained have a warmth and beauty that is priceless. Room for a pool. The full guest house with living room, dining room and one bath is an added bonus with many possible uses, two car garage and room for parking an rv or boat. This home is unique in many ways. The home is featured in pam miners book, 'river & road' chapter one.. This is a unique home for that unique buyer. A home that needs to be cherished. Location, location.
Riverside, 1318 Bougainvillea St, Fort Myers, Florida 33901, image 1
$1,999,999
  • 3 Beds
  • 21/2 Baths
  • 3,104 SqFt
  • $644/SqFt
Entry-Level
House for sale in Riverside
1318 Bougainvillea St, Fort Myers, FL 33901
Listing Courtesy Of: Premier Sotheby's Int'l Realty
Attention discerning homebuyers: envision the potential of elevating this already expansive home with a newly introduced conceptual floor plan for a garage conversion, offering the opportunity for a fourth bedroom addition. If you have been craving the best life for you and the family, this stunning house is just for you. A luxurious new construction in the historic district of fort myers off mcgregor boulevard. On an oversized lot, this three-bedroom plus den, 2.5-bath home with expansive outdoor living is a one-of-a-kind custom gem. The great room floor plan is filled with natural light and open to the chef’s kitchen complete with two full-size ovens and wet bar. The custom pool is what you need to relax and enjoy time with family and friends. The expansive outdoor living also has a kitchen and patio area plumbed for a gas fire pit. Plenty of space for you and guests to stretch out. The home is across from triangle park owned by the community and will never be developed to remain part of this home’s gorgeous views. This is a custom-built home for a family that took a new job before completion and not a typical spec house. Luxury appliances, upgrades and extra details are what make this new construction close to downtown such a gem in the historic neighborhood everyone knows and loves. Schedule a showing to see for yourself. Don't miss watching the video tour.
Riverside, 1249 Osceola Dr, Fort Myers, Florida 33901, image 1
$895,000
  • 3 Beds
  • 4 Baths
  • 3,467 SqFt
  • $258/SqFt
Entry-Level
House for sale in Riverside
1249 Osceola Dr, Fort Myers, FL 33901
Listing Courtesy Of: Flatfee.com
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. Most historic homes have been altered and changed many times over the years, this home has been kept and maintained as original as possible. Hence the new owner with have an original canvas to work with. Keep as is, or? 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, 1215 Caloosa Dr, Fort Myers, Florida 33901, image 1
$885,000$210K
  • 4 Beds
  • 21/2 Baths
  • 3,259 SqFt
  • $272/SqFt
Entry-Level
House for sale in Riverside
1215 Caloosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Riverside Realty Group, LLC
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, 1222 Caloosa Dr, Fort Myers, Florida 33901, image 1
$304,990
  • 4 Beds
  • 2 Baths
  • 1,580 SqFt
  • $193/SqFt
  • $99/mo HOA
Entry-Level
House for sale in Riverside
1222 Caloosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Pulte Realty Inc
Riverside, 1229 Plumosa Dr, Fort Myers, Florida 33901, image 1
$3,300,000
  • 6 Beds
  • 6 Baths
  • 6,041 SqFt
  • $546/SqFt
Entry-Level
House for sale in Riverside
1229 Plumosa Dr, Fort Myers, FL 33901
Listing Courtesy Of: Royal Shell Real Estate, Inc.
Welcome to an extraordinary custom-built mediterranean estate in the heart of fort myers, just one block from the caloosahatchee river and ideally situated off the iconic mcgregor boulevard. This private tropical oasis offers over 6, 000 square feet of air-conditioned living space—including a separate ground-level guest suite—and more than 12, 600 total square feet of exceptional indoor and outdoor living. Meticulously maintained and continuously updated, this residence showcases superior craftsmanship with soaring ceiling heights from 10 to 22 feet, highlighted by custom coffered and tray ceilings throughout and enhanced by elegant indirect lighting and beautifully appointed fixtures. Travertine flooring and rich hardwood floors create a seamless blend of warmth and sophistication. The gourmet kitchen is designed to impress, featuring a sub-zero refrigerator, walk-in pantries, wine cooler, and a dedicated bourbon room—perfect for entertaining. A charming reading nook adds character, while expansive living spaces flow effortlessly into a media room and multiple en-suite guest accommodations. The home offers six bedrooms and six bathrooms, including two luxurious primary suites. Step outside into your own resort-style retreat. The custom heated pool is a true work of art, featuring cascading rock waterfalls, a sun ledge, and exquisite marble inlays commissioned from an australian artist. Surrounded by lush landscaping and complete privacy, the courtyard creates a serene and secluded setting. Motorized screened lanais allow for year-round enjoyment while keeping insects at bay. Additional highlights include: • detached 3-car garage with over 1, 000 sq ft air-conditioned space • separate ground-level guest suite for privacy and flexibility • hurricane-impact, energy-efficient glass throughout • state-of-the-art security camera system • outdoor kitchen and grilling area • pergola with hammock and multiple covered patios and decks • over 1, 000 sq ft front porch living space • rv parking with hookup + tesla charging station • hunter douglas shades and plantation shutters throughout • spa-inspired primary bath with multiple shower heads and body sprayers this one-of-a-kind estate offers the perfect combination of luxury, privacy, and functionality in one of fort myers’ most sought-after locations. Furnishings are negotiable, providing a rare turnkey opportunity. Experience elevated coastal living in a private tropical sanctuary just moments from the river.
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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

HOA Cost Benchmark

$0.06 / Sq.Ft.

Monthly ownership cost
↓25%below peers
↓74%below city avg
This Community
$0.06
Comparable Mid-Tier Avg
$0.08
Fort Myers, FL Avg
$0.23
$0.00
$0.15
$0.30
Lower than peers, lower than the city average
Peer Set · 11 comparable communities
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Preconstruction in Fort Myers

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Ekos On Evans
Ekos On Evans
Ekos On Evans
Condos
  • 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
Monarch Luxury Apartments
Monarch Luxury Apartments
Condos
  • 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
ONE Fort Myers
ONE Fort Myers
Condos
  • 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
The Riley Apartments
The Riley Apartments
Condos
  • 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

Nearby Subdivisions

Entry-Level
River Garden
0.10 miles
For Sale (N/A)
$0 - $0
Premium
Phillips 4th Division
0.30 miles
For Sale (2)
$2.3M - $13.3M
Entry-Level
Valencia Terrace
0.37 miles
For Sale (3)
$515K - $1.1M
For Rent (1)
$10K - $10K
Entry-Level
McGregor Estates
0.38 miles
For Sale (2)
$475K - $490K
Entry-Level
Allen Park
0.39 miles
For Sale (N/A)
$0 - $0
For Rent (1)
$2K - $2K

Schools

Scores

Walk Score®
Car-Dependent. Almost all errands require a car
12
100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure
31
100
Sound Score®
Bearable noise
79
100
Airport Score
Close to airports. Noticeable airport activity
0
100
Traffic Score
Congested area. Frequent traffic delays
26
100
Local Score
Limited local amenities nearby
0
100

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Broker reciprocity logoLocal Realty Service Provided By: Hyperlocal Advisor. Information deemed reliable but not guaranteed. Information is provided, in part, by Greater Miami MLS & Beaches MLS. This information being provided is for consumer's personal, non-commercial use and may not be used for any other purpose other than to identify prospective properties consumers may be interested in purchasing.

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