Riverside Real Estate, Homes, Condos for Sale in Fort Myers, FL

4 Beds ⋅ 2.5 Baths ⋅ 2026029609 MLS

MCGREGOR BLVD HOMES - Welcome to this expertly crafted 4-bedroom, 2.5-bath residence, thoughtfully designed to combine architectural distinction with everyday comfort. A dramatic formal living room with soaring 20-foot ceilings is complemented by a fabulous loft/den that overlooks the space, creating an open and inviting atmosphere. A family room that also overlooks the pool area creates a perfect play space for large family gatherings while the master suite is tucked away from the other bedrooms and is truly your own private retreat. Designed by renowned architect Bruce Gora as his personal family home, this remarkable property is being offered to the public for the first time. The modern architectural design is rich in charm and character, highlighted by a stunning courtyard-style pool setting and two outdoor balconies with peaceful river views. Designer details include wood flooring, a striking metal spiral staircase leading to an upper outdoor patio, and floor-to-ceiling windows that fills the home with natural light. The fully enclosed pool and patio area provides exceptional privacy and features multiple seating areas along with a dedicated space for outdoor grilling—ideal for both relaxation and entertaining, and there is generous storage throughout the property. The home has been carefully maintained, preserving its original character while offering important updates, including an upgraded electrical panel, three air-conditioning units all less than three years old, solar power to help reduce energy costs, and a new roof installed in 2025. Ideally located on Caloosa Drive just off the tree lined streets of McGregor Boulevard, this home sits in one of Fort Myers’ most desirable neighborhoods, only minutes from the dining, shopping, and cultural attractions of Downtown Fort Myers.

1215 Caloosa DR, Fort Myers

Courtesy of Riverside Realty Group, LLC.

$1,075,000

5 Beds ⋅ 3.5 Baths ⋅ 2026022632 MLS

Highly motivated sellers! Welcome to this fabulous estate home located in one of the area’s most sought-after neighborhoods, just moments from the historic Edison & Ford Winter Estates. Located one block from the beautiful Caloosahatchee River. Situated outside of a designated flood zone, this property offers the added peace of mind and convenience of no required flood insurance. NO FLOOD ZONE! This expansive residence offers over 3,900 square feet of living space with five bedrooms and three-and-a-half bathrooms, designed perfectly for a large family or anyone who loves to entertain. As you enter through the elegant French glass front doors from the charming front porch, you are welcomed by a spacious and inviting layout. To the right, you’ll find a beautiful formal living room or den, while the left side features an elegant dining room perfect for gatherings and holiday dinners. The heart of the home is the stunning open-concept kitchen, showcasing glass-front cabinetry, beautiful appliances, and generous space for entertaining, all flowing seamlessly into the oversized family room. The split floor plan offers privacy and functionality. On the right side of the home, you’ll find three spacious bedrooms and two full bathrooms. On the opposite wing, the luxurious primary suite features a cozy double-sided fireplace connecting the bedroom and spa-inspired bathroom, complete with a soaking tub and separate shower. The primary suite also offers direct access to the pool area. An additional bedroom and bathroom are also located on this side of the home. Step outside to your enormous outdoor living space, featuring a sparkling pool surrounded by beautiful travertine tile, creating the perfect Florida retreat for relaxing or entertaining guests. The property also includes a detached garage with endless possibilities—ideal for a mother-in-law suite conversion, private guest retreat, antique car storage, or whatever your vision may be. An additional flex space currently serves as an impressive home gym but could easily be transformed into a studio, office, or recreational area. Additional highlights include gorgeous oak and tile flooring throughout, breathtaking mature oak trees in the front yard, and an unbeatable location just minutes from Downtown Fort Myers dining, shopping, and entertainment. Located just minutes from Downtown Fort Myers, you’ll enjoy quick access to waterfront dining, live music, shopping, breweries, art walks, and community events. Spend weekends exploring the River District, catching sunsets along the water, visiting nearby marinas, or taking a short drive to Southwest Florida’s beautiful beaches, golf courses, and nature preserves. Rarely does a home combine this much space, versatility, charm, and location in one extraordinary package. This is more than just a home—it’s a lifestyle opportunity to experience the very best of Southwest Florida living.

1357 Osceola DR, Fort Myers

Courtesy of RE/MAX Trend.

$409,900

2026016167 MLS

Rare opportunity to build in one of Fort Myers' most desirable in-town locations. Situated on Avocado Dr in the highly sought-after McGregor corridor, this 13,068 sq ft (0.30-acre) lot — 80' x 164' per survey — offers an ideal homesite in an established neighborhood where custom and renovated homes routinely command well over $1 million. A full set of architectural and engineering plans was developed to permit-ready status for this site, confirming its readiness for new construction. Close to downtown Fort Myers, the river district, dining, and shopping, yet tucked into a quiet residential setting. Lots in the McGregor corridor rarely come available — builders, investors, and future homeowners: bring your vision and create something special in the heart of Fort Myers.

3427 Avocado DR, Fort Myers

Courtesy of Home Sold Realty LLC.

$3,300,000

6 Beds ⋅ 6 Baths ⋅ 2026015440 MLS

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.

1229 Plumosa DR, Fort Myers

Courtesy of Royal Shell Real Estate, Inc..

$850,000

3 Beds ⋅ 2.5 Baths ⋅ 2026010182 MLS

Live where a beautiful lake is your backyard! This updated 3 bed/3 bath home sits on wide open water with long, clear views. Nestled within the wonderful CYRC gated community, it’s a quick walk from your front door to the community’s private MARINA, Olympic style swimming pool, TENNIS & PICKLEBALL courts, AND the fabulous Blue Coyote SUPPER CLUB. This is the perfect house for anyone that enjoys an active outdoor lifestyle, entertaining, or simply relaxing on the lanai. You can fish in the lake from your seawall or take off for the Gulf from one of the most hassle-free marinas on the Caloosahatchee. Also within the community is a beautifully maintained park with a ¼ mile walking/jogging loop, garden plots, lakeside dock, and a small playground. Inside the home, the layout provides private spaces for you and for guests, a den/office, as well as open concept living & dining areas with tons of storage. The kitchen is perfectly laid out for serious cooking and includes a Sub-Zero fridge. This stress-free property’s charms extend outside through French doors to a large lanai with newly renovated saltwater pool, spa and natural stone decking. Exterior improvements in 2025 include a new retaining wall, upgraded seawall, and exterior paint. Key preventative upgrades that give peace of mind and long-term value. This low HOA, move-in ready home is offered fully furnished and checks all the boxes!

12541 Marina Club DR, Fort Myers

Courtesy of EXP Realty LLC.

Selling Office: EXP Realty LLC.

$795,000

3 Beds ⋅ 2.5 Baths ⋅ 2026007454 MLS

OLD FORT MYERS — Nestled along prestigious West Riverside Drive, this exceptional Florida-style sprawling residence beautifully blends timeless architectural charm with refined modern updates. Set on an expansive nearly half-acre corner lot, the property is enveloped by lush, mature tropical landscaping that creates a serene, private estate-like setting. Offering over 3,000 square feet of living space, the thoughtfully designed floor plan is light, bright, and ideal for both everyday living and elegant entertaining. Rich hardwood floors flow throughout, while the stunning updated kitchen showcases sleek quartz countertops, quality cabinetry, and a perfect balance of style and functionality. Designed for both comfort and versatility, the home features both a spacious family room and an elegant formal living room, providing multiple gathering spaces for relaxing or hosting. Three screened lanais seamlessly bring the outdoors in, creating peaceful settings to enjoy Florida’s beautiful climate year-round. The spacious primary suite serves as a true retreat, featuring a large walk-in closet and a luxurious spa-inspired bath designed for relaxation. Generously sized guest rooms, abundant natural light, and numerous thoughtful system updates provide comfort, convenience, and peace of mind. Located just moments from the vibrant Downtown River District, this remarkable home delivers the best of Fort Myers living — classic Old Florida character, modern sophistication, and an unbeatable location near dining, shopping, entertainment, and the riverfront lifestyle. A rare opportunity to own a distinctive property in one of the area’s most sought-after neighborhoods.

3209 W Riverside DR, Fort Myers

Courtesy of Cornerstone Coastal Properties.

$2,100,000

5 Beds ⋅ 5 Baths ⋅ 226007020 MLS

MUST SEE! No HOA! Located just off historic McGregor Boulevard, this elevated, all-concrete riverfront estate offers a rare combination of scale, security, and privacy along the Caloosahatchee River. Set on a private, oversized parcel and framed by new fencing and mature landscaping, the property feels intentionally secluded, yet remains only minutes from downtown Fort Myers and the vibrant River District seamlessly combining preserved architectural character with modern conveniences and upgrades. The primary suite is a serene retreat, thoughtfully positioned to take full advantage of both garden and water views. Generous in scale, it offers space for a sitting area and features a luxurious ensuite bath with dual vanities, a soaking tub, a walk-in shower, and ample closet storage—creating a refined, spa-inspired sanctuary. The 4 secondary bedrooms are comfortably sized and well-appointed, providing flexibility for family, guests, executive office space, or private quarters. There placement within the home allows for both privacy and functionality, making the layout ideal for multigenerational living,hosting extended stays, and/or as an investment property. A standout feature is the presence of TWO FULLY EQUIPPED KITCHENS, offering remarkable versatility—perfect for entertaining on a grand scale, accommodating long-term guests, or creating a separate living suite within the home. Having two kitchens also offers the ability to RENT the bottom of the home out and live on the main level! The main living areas are spacious and warm with contemporary finishes and updated systems throughout. Outdoors, the pool, fountains, river views, tropical breezes, and stunning sunset backdrops define the experience, with boating access. Located in one of Fort Myers’ most desirable riverfront areas, this property offers a rare combination of lifestyle, privacy, and thoughtful upgrades. One of the few homes in the area where potential storm-related impact has already been proactively addressed through substantial private mitigation and ongoing city drainage improvements. Designed to provide both comfort and peace of mind, while preserving the full appeal of riverfront living. Additionally, the city of Fort Myers, is in the process of installing a new drainage system to thoughtfully mitigate any flooding concerns during inclement weather. An exceptional opportunity to own a protected, thoughtfully updated historic waterfront estate in one of Fort Myers’ most coveted riverfront settings—where character, comfort, and coastal lifestyle converge.

1205 Caloosa DR, Fort Myers

Courtesy of Coldwell Banker Realty.

$1,354,000

6 Beds ⋅ 3 Baths ⋅ 2026006878 MLS

Step into a piece of history with this captivating 1925 Spanish Colonial home, thoughtfully updated for modern living while preserving its timeless charm. OWNER FINANCING available with a substantial down payment, providing an excellent opportunity to make this dream home yours. Situated in the heart of the historic McGregor District in Old Fort Myers, this exceptional property offers an unmatched blend of elegance and comfort. Nestled on nearly half an acre just a stone’s throw from the river, this beautiful residence boasts 4 spacious bedrooms, 2 bathrooms, a den, and a bright, inviting family room. The home is located in a quiet, highly desirable community known for its socially active lifestyle, with sidewalks and streets that are both kid and pet friendly. The expansive kitchen is a chef’s delight, featuring a center island, double sinks, recessed oven, wood cabinets with stained glass accents, and an eat-in breakfast nook. French doors open to an extensive lanai and an oversized pool, perfect for entertaining or relaxing. Enjoy formal dinners in the stately dining room or unwind in the cozy sitting room by the wood-burning fireplace. A charming private courtyard adds to the home’s unique appeal. A downstairs bedroom provides added flexibility for guests or multigenerational living. The property also offers abundant parking, ideal for a boat, RV, or additional recreational toys. The property includes a separate guest house with 2 bedrooms, 1 bath, a kitchen, and living areas above an oversized 3-car garage, ideal for visitors or in-laws. Recent updates include new roofs and plumbing in 2020, restored hardwood floors, and hurricane-rated windows, ensuring both beauty and peace of mind. The front of the property is scheduled for a full re-landscaping, designed to further enhance curb appeal and create an even more impressive, picturesque estate entrance. The location offers easy access to Fort Myers Country Club, the Edison-Ford Winter Estates, hospitals, top-rated public and private schools, diverse dining and shopping options, RSW Airport, and the pristine beaches of the Gulf of Mexico. Enjoy evening strolls in this wonderful neighborhood lined with mature trees. Don’t miss your chance to own a piece of Fort Myers history in a highly sought-after community. Schedule your private showing today. No water intrusion or storm damage from Ian.

1248 Osceola DR, Fort Myers

Courtesy of List In MLS Realty, LLC.

$545,000

3 Beds ⋅ 2 Baths ⋅ 2026003539 MLS

Located in the Riverside neighborhood near the historic Edison/Ford Estates off McGregor Blvd, this established mid century modern 3 bedroom 2 bathroom home is the perfect choice for peaceful "Old Florida" living. Pride in ownership is readily visible in the upkeep and care of this home. The kitchen is central to the living space as the main living area, dining area and sunroom flow seamlessly together. The kitchen features granite counter tops, new stainless steel refrigerator and dishwasher. Floor to ceiling windows in the sunroom and glass French doors provide a pathway to a gorgeous backyard living space featuring Florida trees including Simpson Stoppers, Dahune Holly, and Bottlebrush trees. The view is framed by a wooden pergola featuring beautiful Rangoon Creeper and a Wisteria-like vine when blooming in spring, summer and fall. The original parquet floors in the bedrooms and living room along with the black walnut kitchen wood flooring sustain the midcentury modern styling of the home. With the split floorplan, the primary bedroom has an adjoining full bath with walk in shower. Plantation shutters in the bedroom offer privacy and southern charm. The 2nd and 3rd bedrooms share an additional full bath with a bathtub and shower combination. All the windows and doors are impact glass. You can rest assured that the home did not experience any flooding from recent past storms. The whole house was re-plumbed in 2023 for peace of mind. This ground level home has no steps, so access is easy and cleaning and maintenance is a breeze. Nearby you will find local treasures such as the Edison and Ford Estates with it's garden center, the Fort Myers Country Club and golf course. Several Lee County schools are nearby as as well. The historic River District in downtown Fort Myers is only 3 miles away. If you are looking for a move in ready home please schedule a tour of 3325 Avocado Drive as this home will not last long!

3325 AVOCADO DR, Fort Myers

Courtesy of Royal Shell Real Estate, Inc..

Selling Office: Palm Paradise Realty Group.

$4,495,000

5 Beds ⋅ 6.5 Baths ⋅ 2025024914 MLS

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.

3402 W Riverside DR, Fort Myers

Courtesy of Royal Shell Real Estate, Inc..

$1,495,000

4 Beds ⋅ 4 Baths ⋅ 2025021554 MLS

Nestled on a sprawling corner lot in Old Fort Myers, this timeless home exudes old-world elegance with grand rooms, ornate ceilings and impeccable craftsmanship. Tropical gardens complete with koi ponds, pergola and wide porches are perfect for entertaining or enjoying lazy afternoons. A sleek chef's kitchen boasts a center island, domed ceiling, Sub-Zero fridge and freezer, plus Bosch induction cooktop, oven, microwave and dishwasher. A prep sink, a warming drawer and tons of cabinetry complete this awesome kitchen. The master bedroom features his and hers oversized closets, dressing room and an adjoining office/4th bedroom. An abundance of storage and built in cabinetry is found throughout the house including a large library and lighted glass display shelving. An oversized laundry room with even more storage is found adjacent to the three car garage. Additional amenities include a 40-kilowatt generator and impact windows throughout. Easy living and low maintenance make this graceful property one of a kind. This timeless Old Fort Myers gem is ready for a new owner to make it their own. Can't be duplicated at this price! See it today!

1299 Plumosa DR, Fort Myers

Courtesy of Cornerstone Coastal Properties.

$1,940,000

4 Beds ⋅ 4.5 Baths ⋅ 2025021038 MLS

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.

1337 Caloosa DR, Fort Myers

Courtesy of Kingfisher Real Estate, Inc.. 239-284-5847

$1,150,000

4 Beds ⋅ 2.5 Baths ⋅ 2025010112 MLS

This exquisite residence is a rare jewel along the coveted historic McGregor corridor—an architectural statement of elegance, sophistication, and timeless Florida living. Built in 2009 as a custom retreat, every detail has been thoughtfully curated to balance refined interiors with a lush outdoor sanctuary. Step into a private paradise where secret gardens and meandering pathways are framed in handcrafted Beldon brick pavers, seamlessly guiding you toward the resort-style pool and spa. Here, the art of outdoor living comes alive: a fully equipped summer kitchen, an expansive covered lounge, and a warm, wood-burning fireplace create the ultimate setting for entertaining under starlit skies. Enclosed within a beautifully landscaped, fenced yard, the verdant greenscape offers both serenity and seclusion. Inside, grandeur unfolds beneath soaring two-story ceilings, where an open living room centers around a dramatic fireplace and gleaming African hardwood "Wenge" floors. The chef’s kitchen is an entertainer’s dream—anchored by an oversized island, custom cabinetry, and sleek Gaggenau steel appliances—designed for gatherings that flow effortlessly between elegance and ease. Distinctive spaces add to the home’s allure: a richly appointed office, plus an additional flexible space ideal as a second office, music studio, or creative retreat, each with custom built-ins. Upstairs, a second-story living area extends the home’s versatility and charm. The primary suite is a sanctuary unto itself, with walls of glass inviting tranquil views of the pool and gardens. A dual-sided fireplace brings warmth and intimacy to both bedroom and spa-inspired bath, where bespoke Wenge cabinetry, Italian sinks, and a luxurious walk-in shower set the stage for indulgence. Every element of the home speaks to craftsmanship and comfort: PGT hurricane impact glass throughout for peace of mind, tongue-and-groove cypress ceilings adding architectural character, and a structured audio system to enrich everyday living. Rarely does a residence so perfectly blend refined design with a tropical oasis lifestyle. This is more than a home—it is an experience, an escape, and an extraordinary offering along one of Southwest Florida’s most storied avenues.

1321 Hanton AVE, Fort Myers

Courtesy of Premier Sotheby's Int'l Realty.

$895,000

3 Beds ⋅ 3 Baths ⋅ 225056672 MLS

Stunning remodel. Designer details. Ultimate location. Enter a residence where timeless charm meets high-design living—this completely reimagined three-bedroom, three-bath beauty in Fort Myers desirable McGregor Corridor is nothing short of extraordinary. Following a complete renovation, this home is a masterclass in craftsmanship, luxury and thoughtful reconfiguration. Every inch has been meticulously upgraded—walls moved, ceilings raised and features elevated—to create a living experience that is relaxed and refined. Inside, you'll be captivated by vaulted ceilings in the great room and primary suite, featuring hand-harvested cypress beams from the local Cypress Slough and crisp white tongue-and-groove wood paneling. Natural textures meet elegant design with beadboard and chair rail wainscoting throughout, a wood-burning fireplace and custom finishes. The gourmet kitchen is a showstopper, quartz countertops with full-height backsplash, a custom banquet, ZLine refrigerator with filtered water and even a left-in reverse osmosis system. The adjacent laundry room—newly added inside for convenience—makes everyday living effortless. The luxury continues outdoors with a new pool by Coastal Custom Pools, complete with marble pavers, a sun shelf with bubblers, a water feature wall and a freestanding hot tub for evening relaxation. Entertain with ease or unwind in style within your fenced-in backyard and dedicated dog run. A replaced front porch with pavers sets the tone before you even step through the door. No detail was overlooked, solid core interior doors, new impact windows, new roof, gutters, trim, tile flooring, upgraded door hardware and whole-home ADT security. There’s even a 50-amp RV plug, generator hookup, irrigation system and whole-house water softener for seamless living. The primary suite is an elegant sanctuary with navy shaker cabinets, quartz counters, Kohler Purist fixtures, custom closets, natural wood shelving and a walk-in shower with dual sinks. Each guest suite is a design lover’s dream featuring custom wallpaper, board and batten accents, built-ins and spa-inspired baths. In one of Fort Myers charming, family-friendly communities, you're a short distance from Triangle Park, the Caloosahatchee River, and all the culture, cuisine and entertainment of downtown. This is not just a remodel, it’s a home of heart and soul, curated for the way you want to live.

1219 Osceola DR, Fort Myers

Courtesy of Premier Sotheby's Int'l Realty.

$735,000

4 Beds ⋅ 4 Baths ⋅ 225047871 MLS

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.

1263 Caloosa DR, Fort Myers

Courtesy of Royal Shell Real Estate, Inc..

Selling Office: Rossman Realty Group Inc.

$1,050,000

4 Beds ⋅ 4 Baths ⋅ 225037023 MLS

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.

1230 Caloosa DR, Fort Myers

Courtesy of LSI Companies Inc..

Selling Office: Cornerstone Coastal Properties.

$375,000

2 Beds ⋅ 1.5 Baths ⋅ 224047710 MLS

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.

1350 Hanton AVE, Fort Myers

Courtesy of Cornerstone Coastal Properties.

Selling Office: Cornerstone Coastal Properties.

$1,550,000

3 Beds ⋅ 3 Baths ⋅ 224029845 MLS

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.

1318 Bougainvillea ST, Fort Myers

Courtesy of John R Wood Properties.

Selling Office: John R Wood Properties.

$1,200,000

4 Beds ⋅ 4 Baths ⋅ 224024418 MLS

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!

1257 Caloosa DR, Fort Myers

Courtesy of Bay Vision Realty.

Selling Office: Premiere Plus Realty Company.

$345,000

224011186 MLS

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.

3427 Avocado DR, Fort Myers

Courtesy of Coldwell Banker Realty.

Selling Office: Cornerstone Coastal Properties.

$700,000

3 Beds ⋅ 2 Baths ⋅ 223095515 MLS

Recently Renovated in 2023 with a New Master Bathroom, New Tile Floors, and Interior Paint, this beautiful property sits along the Caloosahatchee River with over 114 Feet of Waterfront Views. In March 2025, new landscaping, new lighting, and brand new LG Appliances were added. This home is designer Furnished with 3 bedrooms, 2 bathrooms, and a spacious kitchen. This home comes complete with a designated dining room and two living areas, which offer multiple entertaining options. An expansive enclosed screened lanai is where you can sit back and enjoy the nature, serenity, and sunsets. Curated landscaping with Privacy Hedges, Palm Trees, Banana Trees, and Dragonfruit Trees. A Massive Banyan Tree welcomes you at the front of the property. A very quiet road leads to this gorgeous waterfront home with breathtaking backyard Sunsets to the West. There are also pool plans paid for, featuring a 35' x 18' pool with gazebo option that is ready to submit for permitting. Call and Text Agents to see this property.

120 Riverview RD, Fort Myers

Courtesy of Florida Capital Realty.

Selling Office: Florida Capital Realty.

$730,000

3 Beds ⋅ 2 Baths ⋅ 223041915 MLS

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.

3421 W Riverside DR, Fort Myers

Courtesy of DomainRealty.com LLC. carriemartusswfl@gmail.com

Selling Office: Coldwell Banker Realty.

Browse All Riverside Properties for Sale

Riverside Real Estate & Homes