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1205 Caloosa Dr, Fort Myers
$1,999,000
5 Beds ⋅ 5 Baths ⋅ 226029508 MLS ⋅ Riverside BLDG.
A distinctive riverview estate along Fort Myers' historic McGregor corridor, 1205 Caloosa Drive combines architectural character, exceptional scale and a private waterfront setting just minutes from the River District. Set on approximately 0.69 acre along the Caloosahatchee River, this 1936 residence offers approximately 5,680 square feet of living space with 5 bedrooms, 5 full baths, a private pool and no HOA. Extensively renovated over the years while retaining the character of its original architecture, the home provides an impressive collection of living and entertaining spaces. Formal living and dining areas are complemented by a home office, game/media space and two kitchens, creating flexibility for entertaining, extended guests or multigenerational living. Hardwood and tile flooring, impact windows and doors, generous room proportions and abundant natural light contribute to a home that feels substantial without sacrificing warmth. The primary suite takes advantage of garden and water views and offers room for a sitting area, an ensuite bath with dual vanities, soaking tub and walk-in shower, and generous closet space. Four additional bedrooms and baths provide considerable flexibility for family, guests and private work-from-home accommodations. Outdoor living is central to the property. Mature landscaping and established palms frame the oversized homesite, while balconies and outdoor entertaining areas take advantage of views toward the Caloosahatchee River. The pool, covered lanai, fountains and surrounding hardscape create a private setting for entertaining or relaxing while enjoying the riverfront environment. Located just off historic McGregor Boulevard, the property offers convenient access to downtown Fort Myers and the River District while maintaining the privacy and presence of an established residential estate. With direct river frontage and boating access, the location provides an opportunity to enjoy the waterfront lifestyle for which Southwest Florida is known. The residence would benefit from some minor repairs, refreshing and personalization, providing the next owner an opportunity to make this significant property their own while building upon its existing architecture, scale and improvements. Property is being sold AS-IS. Buyers are encouraged to conduct their own inspections and independently verify the condition and functionality of all systems, components, appliances, improvements, pool and waterfront features, as well as permitting, flood information and any other matters important to their purchase. Agents: Please review all private remarks and MLS supplements prior to scheduling a showing or submitting an offer.

1205 Caloosa Dr, Fort Myers
1229 Plumosa Dr, Fort Myers
$3,300,000
6 Beds ⋅ 6 Baths ⋅ 2026038395 MLS ⋅ Riverside BLDG.
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
3209 W Riverside Dr, Fort Myers
$715,000
3 Beds ⋅ 2.5 Baths ⋅ 2026037725 MLS ⋅ Riverside BLDG.
Welcome to 3209 W Riverside Drive and one of the most desirable neighborhoods in SW Florida. Set on an oversized corner lot of nearly half an acre, this beautifully renovated home offers 3 bedrooms, 2.5 baths, an oversized 2-car garage, and over 3,000 square feet of thoughtfully laid-out living space. Upgrades run throughout and include rich hardwood flooring, tongue-and-groove ceiling details, solid wood soft-close cabinetry, quartz countertops, new stainless steel appliances, a whole home water treatment system, a fully renovated primary bath, IMPACT-rated sliding glass doors, and newer AC units. The expansive layout flows with ease offering a spacious living room, formal dining, a formal living space anchored by a wood-burning fireplace, generous bedrooms, abundant storage, an oversized utility room, multiple screened lanais, and a large outdoor space with plenty of room for a pool (see the renderings in the photos). All of this in one of Southwest Florida's most sought-after neighborhoods. The historic McGregor corridor is among the most walkable and well-kept areas in Fort Myers. With quick access to downtown Fort Myers and the River District's regular events and abundant shopping & dining options you’ll love the lifestyle offered here. You're also just minutes from US-41, I-75, Bell Tower Shops, RSW International Airport, and are close to the world-famous beaches of Sanibel Island and Fort Myers Beach. With so much to offer, this one is a must-see.

3209 W Riverside Dr, Fort Myers
1337 Caloosa Dr, Fort Myers
$1,940,000
2026032570 MLS ⋅ Riverside BLDG.
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
1248 Osceola Dr, Fort Myers
$1,354,000
6 Beds ⋅ 3 Baths ⋅ 2026006878 MLS ⋅ Riverside BLDG.
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
1249 Osceola Dr, Fort Myers
$889,500
3 Beds ⋅ 4 Baths ⋅ 2025016791 MLS ⋅ Riverside BLDG.
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.

1249 Osceola Dr, Fort Myers
1219 Osceola Dr, Fort Myers
$895,000
3 Beds ⋅ 3 Baths ⋅ 225056672 MLS ⋅ Riverside BLDG.
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