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 Remember this is a 100-year-old home, antique homes are known for lack of closet space, kitchen is outdated as well, all bedrooms are upstairs.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

3 Beds ⋅ 4 Baths ⋅ 2026046609 MLS

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 Remember this is a 100-year-old home, antique homes are known for lack of closet space, kitchen is outdated as well, all bedrooms are upstairs.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

$409,000

3 Beds ⋅ 2 Baths ⋅ 226039179 MLS

1850 Moreno Avenue, Fort Myers

1900 Clifford Street Unit 603, Fort Myers

$199,000

Location, Location, Location and What a View! Discover the perfect combination of comfort, convenience, and beautiful waterfront living in this charming, fully furnished 2-bedroom, 2-bathroom condominium at Riverside Club in the heart of Downtown Fort Myers. Whether you are looking for a peaceful retirement retreat, a seasonal getaway, or an investment opportunity for seasonal rentals, this condominium has so much to offer! Move-in ready and tastefully furnished, this spacious residence features a generous living room, a separate dining area, and a comfortable, functional kitchen. Neutral colors throughout create a bright and welcoming atmosphere, while tile flooring adds beauty and easy maintenance. And did we mention the view? Imagine relaxing in your own home while enjoying the beautiful scenery that makes this location so special. Residents can enjoy the community swimming pool, perfect for soaking up the Florida sunshine and enjoying the tropical lifestyle. Conveniently located within walking distance of everyday essentials and just minutes from the restaurants, shopping, entertainment, and vibrant atmosphere of Historic Downtown Fort Myers. Beautiful views, a fantastic location, and fully furnished convenience all in one! Don't miss this wonderful opportunity to own your own piece of Southwest Florida paradise.

2 Beds ⋅ 2 Baths ⋅ 2026043008 MLS

Location, Location, Location and What a View! Discover the perfect combination of comfort, convenience, and beautiful waterfront living in this charming, fully furnished 2-bedroom, 2-bathroom condominium at Riverside Club in the heart of Downtown Fort Myers. Whether you are looking for a peaceful retirement retreat, a seasonal getaway, or an investment opportunity for seasonal rentals, this condominium has so much to offer! Move-in ready and tastefully furnished, this spacious residence features a generous living room, a separate dining area, and a comfortable, functional kitchen. Neutral colors throughout create a bright and welcoming atmosphere, while tile flooring adds beauty and easy maintenance. And did we mention the view? Imagine relaxing in your own home while enjoying the beautiful scenery that makes this location so special. Residents can enjoy the community swimming pool, perfect for soaking up the Florida sunshine and enjoying the tropical lifestyle. Conveniently located within walking distance of everyday essentials and just minutes from the restaurants, shopping, entertainment, and vibrant atmosphere of Historic Downtown Fort Myers. Beautiful views, a fantastic location, and fully furnished convenience all in one! Don't miss this wonderful opportunity to own your own piece of Southwest Florida paradise.

1900 Clifford Street Unit 603, Fort Myers

$1,699,000

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.

5 Beds ⋅ 5 Baths ⋅ 226029508 MLS

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 Drive, Fort Myers

$1,354,000

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.

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 Drive, Fort Myers

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