Historical Homes in Southwest Florida

Discover these historic homes, each with a unique story waiting for you to make it your own. Explore these timeless treasures and discover a home that connects you to the past.

$2,250

1 Bed

1 Bath

Bonita Springs

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A cozy and clean cottage, perfect for a couple .Fully Furnished with new furniture and big screen tv. 1 Car Garage. Located on a cul-de-sac on a quiet street Laundry in the garage. Yard fenced on three sides. Enjoy pristine beaches (10 mins away) Bonita Downtown with coffee shops, kayak rentals, botanical gardens and farmers market under 2 miles away, . Naples 5th Ave , RSW, and Fort Myers all about 20 mins away. On a quiet cup-de-sac, supplied with everything you need. Come relax , get some work in if you need to and enjoy the best of what Southwest Florida has to offer! You will love how cozy you feel and how close you are to everything here!

$309,900

2 Bed

2 Bath

Fort Myers

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Charming and Distinctive 1930's Craftsman just a Peaceful stroll away from Stunning Sunsets on the Caloosahatchee River! Immaculately cared for, this one-of-a-kind home sits on almost HALF an ACRE! Plenty of room to Expand, build a Pool or maybe even a much larger home and use this as a secondary In-Law Residence for extended Family and Friends! Park a Boat, RV or additional Toys? This spacious triple lot is well suited for ALL! Currently set up as 2 Bed + Den, can easily be reimagined having 3 Beds 2 Baths. Historic and Refined, details abound from the moment you step on the front porch entry and throughout! Warm and Striking wooden floors throughout, in a word, Gorgeous! Classic Crown Molding and attention to detail abound! Mindful of its Tasteful and Timeless beauty, staying true to its period, while at the same time adding many Modern Conveniences such as a Tankless Water Heater. Generous natural light pours into and over the Stainless/Granite updates of the Open Kitchen. Enjoy Panoramic views, Mature foliage and Towering trees from the Master Suite. Workshop/Shed/Storage with separate 2 Space Carport conveniently sitting only steps away. Kick back on a Front Porch Rocker with your morning coffee/latte/espresso or a glass of wine to wind down at the end of a long day. Require a little more get up and go/cardio? Russell Park only a 5 min walk to launch your Paddle board, Kayak or Canoe! FISH ON! Schandler Hall Park only a 5 minute bike ride to enjoy some Tennis, Pickleball, Basketball, Soccer, Sunshine and More! Extremely Commute Friendly location to both Downtown Fort Myers and I-75 alike. Escape from the Hustle and Bustle to Embrace this up to date Old Florida Classic...with a twist!

$1,799,000

3 Bed

3 Bath

SARASOTA

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This exceptional single-story home in the highly sought-after West of the Trail neighborhood offers the perfect blend of charm, privacy, and convenience. Ideally located near downtown Sarasota, top-rated schools, and world-renowned beaches, this property is an entertainer’s dream and a tranquil wellness retreat. The home features 3 bedrooms, 2.5 baths, and a dedicated den with serene views of the front courtyard. High ceilings, skylights, and sliding glass doors in the living room create a bright and open atmosphere, seamlessly connecting to the outdoors. The heated pool and lush tropical landscaping provide a private oasis, enhanced by southern exposure for sun-soaked relaxation. A second living space, staged as a game room, adds versatility to the layout. The spacious, well-appointed kitchen benefits from an additional planning area and closet pantry space. The owner’s suite is a luxurious escape, with French doors to the pool, an outdoor shower, plus a steam room, and a beautifully decorated ensuite bathroom with a soaking tub. Outdoors, a Zen Garden path leads to a charming gazebo, while the generous covered patio is ideal for al fresco dining. The fully fenced property, secured by electric gates, ensures complete privacy. Walk or bike to nearby restaurants, the downtown farmers market, Selby Gardens, and Southside Village, all within minutes. Siesta Key and Lido Key beaches are 4 miles away, downtown Sarasota is 2 miles, 10 miles to UTC, and 5.8 mile to SRQ, making it easy to embrace the best of Sarasota living.Located in Evacuation Zone D with a brand-new roof, this home combines peace of mind with an unparalleled lifestyle. Don’t miss the chance to make this private retreat your own!

$300,000

3 Bed

1 Bath

TAMPA

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Under contract-accepting backup offers. Welcome home to this adorable 1935 Ybor cottage that has been renovated and has an effective year built of 2010. Located on a quiet street in East Ybor which Tampa Tomorrow has named as one of the top five promising neighborhoods with its fantastic location one mile from historic Ybor, and five minutes to downtown Tampa, Armature Works, Riverwalk and GasWorx Development. Upon first arrival this quaint cottage style home with its inviting front porch and column accents sets the stage for the beauty inside! This cute 3/1 bungalow has fantastic entertainment space with an expansive great room with flexibility for a living room and dining room, family room and bar bistro space or home office. The kitchen features granite counters, stainless appliances, white cabinetry, and double closet pantry. The huge deck off the kitchen is located in the private fully fenced backyard and allows for entertaining inside and outside! The mature oak trees offer shade for enjoying this space year round! The primary bedroom features a double his and hers closet, laminate flooring and window for natural light! Bedroom 2 also features laminate flooring and built in closet and natural light! Accent detail molding on the walls and a beautiful chandelier make this bedroom a relaxing respite at home! Bedroom 3 also features laminate flooring tons of natural light and a closet. This beautifully renovated home has everything you need and want all in 1100 sq ft! Off street parking area, new deck, roof 2021, new soffits 2023,, vinyl exterior siding 2022, new plumbing 2022, new windows 2022, new electric 2022, hot water 2022, and new kitchen appliances 2022! Easy access to I-4, The Crosstown and 275!

$342,000

3 Bed

2 Bath

ARCADIA

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Seller offering $5,000 CREDIT at full listing price—use it for closing costs, prepaids, or a rate buy down! As you stroll up the charming brick walkway and step onto the inviting screened front porch of this 1946 cottage-style home, you can’t help but feel like you’ve discovered something truly magical. Inside, vintage charm dances through every room— from the warmth of beautiful tongue and groove ceilings, built-ins bursting with character, classic penny tile gracing the kitchen, and a retro-style refrigerator that feels like a sweet nod to yesteryear. The gleaming refinished wood floors whisper stories of the past, while tasteful vintage accents throughout the home tie it all together in timeless elegance. Both bathrooms have been beautifully updated, yet they still flaunt their nostalgic 1940s pastel tiles—including a hexagonal window in the oh-so-charming pink bath. The third bedroom features a walk-in closet that doubles as a laundry space, maximizing convenience. You'll find the home offers abundant storage with linen closets and built-in features thoughtfully placed throughout. Every detail throughout the home radiates care and refinement, wrapped in a pristine package of history and charm. Entertaining is effortless in the spacious yard, whether you're relaxing under the expansive 15 x 24 covered patio or hosting gatherings on the wooden deck just off the great room. Out back, a 12 x 20 shed with electricity awaits—perfect for your dream workshop, creative studio, or a private retreat. Nestled in the heart of Arcadia, a town brimming with historic charm, thrilling rodeos, and endless outdoor adventures, this home is a story waiting to be written—will you be the next chapter?

$339,000

3 Bed

2 Bath

SARASOTA

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Under contract-accepting backup offers. Introducing the "Tulip House", a charming and authentic beauty of a home! Incredible RENTAL INVESTMENT OR MULTI-GENERATIONAL opportunity in this established, and centrally located neighborhood. Main house boasts original wood floors, vaulted ceilings adorned with custom stained-glass accents, and updated AC systems. Primary bedroom enjoys a roomy walk in closet and sliding glass doors to access your own tranquil retreat screened-in lanai, and private outside shower and deck. Full size bathroom has all the modern updates and deep shelf storage. 2nd bedroom in main house, also has a walk in closet, with plenty of room for a crib or desk under the large front windows that bring in loads of natural light. Kitchen is delightful with plenty of counter space and an eat-in dining room with more windows making this bright and cheery. The Guest house is equally as appealing with its raised and angled ceilings, updated and modern full bathroom, living/dining room with a wall of windows, and private bedroom with huge walk-in closet and its own entrance to the tropical patio to relax, grill, and enjoy nature separate from the main house. Laundry room is large and shared between the 2 cottages from the guest house. A carport gives shade in between the homes, and a large shed offers lots of room for extra storage in the fenced and peaceful backyard. No HOA. Minutes to Siesta Key and area beaches, downtown and the arts scene, close to shopping, walk to Bee Ridge Park, and schools. Welcome to True Florida living at the "Tulip House"! ( Seller will accept cash or consider owner financing).

$190,000

1 Bed

2 Bath

BRADENTON

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This Braden Castle Park 1925 cottage is waiting for you to make it your next home! Nestled along the picturesque Manatee River, where it meets the Braden River, this 1/2 plus bonus room (small, but has a closet, window and second full bathroom) offers a rare opportunity in a very special 55+ waterfront community. The one car garage has been used as a pottery/craft studio for several years; has electricity, water and an AC split unit. Untouched by the recent storms and not located in a flood zone, this cottage is situated in a neighborhood rich with history. Listed on the National Register of Historic Places, the community is home to charming, unique bungalows that showcase its distinctive character. Residents enjoy a dynamic waterfront lifestyle with direct Gulf access, a private boat ramp, a fishing pier dedicated to the neighborhood’s many Veterans;, boat slips, and an array of recreational amenities. The vibrant community center hosts various events and activities, fostering a warm and welcoming atmosphere. Enjoy coffee on the front patio while enjoying views of the river, fishing and boating a few doors down. In the evening, sit along the riverfront and enjoy your favorite book or social time with your neighbors. Braden Castle Park takes a step back in history and is truly an exceptional place to call home. Yet, you are close to shopping, beaches, a wide variety of restaurants, historic downtown Bradenton and RiverWalk. Truly the best of both worlds.New roof: 2022, updated electrical: 2005

$375,000

3 Bed

2 Bath

Fort Myers

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TWO HOUSES FOR THE PRICE OF ONE!This charming historic property offers incredible value for today’s home buyer and/or investor, featuring a 2-BR, 1-BA main house with a second-story loft, plus a separate 1-BR, 1-BA guest cottage — perfect for extended family or guests.Both homes are move-in ready with fresh interior and exterior paint (2025), new roofs (2022), new hot water heaters (2022), and new GE ranges (2025). The vintage hardwood floors in both homes add warmth and character throughout. In addition, the guesthouse kitchen has been updated with brand-new cabinets, countertops, and built-in microwave oven (February 2025). Landscaping and brick paver walkways were all new in April, 2025. The spacious side yard offers endless possibilities — ideal for extra storage, gardening, or outdoor entertaining.Enjoy the freedom of no HOA fees or restrictions in this centrally located gem. You’ll be within walking distance of public tennis courts, kids playground, Fort Myers Golf Course, and several fantastic restaurants.Important Note: This property is not in a flood zone and had absolutely no water intrusion from recent hurricanes.Also, Truly Nolen Termite coverage is transferable to the new buyer. Don’t miss out — Definitely one of the best opportunities in this price range!

$649,500

3 Bed

3 Bath

Fort Myers

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LIFESTYLE, INCOME & A DEVELOPMENT OPPORTUNITY. This beautifully renovated 2BD/2BA VINTAGE HOME with soaring ceilings, an open floor plan AND ATTACHED 1BD/1BA APARTMENT is situated in an urban oasis of .75 acres of lush mature landscaping in the Historic Downtown River District. Quality updates include roof, gutters & downspouts (2023), hurricane impact windows (2023), Hardie board siding & skirting (2024), new A/C (2023), hardwood floors, stunningly beautiful bathrooms and the list goes on, too numerous to mention here. It's a short walk or easy trolly ride to Downtown Fort Myers with its theaters, restaurants, galleries, museums, boutique shopping, cultural events, Regional Library and the riverfront Ampitheater. Also included is the 288 sq. ft. out-building with RV hook-up with 30-amp outlet, sewer, plumbing and electric PLUS a 180 sq. ft. shed ideal for additional storage. The unique URBAN GENERAL ZONING allows for commercial uses, live/work, development of up to 12 units per acre, making this parcel a one-of-a-kind opportunity. The property is perfect for Artists and Dreamers to use as it sits, or Entrepreneurs and Developers, live the lifestyle, collect the rent and develop the property to its full potential.