Historical Homes in Florida's Big Bend

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.

$250,000

3 Bed

2 Bath

Thomasville

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CLASSIC LIVING CLOSE TO DOWNTOWN! This remarkable historic Hansell House can be yours TODAY! This 3BR/1.5 Bath home has been completely remodeled, yet maintains its original character, including refinished hardwood floors, original and updated lighting, antique doors and hardware. The remodeled kitchen is bright, and offers great space for meal prep including a large walk-in pantry & eat in bar nestled between the formal dining room & kitchen. The full bath & half bath have also been updated but still offer historic charm. The living room and formal dining have plenty of windows offering natural light as well as new, modern light fixtures. The separate laundry room off the kitchen also leads to a small patio in the private, fenced backyard. Home also features a HUGE attic that spans the entire home and basement, both accessible from the interior of the home. Close to schools, parks and shopping! Call your favorite Realtor TODAY for a closer look at this wonderful home!

$500,000

3 Bed

3 Bath

Tallahassee

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OPEN HOUSE Sat. 2-4 PM 4/26 Modern Vibes in the Heart of Tallahassee’s Coolest Neighborhood — Country Club Estates! This beautifully updated home boasts light-filled living spaces, a sleek kitchen with premium finishes, and cozy yet sophisticated touches throughout. Vaulted ceilings, skylights, and floor-to-ceiling windows create an airy atmosphere that’s perfect for both relaxing and entertaining. Step outside to a charming patio beneath a majestic oak tree — an ideal spot for outdoor gatherings. Enjoy unbeatable walkability to downtown, Cascades Park, the Capitol Building, breweries, coffee shops, and restaurants. This home is your perfect urban‌‌‌‌‌‌‌‌‌‌ retreat!

$214,900

3 Bed

1 Bath

Tallahassee

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Bring all offers! Wonderful Midtown, Levy Park Bungalow. Amazing walkable neighborhood with easy access to Lake Ella shops and restaurants. This home comes with mature landscaping and fenced backyard. Off-street parking is a plus. Interior boasts granite counters and convection oven in the galley kitchen along with operational Natural Gas Fireplace. There is a separate super large utility laundry room with Washing Machine and Dryer. Updates include: 2024 Natural Gas Heat and Air system. 2024 Natural Gas Hot Water Heater. Three Bedrooms (third room without closet, which can easily be added with minimal loss of space,) make for spacious, yet private living quarters. 2016 roof. Perfect starter home or investment.

$289,900

3 Bed

2 Bath

Monticello

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Nestled in the heart of historic Lloyd, this beautiful 1914 Charmer boasts the craftsmanship of an older home with the luxuries of brand new finishes! This Beautiful 3 Bedroom, 2 Bath home has been tastefully remodeled, ready for it's new family. It property possesses 4 new electric fireplaces with brand new tiling throughout. Any couple will enjoy the huge double-head shower with a matching double vanity. In the spacious master bedroom, there is a large, custom walk-in closet. Enjoy cooking and entertaining in the fully redone kitchen, with all new SS appliances! This house also offers a 4th flex room that could be used as a separate dining room, play room or office! Other highlights include refinished floors, new lighting, and a new spacious wrap-around porch, Large pantry & butler's pantry, custom mudroom built-ins, and a fireside reading nook in the living room! As well as the huge wrap-around porch in front, there is a nice deck out back for all your entertaining needs. No HOA and plenty of room to park all your toys! Close to I-10 while still maintaining that small-town feel.

$475,000

3 Bed

2 Bath

Tallahassee

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Charming all brick home in downtown Tallahassee! Unfinished basement with lots of potential. A classic 3-bedroom, 2-bathroom home perfectly nestled in the heart of downtown. This timeless property boasts a solid brick exterior and is conveniently located within walking distance of Leon High School, Cascades Park, and an array of local amenities, this property offers both convenience and character. Step inside to find freshly painted interiors, brand-new carpet in the primary bedroom, and beautifully refinished solid oak floors that add warmth and character to the living spaces. The unfinished basement offers endless possibilities for storage or future customization and is not included in the square footage. Outside, the fenced backyard provides a private retreat, ideal for play, gardening, or simply relaxing. Whether you're seeking a move-in-ready home or a property to personalize, this gem is ready to make your own. Don’t miss this opportunity to own a piece of downtown Tallahassee living. First two pictures shown are virtually staged. Buyer to verify room dimensions.

$175,000

3 Bed

1 Bath

Tallahassee

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Rare 3/2 home on 2 lots in the Fairview Subdivision, Corner lot, urban service area, transportation district and walking distance to Leon County Fairground. Updated carpet and paint. Hurry and don't miss it! Why this matters is, strategically located and near to the Florida Capital and FAMU.

$100,000

2 Bed

1 Bath

Tallahassee

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Don't miss this great investment opportunity. This two-bedroom, one-bathroom property is currently tenant-occupied with reliable rental income of $650 per month. This property is being sold as-is, offering buyers the right to inspect. Whether you're looking to expand your rental portfolio or seeking a renovation project with income already in place, this property has potential. Advance notice required due to tenant occupancy.

$305,000

4 Bed

2 Bath

Monticello

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Spacious home located within walking distance of Historic Downtown Monticello. This four bedroom home sits quietly on a manageable half acre lot. Sporting both original hardwood flooring and newly installed LVP flooring, this home blends perfectly for any new home owners. Updated bathrooms and appliances have all been done within the last 5 years. Sizes are approximate.

$425,000

3 Bed

2 Bath

Tallahassee

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Enjoy the look and authenticity of a vintage house in a well established walkable neighborhood, with all of the updates and extra storage that come with more modern construction // Located in the heart of Olde Town Tallahassee, walkable to schools and all of downtown's festivities and dining // Owner has maintained, upgraded and updated the house with great care over the years, including a 2024 roof, 2014 tankless water heater and 2025 kitchen updates including quartz counters and a fresh backsplash // 2016 addition of primary suite with large bathroom with double sinks + a walk-in closet // Gorgeous original tile in hall bath, with clever built-ins including a hamper and linen storage // Original archways and vintage phone stand are some of the other well preserved features, as well as the office/sunroom off of the family room // Welcoming living room with wood fireplace greet guests as they enter the front door // Formal dining room has plenty of room for extra furniture // Kitchen has separate side entry, built in pantry and gas stove // All windows are updated, fully-insulated and each has interior white louvered shutters // Separate long garage that will fit one car + extra storage // Screened side porch overlooks fully-fenced backyard complete with grass and greenery

$369,000

4 Bed

3 Bath

Tallahassee

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Endless Possibilities! This beautiful property could be the right fit for a variety of buyers. Awesome and unique 3 bed, 2.5 Bath Pool Home on almost an acre! Upstairs Living room doubles as a 4th bedroom. Families will enjoy the spacious, updated kitchen and various living spaces along with the pool with brand new liner. Beautiful light-filled office with charming built-ins right off the kitchen. Couples will bask in the massive master bedroom with an equally impressive master bathroom including the Huge soaking tub and double head shower with custom tile work! Laundry room offers a half bath but has all the plumbing and room for a shower and can easily be added back in for a full bath. The upstairs has been tastefully converted into a separate unit with its own dedicated entrance. Upstairs unit rents consistently on Airbnb and can continue to provide the new owner with great income. This unit could also be easily opened back up to the rest of the house. BONUS- Development Opportunity!! Up to 3 small homes could be built or brought on the adjoining lot, also making it the perfect opportunity for investors.

$499,000

3 Bed

3 Bath

Tallahassee

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All brick home with 2-car carport in the heart of Betton Hills! New interior paint (not shown in pictures), 2021 Roof, 2021 Tankless Water Heater, beautiful hardwood floors, 2 living spaces, half bath located in the laundry room. Walking distance to many popular attractions; Whole Foods, Food Glorious Food, Winthrop Park, and many more! This adorable home draped by gorgeous live oak trees is ready for its next owner!

$386,000

4 Bed

4 Bath

Quincy

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Own a piece of history. Walking distance to downtown Quincy. Recently completed top-to-bottom systems and cosmetic renovation allows for a gorgeous marriage of classic style and modern living // Charming original elements including built-in storage nooks and classic decorative tile were painstakingly preserved // Kitchen has butcher block island, fresh cabinets, appliances and counters, plus adjacent laundry closet and breakfast nook with back deck access // Bathrooms got the royal treatment with all new interior elements over the original tile floors // Large corner master suite has two closets, as well as en suite bathroom with separate water closet and a circa-1890's antique renaissance revival sink system plucked from an estate in Alabama and rebuilt by a local cabinet maker to have functioning drawers for proper under-sink. Stay cool in the private pool ( saline ).

$299,650

3 Bed

1 Bath

Tallahassee

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See the 3D virtual tour and video walk-through of this historic gem in Old Town Tallahassee! This charming 3-bedroom bungalow seamlessly blends classic character with modern updates, including a new, architectural shingle roof, updated electrical, remodeled kitchen, and original hardwood floors. Enter the home from the manicured front yard through the inviting, screened-in front porch to be greeted with an open floor plan. The main living area is light and bright with oversized windows, and is located next to the dining area lit with a modern chandelier. The kitchen features an exterior door, white appliances, checkered tiled flooring, stone counters, built-ins, track lighting, and white cabinets. Entertain or relax in the back yard which has green space and a firepit. Located next to Midtown Tallahassee's vibrant dining and shopping, this home is a rare blend of history and convenience.

$995,000

8 Bed

4 Bath

Tallahassee

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Discover the timeless elegance of this classic 1908 residence, boasting a total of approximately 5000 sq. ft. of heated & cooled living area. The captivating Main House features expansive spaces for entertaining, five bedrooms, & a library. Complementing the home are two separate guest apartments: a 1-bedroom/1-bath basement apartment & a detached 2-bedroom/1-bath carriage house apartment, each with full kitchens, perfect for in-laws or generating additional income. The main residence showcases exquisite heart pine wood flooring, high ceilings, & beautiful millwork. Additionally, there are over 1000 sq ft of porches for outdoor relaxation. A sizable three-room workshop offers extra storage & hobby space. The property spans .71 acres, adorned with various fruit trees, oaks & a secluded deck area at the rear, accessible via a landscaped path. With new roofs installed in 2021 by Tadlock Roofing & HVAC systems in 2021 and 2022 by Benson's heat & Air, this home is ideally situated near the Capitol, schools, churches, & hospitals, blending historical charm with contemporary convenience. Total bedrooms and baths are the total for the property, including the 2 guest apartments.

$887,550

4 Bed

4 Bath

Tallahassee

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Open Saturday 3/29, 12 to 2. Great price for this marvelous historic home, home of two governors, which underwent major restoration work around 1980-81 to how it had been while Gov. Bloxham resided there (modern electrical & plumbing though). This can be your residence, a guest house/ airbnb, or an office - it has been used as all three of these. This masonry structure was built by Richard Shine, who also built Goodwood, First Presbyterian Church and the south wing of the old capitol building. 4 fireplaces (have not been utilized in years, unknown if they work). If you want a large home downtown, this is it! Many homes in the Calhoun St Historic Distrcit have returned to residential use in recent years.

$529,900

3 Bed

3 Bath

Panacea

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Find your way home to this Ochlockonee Bay waterfront home nestled high amongst the live oaks. This 3 bedroom 3 bath home features an open floor plan with high ceilings and windows galore taking in water views from nearly every vantage point. In addition to an open and bright living room and master bedroom on the bayside, the heated and cooled sunroom is the perfect location to sit back, relax, and take it all in while in the comfort of the indoors. Situated on one of the highest lots in Ochlockonee bay the property has commanding views down to the water where your dock on the bay awaits. The dock has been fitted with over 80 new pilings and is ready for the next owner to transform it into whatever they want. Great fishing along the entire length of the dock and sunsets to die for along the way to the enormous terminal platform. No elevator required for this ground level home just park and walk right in and start enjoying a relaxing getaway on the bay. Mashes Sands beach is just down the street, along with public boat ramps, and just across the street is the bike and walking trail running 17 miles all the way into St. Marks National Wildlife refuge. Great views, over 2000 sqft home, with a dock in place, on one of the highest lots. If this sounds like what you're looking for then this is definitely worth taking a look.

$995,000

8 Bed

4 Bath

Tallahassee

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Discover the timeless elegance of this classic 1908 residence, boasting a total of approximately 5000 sq. ft. of heated & cooled living area. The captivating Main House plus 2 full apartments. Discover the timeless elegance of this classic 1908 residence, boasting a total of approximately 5000 sq. ft. of heated & cooled living area. The captivating Main House features expansive spaces for entertaining, five bedrooms, and a library. Complementing the home are two separate guest apartments: a 1-bedroom/1-bath basement apartment and a detached 2-bedroom/1-bath carriage house apartment, each with full kitchens, perfect for in-laws or generating additional income. The main residence showcases exquisite heart pine wood flooring, high ceilings, and beautiful millwork. Additionally, there are over 1000 sq ft of porches for comfortable outdoor relaxation. A sizable three-room workshop offers extra storage and hobby space. The property spans .71 acres, adorned with various fruit trees, oaks and a secluded deck.

$320,000

2 Bed

2 Bath

Panacea

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Fabulous bungalow on a Double lot, Walkable to restaurants,Woolley Park, Rock Landing Marina, Easy level living, Two screen porches, Newly fenced yard and new lime rock circular driveway. Perfect investment opportunity or for family enjoyment for years to come. Panacea is a world class in shore fishery. Gorgeous old Fla wood work. All measurements are approximate.

$400,000

3 Bed

1 Bath

Tallahassee

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Charming Betton Hill Opportunity – Priced to Sell! Conveniently located in the heart of desirable Betton Hill, this 3-bedroom, 1-bath home offers an exceptional opportunity for homeowners or investors looking to bring their own style to one of Tallahassee’s most sought-after neighborhoods. Situated on a generously sized lot just under half an acre, this one-story home is full of potential and charm. Step inside to find beautifully refinished real hardwood floors flowing throughout the main living areas, tile flooring in the kitchen and bath, and attractive interior brick accents that add warmth and character. The wood-burning fireplace with glass doors creates a cozy focal point in the living room, while abundant windows fill the home with natural light. The kitchen retains an appeal of it's own, offering a pantry, stove, refrigerator, dishwasher, disposal, and plenty of space to customize. The master bedroom has 2 closets. The covered front entry and covered back porch add extra comfort and functionality, with the back porch offering potential to be converted into a second bathroom and laundry area. The partially fenced back yard is spacious and manicured, with a cleared grassy area enclosed by trees and vegetation, a perfect space for a future in-ground pool! Additional features include:HVAC system replaced in 2018, Roof replaced in 2005, Ceiling fans throughout, Crawl space for easy access to systems, All-electric systems with gas meter available. Walkable to parks, restaurants, shopping, and TMH medical facilities, and just minutes from downtown Tallahassee, this home delivers unbeatable location and affordability in one of the city’s classic neighborhoods. Don't miss this rare chance to create your dream home in Betton Hill!

$185,000

2 Bed

1 Bath

Tallahassee

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This cute little cottage has been owned and occupied by the same person for 75 years! Very well cared for and loved on for all of those years. The lot is gorgeous and full of plant life and blooming just in time for Spring! It has had some updates including HVAC, Well reservoir and pump, water heater, and the windows are double paned and the home is pretty efficient despite its age! The covered deck in the back is 18x15 and the best spot to be looking out at the manicured yard. There is also a 10x15 carport and a storage shed. Come on out and take a look, you won't want to miss this affordable & adorable home!