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.

$775,000

3 Bed

1 Bath

North Fort Myers

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Endless Possibilities on 14.22 Beautiful Acres in North Fort Myers! Welcome to your own private slice of paradise just off Ruden Rd — a rare 14.22-acre gem nestled in a peaceful, country setting while still being close to it all! Located just minutes from Babcock Ranch and Downtown Fort Myers, this fully fenced and gated property is ready for its new owners to fall in love. At the heart of the land sits the most charming 3-bedroom, 1-bathroom cabin, built in 1950 and meticulously maintained. With tongue-and-groove wood accents, built-in cabinetry, a cozy dining area, and a spacious great room featuring a gas fireplace, this cabin exudes warmth and character. Enjoy quiet mornings on the adorable screened-in front porch or unwind with peace of mind thanks to the whole-home generator. The property includes several outbuildings — one conveniently set up with your washer and dryer — plus a tall covered parking area perfect for your RV. With new fencing, an electric gate, and mostly cleared land, this property is ideal for horses, cattle, or simply enjoying wide open space. Situated on a paved road, you get both tranquility and accessibility. Whether you’re dreaming of a hobby farm, a private retreat, or room to roam, this North Fort Myers acreage offers endless opportunity.

$85,000

2 Bed

2 Bath

North Fort Myers

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This 2-bedroom, 2-bathroom home on A DOUBLE CORNER LOT in the heart of North Fort Myers has 1,308 sq. ft. of living space and equal-sized building at the rear of the property that can serve as a working garage, or heavily converted to a second unit, making this an easy TWO INCOME situation. The yard is fully fenced with mature landscaping for privacy. Whether you're looking for a fix-and-flip opportunity, an investment rental, or a primary residence, this home has endless potential. Don't miss your chance to turn this hidden gem into your dream home!

$385,000

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!

$400,000

3 Bed

2 Bath

Fort Myers

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TWO HOMES! ANOTHER HUGE PRICE REDUCTION! NOT IN A FLOOD ZONE! Here's your second chance-contract fell through the day before closing. This is your chance to own a 3 bedroom/2 bathroom pool home right on McGregor Boulevard on nearly a half acre lot (2 lots) with a GUEST HOME offering an additional 2 bedrooms/1 bathroom on the property as well. Just think of the potential investment income while you enjoy living in South Fort Myers, just a short walk to the river, near the Edison Home, and yet NOT IN A FLOOD ZONE and has NEVER been flooded! The roof and gutters are newer (2023). The wood floors in the guest home are original from 1920 and with just a little TLC, would be gorgeous! There's plenty of parking including RV hookup availability and space. The mature palm and oak trees on the property are so beautiful. The spacious covered lanai and large 27'x15' pool will be calling your name at the end of a long day! There are so many things to appreciate about both of these homes and the investment possibilities are numerous! You could even use both of the homes as rentals for maximum passive income potential. Be sure to schedule a showing today to see this home where you'll have no concerns for flood insurance, no HOA, and close to the beaches, downtown river district, shopping, entertainment, golf, and so much more!

$1,525,000

4 Bed

4 Bath

Fort Myers

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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.

$394,900

3 Bed

2 Bath

Fort Myers

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Living near Downtown Fort Myers in a no-flood zone is a super opportunity. This historic home has a rich history, with Thomas Edison's wife coming to tea. The structure behind the home was the kitchen for the main house, which had access to the lot included in the sale that enters from Altamont Ave. Rebuild the structure for additional living space or guest quarters. Walking distance to the Edison Home, Publix, and lots of dining and entertainment downtown. This newly renovated classic historic home features beautiful wood floors and natural light. It is located on five city lots with access from two streets (Clifford St and Altamont Ave). The seller has created a beautiful design that keeps the historic appeal and brings modern trends. The sizeable primary suite has built-in cabinets and a new master bath with a large walk-in shower. High ceilings bring volume to every room. The living room features a working fireplace made of a rare tabby concrete known for its weather resilience. The whole home is open and airy. The larger-than-average lot is zoned neighborhood commercial, allowing for at-home businesses. A large outbuilding could be converted to a work or living space. A colossal fish pond has an artesian well and strategically placed stones. The framing for the second building could make a nice addition to this property and possibly add income with access from the back of the property. This renovation is almost complete, with a few items to make it your own. AC is new. Roof 2020. Windows 2020. Plumbing 1999, Electric 2024, and lots more. There is so much opportunity on this oversized lot for the creative spirit. Make this property your own. Call to view this home before it's too late! $440k recent appraisal on file.

$499,000

4 Bed

2 Bath

Fort Myers

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HISTORIC DEAN PARK - Beautiful Circa 1921 4BR/2BA home situated on a picturesque corner lot. The wrap around front porch invites you to sit for awhile and reminisce about a simpler time. Features include gorgeous original hardwood floors that were recently redone to perfection. The traditional floor plan is spacious and offers great natural light throughout. The well appointed kitchen seamlessly blends vintage charm with all of the things one would desire featuring original upper cabinets, sleek counters and GE Cafe Appliances. Other highlights include a new Roof 2023, Redone Porch 2023, (2) new HVAC systems and duct work and new water heater in 2022. Ideally located a short stroll or bike ride to all the Downtown River District has to offer including dining, shopping, entertainment and art galleries as well as conveniently located close to I-75 and other major thoroughfares. This thoughtfully curated vintage beauty truly is a must see!

$4,500,000

3 Bed

3 Bath

Captiva

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Stunning Gulf Views! Step into timeless island charm with this direct Gulf-front beach cottage on Captiva Island, boasting 114 feet of pristine beach frontage and breathtaking, unobstructed views of the Gulf of Mexico. This rare gem dating back to 1930 captures the essence of Old Captiva with historic character seamlessly blended with thoughtful modern updates, offering the perfect balance of classic coastal vibes and contemporary comfort. Inside, you'll be captivated by the soaring beamed ship-lapped ceilings and natural light that pours in from every angle. The open living space flows effortlessly and the split bedroom floorplan is ideal when hosting guests. The chef conscious kitchen features custom Bluestar appliances, including a built in refrigerator freezer and gas range. Every corner of this cottage has been lovingly restored and updated, preserving its historic soul while adding modern amenities for today’s lifestyle. Outside, enjoy your private Gulf-front sanctuary, where the sound of the waves and breathtaking sunsets become part of your everyday life. Whether you're enjoying your morning coffee on the deck or strolling down your own stretch of beach, this home is all about slowing down and soaking in the beauty around you. Just a short stroll brings you to Captiva Village, where charming shops, top-rated restaurants, and a vibrant community await. Whether you’re searching for a serene retreat, an island getaway, or an investment property, this Captiva beach cottage is the one you’ve been dreaming of.

$450,000

4 Bed

3 Bath

Fort Myers

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**Step back in time at 1421 Steele Street — a true Fort Myers treasure celebrating its 100th birthday.** This enchanting 1925 Craftsman-style home is a rare time capsule, with many of its original features still intact. From the graceful windows to the original wood floors beneath your feet, every inch tells a story. Classic tilework, vintage light fixtures, and a wood-burning fireplace in the living room evoke a bygone era of craftsmanship and charm. The home's flowing floor plan includes four spacious bedrooms, two full baths, and one half bath — all generously sized and filled with character. An attic fan whispers of simpler times before central air, and while this home will require extensive restoration, it offers the bones and soul of a masterpiece waiting to be brought back to life. Relax on the expansive screened front porch and wave to neighbors beneath the dappled shade of the mature tree out front. A porte cochere adds vintage flair and shelter to the driveway, leading to a detached two-car garage — a rare find in historic homes. The property is wrapped in a tall privacy hedge, offering quiet solitude in a setting that feels almost untouched by time. Just minutes away from the vibrant downtown Fort Myers River District, enjoy easy access to boutique shopping, art galleries, live music, and delicious dining. Nearby Edison and Ford Winter Estates honor the spirit of innovation and history, while the Caloosahatchee River invites you to stroll, paddle, or picnic along its scenic banks. For those who appreciate the craftsmanship of the past and dream of breathing new life into a piece of history, 1421 Steele Street is more than a home — it's a legacy. Restore it, cherish it, and become part of its enduring story.

$495,000

2 Bed

2 Bath

Fort Myers

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Nestled amidst mature palms and lush greenery, this beautifully maintained bungalow combines classic charm with modern convenience. Walking distance to downtown Fort Myers and beautiful view of the Caloosahatchee River, this charming spacious 2 bed/2 bath historic home built in 1926 welcomes you with its inviting 363 sqft front porch, perfect for enjoying morning coffee in Florida's sunny days. Step inside to find a spacious floor plan preserved the charm of historic bungalows' inviting interiors and craftsmanship that blends functionality with artistic detail. Upon entering, you're greeted by a spacious living room features beautiful rich warm toned hardwood floors, an original brick fireplace, large windows let in plenty of natural light, enhancing the warm and inviting ambiance. Charming window nooks with built-in seating, perfect for creating a cozy reading corner. The home’s timeless appeal is enhanced by the use of natural woodwork on door and window frames, baseboards, kitchen ceiling, as well as the built-in display cases between the living and dining room, are crafted from high-quality woods with a rich deep stain. The spacious dining room is separated by wide wood frame and two built-in display cases, the artful chandelier complements the timeless feel of the home. The kitchen is newly renovated for modern convenience with granite counters, stainless steel Viking appliances, while still retaining a vintage feel such as farmhouse sink, vintage-style cabinetry with glass-front doors and open shelving. The renovated master bathroom features black hexagonal mosaic floors, glass shower, white modern wall tiles combined with farm house style vanity sink and vintage lighting. The guest bath features hexagonal mosaic floors, subway tile and refinished charming cast-iron tub and pedestal sink. The 440 sqft detached garage has existing electric and water connections, can be converted to ADU. Other features including metal roof, with newer plumbing and electrical wiring installed in 2015. Freshly painted inside & out. Water filtration system in the kitchen, insulation in the attic area. The home boasts a large paved driveway with space for 3-4 cars and a partially fenced backyard. The property is currently being used as a vacation rental. Beyond the immediate charm of the property, this home benefits from its location within a dynamic downtown area set for exciting future developments. City of Fort Myers has plans to expand and enhance the downtown district, adding new retail spaces, waterfront dining, and cultural attractions that will bring even more life to the area. The seller's lender does not require a flood insurance due to the elevation of the property. Zoning allows for residential/office/lodging/childcare/financial/personal care services/artisanal usage. Zoning usage attached.

$363,000

2 Bed

1 Bath

Fort Myers

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Lovingly cared for, updated and charming 1940’s Bungalow style home showcasing original Hardwood Floors. Light and Bright with an Open Floor Plan. Kitchen features Granite Counters, White Shaker Cabinets, Stainless Steel Appliances and open shelving. Kitchen opens to Tiled Great Room with sliders to the new deck. There is a formal living Room and Dining Room, Two Bedrooms, large walk-in closet. There is an additional 201 sq' Screened Room with ceiling fan for lounging and taking advantage of our great Florida weather. Flood Zone X (No Flood Insurance Required). There is also an extra utility room for extra storage and washer dryer. Located steps from the Historic McGregor Boulevard, you will be in a prime location to enjoy quick access to the Downtown River District, Edison Ford Winter Estates. Steps away from the Fort Myers Country Club and Allen Park School. Updates include Metal Roof (2016), Renovated Kitchen and Full House Re-wire by Cornerstone Builders of SWFL. (2017), Updated Bathroom (2024), Hardie Plank Siding (2017), New Deck(2024), New Hot Water Heater (Dec 2023) and Freshly Painted Exterior (2024).

$389,000

2 Bed

1 Bath

Fort Myers

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Charming house in Edison Park, the heart of the Historic District. This mid-century treasure is located just around the corner from the Edison Home Estates, a five-minute drive from downtown, and walking distance to the IB high school, the Arts Magnet elementary school, and the hospital. In addition to its prime location, this house boasts many unique features: a pecky cypress ceiling, a curved wall, and built-in bookshelves. It has a brand new 16’x16’ deck out back, a brand new bathtub and tile, a new refrigerator and new landscaping as well. It is the perfect starter home for a small family, young professional, or newlyweds. Live the Island Lifestyle without Island headaches. New roof in 2018, new water heater in 2024.

$479,000

3 Bed

2 Bath

Fort Myers

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QUAINT UPDATED BUNGALOW. DEAN PARK HISTORIC DISTRICT. Originally built in 1915, this charming historical register home was just the second home built in the original Dean Park. Now fully updated and expanded, it offers 3BBR/2BA including a huge primary bedroom suite, a classic wrap-around front porch and a sprawling 140" X 87' oversize lot, filled with mature trees. The front and two side porches invite you to enjoy the tranquil environment. Paver-stone walked leads up to the pillared porch. A privacy fence encloses a large paver-stone patio, creating your own Shangri-La in the heart of the city. The home was affected by the hurricanes, but remediation preserved the charm of the original woodwork and brickwork, including a fireplace in the entry room with a mantle created from a single piece of wood. Original historic home includes the formal entry room, dining room, two bedrooms, kitchen and bath, both now fully updated. A major 2005 expansion added a gathering/family room, the new primary bedroom, a laundry room and attached garage. The bedroom has 2 walk-in closets. comfortable sitting area and beautifully updated ensuite bath. The kitchen has plenty of wooden cabinets with granite countertops. Buyers will receive a $5000 appliance package so you can get precisely the make and models you want. It is conveniently located between the formal dining room and the gathering room, making the home ideal for entertaining, inside or out. The garage has alley-access and a bright workshop area, perfect for people who tinker or garden. Plenty of parking, hidden from the entertainment patio by the privacy fence. Stroll the quiet pet-friendly streets to absorb the historic envelope of Dean Park. Add a few steps to reach the downtown Ft. Myers River District with its plethora of restaurant and entertainment choices, plus a riverfront park that is both tranquil and vibrant. Motivated sellers. Priced well below competition. Yours to enjoy. SELLERS WANT OFFER. LET'S TALK

$799,000

4 Bed

3 Bath

Fort Myers

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Welcome to one of Rio Vista's treasured 1920's vintage Spanish homes! This generous 4 bedroom home with separate casita and oversized pool is a rare and unique find on the market today. Beautiful original oak floors and saltillo tile throughout add to its overall charm. The kitchen with 48 inch Viking range and hood are the heart of the home, perfect for entertaining friends and family. The spacious first floor master bedroom and bath is a retreat in itself. Leading to the second floor bedrooms is a stunning wood and Spanish tile staircase with leaded glass window. Each room offers its own unique charm ensuring everyone in the family has their own retreat. You will fall in love with the unique character of this old Spanish home with its high ceilings, fireplace and light and airy rooms. Snuggle into one of the cozy little nooks throughout the house or step outside to the oversized pool and lanai to enjoy the peaceful surroundings - a perfect place to unwind. The separate casita with a full bath is a functional space allowing for a variety of uses that can adapt to your lifestyle needs. The desirable location of this home not only allows you to own a piece of Old Fort Myers history, but also places you within easy access to dining, shopping & entertainment including the vibrant Downtown River District.

$295,000

3 Bed

2 Bath

Fort Myers

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Complete Rehab! Captivating Old Florida Charm with GUEST House. Old Florida-style home, perfectly nestled near the Downtown Historic River District. Brimming with timeless character and charm, this gem offers the perfect blend of classic appeal and modern potential. Main house has 2/Bed 1/bath, with Laundry room. The property features an inviting courtyard that’s ideal for outdoor gatherings or private relaxation as well as ample space to create your dream pool. Additionally, and seldomly available, 1 bedroom & one Bath Guest house that the city allows for family members. Main House features include original hardwood floors, high ceilings and a cozy fireplace, some newer windows, New Roof, Exterior paint and a long front screened in porch to enjoy a quiet morning coffee. Whether you're seeking a vacation retreat or a permanent residence, this home’s unbeatable location and unique charm make it a rare find. Located near Art District, Barbara Mann Theater, FSW University, Caloosa Event Center. Don’t miss your chance to own a piece of Florida history—schedule your showing today! Home needs renovation work in main house & guest house.

$825,000

4 Bed

4 Bath

Matlacha

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Here is your chance to own a slice of waterfront paradise in the historic area of Matlacha! This property consists of two cottages, "Pink" and "Green" and they each offer two units within each cottage making the opportunities endless!! You could live and work out of one cottage and rent out the other cottage as one or two units. Zoned C1 so smaller scale commercial uses may also be an option. Both cottages have been completely remodeled with no detail spared and are immaculate. Both cottages offer a full kitchen, two bathrooms, impact resistant doors, impact resistant windows, luxury laminate flooring throughout, washer & dryer and their own patio. Carport has two separate storage closets. From your own back yard you can fish, kayak, boat the amazing bay areas to some of the most sought after islands, catch breathtaking sunrises and sunsets, endless wildlife watching and so much more. All of this and you are located in the heart of Matlacha where you can walk to small retail shops and top rated restaurants.

$6,500,000

4 Bed

3 Bath

NAPLES

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Step into a rare piece of Naples history with this exquisitely renovated, enchanting coastal cottage, once owned by legendary interior designer Albert Hadley. As a co-founder of the iconic Parish-Hadley firm, Hadley crafted interiors for luminaries like Jackie Kennedy and Brooke Astor—an artistic legacy that resonates throughout this home. Seamlessly blending historic charm with modern luxury, this chic residence features a thoughtfully updated main house with three bedrooms and two baths, offering inviting spaces for conversation and relaxation. The chef’s kitchen is a masterpiece, boasting new custom cabinetry and marble countertops. A newly designed wet bar in the dining room, complete with a Subzero wine refrigerator and double drink drawers, makes entertaining effortless. The first-floor bath has been stylishly reimagined with Kohler fixtures, while the second-floor bath exudes equal sophistication. Designed for indoor-outdoor living, the idyllic screened-in porch—complete with a Sunbrite outdoor TV and custom furnishings—invites you to unwind in style. The cozy porch overlooks a sun-drenched pool and patio, all framed by lush tropical landscaping and desirable southern exposure. A private guest cottage offers the perfect retreat, featuring a bespoke kitchenette, built-in queen bed with storage, separate bunk room, and a fully remodeled bath. Thoughtfully upgraded, it includes its own tankless water heater, outdoor shower, and newly updated HVAC system. Timeless details abound, from custom wool rugs and plantation shutters to elegant crown moldings and French doors. Modern updates include a new sun porch roof (2022), a brand-new HVAC system (2023), a complete dormer replacement, and extensive subfloor and tile renovations. A charming white picket fence, alley access, a garage, and a covered carport enhance the home's curb appeal and convenience. Perfectly positioned just three blocks from Naples’ pristine beaches and a short stroll to the world-class dining and shopping of 3rd Street and 5th Avenue, this home is a rare find. Whether as a full-time residence or a luxury retreat that accommodates 14+, this is Old Naples living at its finest. Don’t miss this once-in-a-lifetime opportunity—schedule your private tour today!

$1,500,000

6 Bed

3 Bath

Fort Myers

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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 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 add to the home's unique appeal. The property also 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 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 with sidewalks 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.

$1,500,000

5 Bed

6 Bath

Fort Myers

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This beautiful Compound property sits on a double lot and has amenities you can only dream of. The main house offers 4 bedrooms, 3.5 bathrooms, dining room, great reception room and its own private bar. From the bar, you enter the pool and spa area outside which will lead to the pool home/mother inlaw suite on the other side of the pool. The pool home offers 1 bedroom, 1 luxurious bathroom, full kitchen, living room, great pantry. It has vaulted ceilings and its own entry through a separate gate. Located behind the main living area of the compound, you can find a 12 car garage including a equipment lift. There is also another full bathroom and a huge safe located in the garage. Another 900sqft great room is located on the 2nd floor of the garage. All buildings have been extensively remodeled, hardwood floor & tile throughout. Brand new 3rd bathroom, brand new 5ton AC unit, new water heaters, new washer & dryer. Access for the garage is from the back of the property through melaleuca st. which leads through the huge garden area. Brand new pool equipment. This is a property you can only dream of and offers space for everything you could think of doing! Check it out today!

$430,000

1 Bed

1 Bath

NAPLES

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An Orginal Vintage Cottage located in the heart of the thriving Bayshore Arts District . Built in the 1940’s , This sweetly curated cottage is tucked in amongst a canopy of native plantings and butterfly gardens. Featuring a Front Porch with French Doors and a Living Room with Morning Light , a cozy vibe beckons . Beadboard Ceiling, Custom Moldings, and Open Kitchen add to its feel. An herb window in the kitchen allows for bird watching and beautiful garden views. Primary bedroom and in suite bath with soaking tub and bidet . An interior laundry with plenty of storage and natural light leads to the back garden with lounge area. A magical gnome style garden shed with custom made sally door and electric sits in the tiny forest out back . Enjoy the walkability to Bean to Cup Coffee Shop , Cafes , Celebration park and even the Botanical Gardens! Make this white picket fenced gem your own . May be eligible for historic designation. One of the last remaining authentic Olde Florida Cottages! "LOVE GROWS BEST IN LITTLE HOUSES" Owners would love for the cottage to be loved by the next Owner and remain Intact or Added on , and Owners Certainly Invite All Offers, too !