Clearwater Real Estate Search

Clearwater Historical Properties for Sale

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Newest Clearwater Historical Properties for Sale

101 N Glenwood Avenue, Clearwater
$372,900
4 Beds ⋅ 2 Baths ⋅ Crest Lake Sub SubDv. ⋅ 33755 Zip Code
Virtually Staged. AMAZING IMPROVED PRICE! Charm, natural light, and a corner-lot setting welcome you to this four-bedroom, two-bath Clearwater home. Vinyl plank flooring and plentiful windows create a light, inviting interior, with distinct living and dining spaces that offer flexibility for everyday living and entertaining. The kitchen features stone counters, light cabinetry, a subway tile backsplash, and open shelving for a blend of character and practical storage. The primary bedroom includes its own bathroom, while three additional bedrooms provide options for guests, a home office, or hobbies. An inside laundry room adds everyday convenience. Outside, the fenced backyard and rear deck offer space to create an outdoor retreat for morning coffee, dining, gardening, entertaining, or relaxing beneath the established trees. The corner lot adds to the home’s appeal, with opportunities to refresh the landscaping and personalize the outdoor spaces. Repairs and finishing touches are needed, providing an opportunity to build on the home’s existing charm and updated features. Enjoy a location approximately one block from Crest Lake Park, with lakeside walking paths, a dog park, and playground. Clearwater Country Club offers nearby golf, while downtown Clearwater’s waterfront Coachman Park, and concerts at The BayCare Sound provide a variety of entertainment options. Clearwater Beach is approximately 4–5 miles away, offering Gulf beaches, Pier 60, waterfront dining, and boating activities. Shopping, groceries, and dining are available along Gulf-to-Bay Boulevard, with additional retail options at Clearwater Mall, including Target and Costco. A home with character, flexible space, and plenty of possibilities in a location convenient to Clearwater’s beaches, parks, and entertainment. All distances are approximate and vary by route. All information is believed to be accurate but is not guaranteed. Buyers and agents to verify all facts/information pertinent to their purchase decision.

101 N Glenwood Avenue, Clearwater

306 N Highland Avenue, Clearwater
$349,900
2 Beds ⋅ 1 Baths ⋅ Hillcrest Sub 2 Rev SubDv. ⋅ 33755 Zip Code
Step into this completely updated, meticulously maintained home where pride of ownership shows throughout! This 1940 Florida bungalow flawlessly unites historic soul with extensive modern upgrades. Nestled in a highly convenient location, this property offers seamless proximity to the pristine sands of Clearwater Beach, the charm of downtown Dunedin, and the major metropolitan hub of Tampa. Inside, a sun-drenched, open-concept living space highlights a classic arched doorway, an updated wood-burning fireplace, and masterfully refinished original pine hardwood floors that flow past refinished doors with antique crystal knobs. The custom kitchen boasts a newer stainless steel refrigerator and gas stove, while a newly integrated laundry closet contains a newer full size washer and dryer. The fully renovated bathroom showcases crisp, upscale finishes. Capital improvements deliver absolute peace of mind, featuring a newer roof, newer HVAC system, a newer gas tankless hot water heater, a newer electric garage door, an updated electrical panel, updated plumbing, a freshly painted interior, and partial hurricane-impact windows. Outside, the large private backyard oasis offers unlimited possibilities. A premier asset is the detached garage—wired for electricity and plumbed—offering an excellent head start for a future Accessory Dwelling Unit (ADU) or guest suite. Perfectly positioned just 1.5 miles from up-and-coming, revitalized Downtown Clearwater, this property sits at the gateway of an exciting renaissance. With a wave of new restaurants, bars, hotels, boutique stores, gaming, and entertainment centers just beginning to emerge, the value of this thriving area is rapidly increasing—positioning this immaculate turn-key home as an extraordinary investment property. Schedule your private showing today!

306 N Highland Avenue, Clearwater

1250 Lakeview Road, Clearwater
$205,000
3 Beds ⋅ 1 Baths ⋅ Oakland Heights SubDv. ⋅ 33756 Zip Code
The shady oak on this corner lot was here long before the 1925 bungalow behind it, and by late afternoon the whole yard sits in its shade. This three bedroom, one bath Clearwater home in Oakland Heights is sold as-is to a buyer who would rather build the value themselves and bring every finish in line with their own vision. Inside is a spacious, well appointed open floor plan, with the living area running into the kitchen and family room combination and a separate dining room alongside it, all on one level and with a brand new HVAC replaced in 2024. The spacious and fully fenced corner lot does more work than most at this price. A gate in the fence gives you drive-in access for a boat, an RV, or work equipment, which is not easy to find this close to downtown. Behind the house there is a wide wood deck under the oaks, a storage shed, and a second detached building with its own private entrance. It serves as an office or studio as it stands, and with the right permitting through the City of Clearwater it is a natural candidate for a separate suite, whether that means rental income or room for family. The rest of the yard is open ground for a garden, a playground, or pets, and with no HOA, no minimum lease period, and a Flood Zone X designation, the carrying costs stay predictable whether you hold it or renovate and resell. Clearwater Plaza and Publix sit a few blocks away, close enough that the weekly errands never involve a main road. Ross Norton Recreation Center and Park is a short walk, Belleair Country Club is just south, and Morton Plant Hospital is minutes north. Coachman Park and the BayCare Sound are under three miles, and Clearwater Beach is a straight run west over the Memorial Causeway

1250 Lakeview Road, Clearwater

1241 Nicholson Street, Clearwater
$305,000
3 Beds ⋅ 2 Baths ⋅ Country Club Estates SubDv. ⋅ 33755 Zip Code
Here is one you don't want to miss!!! Welcome to 1241 Nicholson Street, a 3-bedroom, 2-bath home offering recent improvements, flexible living space, a generously sized fenced backyard, and an AMAZING NEW PRICE! A new roof and fresh interior and exterior paint provide a strong start, while the updated kitchen features granite countertops, stainless-steel appliances, ample cabinetry, and a practical layout for everyday use. The adjoining living and dining combination creates a comfortable central gathering space, and the bonus room offers additional flexibility as a home office, playroom, hobby area, media room, or second sitting area. The primary bedroom includes its own private bathroom, while the two secondary bedrooms share a previously refreshed guest bath. Both bathrooms have received updates while still leaving room for future personalization. Additional features include a one-car garage and a large fenced backyard with space to create a patio or grilling area, add gardens or play equipment, provide room for pets, or explore the possibility of a future pool, subject to applicable zoning, permitting, and setback requirements. Conveniently located near shopping, dining, schools, and major roadways, the property is approximately 2 miles from Downtown Clearwater and Coachman Park, about 3 miles from BayCare Ballpark, and approximately 6 miles from Clearwater Beach. Nearby recreational options include Crest Lake Park, the Pinellas Trail, Clearwater Country Club, waterfront activities, and the shops, restaurants, and community events found in Downtown Clearwater and nearby Dunedin. The location also provides access to U.S. Highway 19, Gulf-to-Bay Boulevard, and area employment and entertainment destinations throughout Pinellas County and Tampa Bay. All information is believed to be accurate but is not guaranteed. Buyers and agents are encouraged to verify all measurements, room dimensions, property features, permit history, zoning, school information, distances, and any other facts or information pertinent to their purchase decision.

1241 Nicholson Street, Clearwater

831 Grand Central Street, Clearwater
$374,500
2 Beds ⋅ 2 Baths ⋅ Milton Park SubDv. ⋅ 33756 Zip Code
Rare Clearwater investment opportunity with multiple exit strategies. Whether you are an investor, builder, or end user looking for land value, rental potential, and future upside, this oversized property offers the flexibility to live, lease, expand, or redevelop in one of Clearwater’s active growth corridors. Situated on an 83’ x 127’ quarter-acre lot with rear alley access, this property is currently configured as a duplex with two 1- bedroom, 1-bath units. The property has no rental history due to owner use, but projected rental potential is estimated at approximately $2,500 per unit per month, depending on final use, condition, rental strategy, and market demand. The real value is in the land, zoning, and flexibility. The property offers potential for duplex, triplex, or fourplex use, giving a future owner several possible paths to increase value: maintain the existing duplex, live in one unit and rent the other, lease both units for income, explore conversion or expansion into a triplex or fourplex, or redevelop the oversized lot with new construction. Buyer should verify zoning, permitted uses, density, rental projections, and redevelopment options with the City of Clearwater. The existing block construction and recent updates — including HVAC, cabinetry, and appliances — allow for continued use while preserving long-term upside. This makes the property especially appealing for buyers who want income potential now with the ability to plan future improvements or redevelopment. Location continues to drive demand. The property is conveniently positioned within a short drive to Clearwater Beach and the Gulf, with easy access to Tampa International Airport, Downtown St. Petersburg, shopping, dining, and major employment corridors. This central location supports strong long-term rental appeal and future resale value. Large lots with this level of flexibility — live-in potential, income-producing use, and redevelopment upside — are becoming increasingly rare in Clearwater. For the buyer looking to control land, create income, and unlock future value, this is a Clearwater opportunity worth serious attention.

831 Grand Central Street, Clearwater

403 Magnolia Drive, Clearwater
$3,500,000
7 Beds ⋅ 8 Baths ⋅ Harbor Oaks SubDv. ⋅ 33756 Zip Code
Virtually Staged. A rare opportunity to own one of Harbor Oaks’ most distinguished estates. Built between 1918 and 1925, 403 Magnolia Drive pairs nearly a century of architectural character with the scale and presence of a true estate—all just one block from the water, minutes from Downtown Clearwater, and located in desirable Flood Zone X. Spanning 7,223 square feet across three levels, the seven-bedroom, seven-and-a-half-bath estate is defined by soaring natural light, original hardwood floors, beautifully preserved architectural details, and an exceptional sense of space. Floor-to-ceiling windows line the dual formal living rooms, while a sun-filled solarium with NEW windows and an adjoining Florida room create effortless transitions throughout the main level. A private library and expansive family room offer additional spaces for both intimate everyday living and large-scale entertaining. Each of the home’s seven bedrooms features its own private full bathroom, an extraordinary level of comfort and privacy for family and guests. Upstairs, two generous suites open onto a sweeping wraparound deck and feature beautifully appointed, spa-inspired baths. The entire third floor offers another private retreat with a full bath, fireplace, sun deck, and abundant storage—creating exceptional flexibility for a primary suite, guest quarters, or private living level. At the heart of the home, the kitchen is designed for both serious cooking and entertaining, featuring commercial-grade stainless steel appliances, a Dacor gas range, custom millwork, and an oversized walk-in pantry. A wet bar, tray ceilings, and French doors opening to the courtyard and outdoor living spaces further enhance the home’s ability to host with ease. Outside, the estate unfolds across a prominent corner lot of more than half an acre—an increasingly rare offering in this location. Mature surroundings create a private setting for the resort-style pool and spa, expansive deck, and outdoor entertaining areas, while a circular drive provides an impressive sense of arrival. Moments from Downtown Clearwater’s dining and entertainment, minutes from Clearwater Beach, and surrounded by some of the area’s most notable residences, 403 Magnolia Drive offers a combination of history, scale, land, and lifestyle that is truly one of a kind.

403 Magnolia Drive, Clearwater

322 Roebling Road S, Belleair
$1,925,000
4 Beds ⋅ 4 Baths ⋅ Overbrook Park SubDv. ⋅ 33756 Zip Code
Nestled on just over a quarter acre in the heart of Belleair, this exceptional residence is recognized as one of the Town's historic homes, blending timeless architectural character with modern comforts in one of the area's most sought after locations. Located in an X flood zone, with no history of flooding and flood insurance not required, this remarkable property is ideally positioned near the prestigious Pelican Golf Club and Belleair Country Club, world famous Gulf beaches, boutique shopping, charming neighborhood cafes, and a world renowned hospital, offering an unmatched combination of elegance, convenience, and lifestyle. Surrounded by lush, mature landscaping, the property offers a private resort style setting highlighted by a sparkling pool, expansive outdoor living areas, and an enclosed patio overlooking the backyard oasis. Designed for both relaxation and entertaining, the outdoor spaces create a true retreat like atmosphere. Inside, distinctive architectural details set this home apart, including elegant rounded archways, rich hardwood flooring, and thoughtfully designed living spaces that blend historic character with modern functionality. The open concept kitchen features a gas Wolf range, quality cabinetry, generous workspace, and seamless flow into the main living and dining areas. The flexible floor plan includes three spacious ensuite bedrooms on the upper level, including a well appointed primary suite featuring an exceptionally large custom built walk in closet and an adjoining room ideal for a private study, nursery, fitness space, or wellness room. A room currently utilized as an executive study on the main level can easily be transformed into a fourth bedroom, providing additional flexibility for family, guests, or multigenerational living. Enhancing both comfort and functionality are a whole home generator, integrated dehumidification system, custom wine cellar, oversized three car garage, and abundant storage. The home's exceptional condition reflects years of attentive ownership and care. Combining historic charm with thoughtful modern updates, this remarkable residence is designed for both everyday living and effortless entertaining. From the resort style backyard to the spacious living areas and sought after Belleair location, every aspect of the home reflects quality, character, and enduring appeal.

322 Roebling Road S, Belleair

802 Jurgens Street, Clearwater
$289,900
2 Beds ⋅ 1 Baths ⋅ Clearwater SubDv. ⋅ 33755 Zip Code
Just 10 minutes from world-famous Clearwater Beach, this beautifully remodeled home offers the perfect combination of coastal lifestyle, modern comfort, and investment potential — with NO HOA and NO CDD. This move-in-ready property features 2 bedrooms, 1 fully renovated bathroom, and an additional office/flex room that may be used as a third bedroom, studio, guest space, or potential mother-in-law area with a private entrance. The home has been thoughtfully updated throughout, offering a functional layout designed for comfortable living, rental flexibility, or a future income-producing opportunity. Inside, you will find new flooring, new doors, new appliances, updated plumbing and electrical, a recent A/C, and a beautifully redesigned kitchen with granite countertops, a functional island, and a fresh modern feel. The fully renovated bathroom offers elegant finishes, including a glass shower and a spacious jacuzzi tub. Additional updates include a newer roof, new windows, new grass, gutters, and beautiful curb appeal from front to back. Enjoy an excellent Clearwater location close to top-rated schools, Downtown Clearwater, Coachman Park, Pier 60, restaurants, shopping, hospitals, parks, airports, and some of Florida’s most beautiful beaches. Whether you are looking for a primary residence, vacation home, rental property, or short-term rental/Airbnb opportunity, this home offers exceptional flexibility in one of Florida’s most desirable coastal areas. Live where others vacation.

802 Jurgens Street, Clearwater

909 Hart Street, Clearwater
$485,000
4 Beds ⋅ 3 Baths ⋅ Plaza Park Add Clearwater Improv Co Corr SubDv. ⋅ 33755 Zip Code
Virtually Staged. Unique homes like 909 Hart St in Clearwater do not come along often. Thoughtfully renovated this 4-bedroom, 3-bathroom home is full of character, charm, and stylish updates that set it apart from the typical cookie-cutter property. Best of all, there is no HOA and no CDD, helping keep ownership costs lower. A true standout feature is the oversized remodeled swimming pool, which adds exceptional value and lifestyle appeal. In Florida, having a large updated pool is a major advantage — perfect for cooling off during the long summer months, entertaining guests, hosting pool parties, or simply enjoying your own private backyard retreat year-round. A charming front patio welcomes you in and offers the perfect place to enjoy your morning coffee and Florida’s beautiful weather. Inside, the spacious family room features a large fireplace, creating a warm and inviting space for relaxing or entertaining. The updated kitchen is both functional and stylish, featuring stainless steel appliances, newer cabinetry, granite countertops, and a light gray backsplash. Just beyond the kitchen, the generously sized dining room is ideal for gathering with family and friends. Tile and vinyl flooring flow throughout the home, with no carpet anywhere. Most of the windows have been replaced, adding to the home’s overall value, appeal, and peace of mind for the new owner. The renovated bathrooms feature tasteful contemporary finishes, and the oversized laundry room offers abundant cabinet storage along with a utility sink for added convenience. The private primary suite includes a large sitting area that works perfectly as a home office, workout space, or quiet retreat, with views of the patio and pool. Situated on a large lot, the fully fenced backyard is designed for enjoying the very best of the Florida lifestyle. Complete with an outdoor kitchen, spacious entertaining areas, and the oversized remodeled pool, this outdoor space is made for weekend BBQs, family gatherings, and relaxed evenings at home. Properties with this much personality, outdoor living space, and pool appeal are hard to find.

909 Hart Street, Clearwater

1106 Carlton Street, Clearwater
$167,900
3 Beds ⋅ 1 Baths ⋅ Greenwood Park SubDv. ⋅ 33755 Zip Code
Welcome to 1106 Carlton St, Clearwater, FL 33755, a great opportunity for investors, renovators, or buyers looking for value in the heart of Clearwater, Florida. This 3-bedroom, 1-bath single-family home offers strong potential for those willing to bring a little vision and finishing work to the property. The home was recently renovated, but unfortunately experienced vandalism after the improvements were completed, which has led the seller to make the decision to sell. While the property may currently show with boarded windows, don’t let that discourage you — much of the heavy lifting has already been completed and the home offers a solid foundation for the right buyer. Since purchasing the property in 2017, the owner has made numerous improvements including new flooring, fresh interior and exterior paint, a new HVAC system, a new roof, updated kitchen cabinets and countertops, and a renovated bathroom. With many of the major systems and cosmetic upgrades already addressed, this property presents an excellent chance to come in, complete some minor clean-up and finishing touches, and either rent, renovate further, or resell for potential profit. Located in a convenient area of Clearwater in Pinellas County, the property is close to shopping, restaurants, schools, parks, and major roadways, while also being just a short drive from the world-famous Clearwater Beach and the Gulf of Mexico. Clearwater continues to be one of the most desirable areas in the Tampa Bay real estate market, making opportunities like this increasingly difficult to find. Whether you are searching for your next investment property in Clearwater, a rental opportunity, or a value-add renovation project, 1106 Carlton St is worth taking a look at. Schedule your showing today and see the potential this property has to offer.

1106 Carlton Street, Clearwater

1109 Charles Street, Clearwater
$799,000
3 Beds ⋅ 3 Baths ⋅ Peale Park SubDv. ⋅ 33755 Zip Code
Virtually Staged. This is a rare opportunity to own a truly one-of-a-kind legacy property designed for coastal living in one of Pinellas County's most sought-after locations. Situated on a tropical double lot just blocks from St. Joseph’s Sound and minutes from Downtown Dunedin, this exceptional property offers a combination of land, flexibility, charm, and income potential that is increasingly difficult to find. Perhaps the most valuable feature of this property is its rare grandfathered multifamily designation within a residential zoning district, allowing it to function as either a single-family residence or an income-producing duplex with an additional ADU. Owners have the unique ability to live comfortably in one residence while generating income from the others, creating exceptional income opportunities. Thoughtfully renovated from the studs out by a renowned local builder, the property preserves the timeless character and “Old Florida” charm of the original structures while seamlessly incorporating modern luxury, craftsmanship, and convenience throughout. High-end finishes, thoughtful design, and flexible living spaces create a property that feels both elevated and inviting. The oversized double lot offers endless possibilities for expansion, outdoor entertaining, RV or boat parking, and private resort-style living. Surrounded by tropical landscaping, the outdoor setting is anchored by a brand-new pool with elegant paver decking, creating a private coastal retreat perfect for relaxing, entertaining, and enjoying Florida living year-round. Despite being located just minutes from the waterfront, the property sits outside the flood zone, eliminating the need for flood insurance. The Pinellas Trail is located at the end of the block and provides direct biking/walking access to downtown Dunedin’s acclaimed restaurants, breweries, bars, live music venues, boutique shopping, marinas, award-winning Gulf beaches, and Major League Baseball spring training facilities. The staged renderings showcase the incredible versatility of the property and highlight the many ways the spaces can be customized to fit your vision—whether as a private retreat, multigenerational compound, luxury seasonal residence, or high-performing investment property. Properties offering this level of location, flexibility, land value, and coastal character rarely come to market! This property is listed below appraised value and priced to sell!

1109 Charles Street, Clearwater

456 Gardenia Street, Belleair
$1,999,000
5 Beds ⋅ 5 Baths ⋅ Belleair Estates SubDv. ⋅ 33756 Zip Code
Previous contract canceled due to Buyers property not selling. Welcome to this quintessential Belleair estate, a masterful blend of timeless elegance and modern refinement. Thoughtfully restored with exquisite attention to detail, this historic residence sits on a picturesque, palm tree-lined street. Take advantage of the Belleair lifestyle in your personal golf cart and explore all that the community has to offer including world class golf at Belleair Country Club and The Pelican Golf Club, fine dining, shopping and some of America’s most beautiful beaches. Located in a non-flood, no evacuation zone, the estate offers sweeping golf course views, a resort-sized pool, and a spacious driveway with ample room for vehicles. Inside, you are welcomed by custom marble flooring that flows into a grand formal dining room, ideal for family gatherings. An aesthetically pleasing, professionally designed chef’s kitchen awaits just beyond, complete with a butler’s pantry and adjacent powder room. The first-floor primary suite is a true retreat, featuring refinished 20th-century hardwood floors, a pass-through fireplace, a luxurious en-suite with soaking tub, and a walk-in closet with handcrafted wood shelving. Throughout the home, restored original windows provide an abundance of natural light and frame views of century-old palms and manicured fairways. Two versatile flex spaces—one on each floor—offer options for a home office, nursery, or playroom. Upstairs, four spacious bedrooms each have dedicated bathroom access for convenience. Down a private hallway, a game/media room with half bath provides the perfect secluded entertainment space. Additional highlights include a 400 sq ft living room with wood-burning fireplace and a bright sunroom overlooking the expansive pool and sun deck—an entertainer’s dream. This exceptional property combines history, luxury, and location, offering the rare opportunity to call one of Belleair’s true legacy's home.

456 Gardenia Street, Belleair

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