Glenwood Real Estate, Homes, Condos for Sale in Clearwater, FL

5 Beds ⋅ 5 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

Multigenerational home in the Heart of Glenwood 5 Bedrooms | 5 Bathrooms | Home Office | 3,200 Sq. Ft. Total Welcome to this expansive home in the highly sought-after Glenwood area. Spanning an impressive 3,200 square feet, this property is the ultimate setup for multigenerational living, offering the perfect blend of grand shared spaces and private quarters. The Main Residence (2,715 Sq. Ft.) Step inside the main home into the living room with newly refinished solid Oak wood floors and electric fireplace. A bright, airy, and very spacious footprint that flows effortlessly into a massive, chef-ready kitchen—the first of two in this home. From Kitchen and primary bedroom there is a huge deck perfect for BBQ and just that cup of coffee in the morning. An additional wrap around deck overlooking the park across the street. The house has tons of windows with abundance of natural light. The interior spiral staircase connects both levels where additional bedrooms and large family room/main cave connect to the garage Accommodations & Work: Includes a dedicated home office, perfect for remote work or quiet study, alongside generous bedrooms and beautifully appointed bathrooms featuring durable tile throughout. The main floor has a laundry room and the ensuite has it's own. The Private In-House Suite (588 Sq. Ft.) The self-contained in-house suite offers total independence without sacrificing proximity. Features its own private entrance, allowing occupants to come and go as they please. Comes complete with its own full-sized, large kitchen and a second independent laundry closet. Huge Yard: The massive fully fenced backyard is a blank canvas ready for your dream oasis with pond and waterfall, a grand outdoor entertaining deck, or space for the family and pets to roam freely. The house features a brand new well and new sod throughout the entire yard with flower beds and landscaping The tandem garage can hold 3 cars with abundant storage for the bikes and tolls with plenty of parking with dual driveway and circular drive on the side The house has been recently renovated throughout Properties with this level of spatial flexibility, dual full kitchens, and genuine private-suite capabilities in Glenwood are incredibly rare. Perfect for families looking to co-habitate while maintaining privacy. Roof 2021 AC lower floor 2006 recently clean and sanitize works great AC 2023 main floor. Hot water heater 2018

707 N Glenwood Avenue, Clearwater

$425,000

3 Beds ⋅ 4 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

Welcome to a rare opportunity in the heart of Clearwater’s historic Glenwood neighborhood. Perfectly positioned directly across from Glenwood Park, this 3 bedroom, 3.5 bathroom home sits on an oversized double lot totaling an impressive .41 acres — an exceptional offering in one of Clearwater’s most charming and evolving neighborhoods. Surrounded by a beautiful mix of historic homes, thoughtfully renovated residences, and stunning new construction, Glenwood offers timeless character and a sense of place that is becoming harder to find. Mature trees, unique architecture, and a neighborhood rich with history create an atmosphere that feels both established and full of possibility. This property presents the opportunity to restore and reimagine a home with incredible character while creating something truly special. Whether your vision is preserving its historic charm, designing a luxury renovation, or blending classic architecture with modern finishes, the possibilities here are endless. Set on nearly half an acre, the oversized double lot provides space rarely found this close to everything — room to expand, create incredible outdoor entertaining areas, add a pool, or simply enjoy the privacy and scale of the property. Inside, the home offers generous living spaces and one feature that is almost unheard of in Florida — a basement. Ideal for storage, a workshop, fitness area, game room, wine room, or additional flexible space, this rare amenity makes this property truly stand apart. Even better, the home is located in Flood Zone X, offering added peace of mind with no required flood insurance. Enjoy an unbeatable location just minutes from everything that makes Pinellas County so desirable — only 5 minutes to vibrant Downtown Dunedin and approximately 10 minutes to world-famous Clearwater Beach. Spend your days enjoying local restaurants, breweries, waterfront parks, festivals, shopping, and endless coastal activities. Historic character, a rare basement, an oversized .41-acre double lot, and an incredible location — 615 N Glenwood Ave is ready for its next chapter and waiting for someone to bring their vision to life.

615 N Glenwood Avenue, Clearwater

$405,000

2 Beds ⋅ 3 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

Some Photos Are Virtually Staged. Built in 1948, This Charming Custom Mid Century home located in the established Historic Glenwood neighborhood Offers an Abundance of Features including a Massive 135x133' Lot, Original Wood Parquet Floors, Huge 36x16 Finished/Air Conditioned Basement with Separate Entrance which would be Great for Entertainment Area, Music & Art Enthusiasts, Home Fitness Center, Additional Separate Living Quarters and a number of other uses. There is a Half Bath conveniently located in the basement. The 2 Car Carport is Behind the Home. Separate Workshop with Lockable Door next to basement. The Room with closet off the kitchen Could Easily Be 3Rd Bedroom. The Roof was installed in 2024 and the HVAC was just installed in 2025. Just Minutes to Downtown Clearwater, Clearwater Country Club Golf Course & Gorgeous Clearwater Beach.

1524 Maple Street, Clearwater

$594,900

4 Beds ⋅ 3 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

HUGE PRICE IMPROVEMENT NOW $594,900!! BEAUTIFUL 4BR 2 & 1/2 BATH POOL HOME IN CLEARWATER!! THIS IS A GREAT FAMILY HOME WITH HUGE ROOMS AND LARGE LIVING SPACES!! THE GIGANTIC PRIMARY BEDROOM HAS A BIG WALK IN CLOSET THAT IS CURRENTLY CONVERTED TO A 5TH BEDROOM!! LIVING ROOM IS LARGE WITH COZY FIREPLACE AND OPENS WITH 12FT SLIDERS TO FANTASTIC RECREATION OASIS!! HEATED POOL, OUTDOOR KITCHEN AND TABLE THAT SEATS 12!! THE GARAGE HAS BEEN CONVERTED TO A MEDIA AND GAME ROOM WITH LOTS OF GAMES, AND CUSTOM LIGHTING!! THERE IS A LARGE CIRCULAR DRIVE THAT WILL ACCOMMODATE SEVERAL VEHICLES!! MAKE YOUR APPOINTMENT TO SEE THIS HOME SOON!! HOME HAS BEEN OPERATED AS A VACATION RENTAL, REPORTS AVAILABLE. ASKING PRICE $594,900

505 N Highland Avenue, Clearwater

$761,000

5 Beds ⋅ 4 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

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615 Smallwood Circle, Clearwater

$445,000

3 Beds ⋅ 2 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

Welcome to a 1925 gem in the heart of desirable Clearwater, Florida! Nestled on a peaceful cul-de-sac and surrounded by breathtaking homes, this three-bedroom, two-bath charmer is brimming with potential. With a new flat roof and new A/C installed in 2022, the big-ticket items are already done! Step inside to discover timeless features like two cozy fireplaces and a generously sized kitchen, offering the perfect canvas to create your dream space. Whether you’re envisioning a stunning renovation to call home or a profitable investment opportunity, this historical beauty is priced just right for you. Don’t miss the chance to transform this classic property into a masterpiece of your own. Schedule your showing today—opportunities like this don’t come around often!

1526 Oakwood Street, Clearwater

$850,000

5 Beds ⋅ 4 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

Timeless Elegance Meets Modern Sophistication in the heart of the highly sought-after Glenwood Estates, this extraordinary five-bedroom modern farmhouse seamlessly blends historic charm with contemporary luxury. Set on a generous corner lot at one of the highest points in Clearwater, graced by lush, mature landscaping and towering grand oaks, this home is a sanctuary of beauty and functionality. Lovingly remodeled by the current owners since 2017, including an impressive 1,850-square-foot second-floor master suite, first-floor mother-in-law suite, and double-car garage addition in 2019, the property is as striking as it is practical. The main floor boasts an open, airy layout designed for hosting. Step into the dining area, where a dramatic oak staircase sets a refined tone. The centerpiece is the stunning modern farmhouse kitchen, a chef’s dream outfitted with custom-milled cabinetry from North Carolina, sleek stainless-steel appliances, and an oversized reclaimed oak island. Dolomite countertops, a shiplap ceiling, and artisan pendant lighting complete the space, while LED under-cabinet lighting adds a warm, inviting glow. Adjacent to the kitchen is the welcoming living room, which flows seamlessly into a private office tucked behind charming reclaimed oak barn doors. Through PGT premium hurricane-rated French doors, step onto the garden patio, surrounded by tropical foliage and fruit trees—including banana, lemon, and persimmon—for the ultimate in tranquility. The thoughtfully designed floor plan provides private retreats for every member of the household. On the main floor, two bright bedrooms with garden views share a full bath illuminated by a skylight. A guest half-bath is conveniently located nearby. Upstairs, the master suite is a true oasis. Wide-plank distressed oak flooring, recessed ceiling lights, and ample space for a California king bed create an atmosphere of understated luxury. The spa-like master bath features a freestanding soaking tub, dual sinks, and a tempered glass rain shower, while the adjoining walk-in closet offers custom oak shelving and a vanity station. An additional small bedroom or office is located nearby. The first-floor mother-in-law suite, with its own private entrance, includes a full kitchen with granite countertops, tiled flooring, and modern appliances, making it perfect for extended family, guests, or use as an art studio. A Piece of History with Modern Comfort Originally constructed with heart-of-pine lumber and oak by the McMullen farming family, this home now features modern upgrades throughout: hurricane windows, new electrical wiring, designer fixtures, and a new roof. Crown molding, colonial archways, and built-in shelving enhance the home’s timeless appeal. Situated over 40 feet above sea level and adjacent to a scenic highland, this property is not just a home but a lifestyle. Whether you’re hosting vibrant gatherings, enjoying quiet mornings on the patio, or simply admiring the craftsmanship and thoughtful updates, this one-of-a-kind residence offers it all. Don’t miss your chance to own this masterpiece in Glenwood Estates—schedule your private showing today.

509 N Glenwood Avenue, Clearwater

$580,000

3 Beds ⋅ 2 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

Non Flood Zone, 67ft above sea level home completely unaffected from recent storms! This 3-bedroom, 2-bathroom home combines timeless charm with contemporary conveniences, making it the perfect sanctuary for comfortable living. Step inside to discover a thoughtfully designed and unique interior showcasing beautiful hardwood and tile floors throughout. The inviting sunroom is a standout feature, offering a bright and airy space to unwind and enjoy the view of your expansive yard. The heart of the home is a well-appointed kitchen equipped with a gas stove, ensuring that cooking is both efficient and enjoyable. Double pane windows throughout enhance energy efficiency and provide a serene, quiet atmosphere. For added comfort, the home boasts two newer AC units, ensuring a cool and pleasant environment year-round, and water purification and reverse osmosis systems. In addition to the primary residence, this property includes a detached garage a 1-bedroom unit with a full bathroom downstairs and a bedroom upstairs, perfect for guests, extended family, or as a potential rental opportunity. The massive yard space provides endless possibilities for outdoor activities, gardening, or simply enjoying the open air. The lawn irrigation runs off of a deep well and there's a shallow well to water additional plants, wash cars, and other water activities. Located just minutes from the vibrant downtown areas of Clearwater and Dunedin, you'll have easy access to an array of dining, shopping, and entertainment options. And with the second-best beach in the state—and top 5 in the entire US—just a short drive away, you’ll be able to indulge in sun-soaked days and stunning ocean views whenever you like. Don’t miss the opportunity to make this unique Craftsman home your own. Schedule a viewing today and experience the perfect blend of historic charm!

411 N Glenwood Avenue, Clearwater

$339,000

3 Beds ⋅ 1 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

Back on market due to buyer's financing! High and dry! Completely unimpacted by Hurricane Helene! This house does not require flood insurance, in high elevation! Nestled just moments away from both the sun-kissed shores of Clearwater Beach and the vibrant heart of downtown, this charming 3-bedroom, 1-bathroom home offers the best of coastal living and urban convenience. Upon entering, you are greeted by a warm and inviting living space, bathed in natural light that pours in through the large windows. The kitchen boasts modern appliances and ample counter space, perfect for preparing meals. The three bedrooms are comfortably sized, each offering tranquil retreats for relaxation after a day of beachside adventures or exploring the vibrant area. A shared bathroom features contemporary fixtures and a shower-tub combination. One of the standout features of this property is its expansive fenced-in backyard, providing a private oasis for outdoor activities, entertaining guests, or simply unwinding under the Florida sky. The yard offers plenty of space for gardening enthusiasts or pet owners alike to enjoy. Don't miss your chance to make this delightful Clearwater home yours!

211 N Highland Avenue, Clearwater

$540,000

2 Beds ⋅ 2 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

Stunning Double Lot Home with Brand New $85,000 Solar Panels and Roof! Welcome to 504 N Glenwood Ave, Clearwater, FL 33755! This enchanting 1941 gem boasts not only timeless charm but also modern sustainability. In August 2022, a top-of-the-line $85,000 solar panel system and new roof were installed, blending classic elegance with eco-friendly efficiency. Step inside and be captivated by the unique character of this home. With an open concept layout, the spacious living areas flow seamlessly, perfect for both everyday living and entertaining. The two massive bedrooms offer plenty of space to relax and recharge, each featuring walk-in closets for ample storage. The two well-appointed bathrooms add convenience and style to this inviting sanctuary. Outside, dive into your private oasis! The sparkling pool is ideal for cooling off on warm Florida days or hosting unforgettable pool parties. Set on a generous double lot, the property provides plenty of outdoor space for gardening, entertaining, or simply unwinding in the sunshine. Location is everything! You'll be just minutes away from local shops, an array of fantastic restaurants, and the beautiful Clearwater Beach. Plus, with two airports within a 20-30 minute drive, travel couldn't be more convenient. Looking for even more potential? There's ample room to add an accessory dwelling unit, offering exciting possibilities for additional living space, a guest house, or rental income. The opportunities are endless! Don't miss the chance to make this extraordinary home yours! Schedule a viewing today and experience the perfect blend of historic charm and modern convenience. Call now to book your private tour! Let's make your real estate dreams a reality!

504 N Glenwood Avenue, Clearwater

$835,000

3 Beds ⋅ 2 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

This gorgeous 1941 Coastal Bungalow located in Historic Glenwood was exquisitely restored! Located only a few miles from famous Clearwater beach on a .28 acre fully fenced lot. The home will be sold mostly furnished. The home is zoned for 30 day leasing and has been successful on AirBNB with a 93% occupancy rate, renting at $220 per night in summer and $240 per night Nov-April. Making this home perfect as a vacation home which you can lease and earn from when out of town or simply keep it for yourself! The renovation done was very comprehensive, done by a professional contractor and all permitted. The home was fully restored from the studs in. New plumbing, New electrical, New walls, New lighting, New flooring, New kitchen, New bathrooms, New laundry room, New pool deck, New fencing, New roof, New tankless water heater, New a/c, New siding and New doors and windows. The home was given a fresh start! The roof was put on with hurricane clips and the windows are all impact rated. The windmit from 2021 when the renovation was complete gives an insurane discount for hurricane rated windows and doors. This is not in a flood zone so no flood insurance needed! Located one block from an excellent park to play in with kids and dogs. This is a rare find in Clearwater that you won't want to miss!

305 N Glenwood Avenue, Clearwater

$310,000

2 Beds ⋅ 2 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

Brand New A/C! Come check out this lovely turn of the century well-built home with loads of charm and personality from beautiful hardwood floors to the gorgeous custom crown moldings and ceiling medallions. This home was built in 1948, offers 2 bedroom 2 full baths, living room, dining room, family room, inside laundry and converted garage with an office space, an. Kitchen offers granite counter tops, stainless steal appliances, and cherry wood cabinetry with plenty of storage and pantry. Imagine enjoying your morning coffee in the breakfast room that is just right off the kitchen. Enjoy your fully fenced in back yard while entertaining under your pergola. This amazing home is just 4.4 miles to the sugar bright sands of Clearwater Beach, 17 miles to TPA International Airport, 3.6 miles to downtown Dunedin, less than 2 miles to downtown Clearwater for restaurants and the marina not to mention the upcoming IMAGINE Clearwater Project underway or 22 miles to Hyde Park Village Tampa. This is truly a one-of-a-kind home.

509 N Highland Avenue, Clearwater

$482,000

4 Beds ⋅ 3 Baths ⋅ Glenwood SubDv. ⋅ 33755 Zip Code

One or more photo(s) has been virtually staged. What a standout property! Possible DUPLEX or IN-LAW SUITE! This property comes with 2 separate units. The front property is a 3 bed 2 bath 1285sqft home that has been beautifully remodeled. The high ceilings will be one of the first things you notice when you walk in the door. The kitchen has been updated with new cabinets and quartz countertops, new stainless appliances and a lot of countertop space. The kitchen window allows you to view your beautiful pool while the family plays. The bedrooms are spacious and both bathroom showers have been retiled and updated. Lots of brand new items including a new tankless water heater, waterproof vinyl floors, and a fresh coat of paint inside and out. The back unit is a 1 bed 1 bath 560sqft with a large walk-in closet. This home has also been updated and has a large center island. The cabinets, granite countertops, and stainless steel appliances (not shown in picture) round out this kitchen. New waterproof vinyl flooring throughout and a new tiled shower and updated bathroom complete this unit. This unit also has its own fenced in side yard. The beautiful pool is nestled perfectly in between these two units. The pool was recently acid washed and refilled and a brand new pool pump was installed. Fresh landscaping gives this property a ton of curb appeal. NOT IN FLOOD ZONE, NO CDD, NO HOA, 13 MINS TO CLEARWATER BEACH. Come take a look and fall in love before it's gone!

403 N Highland Avenue, Clearwater

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