Glenwood Homes for Sale in Clearwater - 5 homes

Remarks: PRICE IMPROVEMENT NOW $694000!! 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 $694,000

Listing is courtesy of: KELLER WILLIAMS REALTY PORTFOLIO COLLECTION (727-489-0800)

Listing Agent: Calvin Van Auken (727-641-0912)

Remarks: 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.

Listing is courtesy of: AMOROSE & ASSOCIATES REALTY (727-441-3974)

Listing Agent: Rick Amorose (727-560-0688)

Remarks: This 1920's bungalow brings the kind of charm you just don’t find in newer homes, with original hardwood floors, great natural light from UPDATED WINDOWS, and a comfortable layout from the moment you walk in. The LARGE BACK DECK is a standout feature that's perfect for hosting and enjoying your backyard space. Plus, being in a NO FLOOD ZONE adds real peace of mind. NEW ROOF and IMPACT-RATED WINDOWS as well to give you a great DISCOUNT on your HOME-OWNERS INSURANCE. The location makes everyday life easy—just minutes to downtown Clearwater, quick access to US-19 and Gulf-to-Bay for commuting to beach or Tampa Bay. Not to mention all of the shopping, restaurants, and everyday needs conveninetly close by. Whether you’re buying your first home or looking for a solid investment, this one checks the boxes in all the right ways.

Listing is courtesy of: ACROPOLIS REALTY GROUP LLC (315-396-0493)

Listing Agent: Sal Degaetano (315-396-0493)

Remarks: Step into a private Mediterranean-inspired retreat in the heart of Clearwater. This rare and timeless estate blends 1920s architectural charm with modern luxury, offering an expansive layout, resort-style amenities, and unforgettable outdoor living. Behind custom gates, the home opens to warm stucco textures, handcrafted details, and generous natural light. The main residence features spacious living areas, a grand primary suite, and beautifully updated finishes that honor the home’s original character while elevating its sophistication. At the rear of the property, a beautifully designed mother-in-law suite with its own private entrance offers exceptional versatility. Ideal for extended family, long-term guests, or a secluded home office, this suite enhances the estate’s functionality while maintaining privacy for everyone. Outside, the property transforms into a true sanctuary. A tropical grotto-style pool with waterfall and spa anchors the lush backyard, creating a serene backdrop for both quiet mornings and lively gatherings. The added pool house provides flexible space for guests, a studio, or a private retreat steps from the water. Entertaining reaches a new level with the custom outdoor kitchen, thoughtfully designed with premium materials and ample prep space. Whether hosting intimate dinners or large celebrations, this outdoor haven delivers the ambiance of a boutique resort. Located minutes from Clearwater’s award-winning beaches, vibrant downtown, and top schools, this estate offers a rare blend of privacy, character, and luxury living. Truly a one-of-a-kind luxury property!

Listing is courtesy of: BELLE ISLE REALTY, LLC (727-224-9522)

Listing Agent: Amy Schroth (727-688-5784)

Remarks: Live in Resort-Style Luxury While Earning Passive Income! Welcome to paradise in the heart of Clearwater — just 10 minutes from the world-renowned Clearwater Beach, within walking distance to Clearwater Country Club, and in an A-RATED school district. This beautifully updated and income-generating MULTIFAMILY QUADPLEX resort combines timeless elegance with modern upgrades, offering a truly unique blend of residential comfort and business potential. Whether you're looking to live in style while offsetting your mortgage or expand your portfolio with proven 5-star short and long term rental success, this property delivers. Zoned for FIVE UNITS, with the potential of earning over $200,000 in annual rental income, this high-performing asset comes fully furnished and turnkey — ready for immediate occupancy for multigenerational living or continued rental use. Set on a spacious 1/3 acre CORNER LOT, the centerpiece is a 1925 Mediterranean masterpiece bursting with original charm and character. Inside you’ll find terracotta tile floors, original red oak hardwood floors and red oak accents through out, soaring ceilings, 10" baseboards, rope twist door and window molding, a cozy fireplace, natural gas burning appliances, AND an ATTACHED MOTHER IN LAW SUITE WITH A PRIVATE ENTRANCE! The chef-inspired kitchen features a gas range, granite countertops, stainless steel appliances, and ample cabinet space. The primary home features an attached mother in law suite that can either be utilized with main home access or can remain separate to create two units. The other two apartments are located in the detached building adjacent to the pool. Each of the four units on this property boasts private entrances and has been thoughtfully remodeled with modern touches and inviting décor — perfect for vacationers or long-term tenants alike. Step outside to your private oasis: a resort-style pool with a brand new gas heater surrounded by a pavered entertaining deck complete with an outdoor kitchen and bar, brand new $12,000 hot tub, pool table, and a variety of games — ideal for hosting guests or relaxing in style. Additional features include a woodworking shed and storage shed for hobbyists or added storage, a 40-foot parking space for an RV or camper with electrical hookups and water, and fully landscaped grounds offering privacy and charm. This multifunctional property is a rare gem in one of Clearwater’s most desirable locations, nestled within the historic Glenwood neighborhood. Whether you want a luxe home with unmatched character, an income stream, or both — this quadplex is the ultimate lifestyle and investment package.

Listing is courtesy of: COMPASS FLORIDA LLC (305-851-2820)

Listing Agent: Katie Patterson (727-771-5660)