Location: Glenwood, Clearwater
Do Not Show Listings
505 N HIGHLAND AVE, CLEARWATER, FL 33755
$674,000176 Days on yellowkey MLS ID: TB8453434
REDUCED by $10,000 (1.5%) on 04/29/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2361 Built: 1961 Tax: $8,202 (2024)Community: GlenwoodSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,202
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: PRICE IMPROVEMENT NOW $674000!! 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 $674,000
Listing is courtesy of: KELLER WILLIAMS REALTY PORTFOLIO COLLECTION (727-489-0800)
Listing Agent: Calvin Van Auken (727-641-0912)
615 N GLENWOOD AVE, CLEARWATER, FL 33755
$499,0009 Days on yellowkey MLS ID: TB8510985
1 Days Off yellowkey (back on 5/26/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2197 Built: 1947 Tax: $227 (2025)Community: GlenwoodSingle Family
Taxes:$227
Tax Year: 2025
Remarks: Under contract-accepting backup offers. 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.
Listing is courtesy of: KATIE DUCHARME REALTY, LLC (727-492-8490)
Listing Agent: Katie Ducharme Procissi (727-492-8490)
1500 MAPLE ST, CLEARWATER, FL 33755
$1,399,000250 Days on yellowkey MLS ID: TB8429998
Bed: 6 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3850 Built: 1925 Tax: $3,823 (2024)Community: GlenwoodSpa: YesSingle Family
Taxes:$3,823
Elementary School: Skycrest Elementary-PN
High School: Clearwater High-PN
Middle School: Dunedin Highland Middle-PN
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)
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