Highland Glen Real Estate, Homes, Condos for Sale in Clearwater, FL

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

Wooowww, what an amazing END UNIT WITH EXTRA WINDOWS! Lots of light!!! And look at these high ceilings throughout! This unit has a spacious open-concept design! Located in Clearwater, right next to the Dunedin city border, 3 bed 2.5 bath with attached 1 car garage in the highly desirable Highland Glen community. Enjoy the maintenance-free living! This corner unit is in excellent condition and MOVE-IN READY! Primary bedroom is Large and spacious, and comes with a walk-in closet. The primary bath has a double sink, garden bath tub and a separate glass shower. Convenient in-unit laundry. Roof 2024, newer appliances & LOW HOA FEE. Great Clearwater/Dunedin location. Just minutes to the world famous Clearwater Beach and Downtown Clearwater where EVO Entertainment with the largest movie screen is coming! To the other direction, also just minutes to Downtown Dunedin. DOG FRIENDLY COMMUNITY!

1516 Talisker Drive, Clearwater

$314,900

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

Under contract-accepting backup offers. Welcome home to this beautiful 3-bedroom, 2.5-bathroom townhome, ideally located on the Clearwater/Dunedin border. With abundant natural light, and 10-foot ceilings on both levels, this home feels bright, spacious, and inviting. The open-concept main level features a comfortable living and dining area that flows into the kitchen, perfect for everyday living and entertaining. The spacious Primary Suite offers a relaxing retreat with a double vanity, deep garden tub, separate shower, and large walk-in closet. Two additional bedrooms provide plenty of space for family, guests, or a home office. This fantastic location is just minutes from TD Ballpark, the Pinellas Trail, Downtown Dunedin, and award winning beaches! Located in a NON-FLOOD zone and NON-EVACUATION zone will give you extra peace of mind! The low monthly HOA fee includes exterior maintenance and grounds maintenance which offers stress free living! This unit is turnkey, well-maintained, and ready for its next owner. Schedule your showing today!

2023 Strathmill Drive, Clearwater

$309,900

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2.5-bath end-unit townhome with a 1-car garage in the highly desirable Highland Glen community. Offering an abundance of natural light and a spacious open-concept design, this corner unit features a bright living and dining area that flows seamlessly into a well-appointed kitchen with rich wood cabinetry, granite countertops, stainless steel appliances, and reverse osmosis water filtration at both the sink and refrigerator. Elegant tile flooring extends throughout the first floor, while warm wood flooring continues upstairs. The generous primary suite offers a walk-in closet and a private en-suite bath with dual vanities, a soaking tub, and a separate walk-in shower. Additional highlights include built-in surround sound speakers in the living room and primary bedroom, a whole-home water softener, an A/C system with UV germ control for enhanced comfort, and the added peace of mind of a new roof installed in 2024. Upstairs also features two additional bedrooms, a full bathroom, and a convenient laundry room complete with washer and dryer. Ideally located on the Clearwater/Dunedin border, Highland Glen offers easy access to Downtown Dunedin, Clearwater Beach, the Pinellas Trail, TD Ballpark, shopping, dining, and everyday conveniences. The low HOA fee includes exterior maintenance, making for easy, low-maintenance living in one of Clearwater's most convenient locations.

1515 Bowmore Drive, Clearwater

$309,000

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

LOCATION...LOCATION...LOCATION! Experience the ideal Florida lifestyle in this bright and airy end unit townhome, perfectly situated in the Clearwater Dunedin area. Abundant natural light fills the home, creating a welcoming atmosphere throughout. This well-maintained townhome features three bedrooms, two and a half baths, and a one-car garage. The main level and bathrooms are finished with tile flooring and the spacious primary bedroom boasts wood-look vinyl, dual sinks, a relaxing garden tub, and a walk-in closet with shelving. The open-concept lower level is designed for entertaining or quiet dinners, with solid wood cabinets with a convenient built-in wine rack. The garage provides ample storage and includes an EV charging station. Enjoy stunning pond views from your back patio, where you can watch birds, turtles, and other wildlife as you sip your morning coffee or unwind in the evening Situated just minutes from world-class beaches, downtown Dunedin, festivals, Spring Training at BayCare Ballpark, restaurants, shopping, and more, this home provides comfort and convenience in a highly sought-after location. Plus, NO flood insurance! Begin your new chapter in this exceptional, move-in ready home perfectly situated in a prime location. Don't miss the opportunity to view your new home-schedule your tour today.

1508 Talisker Drive, Clearwater

$312,000

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

Spectacular End-Unit Townhome – Coastal Living Meets Modern Luxury WELCOME HOME! Experience the ultimate Florida lifestyle in this beautifully finished 3-bedroom, 2.5-bathroom end-unit townhome, perfectly situated on the Clearwater/Dunedin border. Bathed in natural light from extra windows and featuring soaring 10-foot ceilings on both levels, this home offers an expansive, airy feel that is rare to find. CHEF’S DREAM & DESIGNER DETAILS Enter through the welcoming foyer and discover an open-concept living, dining, and kitchen combo designed for effortless entertaining. The attention to detail is spectacular, including a downstairs half-bath with custom wainscoting and trim, a custom-crafted staircase, and gorgeous luxury vinyl plank flooring throughout the entire second floor. THE PRIMARY RETREAT The oversized Primary Suite is a true sanctuary, featuring a double vanity, deep garden tub, separate stand-up shower, and a large walk-in closet. Two additional upstairs bedrooms offer the perfect flexibility for a guest room, a quiet home office, or a creative space. LIFESTYLE & LOCATION You are truly in the heart of it all. Sports & Outdoors: Minutes from TD Ballpark (Spring Training home of the Toronto Blue Jays) and the scenic Pinellas Trail. Sun & Sand: Just 15 minutes to the world-famous Clearwater Beach. Dining & Shopping: Enjoy the charm of downtown Dunedin and Clearwater’s vibrant local scene just a short drive away. PEACE OF MIND BUILT-IN Rest easy with significant recent upgrades and safety features: Newer Roof (March 2024) and fresh interior/exterior paint. Located in Flood Zone X (no flood insurance typically required). Aluminum Hurricane Shutters included for maximum protection. Low monthly HOA fee covers all exterior maintenance. Zoned for excellent local schools with nearby private and charter options. This beautiful townhome is turnkey and ready to go for its next owner. Schedule your appointment quickly—this one won’t last!

2029 Strathmill Drive, Clearwater

$274,999

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

CLEARWATER DIAMOND IN THE ROUGH! PRICE IMPROVEMENT!! MOTIVATED SELLER!! Solid Block Construction in Prime Clearwater Location! Welcome to 1507 Talisker Dr. This spacious 3-bedroom, 2.5-bath, 1-car garage townhouse is located in the desirable Highland Glen community. Built in 2008 with durable block construction, this home offers 1,416 sqft of living space and a functional layout ready for your personal touch. The roof was replaced in March of 2024, providing peace of mind for years to come. While it does need some cosmetic updates, the home features strong bones, solid structure, and great potential! Enjoy unbeatable convenience with close proximity to some of Pinellas County’s most desirable destinations. You are approximately 1.5 miles from Downtown Dunedin, Edgewater Dr, and the Intercoastal. 3 miles from US 19, major shopping and dining. 3 Miles from Downtown Clearwater, 5 miles from the world-famous Clearwater Beach, and 18 miles from Tampa International Airport. Whether you're heading to the beach, enjoying Dunedin’s vibrant dining scene, or commuting across the Tampa Bay area, this location puts you right in the middle of it all. With major systems already addressed and just cosmetic updates needed, this is your chance to own a well-built home in a high-demand area at a great value! Don't wait to schedule your showing today!

1507 Talisker Drive, Clearwater

$294,500

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

One or more photo(s) has been virtually staged. Welcome home! This 3 bedromm 2.5 bathromm has brand new carpet through out all the bedrooms and the staircase. Unit has a brand new air Conditioner unit. It’s been freshly painted. New roof 2024. This unit is move in ready! Master bedroom has huge walk in closet and spacious bathroom. Attached 1 car garage. Open layout connecting living, dining, and kitchen that makes it for perfect for entertaining. Convenient access to Clearwater beaches and major roads for easy commuting.

2036 Strathmill Drive, Clearwater

$285,000

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

One or more photo(s) has been virtually staged. Highland Glen offers energy-efficient features in a well-maintained community that is ZONED NON-FLOOD with HURRICANE SHUTTERS available for installation as needed during Hurricane Season in Florida. "ASK ABOUT THE ASSUMABLE MORTGAGE! (subject to lender approval). Buyer must qualify under FHA guidelines and cover seller equity. Why pay higher interest rates when you can assume the current mortgage at an amazing (FHA) rate from 2020. Welcome to 2005 Strathmill Drive, a well maintained 3-bedroom, 2.5-bath, with a 1-car garage, and a transferrable ADT alarm system. Nestled in the sought-after Highland Glen community of Clearwater. Highland Glen offers energy-efficient features in a well-maintained community that is Zoned NON-FLOOD with hurricane shutters available for installation as needed. This residence offers a blend of spacious bedrooms and is situated in a prime location. This townhome interior was recently painted throughout (June 2025). The HOA has painted the exterior of the building (July 2025). Current owner has installed and equipped with Samsung Smart stainless-steel appliances (2022), including a new dishwasher (2024), upgraded faucet (2022), and garbage disposal (2023). All toilets have been replaced with modern, energy-efficient models (2023). A complete HVAC replacement was done in 2020, featuring a UV light air purification system (2022) and an exterior surge protector (2023). The system has been professionally serviced biannually, with a transferable care plan valid through April 2027. The owner has consistently maintained the dryer and air vents on a service plan ensuring better air quality and safety for the home. This floor plan layout with the owner's suite has its own private bathtub and shower with a large walk-in closet. The other two bedrooms upstairs have ample space to fit a full or queen size beds. The home has its own smart thermostat and security system to provide you with peace of mind while enhancing your comfort and security. The low HOA fee covers outside pest control, exterior building and grounds maintenance. Situated just minutes from Downtown Dunedin, 10 minutes from Honeymoon Island and a short drive to Clearwater Beach. With easy access to shopping, dining, and entertainment. Nearby attractions include the Pinellas Trail, Coachman Park, and the Clearwater Marine Aquarium. Commuters will appreciate the proximity to US-19 and Tampa International Airport, approximately 15 miles away. Living at Highland Glen in Clearwater offers an unbeatable combination of location, value and lifestyle-making it one of the area's smartest housing choices for homebuyers.

2005 Strathmill Drive, Clearwater

$330,000

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

Welcome to 2039 Strathmil Drive in the Highland Mill townhome community of Clearwater. Located 5 minutes to downtown Dunedin and about 8 minutes to downtown Clearwater, this cozy and beautiful 3 bedroom/2.5 bath/1 car garage townhome is MOVE-IN ready and is available for YOU! As you enter the home, you will notice the beautiful laminate floors on the first floor and the spacious OPEN concept living room/dining room combo. The kitchen comes with maple cabinets, black appliances, and a LARGE breakfast bar. Upstairs is a split bedroom plan with a laundry room for your convenience. WASHER & DRYER remain with the property. The primary suite features a LARGE, WALK-IN closet; primary bath with double vanity, soaker tub & Separate Shower. A private one car garage for a vehicle and extra storage & Low Monthly HOA. Located minutes to quaint DOWNTOWN DUNEDIN. Dunedin has a vibrant OLD FLORIDA/ SMALL TOWN feel. Close to Award Winning Restaurants, BEAUTIFUL parks, Fun FESTIVALS, FARMERS Market, CLEARWATER BEACH, DUNEDIN CAUSEWAY & HONEYMOON ISLAND! This is a MUST SEE! This is the home you deserve and the low maintenance lifestyle!! NO FLOOD INSURANCE required! Schedule a showing TODAY!!!

2039 Strathmill Drive, Clearwater

$330,000

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

LOCATION! LOCATION! Less than .25 OF A MILES FROM DUNEDIN!!!! GORGEOUS 3 BEDROOM, 2.5 BATH, 1 CAR GARAGE - Townhome BUILT 2007 with a patio and a view! Neutral color scheme with TILE floors on the Main floor. OPEN Concept floorplan! Kitchen OVERLOOKS to the Great room with a direct view of the POND. Kitchen Features STAINLESS STEEL APPLIANCES, LIGHT Color countertops, LARGE Kitchen Breakfast Bar, MAPLE Cabinetry & PANTRY. LOTS of NATURAL light! Split bedroom plan upstairs with full laundry room for your convenience. WASHER & DRYER remain with the property. The MASTER Suite features a LARGE, WALK-IN Closet. MASTER Bath with DOUBLE VANITY, SOAKER Tub & Separate Shower. All bedrooms have VAULTED Ceilings! SMOOTH/ KNOCK DOWN Ceilings throughout, A/C (2023), A private one car garage for a vehicle and extra storage & Low Monthly HOA. Enjoy BBQ's and relaxing on the Back patio which overlooks the serene pond for bird and turtle watching or stroll down to Bayshore & Union to watch the Sunset! MINUTES to Quaint DOWNTOWN DUNEDIN. Dunedin has a vibrant OLD FLORIDA/ SMALL TOWN feel. Close to Award Winning Restaurants, BEAUTIFUL parks, Fun FESTIVALS, FARMERS Market, CLEARWATER BEACH, DUNEDIN CAUSEWAY & HONEYMOON ISLAND! This is a MUST SEE! This is the home you DESERVE and the LOW Maintenance Lifestyle!! NO FLOOD INSURANCE Required which saves you money!

1510 Talisker Drive, Clearwater

$330,000

3 Beds ⋅ 2 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

Super 3 bed/2.5 bath/1 car garage townhouse in Clearwater near Dunedin. Open ground floor layout with an upgraded kitchen that has new stainless-steel cabinets. There is an eating counter and a closet pantry. Convenient half-bath on the first floor. Sliding doors go out to a private patio. This is a corner unit giving windows on 3 sides and extra light. There are 12-foot ceilings upstairs and down. The second floor has a split plan with 2 bedrooms at the back and the master bedroom at the front. The spacious master bedroom has a bathroom ensuite and a walk-in closet. The laundry room is conveniently located on the 2nd floor. The 1 car garage has extra storage space. New roof in 2024. New AC air handler and outside condenser in 2023! This townhouse has the one of the lowest HOA fees around at $185/mo.! Clearwater downtown 5 minutes, Dunedin downtown 5 minutes, Clearwater Beach 10 minutes, downtown St Pete 30 minutes, Tampa & Tampa International Airport is 30 minutes. Great value!!!

1526 Bowmore Drive, Clearwater

$320,000

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

Welcome to your dream home! This stunning 3-bedroom, 2.5-bathroom, 2-story townhome is the epitome of modern living. Nestled in a prime location, just minutes away from the renowned Clearwater Beach, Golf Course, and top-rated schools, this property offers both luxury and convenience. As you step inside, you'll be greeted by an open-concept kitchen featuring solid wood cabinets, a spacious breakfast bar, ample storage space, and stylish recessed lighting. The first floor features a guest powder room for added privacy and convenience to your guests. The bedrooms are strategically located upstairs, providing privacy and tranquility. The private master bedroom is a true retreat, boasting a generously sized walk-in closet and an en-suite bathroom that feels like a spa oasis. Pamper yourself in the large soaker tub, enjoy the convenience of a dual vanity, and indulge in the luxurious walk-in shower. With a one-car garage, this townhome offers both convenience and security for your vehicle. Enjoy the benefits of low HOA monthly fees, covering exterior maintenance and grounds upkeep. The "Location! Location! Location!" tagline is not an exaggeration – Situated in a PRIME LOCATION, this property is just minutes away from downtown Clearwater and Dunedin's shopping and restaurants and a short 7-minute drive to the breathtaking Clearwater Beach, with easy access to Tampa. Whether you're looking for your dream home or a savvy investment property, this townhome ticks all the boxes. Don't miss the opportunity to make this your new home sweet home.

1505 Bowmore Drive, Clearwater

$322,000

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

Welcome to Your Dream Home in the Highland Glen community. This stunning 3-bed, 2.5 bath with a single car garage is a true masterpiece! This beautiful townhome boasts an open concept kitchen with solid wood cabinets, stainless-steel appliances, newer Samsung smart refrigerator, large breakfast bar, storage space, and recessed lighting. From ceramic flooring to tasteful light fixtures, this home exudes sophistication at every turn. Enjoy the comfort of ceiling fans, a smart thermostat, and the warm embrace of wood blinds, all enhanced by an abundance of natural light. Discover the ultimate retreat in the private master bedroom, boasting a generously sized walk-in closet and an en-suite bathroom featuring a large soaker tub, dual vanity, and a luxurious walk-in shower. When you step out back through the rear triple sliding door you will find a large deck and privacy making it the perfect space to soak up the beautiful Florida weather. Location! Location! Location! Conveniently located just minutes from world famous Clearwater beach, Toronto Blue Jays Spring Training Ballpark, Clearwater County Club and Golf Course, top rated schools, shopping and award-winning restaurants. This is the perfect home for you! Call today for your exclusive viewing.

1525 Talisker Drive, Clearwater

$305,000

3 Beds ⋅ 3 Baths ⋅ Highland Glen SubDv. ⋅ 33755 Zip Code

3 bed, 2 and a half bath, 1 car garage, 2 story townhome. Built-in 2007. Downstairs is open with high ceilings and tile flooring. All bedrooms are upstairs. The master bedroom is spacious with a big jacuzzi tub. 5 minute drive to downtown Dunedin and about 8 minutes to downtown Clearwater. Great investment property.

2011 Strathmill Drive, Clearwater

Browse All Highland Glen Properties for Sale

Highland Glen Real Estate & Homes