$1,198,000
Off-Market Date: 06/08/2026209 Highland Woods Drive Safety Harbor, FL 34695
Pending MLS# TB8513515
4 beds 4 baths 3,168 sq ft Single Family
Details for 209 Highland Woods Drive
MLS# TB8513515
Description for 209 Highland Woods Drive, Safety Harbor, FL, 34695
Under contract-accepting backup offers. Welcome to Highland Woods, one of Safety Harbor's most sought-after communities offering a great location and gated. The home is where luxury, comfort, and privacy come together in this exceptional pool home offering a three-way split floor plan, 4 bedrooms, a spacious bonus room, and 4 full bathrooms. From the moment you arrive, the home's impressive curb appeal shines with a beautifully landscaped homesite and an elegant brick-paver driveway. Step through the grand double-door entry into a stunning formal living and dining area, where expansive sliding glass doors frame picturesque views of the covered lanai, sparkling pool, and spa—creating the perfect backdrop for entertaining and everyday living. At the heart of the home is an oversized kitchen featuring abundant cabinetry, generous storage, and a sunny breakfast nook overlooking the pool and lanai. The kitchen flows seamlessly into the light-filled family room, where additional sliding glass doors provide easy indoor-outdoor living and access to the resort-style outdoor space. Designed with functionality in mind, the home's thoughtful layout offers two spacious secondary bedrooms on the side of the home, each featuring charming window seats and ample closet space, along with a shared full bath. A fourth bedroom is privately situated toward the rear of the home and enjoys convenient access to a full bath that also serves as a pool bath with direct exterior access. The luxurious primary suite is a true retreat, complete with a sitting area, private French door access to the lanai, and a stylish sliding barn door leading to the spa-inspired en suite bath. Here you'll find a deep soaking tub, walk-in shower, dual vanities, dedicated makeup vanity, and an oversized walk-in closet with custom built-in shelving. Additional highlights include a spacious laundry room, an oversized three-car side entry garage, and a versatile second-floor bonus room with its own full bath and walk-in shower. This flexible space is ideal as a media room, guest suite, home office, or potential fifth bedroom. Outside, enjoy Florida living at its finest with a covered brick-paver lanai, sparkling pool, relaxing spa, and private backyard surrounded by mature landscaping. The expansive outdoor living area provides the perfect setting for al fresco dining, entertaining, or simply enjoying the beautiful Florida weather year-round. Ideally located just minutes from charming downtown Safety Harbor, residents enjoy easy access to local shops, dining, community events, waterfront parks, and the natural beauty of Philippe Park. This remarkable home offers the space, flexibility, and lifestyle today's buyers are seeking. Schedule your private showing today and experience everything this exceptional Highland Woods residence has to offer. Other features include Solar fully paid off with average $50 a month electric bills and the home has back up generators that store the excess solar so that in power outages you have power, giving both a savings and convenience - Plantations shutters in various places, guest suites with additional split systems offering flexibilty for guests on the temperature of their rooms; Come check out this resort like living home today! Roof 2018, Solor 2020, AC 2021 WIFI speakers in home and on back deck.
Listing Information
Property Type: Residential, Single Family Residence
Status: Pending
Bedrooms: 4
Bathrooms: 4
Lot Size: 0.29 Acres
Square Feet: 3,168 sq ft
Year Built: 2000
Garage: Yes
Stories: 2 Story
Construction: Block
Subdivision: Highlands At Safety Harbor The
Foundation: Slab
County: Pinellas
School Information
Elementary: Safety Harbor Elementary-Pn
Middle: Safety Harbor Middle-Pn
High: Countryside High-Pn
Room Information
Main Floor
Primary Bedroom: 18.2x13.7
Kitchen: 18.2x16.9
Living Room: 11.1x19.1
Bathrooms
Full Baths: 4
Additonal Room Information
Laundry: Laundry Room
Interior Features
Appliances: Built-In Oven, Washer, Cooktop, Dishwasher, Dryer, Microwave, Refrigerator
Flooring: Carpet,Tile
Additional Interior Features: Ceiling Fan(s), Walk-In Closet(s), Tray Ceiling(s), Built-in Features, Split Bedrooms, High Ceilings, Separate/Formal Dining Room, Main Level Primary, Living/Dining Room, Kitchen/Family Room Combo, Separate/Formal Living Room, Stone Counters, Wood Cabinets
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Cable Connected,Electricity Connected,Sewer Connected,Water Connected
Cooling: Central Air, Ceiling Fan(s)
Heating: Central
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 3
Parking Description: driveway
Roof: Shingle
Pool: In Ground, Screen Enclosure, Gunite
Fencing: fenced
Additional Exterior/Lot Features: Landscaped
Community Features
Community Features: Sidewalks, Gated
Security Features: Gated Community
Homeowners Association: Yes
HOA Dues: $140 / Monthly
Driving Directions
Us Hwy 19 to 580 East toward Safety Harbor. Make a right onto Phillippe Pkwy and follow to Fairview St - make a right and take the first left onto Highland after going through gate. Home will be on your right.
Financial Considerations
Terms: Cash,Conventional
Tax/Property ID: 27-28-16-39353-000-0360
Tax Amount: 9462
Tax Year: 2025
A broker reciprocity listing courtesy: KELLER WILLIAMS REALTY- PALM H
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Sales History & Tax Summary for 209 Highland Woods Drive
Sales History
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Tax Summary
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 209 Highland Woods Drive
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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