Location: Highland Lakes, Palm Harbor
Do Not Show Listings
1223 TIMBERBROOKE DR, PALM HARBOR, FL 34684
$429,90034 Days on yellowkey MLS ID: TB8483228
REDUCED by $10,000 (2.3%) on 04/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1468 Built: 1977Monthly Fee: $164 Tax: $1,667 (2025)Community: Highland LakesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,667
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Beautifully updated and RARE 3-bedroom, 2-bath home with an attached 2-car garage, featuring an open and split floor plan and stunning, picturesque views of a peaceful PRESERVE where wildlife is frequently seen! Light and bright upon entry, the home showcases oversized hurricane-impact windows and a spacious living and dining room combination perfect for entertaining. Recent updates include stylish laminate plank flooring, an updated kitchen and bathrooms, recessed lighting, and freshly painted interior and exterior. The beautifully renovated kitchen features solid wood cabinetry, sleek stainless-steel appliances, spacious pantry closet, updated countertops, recessed lighting, and under-cabinet lighting. The primary suite is a true retreat with both a walk-in closet and an additional built-in closet, along with an updated en-suite bath boasting a granite-topped vanity, modern lighting, and a walk-in shower. The updated hall bath showcases travertine flooring, a granite vanity, and a glass-enclosed walk-in shower with custom tilework, conveniently located between an additional bedroom and the main living area. The THIRD BEDROOM is privately positioned at the rear of the home, offering tranquil preserve views and a generously sized built-in closet for storage. Enjoy the serene natural surroundings year-round from the heated and cooled family room or the bonus lanai, which is not included in the home’s heated square footage. Additional features include a cost-saving deep irrigation well, new patio and side doors (2024), a new garage door (2021) and garage door opener (2025), a 3-ton HVAC system (2017), and an updated electrical panel (2017)! This home sits safely high & dry in a NON-flood zone and NON-evacuation zone, plus offers a recently passed 4-point inspection available for your review and transferrable to buyer. Residents of Highland Lakes enjoy an exceptional country club lifestyle with a remarkably low HOA fee of just $164 per month, including UNLIMITED FREE GOLF on three private executive courses, tennis, pickleball, bocce, and shuffleboard courts, and a vibrant clubhouse offering entertainment, fitness classes, and social events. The lakeside lodge on Lake Tarpon features a private boat ramp, fishing pier, and community pontoon boats. Additional amenities include free RV and boat storage and a golf cart-friendly community design. Ideally located near world-class Gulf beaches, upscale dining and shopping, top-rated healthcare, major sports venues, two international airports, and a cruise port, this exceptional property offers the perfect blend of elegance, comfort, and active Florida living. Don’t miss this rare opportunity—schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Amanda Justus (727-330-4478)
2938 MACALPIN DR W, PALM HARBOR, FL 34684
$499,00012 Days on yellowkey MLS ID: TB8491531
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1944 Built: 1979Monthly Fee: $164 Tax: $2,779 (2025)Community: Highland LakesSingle Family
Taxes:$2,779
Remarks: Beautifully updated 3-bedroom, 2-bath home offering nearly 2,000 square feet of upscale living in Palm Harbor’s premier 55+ golf community, Highland Lakes. This residence features one of the community’s most desirable floor plans, highlighted by a renovated open-concept kitchen that flows seamlessly into the main living area, an indoor laundry room, attached 2-car garage, and an oversized heated and cooled Florida Room with endless possibilities! Large, updated windows invite abundant natural light throughout. The eat-in kitchen shines with granite countertops, beautiful wood cabinetry, stainless steel appliances including a brand-NEW (2026) stove, recessed lighting, extensive built-in pantry storage, and a convenient passthrough window to the Florida Room—perfect for entertaining. The primary suite is a private retreat with a beautifully updated en-suite bath featuring a newer vanity with a stone countertop, modern lighting, a walk-in shower, and a spacious walk-in closet with custom cabinetry, plus sliding doors leading to the Florida Room. The guest bedroom is equally versatile, with a nearby hall bath and a slider that allows it to function as a second en-suite with its own large walk-in closet. Major upgrades include a NEW roof (2024), luxury vinyl plank flooring (2025), updated electrical panel (2017), third bedroom renovation (2026), fresh landscaping (2025), new hall bathtub (2025), freshly painted exterior (2025), kitchen renovation (2017), both hurricane-impact and resistant windows, and a new generator (2019) plus so much MORE! A transferable 4-point inspection is also available for added peace of mind. Located in a non-evacuation zone, this home offers security and comfort year-round. Highland Lakes residents enjoy a vibrant, resort-style lifestyle with a low HOA fee that includes unlimited golf on three private executive courses, access to tennis, pickleball, bocce, and shuffleboard, an active clubhouse with social events and fitness classes, and a lakeside lodge on Lake Tarpon with a private boat ramp, fishing pier, and community pontoon boats. Additional perks include free RV and boat storage and golf cart-friendly streets. Conveniently located near award-winning Gulf beaches, dining, shopping, medical facilities, major airports, and a cruise port, this exceptional home offers the perfect blend of elegance, convenience, and active Florida living. Move right in and start enjoying it all - don't wait and schedule your private showing today!
3132 BRUNSWICK CIR, PALM HARBOR, FL 34684
$474,90034 Days on yellowkey MLS ID: TB8483229
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1858 Built: 1981Monthly Fee: $164 Tax: $2,083 (2025)Community: Highland Lakes Unit 14 Ph 2Single Family
Taxes:$2,083
Remarks: One or more photo(s) has been virtually staged. Welcome to this GRAND and SPACIOUS 3-bedroom, 2-bath split and open-concept home PLUS an office, designed for comfortable living and effortless entertaining. Upon entry through the updated glass front door, you’re immediately greeted by light-filled open spaces and large updated windows showcasing peaceful green views with no immediate rear neighbors. The home features not a speck of popcorn ceilings and zero carpet, creating a clean and modern feel throughout. Additional highlights include a large indoor laundry room, attached full two-car garage, and a BRAND NEW (2026) 3.5-ton Daikin HVAC system for peace of mind. The private master retreat, thoughtfully split from the additional bedrooms, offers tranquil green views and features TWO oversized walk-in closets, a bonus office/flex space, and an updated en-suite bath with dual sinks, granite countertops, updated lighting, and a walk-in shower. The open-concept layout provides a convenient pass-through window to the family room with bar-top seating, a large kitchen island for easy meal prep, solid-wood cabinetry, and both recessed and over-cabinet lighting. The updated hall bath is ideally situated between the two additional bedrooms and main living areas, featuring an updated vanity with granite countertop, modern lighting, and a tub/shower combination. The spacious indoor laundry room includes built-in cabinetry, a generous linen closet, and a utility sink for added convenience. The home is safely high and dry in a non-flood and non-evacuation zone and is just a short stroll to the main clubhouse, offering easy access to all the exceptional amenities of Highland Lakes! As a resident of Highland Lakes, you’ll enjoy FREE UNLIMITED GOLF on three private executive golf courses, an active clubhouse filled with social events and clubs, along with fitness and hobby programs in a welcoming country club setting. At the Lake Tarpon Lodge, residents also have access to a second heated pool, picnic areas, a fishing pier, community pontoon boats, and secure RV and boat storage, all included with your membership. With stylish upgrades, spacious living areas, and unmatched amenities, this home presents an incredible opportunity to enjoy the vibrant 55+ lifestyle. Schedule your private showing today!
1632 HEATHER PL, PALM HARBOR, FL 34684
$425,000Listed 04/08/2026 8:32AM MLS ID: TB8493682
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1508 Built: 1973 Tax: $4,834 (2025)Community: Highland LakesSingle Family
Taxes:$4,834
Elementary School: Highland Lakes Elementary-PN
High School: Palm Harbor Univ High-PN
Middle School: Carwise Middle-PN
Remarks: Positioned on a quiet cul-de-sac within the highly desirable community of Highland Lakes in Palm Harbor, this updated 2-bedroom, 2-bath home presents a rare opportunity combining flexibility, storm-prepared improvements, energy efficiency, and optional lifestyle amenities. While located within Highland Lakes, this property is not currently part of the HOA—allowing ownership without mandatory fees, restrictions, or age requirements. Buyers also have the option to join and enjoy the community’s well-known amenities, including golf, pickleball, boat and RV storage, and more, with applicable requirements. Set on a spacious lot, the home offers both privacy and usability, complemented by a layout designed for comfortable everyday living and effortless entertaining. Inside, approximately 1,508 square feet of living space features a cohesive design with neutral tones, consistent flooring, and thoughtful updates throughout. The kitchen has been refreshed with modern cabinetry, granite countertops, stainless steel appliances, and a functional layout that flows naturally into the living and dining areas. Recessed lighting, updated interior doors and hardware, and improved finishes enhance the home’s move-in ready appeal. Significant upgrades provide meaningful peace of mind. NEW hurricane impact windows were installed in every room in 2025, and the roof structure has been reinforced with hurricane clips, offering enhanced storm protection and potential insurance advantages. The home is also located in a NON-FLOOD ZONE and NON-EVACUATION ZONE—an increasingly important consideration for today’s buyers. Solar panels contribute to energy efficiency and are expected to be paid off at closing, offering long-term cost savings. Both bathrooms have been updated with high vanities, granite countertops, new toilets, and refreshed finishes. One features a walk-in tile shower, while the other includes a tub, providing flexibility for different preferences. The bedroom layout offers separation and privacy, with the primary suite delivering generous space, ample storage, and a comfortable retreat. Additional key updates include a 2023 HVAC system and a 2021 water heater. Outdoor living is a standout feature. A covered and screened rear porch extends the living space, creating a comfortable setting for relaxation or entertaining. Beyond that, the fully fenced backyard offers privacy and versatility, ideal for pets, gatherings, or future customization. The above-ground pool enhances the Florida lifestyle, while a detached shed provides additional storage. An oversized 2-car garage adds further functionality. Ideally located near schools, shopping, dining, and medical facilities, this home is also just a short drive from Honeymoon Island, Caladesi Island State Park, the Dunedin Causeway, and the vibrant downtown areas of Palm Harbor, Dunedin, and Tarpon Springs, with Tampa International Airport approximately 45 minutes away. Opportunities within Highland Lakes offering this level of flexibility, protection, and lifestyle potential are limited, making this a compelling option for full-time residents, seasonal buyers, and those ready to act in today’s market.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Paul Virgadamo (727-919-8994)
999 GILLESPIE DR, PALM HARBOR, FL 34684
$479,9007 Days on yellowkey MLS ID: TB8492306
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1732 Built: 1983Monthly Fee: $164 Tax: $6,872 (2025)Community: Highland Lakes Unit Fifteen Ph 1Single Family
Taxes:$6,872
Remarks: 3 BEDROOMS 2 BATHROOMS FL 34684
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
2928 MACALPIN DR S, PALM HARBOR, FL 34684
$389,00017 Days on yellowkey MLS ID: TB8489035
1 Days Off yellowkey (back on 4/7/2026)
REDUCED by $1,000 (0.3%) on 04/02/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1352 Built: 1979Monthly Fee: $164 Tax: $2,034 (2025)Community: Highland LakesSingle Family
Taxes:$2,034
Remarks: You’ve heard the buzz about Highland Lakes now it’s time to see what all the excitement is about (and yes it really is that good). Welcome to a home that checks every box for the 55+ lifestyle you’ve been dreaming about. Perfectly positioned on one of the largest high and dry lots in the neighborhood this property gives you something that’s getting harder to find space privacy and peace of mind. No flood worries here just room to breathe and enjoy your slice of Florida sunshine. Step inside and you’ll find a home that’s been thoughtfully updated where it matters most. The kitchen and bathrooms have already been refreshed so you can skip the renovations and go straight to enjoying life. With both a separate living room and family room there’s plenty of space to entertain guests or spread out when you need a little quiet time because let’s be honest we all do sometimes. then there’s the patio a generous 21x10 covered and enclosed space that’s just begging for morning coffee afternoon reading or evening cocktails. It’s your personal retreat minus the plane ticket. Even better the big ticket items are already taken care of. With a brand new roof in 2025 you can enjoy years of low maintenance living. Translation more time for golf less time for contractors. Now let’s talk lifestyle because this is where Highland Lakes truly shines. For just 164 dollars per month you’ll unlock access to an amenity rich resort style community that keeps life as active or relaxed as you want it to be. Enjoy unlimited golf on three private executive courses yes unlimited heated pools and spa for year round relaxation tennis pickleball bocce and shuffleboard bowling leagues fitness classes and hobby studios from arts and crafts to woodworking and a lively clubhouse filled with clubs events and social opportunities. And it doesn’t stop there the Lake Tarpon Lodge adds even more perks including a second heated pool private boat ramp fishing pier picnic areas community pontoon boats and even free secure boat storage because retirement should come with toys. Location You’re exactly where you want to be safely above the floodplain in a non evacuation zone yet just minutes from award winning Gulf beaches top notch dining shopping cultural attractions professional sports and excellent medical facilities. Plus two international airports are within easy reach for when adventure calls. This isn’t just a home it’s a lifestyle upgrade. So go ahead live the Florida life you’ve worked so hard for. The only thing missing is you. ps. Be sure to show to stop by the main clubhouse at 3300 MacGregor Dr and the Lake Tarpon Lodge at 127 Lakeside Dr.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Carl Gresen (727-424-6330)
2137 MALCOLM DR, PALM HARBOR, FL 34684
$434,80085 Days on yellowkey MLS ID: TB8462729
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1319 Built: 1978Monthly Fee: $164 Tax: $2,812 (2024)Community: Highland Lakes Unit SixSingle Family
Taxes:$2,812
Tax Year: 2024
Remarks: **Price Improvement - BRING OFFERS** This is the one you’ve been waiting for in the ever active, Golfcart friendly 55+ Highland Lakes! This MOVE-IN READY gem WITH 200 EXTRA SF OF SPACE, offers a seamless blend of sophisticated design, comfort and value. Practicality meets peace of mind with a 2021 ROOF, usable well for LOW-COST irrigation, 16-SEER Trane AC, reinforced garage door, JELD-WEN 'tip out' windows, 2018 electric panel/water heater and back room that ADDS 200+ SF OF HEATED AND COOLED SPACE. Enter through the SCREENED front porch to find inside newer vinyl flooring and porcelain tile throughout — absolutely no carpet! The heart of the home has been modified to provide a stunning open-concept kitchen featuring soft-close cabinetry, premium Quartz Berwyn countertops with breakfast bar, complimented by chic tile backsplash, high-end GE Profile appliances in Slate and white cabinetry providing ample storage with a dual-pantry system (kitchen and laundry). Both bathrooms have been beautifully remodeled. The Primary bedroom features an ensuire bath with STEP-IN SHOWER. Enjoy the spacious light-filled Florida room in back that is fully finished with a dedicated AC split, overlooking a private greenbelt with a separate patio. Outside bask in the green space that features lemon, mango, and avocado trees and fragrant Jasmine. Beyond the fairways, this vibrant GOLF CART community offers an unparalleled lifestyle. Residents enjoy a rich tapestry of activities, from competitive play on the tennis, pickleball, and bocce courts to refreshing afternoons by the Olympic-size geothermal heated pool and spa. Life here extends to the water, where you can explore Lake Tarpon on one of two community pontoon boats, including curated lunch excursions to lakeside favorites. Whether you’re honing a craft in the woodworking shop or relaxing at the lakeside lodge, every amenity is designed for your leisure. Buyers may be eligible for Mortgage savings with this purchase, ask Agent.
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Katrina Jauregui (949-633-3204)
2149 MALCOLM DR, PALM HARBOR, FL 34684
$409,00051 Days on yellowkey MLS ID: TB8475863
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1535 Built: 1978Monthly Fee: $164 Tax: $5,408 (2024)Community: Highland Lakes Unit SixSingle Family
Taxes:$5,408
Remarks: **Price Improvement - BRING OFFERS** Brand NEW ROOF and Peaceful Greenbelt Views in Highland Lakes! Opportunity knocks in our area's most sought-after active 55+ community! Mortgage savings may be available for buyers of this listing. This beautifully updated Concord model offers over 1,500 square feet of brilliantly designed living space and fantastic modern upgrades. From the moment you arrive, you are greeted by lovely curb appeal, a freshly painted driveway, and a welcoming front patio—the absolute perfect spot to sip your morning coffee and wave to your friendly new neighbors. Best of all? The roof is brand new (just one week old!), and the HVAC Is from 2020, electric panel updated in 2021 giving you total peace of mind for years to come! As you open the front door, gorgeous luxury vinyl floors lead you into a generous living room that easily accommodates both seating and dining areas. At the heart of the home is a beautifully remodeled kitchen featuring gleaming granite countertops. It perfectly opens up to a versatile dining or sitting area that flows seamlessly into the back lanai. A newer sliding glass door invites you out to your rear patio, where you can relax and look out over a large, peaceful greenbelt. Tucked quietly on one side of the home are two generous-sized bedrooms. The primary suite serves as a true retreat, boasting a beautifully remodeled en-suite bathroom with stunning contemporary tile in the walk-in shower. Add in the convenience of a large inside laundry room complete with a utility sink, and this home truly checks every box! Where else can you find this much value? Your Highland Lakes HOA membership remains low and unlocks a premier lifestyle that feels like a year-round vacation. Your GOLF CART community amenities include Free Golf for Two: No greens fees on the private 27-hole executive golf course, Two community pools, tennis courts, and shuffleboard, Lake Tarpon Access: Enjoy private boat access to the lake, plus RV and boat storage, an active clubhouse and lodge featuring performing arts, bowling leagues, fitness facilities, arts & crafts, and so much more! TURNKEY negotiable. Schedule your showing today and start living the Highland Lakes lifestyle!
3400 RUGBY CT, PALM HARBOR, FL 34684
$375,00023 Days on yellowkey MLS ID: TB8484795
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1420 Built: 1981Monthly Fee: $164 Tax: $4,157 (2025)Community: Highland LakesSingle Family
Taxes:$4,157
Remarks: Welcome to your slice of paradise in Highland Lakes - widely regarded as the best-kept secret in Pinellas County! This beautifully maintained 2-Bedroom, 2-Bath home offers 1420 sq ft of comfortable living space and a spacious 2-car garage, all ideally situated on a premium pie-shaped lot at the end of a quiet cul-de-sac. Step inside and be greeted by VAULTED CATHEDRAL CEILINGS that create an inviting open layout. A wall between the kitchen and living room has been removed, creating a seamless flow and enhancing the home's spacious, airy feel. The UPDATED Kitchen features Stainless Steel Appliances, GRANITE COUNTERTOPS, Shaker Cabinets with an additional cabinet added for storage and "working counter space". The Kitchen opens to Dining Room/Living Room AND the Family/FLEX Room, perfect for an office or den. Both Bathrooms have also been tastefully updated, offering a fresh, contemporary feel. Relax and unwind in the SCREENED-IN Florida Room, an ideal space to enjoy your favorite beverage and watch the Florida Wildlife. Enjoy peace of mind with NO FLOOD INSURANCE Required and a NON EVACUATION ZONE, along with valuable updates including HURRICANE IMPACT WINDOWS and SLIDING GLASS DOOR, the Roof was replaced in 2018, and the AC System in 2014. The expansive Pie-Shaped lot enhances privacy and offers ample room to add a pool, plant a garden, or expand the home, giving you endless possibilities to create your dream outdoor oasis. Located in the highly desirable 55+ community of Highland Lakes, where residents enjoy FREE GOLF, FREE BOAT/RV STORAGE/, PICKLEBALL, TENNIS, HEATED POOLS, PONTOON BOATS FOR LAKE CRUISES, with OVER 50 CLUBS AND ACTIVITIES INCLUDING: A FULL WOOD WORKING WORKSHOP, CERAMICS, STAINED GLASS STUDIOS, CARDS, CLUBS, and DANCES. All of this and just 3 miles to Dunedin Causeway, World Famous Honeymoon Island, Walls Springs, Fred Howard Park with Sunset Beach, 2 International Airports with 30 minutes - all this and so much more!
Listing is courtesy of: RAGSDALE RESIDENTIAL REALTY (727-742-3789)
Listing Agent: Sheri Ragsdale (727-742-3789)
1303 GLENGARRY DR, PALM HARBOR, FL 34684
$439,90048 Days on yellowkey MLS ID: TB8477898
REDUCED by $9,600 (2.1%) on 04/03/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1687 Built: 1979 Tax: $6,600 (2025)Community: Highland LakesSingle Family
Taxes:$6,600
Remarks: HUGE PRICE REDUCTION - THE TIME IS NOW TO SEE THIS HOME!!! ABSOLUTELY EVERYTHING in this home has been done for you! Just bring your suitcases and move right into this beautifully updated home. Furniture negotiable. This home is a short walk to the main clubhouse in a 55+ retirement golf community designed to meet all your needs and desires. The home has been totally updated with quality materials and features a modern aesthetic look that clearly shows pride of ownership. Recent upgrades include: a new roof (2022), thermal solar tubes (2021), leaf guards for gutters (2022), windows (2022 & 2023), air conditioner (2024), hot water heater (2020), flooring (2020), outdoor patio (2021), deep water well pump (2023), bathroom ceiling fans (2026), concrete driveway (2020), and landscaping (2026). The convenient kitchen, nestled between the family room and dining area, includes a pass-through to the enclosed sunroom. Here you'll find newer light cabinets and Quartz countertops, plus modern track lighting in both the kitchen and living room. The spacious sunroom offers a view of the beautifully landscaped private patio—perfect for entertaining guests and enjoying outdoor meals. The master bedroom provides ample closet space and an updated bathroom with a walk-in shower. Adjacent to the master is a peaceful, versatile private area overlooking the lovely patio. The family room adjacent to the kitchen is roomy enough for TV and a small eating area. The two-car garage also accommodates a golf cart and plenty of storage. Residents enjoy Highland Lakes' many amenities, such as free golf on three 9-hole executive certified courses, an Olympic-sized heated pool and hot tub, a multi-use auditorium, and a wide range of activities, clubs, and social events. Highland Lakes is considered Pinellas County’s premier retirement community. Don’t miss the chance to visit this special home!
Listing Agent: Sue Hirsch (727-255-3027)
1735 ABERDEEN CT, PALM HARBOR, FL 34684
$499,9007 Days on yellowkey MLS ID: TB8493231
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1556 Built: 1980 Tax: $6,372 (2025)Community: Highland LakesSingle Family
Taxes:$6,372
Remarks: Welcome to this beautifully maintained rare 3-bedroom home that is perfectly situated on a manicured corner lot offering both curb appeal and surprising privacy. Lush landscaping creates a serene setting making this home feel like your ow private retreat Peace of mind comes easy with major updates already completed: brand new roof (2004), A/C 2020, water softener 2021, new oven 2024, and microwave 2022. An irrigation system installed in 2013 helps keep the grass looking their best. Step inside to an updated open concept kitchen that flows seamlessly into the living space ideal for both everyday living and entertaining. Additional highlights include a retractable awning 2020 for shaded outdoor comfort, a larger garage with room for a golf cart and privacy screens on both the garage and front entry. these 3 bedrooms is a rare find. Enjoy the 3 Executive Golf courses, pickleball and tennis courts, two heated pools, a pontoon boat on Lak Tarpon or bring your boat or RV in the storage. Enjoy the woodshop or ceramic and stain glass shop. You can enjoy all the clubs and entertainment in the Clubhouse. This community offers around the clock opportunities for an active lifestyle
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Diane Thompson (727-409-2779)
1207 GILLESPIE DR N, PALM HARBOR, FL 34684
$534,90013 Days on yellowkey MLS ID: TB8491462
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2072 Built: 1985Monthly Fee: $150 Tax: $4,394 (2025)Community: Highland Lakes Unit Fifteen Ph 3Single Family
Taxes:$4,394
Remarks: BEAUTIFUL 2BR-2BBA DIRECTLY ON HIGHLAND LAKES GOLF COURSE...TOTALY UP-DATED...HURRICANE WINDOWS, GENERAX, CABINETS IN GARAGE, ATIC W/PULL DOWN, TV AND OFFICE CABINETS STAY, GOLF CART SHED, FRIG 1YR , STOVE 2YR, W/D 2YR, MICROWAVE 1YR, TANK LESS HOT WATER 3MONTHS, EXTRA "SHE" SHED, WELL FOR SPRINKLERS, PAVERS ON DRIVEWAY...TOO MUCH TO LIST ALL..A PURE JOY TO SHOW...
Listing is courtesy of: A BETTER WAY REALTY INC (727-481-4768)
Listing Agent: William Decker (727-481-4768)
3569 OAK LAKE DR, PALM HARBOR, FL 34684
$399,00062 Days on yellowkey MLS ID: TB8472815
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1466 Built: 1987Monthly Fee: $164 Tax: $2,919 (2024)Community: Highland Lakes Unit EighteenSingle Family
Taxes:$2,919
Remarks: One or more photo(s) has been virtually staged. UPDATED in 2026!!! NEW KITCHEN including quartz countertops, stainless steel appliances, cabinets with soft close doors and drawers! NEW BATHROOMS! NEW CARPET in bedrooms. Welcome to 3569 Oak Lake Drive, a delightful single-family home nestled in the heart of Palm Harbor's esteemed Highland Lakes community. This residence offers a harmonious blend of comfort, style, and active living in one of Florida's most sought-after 55+ neighborhoods. Step inside to discover a spacious split-bedroom floor plan designed for both privacy and comfort. This is basically a 2-bedroom home built within a 3-bedroom floorplan so all the rooms are large. The open-concept living and dining areas are bathed in natural light, creating a warm and inviting atmosphere. The kitchen boasts ample cabinetry and a cozy breakfast nook, perfect for morning coffee. The primary suite features a walk-in closet and an en-suite bathroom, while the second bedroom offers flexibility for guests or a home office. The Florida room provides additional living space, ideal for relaxing or entertaining guests. The landscaped yard offers a serene setting with mature trees and lush greenery. Highland Lakes is renowned for its resort-style amenities… Enjoy free access to three private nine-hole executive golf courses, along with a community pool, tennis, pickleball, bocce ball, and shuffleboard courts. For those who love the water, community pontoon boats offer a relaxing way to explore Lake Tarpon. Feeling creative? Dive into hands-on fun with ceramics, stained glass, and woodworking studios. With over 40 active clubs and complimentary RV and boat storage, there’s something here for everyone to enjoy year-round. Located just minutes from Gulf beaches, shopping, dining, and top-rated medical facilities, 3569 Oak Lake Drive offers the perfect blend of tranquility and convenience. Don't miss this opportunity to enjoy the Florida lifestyle in a vibrant, active community. Close to all the Tampa Bay Area has to offer; Championship golf courses, Tampa International Airport, NHL, NFL, MLB events, Grand Prix, PGA events, fine dining, concerts, parks, biking trails, BMX events, and more. Begin Your Paradise Life Today.
Listing is courtesy of: PARADISE LIFE REALTY (727-698-2996)
Listing Agent: Lou Tutko (727-698-2996)
3098 E DORCHESTER DR, PALM HARBOR, FL 34684
$399,900187 Days on yellowkey MLS ID: TB8433251
0 Days Off yellowkey (back on 3/31/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1567 Built: 1980Monthly Fee: $164 Tax: $3,136 (2024)Community: Highland Lakes Unit 14 Ph 1Single Family
Taxes:$3,136
Remarks: Under contract-accepting backup offers. One of the many Highlights of this spacious 1567 Sq Ft, 2-bedroom, 2-bath, Split Plan home is the LARGE ENCLOSED FLORIDA ROOM, which is the Perfect Peaceful Place to Relax, Watch Wildlife, and Enjoy the VIEWS of your PRIVATE Backyard. Recent updates ensure peace of mind and efficiency, including the NEW ROOF (2024), NEW WINDOWS (2025) with PLANTATION SHUTTERS on EVERY WINDOW, gives off that Breezy, Coastal vibe and secure with permanently affixed accordion HURRICANE SHUTTERS, NEW AC with ALL NEW DUCTS (2018), UPDATED ELECTRICAL PANEL, and NEW Rainbird Sprinkler System (on a WELL). The kitchen has been expanded to include more cabinets with GRANITE Counter Tops - providing ample storage for all your cooking appliances and a Rare WALK IN PANTRY! STAINLESS STEEL APPLIANCES and a Stainless Steel Refrigerator that RESISTS Fingerprints, and an oven that is practically brand new! Doing Dishes isn't a chore when you're enjoying the expanded view out of the Florida Room and your PRIVATE Backyard. The CERAMIC TILE THROUGHOUT is easy to maintain and goes with any decor. The Primary bedroom's bath has a TILED SHOWER and GRANITE. The Oversized Garage easily fits 2 cars or a Golf Cart. Additional storage with a pull-down attic. Plus, a water softener to help with the Hard Florida water. Come and Discover HIGHLAND LAKES ON LAKE TARPON, the $164 monthly HOA fee GIVES you FREE GOLF on 3 community-owned and maintained executive GOLF COURSES (with Par 4s!), 2 HEATED POOLS, PICKLEBALL, TENNIS, CERAMICS, FREE BOAT OR RV STORAGE! 2 PONTOON BOATS FOR CRUISING THE LAKE, with over 40 clubs, there is something for everyone. Located near Beaches, 2 International Airports, shopping, restaurants, all this plus SO MUCH MORE! Plus, located in a NON-EVACUATION ZONE with NO FLOOD INSURANCE REQUIRED!
1563 WICKLOW DR, PALM HARBOR, FL 34684
$499,00076 Days on yellowkey MLS ID: TB8467874
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1964 Built: 1985Monthly Fee: $164 Tax: $5,324 (2024)Community: Highland Lakes Unit Fifteen Ph 4Single Family
Taxes:$5,324
Remarks: Under contract-accepting backup offers. Stop scrolling — this is the one. A stunning open-concept retreat with high-end updates, bonus living space, and premier access to beaches, travel, and entertainment. Welcome to luxury, ease, and elevated living in the coveted Highland Lakes 55+ community. This stunning, fully updated open-concept residence delivers 1,964 sq ft of refined interior space plus a 260 sq ft air-conditioned enclosed porch, creating an exceptional setting for both everyday comfort and effortless entertaining. From the moment you enter, the home impresses with stylish new flooring (2021), abundant natural light from updated windows (2021), and a seamless flow into a beautifully reimagined kitchen featuring granite countertops, elegant new cabinetry, and premium appliances (2021–2023). Every detail reflects thoughtful upgrades and timeless design. The spacious primary suite, well-appointed guest bedroom, and two full baths offer comfort and privacy, while the oversized utility room and 2-car garage provide rare practicality without sacrificing style. Major system improvements — including a new roof (2024) and water heater (2022) — ensure true move-in-ready confidence. The enclosed, air-conditioned porch extends your living space year-round, perfect for morning coffee, evening gatherings, or quiet relaxation. Ideally positioned near two international airports, breathtaking Gulf beaches, museums, and top concert and entertainment venues, this home offers the ultimate blend of luxury, location, and low-maintenance lifestyle within one of the area’s most desirable active communities. This is more than a home — it’s the lifestyle upgrade buyers have been waiting for.
Listing is courtesy of: TREASURED HOME COLLECTION (727-210-3282)
Listing Agent: Holly Davis (727-430-6393)
3529 OAK LAKE DR, PALM HARBOR, FL 34684
$420,00056 Days on yellowkey MLS ID: TB8474960
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1671 Built: 1987Monthly Fee: $164 Tax: $2,348 (2025)Community: Highland LakesSingle Family
Taxes:$2,348
Remarks: Welcome to this turn key vacation home featuring a clean 4 point inspection, 2-bedroom, 2-bathroom in the highly desirable Highland Lakes community where comfort and lifestyle come together which is perfect for seasonal living or a second home with furniture options available for a seamless, move in ready experience. This well-maintained residence features a newly added roof in 2024, new A/C in 2020 and a welcoming covered porch, perfect spot to relax, enjoy the sunlight and peaceful neighborhood setting. The home features two dining areas, a bright Florida room, and a spacious living room offering flexible spaces for both everyday living and entertaining. Enjoy low maintenance living in this home with tile flooring throughout perfect for easy upkeep. Nestled in a friendly established community this home offers access to Highland Lakes’ resort-style amenities and active lifestyle. Residents enjoy 3 nine hole executive golf courses and golf cart access, Olympic site heated swimming pool, spa, tennis and pickle ball courts, bocce and shuffleboard courts, meeting rooms, craft rooms, professional woodshop, library, billiards rooms and multi purpose auditorium for dances, shows, movies and other activities. Beautifully maintained common areas and a community lodge and great room ideal for social gatherings and private events. With guest recreation options and boat lot access available there are plenty of opportunities to enjoy the outdoors and connect with neighbors. A reasonable monthly homeowner association helps maintain the community’s quality and amenities, ensuring a well-kept and welcoming environment. Whether you’re seeking an active social lifestyle or a quiet place to unwind, this home offers the perfect opportunity to enjoy comfortable living in one of the area’s most sought after neighborhoods.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-847-4444)
Listing Agent: Smitha Suvarna (813-508-6630)
2954 CURLING CT, PALM HARBOR, FL 34684
$299,99945 Days on yellowkey MLS ID: TB8479013
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1069 Built: 1976Monthly Fee: $164 Tax: $3,134 (2025)Community: Highland LakesSingle Family
Taxes:$3,134
Remarks: UPDATED! This inviting two-bedroom, two-bath home, located on a quiet cul-de-sac in Highland Lakes, Palm Harbor’s premier 55+ golf course community, offers comfort, style, and an exceptional Florida lifestyle. Move-in ready with major updates already completed, including a NEWER ROOF (2020), NEWER A/C (2022), FRESH PAINT, BRAND NEW TEXTURED CEILINGS, a NEWER WATER HEATER, and an UPDATED ELECTRIC PANEL—providing added peace of mind from day one. The open living room and dining room combination features a wall of glass sliders that flood the space with natural light and showcase peaceful views of the enclosed lanai and backyard. New laminate flooring extends throughout the main living areas and into the kitchen. The updated kitchen is bright and welcoming, featuring white cabinetry, two windows, a dinette area, and a prep counter with pendant lighting that opens to the dining area. Black accents and stainless-steel appliances create a crisp, modern look. Ample cabinetry, generous counter space, and direct garage entry combine to create a kitchen designed for both daily living and easy entertaining. Both bathrooms feature updated vanities with the primary en-suite including a walk-in shower, while the secondary bath features a tub/shower combination. Well-placed storage includes a large hall closet, linen closet, and two closets in the primary suite, one of which is a walk-in. The spacious enclosed lanai offers a sunroom-style setting with surrounding windows, creating a versatile bonus space ideal for reading, relaxing, or enjoying morning coffee. Just outside the lanai, a paver patio with fire pit provides an inviting outdoor gathering area. Low HOA fees include golf membership with no green fees and outstanding amenities including lighted tennis and pickle ball courts, two pools, shuffleboard, a clubhouse with fitness center and auditorium, access to the Lake Tarpon Lodge with boat ramp and dock with community pontoon boats on Lake Tarpon, secure RV and boat storage, and more. Located in a non-evacuation flood zone and centrally positioned near shopping, dining, medical facilities, and just minutes from top Gulf beaches. Schedule your private showing today.
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Dean Ribble (727-420-5549)
984 GILLESPIE DR, PALM HARBOR, FL 34684
$490,00022 Days on yellowkey MLS ID: TB8487388
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1593 Built: 1983Monthly Fee: $164 Tax: $3,140 (2025)Community: Highland Lakes Unit Fifteen Ph 1Single Family
Taxes:$3,140
Remarks: Beautifully maintained 2-bedroom, 2-bath, 2-car garage home ideally situated on the golf course in the highly sought-after 55+ community of Highland Lakes. Outstanding curb appeal welcomes you with mature, lush landscaping and a paver driveway. Major updates include a 2020 roof, 2025 A/C, 2020 hot water heater and impact-rated windows throughout most of the home, complemented by stylish plantation shutters. The spacious primary suite offers direct access to the Florida room through sliding glass doors, along with tranquil golf course views, a large walk-in closet, and an additional built-in closet. The en-suite bath has been tastefully semi-updated with granite countertops, wood cabinetry, and a walk-in shower. The living and dining rooms share attractive wood-look laminate flooring, and the living area also opens to the Florida room through another set of sliders, creating a seamless indoor-outdoor feel and showcasing the beautiful golf course setting. The remodeled kitchen is both spacious and inviting, featuring wood cabinetry, granite countertops that coordinate with both bathrooms, stainless steel appliances, disposal, newer recessed lighting, and a cheerful eat-in area. Just off the kitchen, you’ll find the dedicated inside laundry room with washer, dryer, utility sink, and storage cabinets, as well as separate access to the 2-car garage which houses a newer electrical panel and water heater. Nearby, the guest wing includes a generously sized second bedroom with built-in closet and an updated guest bath with granite countertop, newer faucet and vanity, recessed lighting, and a tub/shower combo with sliding shower doors. The large family room features vaulted ceilings and is highlighted by a striking oversized window installed by the owner, perfectly framing the golf course and pond views. Both family room windows are outfitted with stylish motorized accordion blinds. The massive Florida room spans the length of the home and is filled with natural light from its many windows, offering expansive views of the golf course. Located in a non-flood zone and no evacuation zone, this home is in one of communities most desirable settings. Highland Lakes is known for its active lifestyle and impressive amenities, including three private 9-hole golf courses, two clubhouses with a wide variety of social activities, two community pools with the main pool featuring a heated spa, plus tennis, pickleball, bocce, and shuffleboard. Beautiful Lake Tarpon is nearby, and residents enjoy access to two community pontoon boats, a private boat ramp, and RV/boat storage, all included in the monthly fee. Hurry to schedule your showing, because this one won't last long!
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)
Listing Agent: Ryan Nowlin (727-647-8089)
1658 MACDONNELL CT, PALM HARBOR, FL 34684
$498,00091 Days on yellowkey MLS ID: TB8462135
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1875 Built: 1981Monthly Fee: $164 Tax: $3,480 (2025)Community: Highland LakesSingle Family
Taxes:$3,480
Remarks: BEST VALUE within Highland Lakes! Unique, beautifully designed home that must be seen in person to fully appreciate! One of the finest homes in this resort-style 55+ community, offering free golf and hundreds of amenities! This beautifully updated, open-concept residence features nearly 1,900 square feet of living space, PLUS a bonus screened lanai not included in the heated square footage. Perfectly situated in Highland Lakes on a peaceful, private cul-de-sac, the home is surrounded by lush greenery with no neighboring homes visible from the front or backyard. Truly unique and full of charm—this is a property that must be seen to be fully appreciated! Large newer windows and skylights flood the home with natural light throughout the day. Quality upgrades shine in the spacious open-concept design that seamlessly blends the living room, family room, Florida room, dining area, and kitchen, creating an ideal setting for entertaining. The chef’s kitchen features a huge island open to the main living space, striking granite countertops, solid wood cabinetry, sleek stainless appliances, recessed lighting, and absolutely no popcorn ceilings, complemented by elegant chair rail detailing throughout. Two bedrooms are thoughtfully separated by a large dressing room, a bathroom, and two closets, while the versatile Florida room can serve as a THIRD BEDROOM, office, or game room and opens to a large private screened porch, also accessible from the primary bedroom. Additional highlights include a convenient inside laundry room with utility tub, a spacious two-car garage with workbench and pull-down stairs to a full attic, a cost-saving deep well, and an expanded patio perfect for grilling. Situated at one of the highest elevations in Pinellas County, this home is not in a flood zone offering peace of mind. No insurance worries here with a NEW electrical panel in 2024, 3.5 TON HVAC in 2016 and with a recently passed four-point inspection available and transferable to the buyer! Located in the highly desirable Highland Lakes active adult community, residents enjoy a vibrant lifestyle with a huge clubhouse offering concerts, shows, dinners, exercise classes, and fairs, plus a lodge on Lake Tarpon with complimentary pontoon rides across its scenic five-mile waters. Amenities include heated pools, pickleball, tennis, bocce, volleyball, yoga, cornhole, and water aerobics, along with creative outlets such as a full woodworking shop, art, ceramics, glass classes, a library with computers, and numerous clubs including chef’s, drama, and photography. The friendly community hosts neighborhood block parties—Block 32 is known as “the friendliest block”—and offers affordable RV and boat storage for only an initial $25 deposit and a minimal $25/YEAR fee. Best of all, residents enjoy three private, pristine championship golf courses with free unlimited play. With a low HOA supported by dedicated volunteers and the option to reserve the Lake Tarpon lodge for private events, this home offers not just a place to live, but an exceptional lifestyle. Schedule your private showing today and start your next chapter!
142 STAFFORD CIR, PALM HARBOR, FL 34684
$357,900130 Days on yellowkey MLS ID: TB8450333
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1294 Built: 1977Monthly Fee: $164 Tax: $5,331 (2024)Community: Highland LakesSingle Family
Taxes:$5,331
Remarks: Welcome home to this updated, move-in ready Palm Harbor retreat in the sought after 55 plus community of Highland Lakes. From the moment you arrive, it is clear this two bedroom, one and a half bathroom home on almost ¼ acre of land has been truly cared for. Inside, nearly 1,300 square feet of inviting living space unfolds in a layout that feels both open and comfortable. The living and dining area flows seamlessly into a spacious family room where a vaulted ceiling and bay window fill the space with soft natural light. It is the perfect spot for morning coffee, quiet afternoons or hosting friends. The kitchen feels fresh and functional with a new range and a pantry that offers generous storage space. Both bathrooms have been thoughtfully updated over recent years, including the main bath which features an easy access low curb shower and safety bars for peace of mind. Throughout the home you will find wood laminate flooring and tile, generous closets in both bedrooms plus extra hallway storage and a convenient interior laundry room with washer and dryer included. The oversized one car garage provides space for a vehicle and a golf cart, and the widened driveway and expanded front porch give you extra room to welcome guests. Major expenses have already been taken care of, with a 2025 AC, a 2023 roof, and a 2024 sprinkler system update. This home not only offers comfort inside but also acts as a gateway to an unbeatable lifestyle. Highland Lakes is known for its incredible affordable amenities and vibrant social atmosphere. Residents enjoy free golf on three private executive courses, active pickleball and tennis leagues, shuffleboard, bocce, bowling, fitness programs, arts and crafts, a woodshop and a well loved library. The Lake Tarpon Lodge offers a peaceful retreat with a second heated pool, picnic areas, a fishing pier and community pontoon boats. There is even free RV and boat storage along with a private boat ramp and open dock. All of this is perfectly located just minutes from Gulf beaches, Honeymoon Island, the Pinellas Trail, endless shopping and dining options, cultural attractions, medical facilities and two international airports. Highland Lakes sits high and dry in a non evacuation zone so everyday living stays worry free. With so much to offer, this home gives you comfort, convenience and a community you will truly love. Your best life is waiting right here in Highland Lakes, schedule your showing today!
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Mimi Desetto (727-417-5194)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.