Saddlebrook Homes under $500,000

Saddlebrook Homes under $500,000

Welcome to Saddlebrook, a vibrant and welcoming subdivision nestled in the heart of sunny Florida! This charming community offers the perfect blend of tranquility and accessibility, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle without sacrificing convenience.

Saddlebrook boasts a variety of beautiful homes, with many options available for under $500,000. Whether you’re a first-time homebuyer or looking to downsize, you’ll find well-designed properties that cater to diverse tastes and preferences. From cozy single-family homes to modern townhouses, each residence is thoughtfully constructed to provide comfort and style.

The community is surrounded by lush landscapes and scenic views, creating a serene atmosphere that encourages outdoor activities and social interactions. Residents can enjoy the numerous parks, walking trails, and recreational facilities that Saddlebrook has to offer. With a strong sense of community, neighbors often gather for events and activities, fostering lasting friendships and a welcoming environment.

Conveniently located near major highways, Saddlebrook provides easy access to shopping, dining, and entertainment options. Whether you’re in the mood for a leisurely day at the beach or a night out in the vibrant downtown area, you’re never far from the action.

Discover the charm of Saddlebrook, where affordable living meets a rich community spirit. With homes under $500,000, this subdivision is not just a place to live; it’s a place to thrive. Come and explore your future home in Saddlebrook today!

Newest Saddlebrook Homes under $500,000

5020 Mill Pond Road Unit 3172, Wesley Chapel
$280,000
2 Beds ⋅ 2 Baths ⋅ Saddlebrook SubDv. ⋅ 33543 Zip Code
THIS IS A COMPLETELY UPDATED GOLF COURSE TWO-BEDROOM GOLF-COURSE CONDOMINIUM THAT WAS PURCHASED FOR THE OWNERS WHILE OTHERS ATTENDED THE SADDLEBROOK ACADEMY AND GRADUATED. BEAUTIFULLY UPDATED CONDOS IN LAKESIDE VILLAGE. PRICED COMPETIVELY AND IT IS SOLD FURNISHED WITH THE EXCEPTANCE OF THE OWNERS PERSONAL BELONGINGS AND WALL ART AND PERSIAN AND OTHER RUGS WHICH TOOK THEM YEARS TO PURCHASE AND HAVE SPECIAL MEANING TO THEM. MAKE AN APPOINTMENT TO VIEW AS SOON AS POSSIBLE. MEMBERSHIPS ARE AVAILABLE WITH MANY CHOICES TO CHOOSE FROM. YOU ARE ONE MILE FROM THE INTERSTATE TO GET TO THE INTERSTATE, AND CLOSE TO ALL THE ACTIVITIES OUTSIDE OUR GATES.

5020 Mill Pond Road Unit 3172, Wesley Chapel
5333 Cobblestone Court, Wesley Chapel
$325,000
3 Beds ⋅ 3 Baths ⋅ Saddlebrook SubDv. ⋅ 33543 Zip Code
NEW ON THE MARKET A TWO-STORY FURNISHED CLUSTER HOME WITH 3 BEDROOMS, TWO AND A HALF BATHS, AND READY FOR YOU TO MOVE IN NOW. THE SELLERS HAVE JUST GONE NORTH TELLING ME THEY HAVE DIFFICULTY TRAVELING AT THEIR AGE AND FEEL THIS MAY BE THE TIME TO GIVE UP THEIR SECOND HOME AFTER COMING TO SADDLEBROOM FOR OVER 30 YEARS. FIRST IN A CONDO AND NOW TO THIS HOME. THEY HAVE MADE IT READY FOR THE NEXT BUYER TO COMFORTABLY MOVE IN AND NOT HAVE TO WORRY WITH FURNISHING, IT ALL STAYS. JUST BRING YOUR SUITCASES AND YOUR TENNIS RACKETS AND GOLF CLUBS. THERE IS A COMMUNITY SWIMMING POOL AT THE END OF THE ROAD FOR YOUR USE. IF YOU DECIDE TO JOIN THE SADDLEBROOK CLUB THERE ARE MANY MEMBERSHIP CHOICES AVAILABLE. THE HOA DUES INCLUDE THE EXTERIOR MAINTENANCE OF THE BUILDING SUCH AS PAINTING, ROOF, LAWN MOWING, IRRIGATION, HOMEOWNER HAZARD INSURANCE, ROAD MAINTENANCE, POOL MAINTENANCE, STREET LIGHTING, SUB-TERRANEAN WARRANTYSECURITY ROVING GUARD TOO. TRASH PICKUP TWICE A WEEK AND RECYCLABLES ONCE A WEEK TOO. CLOSE TO US OUTSIDE OUR GATES ARE THE MANY RESTAURANTS, HOSPITALS, SHOPPING CENTERS, GROCERY STORES, ETC.

5333 Cobblestone Court, Wesley Chapel
29129 Bay Hollow Drive Unit 3204/3206, Wesley Chapel
$270,000
3 Beds ⋅ 3 Baths ⋅ Saddlebrook SubDv. ⋅ 33543 Zip Code
This stunning three-bedroom, three-bathroom condo in Saddlebrook offers breathtaking golf course views from two private balconies. The open floor plan features two bedrooms and two bathrooms on one side of the condo, along with a privacy lockout door leading to the additional third bedroom and bathroom, which can be used as a separate living area. Tastefully updated with luxury vinyl floor throughout and beautifully furnished, the furniture may be included with the sale. The kitchen features granite countertops, beautiful cabinetry, and new 2026 appliances. A washer and dryer are conveniently located inside the condo. Whether you are looking for a full-time residence, a vacation retreat, or an investment property, this condo offers the flexibility to live in the condo or rent out one or both sides. Saddlebrook Golf and Tennis Resort is home to Saddlebrook Preparatory School for junior athletes, offering an exceptional setting for those who enjoy an active lifestyle. Come golf, play tennis, pickleball, paddle, and enjoy all that the resort has to offer. Club memberships are available. Located in the heart of Wesley Chapel, Saddlebrook is close to I-75, Wiregrass Mall, Tampa Premium Outlets, AdventHealth, BayCare Hospital, Moffitt Cancer Center, AdventHealth Center Ice, and the area’s newest shopping and dining destinations. Call today to schedule your private showing!

29129 Bay Hollow Drive Unit 3204/3206, Wesley Chapel
29130 Bay Hollow Drive Unit 3314, Wesley Chapel
$264,900
2 Beds ⋅ 2 Baths ⋅ Saddlebrook SubDv. ⋅ 33543 Zip Code
Imagine living at a resort year-round, where your days are filled with Florida sunshine, beautiful surroundings, and effortless living without the lawn work or weekend chores. Welcome to this exceptional second-floor 2-bedroom, 2-bath residence offering 1,400 square feet and one of Saddlebrook’s most desirable floor plans. This condo offers spacious living areas, excellent separation between the bedrooms, and an expansive balcony that creates a seamless extension of the indoor living space. The true showstopper, however, is the spectacular panoramic view. From your elevated second-floor setting, take in sweeping views across the peaceful pond, lush golf course, Lakeside Pool, Fitness Courts, and beautiful tropical landscape. The combination of shimmering water, manicured fairways, and lush surroundings creates a picturesque and serene backdrop from morning to night. The oversized balcony is the perfect place to enjoy morning coffee, evening cocktails, or simply unwind while taking in one of Saddlebrook’s most beautiful views. Whether enjoyed as a full-time residence, seasonal retreat, or investment property, this condo offers an exceptional combination of space, views, and low-maintenance resort living. Saddlebrook Resort is in the midst of an exciting $92 million transformation, bringing a fresh new energy to its iconic 480 acres of Florida paradise. Recent enhancements include Brew Café, the new Pool Bar & Kitchen, The Goal Sports Tavern, Rare 1981 upscale restaurant, beautifully renovated guest rooms, and a reimagined golf experience featuring three interchangeable nine-hole courses. The resort is also home to 43 tennis courts and 8 pickleball courts. The community offers 24-hour guard-gated security and an ideal location convenient to I-75, The Grove, The Shops at Wiregrass, Tampa Premium Outlets, dining, hospitals, and everyday conveniences. Optional memberships are available directly through Saddlebrook Resort for those who wish to enjoy golf, tennis, pickleball, spa services, dining, and additional resort amenities. Experience one of Saddlebrook’s premier second-floor floor plans, breathtaking panoramic pond and golf course views, and the rare opportunity to enjoy the feeling of a luxury resort every day of the year.

29130 Bay Hollow Drive Unit 3314, Wesley Chapel
740 Preakness Circle, Deland
$369,900
4 Beds ⋅ 2 Baths ⋅ Saddlebrook SubDv. ⋅ 32724 Zip Code
Open House Sunday, October 11th from 1:00-3:00pm rain or shine!! Welcome home to this beautiful Pinehurst home by Taylor Morrison in the desirable established Saddlebrook community. With 2,029 square feet of living space, this plan is known for its signature central rotunda foyer flowing into the large kitchen/family room combo, and the primary suite tucked privately at the back of the home. This home features 3 bedrooms, 2 baths PLUS flex room for office/den/4th bedroom and 2 car garage that even a standard truck can fit in! This premium lot offers a large screened lanai overlooking a fully fenced backyard and wooded preserve for privacy along with a buffer across the street with mature landscaping. Some recent updates include a top of the line HVAC system (5/2026) with UV light filter, whole house surge protector and new water heater. The Saddlebrook community pool and playground is a very popular place to visit with neighbors and park benches are located near the community ponds to take breaks while enjoying the daily dog walks. Located close to award winning Downtown DeLand Mainstreet for year-round parades and festivals, Stetson University, DeLand High School, and 30-40 minute drive to Orlando area attractions and some of the world's most famous beaches!

740 Preakness Circle, Deland
29300 Bay Hollow Drive Unit 3257, Wesley Chapel
$315,000
3 Beds ⋅ 3 Baths ⋅ Saddlebrook SubDv. ⋅ 33543 Zip Code
Before reaching your destination, you’ll pass through the gates of Saddlebrook Resort where mature trees, lush landscaping, and tranquil water views create a peaceful resort-style setting. Tucked away near the end of a quiet private road in the desirable Lakeside area, this thoughtfully updated condo offers a unique and flexible layout ideal for full-time living, seasonal use, or income potential. The main side of the condo features 2 bedrooms and 2 full bathrooms with a spacious split-bedroom design, comfortable living and dining areas, curated finishes, solid wood cabinetry, luxury vinyl flooring, updated baths, indoor laundry, and a lanai designed to capture the breathtaking surroundings. The gorgeous pond frontage with sweeping golf course views creates the perfect backdrop for quiet morning coffee, potent evening cocktails, or lazy Sunday afternoons. Adding to the versatility, the condo also includes a separate private entrance leading to an additional oversized bedroom and full bathroom which is ideal for guests, multigenerational living, a private office, or rental income opportunities. Use all 3 bedrooms for yourself or rent one side while enjoying the other. Being sold furnished, this condo is move-in ready and perfect as a vacation getaway, seasonal retreat, or investment property. Photos can showcase the view, but they can’t fully capture the feeling of being here. With Saddlebrook’s gated resort atmosphere, golf course, tennis and pickleball facilities, fitness center, dining options, salon, boutique services, mature landscaping, private roads, and peaceful water and fairway views, this home truly feels like a daily escape. Owners can also enjoy the excitement of Saddlebrook’s ongoing $92 million revitalization featuring redesigned golf courses by Rees Jones, upgraded dining venues, refreshed accommodations, and enhanced resort amenities. Conveniently located near shopping, dining, I-75, Tampa Premium Outlets, AdventHealth, and everything Wesley Chapel has to offer. Whether you’re searching for a seasonal retreat, vacation getaway, investment opportunity, or low-maintenance Florida lifestyle, this is an incredible opportunity to own in one of Tampa Bay’s most recognizable golf and tennis communities. Call today for your private showing.

29300 Bay Hollow Drive Unit 3257, Wesley Chapel
29130 Bay Hollow Drive Unit 3312, Wesley Chapel
$265,000
2 Beds ⋅ 2 Baths ⋅ Saddlebrook SubDv. ⋅ 33543 Zip Code
Wake up to panoramic pool and golf course views from this beautifully furnished second floor condo in the heart of Saddlebrook Resort. This 2-bedroom, 2-bath residence offers one of the most spectacular vantage points in the community, overlooking the sparkling pool with sweeping golf course views beyond which makes it the perfect backdrop for your morning coffee or evening unwind. Inside, the light-filled layout features an open living and dining space designed to maximize the scenery, elegant plantation shutters throughout, and a furnished interior makes this an effortless full-time residence, seasonal retreat, or investment opportunity. The spacious primary suite offers tranquil views and a private bath, while the second bedroom provides flexibility for guests or a home office. Located behind the gates of the iconic Saddlebrook Resort, owners enjoy a setting known for its lush landscaping, resort lifestyle, and exciting revitalization underway. Saddlebrook’s $92 million transformation includes redesigned golf courses by Rees Jones, upgraded dining venues, refreshed accommodations, tennis and pickleball facilities, fitness amenities, and more. Conveniently located near shopping, dining, I-75, Tampa Premium Outlets, AdventHealth, and all that Wesley Chapel has to offer. Whether you’re looking for a vacation getaway, winter escape, or maintenance-free Florida lifestyle, this condo delivers incredible views, resort-style surroundings, and the opportunity to own in one of Tampa Bay’s most recognizable golf communities. Call today for your private showing.

29130 Bay Hollow Drive Unit 3312, Wesley Chapel
29903 Baywood Lane, Wesley Chapel
$450,000
3 Beds ⋅ 3 Baths ⋅ Saddlebrook SubDv. ⋅ 33543 Zip Code
Don’t miss your opportunity to own a coveted Saddlebrook address in the highly sought-after Fairway Village. This beautifully maintained end-unit cluster home offers 2,356 square feet of effortless, maintenance-free living, perfectly positioned to capture peaceful golf course views while maintaining exceptional privacy. Featuring 3 spacious bedrooms, 3 full baths, and a 2.5-car garage with room for both your golf cart and extra storage, this home blends generous space with a functional layout designed for everyday living and entertaining. The expansive 25x17 family room is the heart of the home, complete with a striking wood-burning fireplace, built-in bar, and sliding glass doors that open to a screened lanai, an ideal setting for morning coffee or evening gatherings overlooking the fairway. The kitchen flows seamlessly into the main living and dining areas, offering tiled floors, a breakfast bar, and ample space to make it your own. The oversized primary suite features three closets and a spacious en-suite bath with a garden tub, separate walk-in shower, and natural light from above. Each bedroom enjoys its own private bath, including one with French doors leading to a charming courtyard retreat, perfect for guests or a quiet escape. Additional highlights include a dedicated laundry room, a well-sized garage, and major updates with a new A/C (2024) and roof (2014). Located in one of Saddlebrook’s most desirable communities, this home offers a rare opportunity to enjoy a serene golf course lifestyle with low-maintenance convenience and ready for your personal touch.

29903 Baywood Lane, Wesley Chapel
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