Homes for Sale Near Windy Hill Middle in Clermont - 183 homes

Remarks: This beautifully maintained, like-new home features 3 bedrooms upstairs and a versatile flex room on the first floor, perfect for a home office, TV room, or playroom. The kitchen showcases beautiful finishes and plenty of natural light, making it a bright and inviting heart of the home. The master suite offers a spacious retreat with a large walk-in closet, while the laundry conveniently upstairs adds to the home's practical layout. Step outside to a large backyard, ideal for outdoor entertaining or relaxing in the Florida sun. Perfectly designed for modern living, this home combines style, functionality, and comfort in a desirable Clermont location. Don’t miss the opportunity to make it yours!

Listing is courtesy of: POINTON REALTY INC (407-395-2860)

Listing Agent: Andrea Pointon (407-446-4414)

Remarks: LUXURY RENOVATION WITH 3 FULL BATHS & INCOME POTENTIAL – NO CDD & LOW HOA! Welcome to 10618 Reagans Run Drive, a masterfully upgraded residence in Clermont where no expense has been spared. Featuring over $40,000 in premium improvements, this home offers the perfect combination of sophisticated design, top-tier mechanical reliability, and a smart layout for maximum ROI. UNMATCHED UPGRADES & LUXURY FEATURES: MECHANICAL EXCELLENCE: Total peace of mind with a BRAND NEW ROOF (Installed 2025) with a 40-year life expectancy and a NEW HVAC SYSTEM featuring a 10-year warranty. LUXURY INTERIOR FEATURES: The entire home features stunning Luxury Italian Porcelain tile flooring (no carpet!). GOURMET KITCHEN: A chef’s dream! Completely renovated with Exquisite Wood Cabinetry, high-end Quartz countertops, and premium Stainless Steel appliances. BONUS INCOME SUITE: The garage has been professionally converted into a fully independent Studio/Efficiency with its own full bathroom and private side entrance. Ideal for generating rental income to pay your mortgage or as a private guest suite. OUTDOOR ENTERTAINING: Relax on the covered back porch with premium pavers and a built-in Outdoor Kitchen (sink and cabinets), all overlooking a large, fully fenced backyard. FINANCIAL ADVANTAGES: NO CDD fees and a remarkably low HOA of only $298/Annually. Move-in ready with "Zero" deferred maintenance. LOCATION: Enjoy the best of Clermont’s rolling hills, lakes, and shopping, with easy access to major highways for a quick commute to Orlando. Conveniently located near US-27 and SR-50, with easy access to supermarkets, restaurants, Clermont Landing, and Downtown Clermont. Enjoy nearby recreational areas such as Lake Louisa State Park and the Clermont Chain of Lakes, and benefit from being just 30–40 minutes from Orlando’s top attractions including Walt Disney World and Universal Studios. This is a rare "Turn-Key" opportunity that pays for itself. Schedule your private showing today!

Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)

Listing Agent: Brigida Lopez (321-945-3989)

Remarks: Move-In Ready! Welcome to the final Miles plan in Ridgeview and experience the perfect blend of style and functionality in this beautifully designed open-concept home featuring 4 bedrooms and 3 full baths, enhanced by tile flooring in the main living areas, and 9'4" ceilings throughout. The Spacious Great room flows seamlessly to the covered rear Lanai - perfect for entertaining and outdoor living. The well-appointed kitchen showcases upgraded 42" cabinets, quartz countertops, a stylish tile backsplash, and stainless appliances—ideal for entertaining and everyday living. The Primary suite offers a serene retreat with ensuite bathroom featuring adult-height vanity with dual sinks, quartz countertops, and walk-in shower with wall tile surround, frameless glass enclosure, and multiple shower heads. A home that effortlessly combines comfort, luxury, and thoughtful design. Located in the desirable Ridgeview community, residents enjoy outstanding amenities including a pool and playground. Just steps from Lake Louisa State Park and adjacent to the exciting new Olympus Project, Ridgeview also offers direct access to Schofield Road—connecting Clermont to Winter Garden. Enjoy the convenience of nearby shopping, dining, and easy access to major thoroughfares for a connected and active lifestyle.

Listing is courtesy of: RISEWELL HOMES FLORIDA LLC (888-827-4421)

Listing Agent: Stephen Wood (321-231-2077)

Remarks: Under Construction. This new two-bedroom home offers convenient single-story living. A secondary bedroom and a study are secluded near the front of the home, leading to an inviting open-concept floorplan that boasts convenient access to a covered patio for seamless indoor-outdoor living. The owner’s suite is nestled into a private rear corner, complete with a full bathroom and walk-in closet. A spacious two-car garage completes the home. Each home comes with Lennar’s Everything’s Included® promise, which includes new appliances as well as quartz countertops, blinds, and more in the price of your home. Wellness Ridge is one of the most modern and anticipated new communities. R19 insulation is used to provide a quiet, comfortable and highly energy efficient home. LP Siding provides durability and impact resistance for your beautiful Florida home. Welcome to the much anticipated - Sanctuary at Wellness! Nestled in the heart of Clermont, FL, Sanctuary at Wellness Ridge is an exclusive 55+ master-planned community designed for those who prioritize a luxurious, health-focused lifestyle. The state-of-the-art clubhouse is the vibrant heart of the community, where residents gather for events and activities. It features a fitness center and a golf simulator for year-round enjoyment. Sanctuary at Wellness Amenities include: clubhouse, resort style pool, sports courts (basketball, pickleball, bocce ball), fitness center, and walking trails.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Under Construction. Check out this amazing new single-story Next Gen®! The McCartney features a private suite with its own entrance, living area, kitchenette, bedroom, bathroom and laundry, perfect for multigenerational households. The main home is host to an inviting open-concept layout with easy access to a covered patio for seamless indoor-outdoor living. Two secondary bedrooms are located off the foyer, and a lavish owner’s suite is tucked into a private rear corner, complete with a full bathroom and walk-in closet. Each home comes with Lennar’s Everything’s Included® promise, which includes new appliances as well as quartz countertops, blinds, and more in the price of your home. Wellness Ridge is one of the most modern and anticipated new communities. R19 insulation is used to provide a quiet, comfortable and highly energy efficient home. LP Siding provides durability and impact resistance for your beautiful Florida home. Welcome to the much anticipated - Sanctuary at Wellness! Nestled in the heart of Clermont, FL, Sanctuary at Wellness Ridge is an exclusive 55+ master-planned community designed for those who prioritize a luxurious, health-focused lifestyle. The state-of-the-art clubhouse is the vibrant heart of the community, where residents gather for events and activities. It features a fitness center and a golf simulator for year-round enjoyment. Sanctuary at Wellness Amenities include: clubhouse, resort style pool, sports courts (basketball, pickleball, bocce ball), fitness center, and walking trails.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Brand new, energy-efficient home available NOW! Retreat to your luxurious primary suite upstairs with an oversized walk-in closet and dual sinks in the bath. Now selling, Cagan Crossings West offers spacious open-concept townhomes from the mid $300s, on US-27 in Clermont, FL. This desirable location allows residents to be minutes from Clermont's chain of lakes, Downtown Clermont, and Disney World. This community will feature a resort-style pool and cabana as well as a tot lot. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Under Construction. *READY BY THE END OF FEBRUARY 2026* The 2,278 sq. ft. Glacier Bay offers thoughtfully designed single-story living with 4 bedrooms, 3 baths and a 3-car garage. A walk-in pantry enhances the open, flowing space and connectedness of the kitchen and dining area. A covered lanai provides excellent outdoor living space. The primary room has a large walk-in closet and linen storage.

Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)

Listing Agent: Amanda Warren (321-662-0779)

Remarks: Under Construction. The 2,278 sq. ft. Glacier Bay offers thoughtfully designed single-story living with 3 bedrooms, 2.5 baths and a 3-car garage. A walk-in pantry enhances the open, flowing space and connectedness of the kitchen and dining area. A flex room offers versatile space perfect as an office, game room or additional sitting area. A covered lanai provides excellent outdoor living space. The owner’s suite has a large walk-in closet and linen storage.

Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)

Listing Agent: Amanda Warren (321-662-0779)

Remarks: Under Construction. The 2,278 sq. ft. Glacier Bay offers thoughtfully designed single-story living with 3 bedrooms, 2.5 baths and a 3-car garage. A walk-in pantry enhances the open, flowing space and connectedness of the kitchen and dining area. A flex room offers versatile space perfect as an office, game room or additional sitting area. A covered lanai provides excellent outdoor living space. The owner’s suite has a large walk-in closet and linen storage.

Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)

Listing Agent: Amanda Warren (321-662-0779)

Remarks: Under Construction. This Glacier Bay offers thoughtfully designed single-story living with 4 bedrooms (flex room upgraded to the 4th bedroom), 3 bathrooms (instead of 2.5) and a 3-car garage. A walk-in pantry enhances the open, flowing space and connectedness of the kitchen and dining area. The covered lanai provides excellent outdoor living space. The primary room has a large walk-in closet and linen storage.

Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)

Listing Agent: Amanda Warren (321-662-0779)

Remarks: Your Search is Over — This Home Has It All! Trust Me! Welcome to this beautifully maintained home, lovingly cared for by its owners and located in the peaceful Sawgrass Bay community in beautiful Clermont. From the moment you step inside, you’ll feel the warmth and comfort of this cozy residence. The spacious, open-concept kitchen is the heart of the home—inviting you to gather with family and friends around the oversized island, perfect for cooking, entertaining, and creating memories. Step outside to the extended screened-in lanai, a tranquil outdoor retreat that offers the perfect setting to relax, enjoy your morning coffee, or host an evening get-together. The fully fenced backyard with privacy screen adds both peace of mind and charm. This stunning home features 4 spacious bedrooms and 3 full bathrooms, luxury vinyl flooring on the first floor, high ceilings on both levels, a smart hybrid water heater, irrigation system, and a whole-house water filtration and softener system. The washer and dryer are included, and the garage offers floating storage shelves and gutters all around. Located in the family-friendly Sawgrass Bay community, residents enjoy a community pool and playground—making this home the perfect blend of comfort, style, and lifestyle.

Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS (407-822-1063)

Listing Agent: Yesenia Barrios (321-276-1977)

Remarks: PREMIUM LOT, NO REAR NEIGHBORS. Built in 2023 this home is Turn key and ready for a new owner! Featuring stunning preservation views. This spacious property includes 5 bedrooms, 3 bathrooms, an upstairs loft, and a 2-car garage, thoughtfully designed with modern conveniences such as a washer, dryer, refrigerator, window blinds, and ample storage throughout. Solar panels to save on electricity and water softener system throughout the entire home. The open-concept first floor seamlessly integrates the kitchen, café, and gathering room, creating an ideal space for entertaining. The kitchen boasts a center island, storage pantry, stainless steel Whirlpool appliances, elegant cabinetry, and granite countertops. Step out to the lanai, located just beyond the café, for effortless indoor and outdoor entertaining. The main level also features a bedroom and full bathroom, perfect for accommodating guests or creating a private home office. Upstairs, the second floor offers ample space for the entire family, including a spacious loft, laundry room, three additional bedrooms, a third full bathroom, and the luxurious Owner’s Suite. The Owner’s Suite is a true retreat, complete with a large walk-in closet, en suite bathroom featuring a double quartz-topped vanity, dual sinks, a linen closet, and a walk-in shower. This home comes equipped with premium features, including a washer, dryer, refrigerator, blinds, a direct vented range hood, and our professionally curated Preferred design package. The kitchen is adorned with Villanova cabinetry, Majestic granite countertops, and Maple quartz countertops in the bathrooms. The first-floor living areas, bathrooms, and laundry room are graced with Boston Perla ceramic tile flooring, while stain-resistant Bare Mineral carpet adds comfort to the bedrooms and loft. This spacious Tybee home is perfect for relaxing and entertaining with family and friends. Located in the gated community of Cagan Crossings, this property offers affordable living with easy access to nearby attractions, shopping, and dining. The community features family-friendly amenities, including a pool with a cabana, playground, covered picnic area, and scenic wetland views. With highly ranked schools nearby, a convenient location just off Hwy-27, nine miles from I-4, and less than ten minutes to Disney, this is an opportunity you don’t want to miss!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Rodrigo Oliveira (407-517-8491)

Remarks: Available NOW! Welcome to this brand new, never-lived-in 4-bedroom, 3-bath Aspen model in the highly sought-after Wellness Ridge community. Priced below appraised value, this home includes full lawn care and ultra-fast 1.2G fiber internet, offering outstanding value and low-maintenance living. Be the very first to live in this thoughtfully designed home featuring a spacious foyer, desirable three way split floorplan, and an open concept kitchen complete with a large quartz island, stainless steel appliances, upgraded finishes, and premium paint throughout. Enjoy peaceful privacy with no rear neighbors from the covered back porch, perfect for taking in beautiful Florida sunsets. The front of the home offers a 2 car garage, paver driveway, and wide community sidewalks that enhance the neighborhood’s charm and walkability. Ideally located just minutes from world class theme parks and Lake Louisa State Park, residents enjoy resort style amenities including two swimming pools with cabanas and a lap pool, pickleball, tennis and basketball courts, soccer field, clubhouse with a state of the art fitness center, playground, and scenic walking trails. The home is also conveniently situated near the upcoming Olympus master development, a 243 acre mixed use sports, entertainment, retail, hospitality, and wellness destination expected to bring exciting dining, recreation, and entertainment options to the area. Do not miss this opportunity to own a truly move in ready, never lived in home in one of Central Florida’s most vibrant and rapidly growing communities! Closing cost assistance available!

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Danielle Ramesar (352-638-3080)

Remarks: Skip the delays, added costs, and limitations of new construction on a narrow 50’ lot—this exceptional property delivers space, privacy, and immediate enjoyment. Perfectly positioned on a generous 100’ wide, 0.26-acre corner lot at the end of a quiet cul-de-sac in the highly desirable South Ridge community, this home truly stands apart. Step into a home that truly has it all—space, style, and the Florida lifestyle you’ve been dreaming of. From the moment you arrive, the oversized three-car driveway and mature landscaping set the tone for what’s inside. Through the grand double entry doors, you’re welcomed by a bright, open layout filled with natural light and upgraded with no carpet throughout for a clean, modern feel. Designed with flexibility in mind, the formal living and dining areas can easily transform into a private office, den, or flex space to fit your lifestyle. At the heart of the home, the expansive open-concept kitchen is a true showstopper—perfect for entertaining and everyday living alike. Enjoy 42” cabinetry, stainless steel appliances, a natural gas range, granite countertops, a large center island with bar seating, and a separate prep island. Whether hosting friends or enjoying a quiet morning, the cozy breakfast nook and spacious family room create the perfect gathering spaces. Then step outside—and this is where the home truly shines. Your private backyard oasis awaits, featuring a stunning saltwater pool with a waterfall, tanning ledge, and built-in seating. The covered lanai offers the ideal space for outdoor dining or relaxing in the shade, while the fully fenced yard provides privacy and room for pets or play. The thoughtfully designed split floor plan offers both comfort and privacy. The oversized primary suite is a retreat of its own, complete with a bay window, direct pool access, new vinyl flooring, and dual walk-in closets. The en-suite bathroom delivers spa-like luxury with separate vanities, a makeup station, garden tub, walk-in shower, and private water closet. On the opposite side of the home, three additional bedrooms and two full bathrooms provide the perfect setup for family or guests. Additional features include a dedicated laundry room and a spacious three-car garage with plenty of storage. Enjoy peace of mind with major updates already completed: new roof (2025), water heater (2023), HVAC (2018), fresh interior paint, updated lighting, new primary flooring, and new front sod. Location is everything—and this home delivers. Ideally situated near shopping, dining, golf courses, state parks, and the Chain of Lakes, you’ll also be just minutes from the National Training Center, hospitals, and everyday conveniences. With easy access to US-27, Highway 50, the Turnpike, 408, and 429, commuting is seamless. Plus, enjoy the convenience of being within walking distance to East Ridge High School and close to top-rated middle and elementary schools. Homes like this—with a pool, upgrades, space, and location—don’t come around often. Schedule your private showing today.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Nick Whitehouse (407-902-4639)

Remarks: Exceptional opportunity to acquire a fully furnished, turnkey 3-bedroom, 3-bath residence in the sought-after Hidden Forest community of Clermont. This contemporary townhome showcases an open-concept layout with abundant natural light, a modern kitchen featuring stainless steel appliances, and a private screened splash pool designed for relaxation and guest enjoyment. Approved for short-term rental use, this property demonstrates a consistent record of high occupancy and strong income performance. It is currently managed by a reputable property management company that will remain in place and continue overseeing all existing and future reservations, ensuring a seamless transition for the new owner. Combining modern finishes with a serene natural setting just minutes from Disney and Central Florida’s premier attractions, this home represents an exceptional investment opportunity and a valuable addition to any portfolio.

Listing is courtesy of: MP FLORIDA PROPERTY & REALTY INC (954-701-0824)

Listing Agent: Katia Puppio (407-453-6261)

Remarks: Under Construction. Welcome to Parkside Trails! Explore the charm of this premier Clermont location, offering exclusive amenities and quick access to shopping, dining, and entertainment. With a mix of new construction, single-family and townhomes, plus a variety of exclusive amenities, families will love coming home. Now Selling Onsite with 4 Models Open Daily! At Pulte, we build our homes with you in mind. Every inch was thoughtfully designed to best meet your needs, making your life better, happier and easier. Our new construction Foxtail interior unit townhome features 3 bedrooms, 2 full bathrooms, a powder room, an open concept kitchen, café and gathering room, a private courtyard, and a 2-car rear-facing garage. The first floor is ideal for entertaining, featuring a spacious gathering room, café and kitchen, with a large center island, storage pantry, Elkins White cabinets, a decorative tile backsplash, Blanco Maple quartz countertops and Whirlpool stainless-steel kitchen appliances. A powder room and laundry on the first floor add to the thoughtful convenience. Enjoy entertaining loved ones from your private, fenced rear courtyard. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and en suite bathroom with a double sink Blanco Maple quartz-topped vanity, private water closet and a walk-in shower. Two additional bedrooms, the secondary bathroom and extra storage offered by a linen closet are on the opposite side of the second floor, offering privacy and space for everyone. Professionally curated design finishes for this popular Foxtail townhome include tile flooring throughout the first floor and bathrooms and soft, stain-resistant, Shaw brand carpet in the bedrooms and second floor living areas, and so much more.

Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)

Listing Agent: Adrienne Escott (407-250-9131)

Remarks: Under Construction. Welcome to the Steely, an innovative two-story Next Gen® home. This home features a private suite with a separate entrance, living area, kitchenette, bedroom, bathroom and laundry, ideal for multigenerational households. The main home is host to an inviting open-concept layout that blends the kitchen, living and dining areas, while a luxe owner’s suite at the back of the home offers a private retreat with a full bathroom and walk-in closet. A secondary bedroom is tucked away to the side of the home on the first floor. Two additional bedrooms share the second level with a versatile game room. Each home comes with Lennar’s Everything’s Included® promise, which includes new appliances as well as quartz countertops, blinds, and more in the price of your home. Wellness Ridge is one of the most modern and anticipated new communities. R19 insulation is used to provide a quiet, comfortable and highly energy efficient home. LP Siding provides durability and impact resistance for your beautiful Florida home. Welcome to Wellness Ridge the community that was designed to provide a Healthy & Active Lifestyle!! Community Features include: Sports Courts, Clubhouse, Fitness Center, Conservation Areas, Playground, Resort Style Swimming Pool and Multi-Use Trails. This beautiful home is very close to Lake Louisa State Park. Clermont is one of the fastest-growing cities in Central Florida. Strategically located close to Orlando and theme parks, it is known for its picturesque hills and pristine lakes. Schedule your appointment today!

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Brand new, energy-efficient home available! Retreat to your luxurious primary suite upstairs with an oversized walk-in closet and dual sinks in the bath. Now selling, Cagan Crossings West offers spacious open-concept townhomes from the mid $300s, on US-27 in Clermont, FL. This desirable location allows residents to be minutes from Clermont's chain of lakes, Downtown Clermont, and Disney World. This community will feature a resort-style pool and cabana as well as a tot lot. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Welcome to “Lakehouse Landing” an income-producing retreat in the sought-after Orange Tree community. Boasting a new roof, a newly resurfaced pool, 5 bedrooms, 4 full bathrooms, this spacious home is designed to deliver unforgettable vacation experiences to guests from all over. This home is situated on a cul-de-sac, and looks out over a conservation area and lake with waterfront views. The well located private pool provides wonderful sunset views over the lake for relaxing evenings and great indoor/outdoor entertaining with all of Florida’s sunshine. The community offers a low yearly HOA and has a tennis court, pickleball court, a 5 acre playing field, soccer pitch and two playgrounds. There is a lake where you can fish, and a beautiful conservation area, making Orange Tree a very desirable place to stay. With a proven record of strong rental income and high occupancy, this turn-key property is a revenue generating investment with bookings scheduled deep into 2027. The property is sold with all the contents. Located just 8 minutes from the Walt Disney World Resort main gates, close to Universal Orlando, SeaWorld, and world-famous International Drive, the property puts guests in the heart of Central Florida’s most popular attractions. Restaurants, outlet shopping, pharmacies, grocery stores, theatres, and entertainment venues are all minutes away. Don’t miss this incredible opportunity to own an established investment property in one of Florida’s most desirable vacation destinations. Schedule your showing today!

Listing is courtesy of: PARK PLACE REALTY ASSOCIATES (407-878-0607)

Listing Agent: Barrett Espinola (407-617-3189)

Remarks: Under Construction. Check out this amazing new single-story Next Gen®! The McCartney features a private suite with its own entrance, living area, kitchenette, bedroom, bathroom and laundry, perfect for multigenerational households. The main home is host to an inviting open-concept layout with easy access to a covered patio for seamless indoor-outdoor living. Two secondary bedrooms are located off the foyer, and a lavish owner’s suite is tucked into a private rear corner, complete with a full bathroom and walk-in closet. Each home comes with Lennar’s Everything’s Included® promise, which includes new appliances as well as quartz countertops, blinds, and more in the price of your home. Wellness Ridge is one of the most modern and anticipated new communities. R19 insulation is used to provide a quiet, comfortable and highly energy efficient home. LP Siding provides durability and impact resistance for your beautiful Florida home. Welcome to Wellness Ridge the community that was designed to provide a Healthy & Active Lifestyle!! Community Features include: Sports Courts, Clubhouse, Fitness Center, Conservation Areas, Playground, Resort Style Swimming Pool and Multi-Use Trails. This beautiful home is very close to Lake Louisa State Park. Clermont is one of the fastest-growing cities in Central Florida. Strategically located close to Orlando and theme parks, it is known for its picturesque hills and pristine lakes. Schedule your appointment today!

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)