Homes for Sale Near Winter Park High in Orlando - 111 homes

Remarks: TIMELESS ELEGANCE MEETS MODERN LUXURY, a newly renovated masterpiece nestled in one of Orlando's most coveted neighborhoods - Baldwin Park. This elegant home harmonizes timeless architectural beauty with the finest modern upgrades, offering the perfect blend of sophistication and comfort. Upon entry, you’ll be greeted by an open-concept layout bathed in natural light, accentuated by custom finishes, extensive millwork and premium fixtures throughout. Enjoy the formal dining room featuring an illuminated, glass-enclosed, 96 bottle cable wine rack that’ll make any wine enthusiast fall in love. The chef-inspired kitchen is a true showstopper, featuring top-of-the-line appliances like a Viking 6 burner gas range and a Sub Zero refrigerator, custom cabinetry, and an oversized quartz island that is perfect for both cooking and entertaining. Look out the French doors on to the captivating backyard where you’ll find a pool w/ a spill over spa and sun shelf, a paved pool deck and manicured landscaping. Adjacent to the kitchen, the spacious living areas flow seamlessly, creating an inviting space for gatherings. Tucked away from the family room you’ll find the laundry room and walk out to the three car garage. Retreat to the primary bedroom, where your comfort is paramount. The primary bath includes a generous walk in closet, a glass-enclosed rain shower, dual vanities, and premium finishes that evoke a sense of tranquility. Travel up the curved staircase that features exquisite wall paneling to the left, an iron stair rail to the right and a stunning chandelier overhead. Upstairs you’ll find three bedrooms, two full baths, and a spacious flex room. This exquisite home is not only about style and luxury, it’s about location. You’re just steps away from the dynamic Baldwin Park, a community known for its tree-lined streets, eclectic shops, upscale dining, and recreational parks. With its prime position, you can enjoy all the conveniences and culture Baldwin Park offers, while being only minutes from downtown Orlando, Winter Park, and major highways for easy access to all of Central Florida. 3D Tour was done prior to painting, still photos show current paint. Schedule your private tour today!

Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)

Listing Agent: Daniel Sposato (407-721-0630)

Remarks: Under Construction. Welcome to The Lorinda by David Weekley Homes, a refined two-story residence balanced at ~3,465 sq ft with 5 bedrooms, 4 full baths, and a spacious 3-car garage. The first floor unfolds with a gracious foyer leading into a refined open-concept great room and dining space flanked by a gourmet kitchen with a center island that's made for gathering. A flexible guest suite or study and a well-appointed powder room round out this level. Upstairs lies the serene main suite, likely featuring elevated design touches and generous closets. Accompanying it are three additional bedrooms, each with easy access to full baths—perfect for families or entertaining overnight guests. With a thoughtful layout, upscale appointments, and room for both everyday life and special occasions, The Lorinda effortlessly blends elegance and practicality. Contact the David Weekley Homes at Downtown Orlando Team to learn about the industry-leading warranty included with this new construction home in Orlando, FL!

Listing is courtesy of: WEEKLEY HOMES REALTY COMPANY (866-493-3553)

Listing Agent: Robert St. Pierre

Remarks: Under contract-accepting backup offers. Ideally positioned in the heart of Baldwin Park’s Village Center, just moments from its vibrant downtown core, this beautifully updated 4-story townhome perfectly blends modern style with everyday convenience. This unique townhome includes the ONLY ROOFTOP TERRACE on the block...what a special added bonus! In the past year, over $65,000 in high-impact updates have transformed this unit for elevated, turnkey living. Enjoy beautiful NEW hardwood floors and wooden stair treads, a NEW 4-zone HVAC system, a NEW hot water heater, a NEW refrigerator, fresh NEW paint, NEW updated lighting and fans throughout! Other improvements include all NEW white cordless blinds on the windows and exterior doors, NEW carpet in the bedrooms, and the HOA recently installed a NEW roof! This 4-Story floorplan is one of the larger townhome styles in the community, with 2300+ SF, 3 bedrooms, each with a private en-suite bath, a front covered porch, and a versatile 4th-floor bonus room/den with a ½ bathroom and don't forget the private roof top terrace. The 1st floor features a private guest suite complete with a full en-suite bath and walk-in closet, ideal for visitors, a home office, or multigenerational living. The main living area sits on the 2nd level, thoughtfully designed for both entertaining and daily comfort with an open-concept layout that connects the living and dining areas to a refreshed kitchen with a clean, modern aesthetic. Off the living room, a front-facing balcony provides a charming outdoor extension of the second level. On the 3rd floor you’ll find the sunny Primary Suite with a stunning renovated en-suite bath, featuring a large walk-in shower, a separate sleek soaking tub, and a large linen closet. The 3rd floor is complete with the laundry area and the 3rd bedroom suite. The 4th floor provides exceptional flexibility, functioning as a media room, secondary living area, or a 4th bedroom with a ½ bathroom. The rooftop terrace offers a rare outdoor retreat, perfect for morning coffee watching the sunrise, or relaxed evenings under the skyline. A rear-entry 2-car garage adds convenience, while ample guest parking is available both in front of the home and nearby. Residents of Baldwin Park enjoy an unmatched lifestyle with access to multiple community pools, fitness centers, scenic walking and biking trails, parks, playgrounds, and the picturesque Lake Baldwin. Just a short distance to popular restaurants, boutique shops, grocery options, and everyday conveniences, this highly sought-after neighborhood also offers access to top-rated schools—all just minutes from Winter Park and Downtown Orlando. This is an exceptional opportunity to enjoy refined, low-maintenance living in one of Central Florida’s most desirable communities—where thoughtful updates, flexible living spaces, and an unbeatable location come together effortlessly.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Marystuart Day (407-620-8683)

Remarks: Under contract-accepting backup offers. Positioned on one of Baldwin Park’s desired streets, this impressive estate delivers over 4,000 square feet of intentional design, elevated finishes and undeniable presence. Inside, sophistication reigns with four oversized bedrooms, 3.5 designer baths, a private executive office, bonus loft, and a two-car oversized garage built for collectors and convenience alike. From moment you arrive, the home impresses with beautiful curb appeal, highlighted by a welcoming, expansive front porch and multiple private outdoor spaces to relax and unwind. The first floor offers a formal dining room, formal living room, private office, primary suite, family room, kitchen and a spacious laundry room with ample storage. The heart of the home is a well-equipped kitchen with custom cabinetry, a large center island, pantry, oven with warming drawer, and a butler’s coffee/wine bar that flows into an ornate formal dining room, ideal for entertaining. The kitchen opens seamlessly to the inviting family room and overlooks two enchanting Parisian-inspired courtyards with fountains, creating a private outdoor retreat ideal for gatherings. The first-floor primary suite is a luxurious sanctuary with a Jacuzzi tub, separate shower, dual vanities and a custom walk-in closet. Upstairs features three additional bedrooms, two full baths, including a Jack-and-Jill, and a spacious bonus loft, offering comfort and flexibility. Two main air conditioner units (2025, 2026), a water heater (2018) and a recently installed roof (2021). Go outside and you’re moments from Baldwin Park’s Village Center, top-rated schools, boutique shopping, chef-driven dining, resort-style pools, elite fitness centers, scenic lakes and iconic Cady Way Trail. Golf cart to dinner. This is Baldwin Park at its absolute finest!

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Jj Mackle (321-217-9553)

Remarks: Under contract-accepting backup offers. Introducing an exquisite Lexeer residence, now offered with a refined pricing approach designed to provide buyers with enhanced flexibility and optional turnkey living. Spanning approximately 3,500 square feet, this two-story home showcases transitional elegance with 5 bedrooms and 5.5 bathrooms, thoughtfully designed for both everyday comfort and elevated entertaining. A resort-style pool and outdoor kitchen create a seamless indoor-outdoor lifestyle ideal for year-round Florida living. Inside, the open-concept floor plan unfolds with intention, where abundant natural light and refined textures create an atmosphere of calm sophistication. The main living areas flow effortlessly into a chef’s kitchen featuring Thermador appliances, a spacious walk-in pantry, wine bar, and a durable designer composite scratch-resistant sink with a Signature brushed gold faucet. Stunning Calacatta Laza Oro countertops highlight the oversized waterfall island, while a dropped ceiling with integrated LED lighting, designer fixtures, and subtle metallic accents elevate the home’s curated aesthetic. The first-floor primary suite serves as a private retreat, offering elegant finishes and direct access to the backyard oasis. The spa-inspired bathroom features Calacatta Laza Oro countertops, marble shower flooring, and an expansive double shower with dual showerheads and hand-held fixtures in a refined brushed gold finish. An oversized soaking tub anchors the space, while an expansive walk-in closet with custom built-ins, integrated lighting, and glass display elements provides a luxurious setting to showcase your wardrobe and accessories. Upstairs, an oversized loft offers flexible space ideal for a media room, secondary lounge, or study. Four generously sized en-suite bedrooms each include walk-in closets with built-ins. The second level also features a full laundry room with Samsung front-load washer and dryer, along with a large storage area complete with custom shelving. Outdoor living is equally intentional. Sliding glass doors open to a covered lanai with a summer kitchen, overlooking a resort-style pool and marble paver patio, creating a refined outdoor setting designed for both relaxation and entertaining. For those seeking a fully turnkey experience, a designer furniture package curated by Max Home Designs is available separately, featuring custom-selected pieces, elegant ceiling-to-floor linen drapery, and a 77inch LG Smart TV. Located within the highly desirable Audubon & Winter Park School District, 2415 Laura Street presents a rare opportunity to own a meticulously crafted new construction home where elegance, functionality, and timeless design exist in perfect balance. Seller is open to creative structuring, including potential financing incentives that may enhance overall affordability.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Leighton Hope (407-619-7897)

Remarks: Under contract-accepting backup offers. Welcome home to this charming, first floor, corner-unit condo in the heart of Baldwin Park! This impressive home features an oversized wrap around patio, an attached one car garage and has been fully updated throughout! Move in stress-free with a New HVAC (2022), New Paint (2022), all New Luxury Vinyl Plank Flooring throughout (2022), Brand new Refrigerator, Microwave, Range (2024), New Disposal (2026), New Washer & Dryer (2023 Stackable HE Samsung), New Garage Door Motor (2024), and all New Ceiling Fans inside + out (2023). When entering the condo, you’re welcomed by a spacious open floor plan, bright natural light and a living/dining room combo that is perfect for entertaining. The newly updated kitchen was made more spacious by opening up a half wall and features brand new appliances throughout, granite countertops, a pantry and plenty of cabinet storage! A unique feature of this home is having not only an indoor laundry room with a brand new stackable unit, but also direct garage access! This split floor plan home features 3 bedrooms and 2 bathrooms. The owners suite is extremely spacious, has its own private patio, a custom walk-in closet and an ensuite bath with a double vanity and glass enclosed shower. The other bedroom near the owners suite features a large closet with plenty of storage. The 3rd bedroom has a custom built in desk area located in the closet making it a great bedroom or office/flex space. This gorgeous condo is located in the middle of everything Baldwin Park has to offer! Live just minutes to Downtown Baldwin, Blue Jacket Park, Audubon Park, Winter Park and so much more. Zoned in the highly desirable, Baldwin Park Elementary, Glenridge Middle & Winter Park High school districts. The HOA includes access to the beautiful pool, fitness center and countless parks all walking distance from the condo. Don’t miss out on your chance to own this turn-key condo with stunning natural light, spacious outdoor patios, updated finishes, all new major systems, an open floor plan, ample amounts of storage, all walking distance to the best of Baldwin Park. Schedule your tour today!

Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)

Listing Agent: Lindsey Hahn (847-951-1933)

Remarks: Bright, stylish, and move-in ready, this first-floor 2-bedroom, 2-bath condo in the sought-after Colonial Landings community was completely remodeled in 2022 and is ready for immediate enjoyment. Modern luxury vinyl flooring runs throughout, creating a cohesive, low-maintenance living space. The spacious primary bedroom features a walk-in closet, a dedicated makeup vanity with its own sink, and an en-suite bath with a relaxing garden tub/shower. The second bedroom has private access to the second full bath, which also opens to the main living area for guest use, offering a smart and flexible layout. The bright, oversized family room provides an open, airy feel with plenty of room for both living and dining. The kitchen and dinette area include a convenient in-unit laundry closet, adding everyday practicality. This well-designed floor plan maximizes comfort, privacy, and functionality. The condo includes one assigned primary parking space plus ample guest parking. The unit overlooks the community tennis courts and pool, giving you a resort-style atmosphere right outside your door. Colonial Landings residents enjoy a range of amenities, including two tennis courts, a basketball court, a sparkling community pool and spa with restrooms, BBQ grills, and a covered BBQ pavilion. The community's central Orlando location offers easy access to major roadways, shopping, dining, entertainment, employment centers, public transportation, and area attractions. This condo is conveniently located near the University of Central Florida (UCF), Valencia College, and Full Sail University, making it an excellent option for owners or investors seeking proximity to major campuses. Downtown Orlando and Orlando International Airport are within a reasonable drive, and nearby Little Econ Greenway provides miles of walking trails, riverside recreation, picnicking, and wildlife viewing for those who enjoy the outdoors. With its recent remodel, modern finishes, strong amenity package, and prime Orlando location, this updated first-floor condo in Colonial Landings offers an outstanding opportunity for comfortable living or a solid addition to an investment portfolio.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Angela Carney (407-760-9822)

Remarks: Under contract-accepting backup offers. TIMELESS MEDITERRANEAN TWO-STORY home with PRIMARY BEDROOM ON FIRST FLOOR. Come see this 3-bedroom, 2.5 bath home situated in phase one of Baldwin Park on quiet Trapp Ln. Warm details flow throughout, from the wrought iron entry to the Spanish Mission courtyard with a wood burning fireplace. The 2386 sq. ft. layout offers a formal living room, dining room, office nook and a downstairs primary suite with an updated bath and roomy walk in closet. Features include wood floors in the entire home, granite counters, upgraded cabinets, stainless steel appliances and shutters throughout. A coffee bar links the kitchen and dining room, and the private courtyard creates a quiet hideaway for relaxing or hosting. The oversized 3 car garage adds generous storage. Just steps from the Fox Mews, Enders Park and Village Center favorites including restaurants, shops and daily conveniences. Quick access to nearby districts, parks, airports and well known golf courses.

Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)

Listing Agent: Brian Cirillo (321-231-1068)

Remarks: Welcome to a home that blends timeless character, warmth, and opportunity in one of Orlando’s most charming and centrally located neighborhoods. Nestled on an expansive oversized lot in the desirable Colonial town/Tinker Heights corridor, this beautifully positioned residence offers the rare combination of space, privacy, and city convenience. From the moment you arrive, you’ll feel the potential and serenity this property offers. Mature trees, generous outdoor space, and a welcoming presence set the tone for a lifestyle of comfort and connection. Inside, natural light fills the living spaces, creating an inviting atmosphere perfect for both everyday living and memorable gatherings with family and friends. This residence offers the flexibility to enjoy as-is or transform into your personal sanctuary. Whether you envision a modern luxury renovation, an outdoor oasis with a custom pool, or a peaceful retreat just minutes from the vibrant energy of downtown Orlando, this property provides the perfect canvas. Located just moments from Baldwin Park, Lake Highland, the Milk District, and Downtown Orlando, you’ll enjoy effortless access to fine dining, boutique shopping, parks, lakes, and top schools — all while tucked into a quiet, established neighborhood that continues to appreciate in value.This is more than a home — it’s an opportunity to create your lifestyle in one of Central Florida’s most sought-after locations.**Seller is motivated and willing to assist with buyer closing costs**, making this an exceptional opportunity for homeowners seeking value, flexibility, and long-term upside in a premier Orlando location. Come experience the charm, space, and possibilities of 4201 Park Lake Street — where your next chapter begins.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Rey Zapata (407-288-7384)

Remarks: Under contract-accepting backup offers. Pristine, model perfect, and absolutely move-in ready, this stunning three-bedroom, two-full and one-half-bath home is the opportunity buyers have been waiting for in one of the sought-after locations in Baldwin Park and Orlando! From the moment you go inside, high coffered ceilings, extensive crown molding and baseboards, and graceful archways create a refined yet welcoming atmosphere. The bright, open concept floor plan is filled with natural light and designed for effortless living and entertaining. The inviting foyer leads to a spacious family room that flows seamlessly into a beautifully appointed kitchen featuring a large island, walk-in pantry and abundant cabinetry, ideal for gatherings with family and friends. The oversized private primary suite is a retreat, featuring a spa-inspired bath with a soaking tub, spacious walk-in shower, dual vanities, two walk-in closets and a separate water closet. A generous separate dining room, two guest bedrooms, a laundry room complete with washer, dryer and sink, a convenient powder bath and a two-car garage, provide comfort and functionality. Double-pane windows and blinds throughout enhance energy efficiency and comfort. Go outside to your covered, paved patio that opens into the expansive, beautifully finished paved backyard, ideal for entertaining or simply relaxing in your own private oasis. Zoned for incredible schools and just near the scenic Cady Way Trail, as well as minutes to Baldwin Park’s charming restaurants, shops including Publix, and lakes, with easy access to Winter Park, downtown Orlando, Orlando International Airport, and major highways, this home delivers the ultimate blend of elegance, location and lifestyle. Schedule your private showing today and be ready to fall in love!

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Jo Ann Lamar (321-231-0052)

Remarks: Welcome to 2018 Brink Aly, a move in ready 3-bedroom, 3.5-bath City Home in the heart of Baldwin Park. A charming, tree-lined walkway leads you to this inviting Charleston-style residence. The main living level is thoughtfully designed for everyday comfort and entertaining, featuring hardwood floors throughout the kitchen, dining, and living areas, along with a convenient half bath. The kitchen offers a quartz island, rich dark cabinetry, stainless steel appliances, and a built-in desk area for added functionality. Just off the kitchen, enjoy a private second-floor porch—perfect for grilling or relaxing outdoors. Upstairs, the third floor includes the spacious primary suite, a secondary bedroom, and a laundry area. The first floor features a private guest suite complete with a full bath and walk-in closet. An attached two-car garage provides ample storage. Recent upgrades provide peace of mind, including a brand new water heater, new AC system, and fresh interior paint, making this home truly move-in ready. Ideally located just steps from the Grace Hopper heated Olympic-sized pool, fitness center, and community room, and only two blocks from Baldwin Park’s Village Center with Publix, CVS, dining, and entertainment. You’re also just one block from Blue Jacket Park and a short walk to Lake Baldwin Park with its popular dog park and scenic walking trail. Don’t miss this opportunity to own in one of Orlando’s most sought-after communities!

Listing is courtesy of: AFFINITY REALTY LLC (407-706-6961)

Listing Agent: Matthew Fong (321-274-3287)