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

Remarks: One or more photo(s) has been virtually staged. Looking for a move-in ready 1-bed condo in Orlando near UCF under $200K? This bright first-floor unit offers updated flooring, privacy with no rear neighbors, community amenities, and quick access to major highways, all within the Winter Park High School district. New vinyl plank flooring installed in 2026 enhances the main living areas, while the bedroom features laminated flooring updated in 2022. The A/C was replaced in 2019, adding long term value and comfort. Natural light fills the space, creating an open feel throughout. Assigned parking is included, with visitor spaces nearby for added convenience. Residents enjoy access to a swimming pool, tennis courts, and basketball courts. Located near SR 417, E Colonial Drive, and University Blvd, and minutes from UCF, Valencia College, and Full Sail University. Priced at $175,000, this 1-bed condo in Orlando presents a strong opportunity for buyers seeking location, function, and value in a high demand area. Schedule your showing today.

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-841-0888)

Listing Agent: Nora Rios (407-274-1174)

Remarks: Under contract-accepting backup offers. Charming & Convenient: Your Dream Home Awaits in East Orlando! Discover the perfect blend of comfort and convenience in this charming 3-bedroom, 2-bath single-family home in East Orlando. Featuring a 2-car garage and 1,318 sq ft of living space, this property is an ideal opportunity for families or investors looking for a prime location near top schools, UCF, and major highways. TURNKEY...Recently updated kitchen, bathrooms, interior paint, AC, and Roof.

Listing is courtesy of: MAGIC REALTY LLC (407-588-7177)

Listing Agent: Mike Martin (407-588-7177)

Remarks: Reduced!! Reduced!! Owner says SALE!! Stunning 3/4 Waterfront Acre on Lake Irma–Live in this 4 bedroom 2 bath home or bring your builder and build your new Dream Home. Embrace the ultimate in luxury living with this rare opportunity to own a pristine waterfront lot on the serene shores of Lake Irma in beautiful East Orlando. This exquisite lot offers the perfect canvas to build your custom dream home in a tranquil setting. This lot combines the peaceful ambiance of lakeside living with the convenience of being just minutes away from Winter Park's vibrant restaurants, and top-rated schools, including Trinity Prep School (just a 5-minute drive), 20 minutes to MCO airport, and a short trip to shopping, dining, and entertainment. With direct access to the water, indulge in endless recreational activities such as boating, fishing, kayaking, or simply relaxing by the shore. With approximately 1/4 acre of buildable land and a wide lot, you have ample space to design and build your dream home, lush gardens, outdoor living areas, and more. The possibilities are endless. The lot boasts mature trees, providing privacy. Wake up to the soothing sounds of nature and experience stunning sunsets over the lake each evening. Work with your preferred architect and builder to create a home that perfectly reflects your style and needs. Whether you envision a modern architectural masterpiece or a charming lakeside cottage, this lot can accommodate your vision. Lake Irma is a hidden gem in East Orlando, offering natural beauty with its migratory birds, conservation lands, a private slalom ski course and many newly constructed custom homes. This lake secluded retreat is still close to everything in east Orlando/Winter Park. Don’t miss this extraordinary opportunity to create your own waterfront sanctuary on Lake Irma. Contact us today to schedule a private viewing and start planning the home of your dreams.

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

Listing Agent: Dan Haber (321-624-0966)

Remarks: Welcome to this charming 2-bedroom, 2-bathroom condo nestled in the Union Park area of Orlando, offering comfort, convenience, and access to natural beauty. The home features a spacious kitchen/dinette combo and a versatile living/dining area complete with a built-in wet bar—perfect for entertaining. The primary bedroom boasts a walk-in closet, a makeup vanity with its own sink, and an en-suite bathroom with a relaxing garden tub/shower. The second bedroom enjoys private access to the second full bathroom, which also serves guests through a separate entry from the main living space. Residents of this community enjoy access to fantastic amenities including two tennis courts, a basketball court, a sparkling community pool and spa with restrooms, BBQ grills, and a covered BBQ pavilion. The condo overlooks a tranquil green space that leads down to the scenic Little Econlockhatchee River and the 7.4-mile Little Econ Greenway Trail, offering riverside recreation, wildlife watching, and connections to Jay Blanchard Park. Ideally located just 2 miles from Valencia College East Campus and within 5 miles of both UCF and Full Sail University, this condo offers an unbeatable combination of lifestyle and location.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Frank Baloun (407-488-4969)

Remarks: Under contract-accepting backup offers. Welcome to easy Baldwin Park living! This beautifully maintained 2-bedroom, 2.5-bath townhouse sits in the perfect location—just one block from Enders Park and one block from the Cady Way Trail. Enjoy all the perks of low-maintenance living with your own private screened-in patio and backyard lawn, ideal for morning coffee, weekend lounging, or letting kids and pets play freely. Even better, the two-car garage opens directly to a green space, perfect for tossing a ball with your dog or enjoying a little extra breathing room. Step inside to high ceilings, luxury vinyl plank flooring, and a welcoming foyer/workspace with built-ins. The deep living room flows into the dining area and a bright, BRAND NEW updated kitchen featuring new quartz countertops, a new farmhouse-style deep sink, new kitchen hardware, solid wood cabinets, stainless steel appliances, an eat-in bar, and pantry. A reverse-osmosis drinking-water system and whole-home water softener (installed about a year ago) add extra convenience. A half bath and additional storage closet complete the first floor. Upstairs, you’ll find two spacious primary suites, each with walk-in closets, ceiling fans, and bathrooms with double vanities and shower/tub combos. Laundry is upstairs for ease. Major updates are already done for you, including a new roof, 2024 AC, and 2023 hot water heater. The garage features epoxy flooring, and plantation shutters accent the front-facing windows for a classic Baldwin Park look. The $600/month HOA covers lawn maintenance, roof and exterior maintenance, and access to all Baldwin Park community pools, fitness centers, playgrounds, and clubhouses. If you’ve been searching for a move-in-ready townhome with charm, thoughtful upgrades, green space, and unbeatable walkability—this is the one.

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

Listing Agent: Cara Edwards (407-616-3204)

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: 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)