Homes for Sale Near Winter Park High in Orlando - 104 homes

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)