Homes for Sale Near Winter Park High in Orlando - 114 homes

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. Beautifully remodeled mid-century modern 3-bedroom, 2-bath residence offering 1,403 square feet on a generous 50' x 140' lot. This immaculately maintained this light-filled home features an open split floor plan designed for comfortable everyday living and effortless entertaining. The stylish modern kitchen is appointed with 42-inch white shaker all-plywood cabinetry, brushed nickel hardware, solid dovetail drawers with undermount soft-close glides, soft-close hinges, white quartz countertops, a deep stainless steel sink, Hansgrohe faucet, and stainless-steel appliances. Large windows and new Jeld-Wen insulated low-E vinyl windows throughout enhance the bright and airy feel of the home. The spacious primary suite includes a walk-through closet with built-in storage and leads to a beautifully renovated 11' x 16' ensuite bath featuring a dual-sink white shaker vanity with quartz counters, extensive storage, an oversized 8-foot walk-in shower with high-gloss porcelain tile, modern Kohler fixtures, recessed lighting, and neutral porcelain tile flooring. A door from the primary bath provides direct access to the rear patio and garden. Throughout the home, large plank wood-look porcelain tile creates a cohesive and elegant finish across the living spaces, bedrooms, and hall bath. The secondary bedrooms open through 6-foot sliding glass doors to a generous 9' x 17' patio and share a fully renovated bathroom with a 6-foot walk-in shower finished with marble-look porcelain tile and a penny tile shower floor. Interior and exterior paint (2022) paver driveway, Roof replaced (2021) with aluminum soffits and fascia, Central HVAC system with new ductwork (2022), new electrical panels, new hot water heater, new two-panel interior doors, 4-inch baseboards, new PEX water lines, and new ceiling fans. Outside, An impressive looking shed provides great storage, St. Augustine lawn, 6-foot wood privacy fence, and sprinkler system create a wonderful outdoor setting. The large back covered patio offers plenty of room to relax, play, or entertain family and friends. Located just moments from Baldwin Park Village, residents will enjoy convenient access to shopping, waterfront dining, and some of Central Florida’s most loved destinations, including Downtown Orlando, Winter Park, Audubon Park, East End Market, the Milk and Hourglass Districts, SR 408, I-4, and Orlando International Airport. The Cady Way Trail is just steps away, offering miles of walking, running, and cycling trails. Zoned for highly regarded schools including Baldwin Park Elementary, Glenridge Middle, and Winter Park High. No HOA fees.

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

Listing Agent: Emma Kaplan (407-942-7542)

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: Welcome to the Summerlyn Homesite 12 in Baldwin Park area! This beautifully designed 3-bedroom, 2.5-bath townhome by award-winning David Weekley Homes offers a bright, open-concept layout with expansive windows that fill the home with natural light. The main level features spacious family and dining ideal for everyday living and entertaining. Upstairs, the owner’s retreat provides a private and peaceful space with a generous en-suite bath and additional bedrooms and a versatile loft offer flexible living—perfect for guests, family, or a home office. Located just steps from the desirable Baldwin Park community, residents enjoy access to scenic parks, fitness trails, dining, shopping, and a weekly farmers market—all just steps from your door. Experience quality craftsmanship, energy efficiency, and an unbeatable location.

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

Listing Agent: Robert St. Pierre

Remarks: Under contract-accepting backup offers. WATERFRONT!!Welcome to this beautifully designed 4 bedroom, 3 1/2 bath with office, Baldwin Park home on a corner lot with gorgeous lakeview. Enjoy a morning walk around the lake at your doorstep. New Roof to be installed (2026), New AC to be installed (2026). Prepare to be impressed as you enter from the charming, stone front porch to 2590 SF of bright and inviting space! The open floorplan is perfect for entertaining or spending time with family. The gourmet kitchen is the heart of the home featuring a large center island, granite countertops, stainless steel appliances, 42-inch wood cabinets and pantry. The main living areas boast beautiful wood flooring and a wood burning fireplace. The first-floor flex space is perfect for a den or playroom. Additional office space downstairs. Beautiful wood shutters adorn the windows and crown molding throughout the home !The owners suite's features a luxurious bath features a soaking tub, separate glassed-in shower, dual vanities, and an extra spacious walk-in closet. The upstairs loft offers a versatile space that can serve as a play area or family room. Bedrooms 2 and 3 share a Jack n Jill bath. The laundry room is on this level for added convenience. The owner chose high end finishes when it was built. Entire home is adorned with wood flooring that can be stained to any tone of wood you desire. The spacious garage offers ample room for multiple vehicles while also providing dedicated storage areas to keep your belongings organized. No front or rear neighbors for incredible privacy. This home has a perfect location just steps from the lake and walking distance to enjoy the city center on New Broad Street with restaurants, shopping, banks, pharmacies, and docks to enjoy Lake Baldwin. Baldwin Park offers 3 community pools, clubhouse, playgrounds, 2 workout facilities, bike/walking trails and has easy access to Downtown Orlando, Winter Park, and Orlando International Airport.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: Ingrid Livingston (407-595-5972)

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: Spacious David Weekley Townhome on Corner Homesite in Baldwin Park Area! Located just minutes from premier dining, shopping and entertainment. The beautifully designed Shadyvilla plan offers 3-bedroom, 2.5-bath offers both comfort and convenience. This home features abundant natural light, large windows creating a warm and inviting atmosphere. The main floor boasts stylish laminate flooring, a dedicated study, and an open-concept layout perfect for entertaining. The modern kitchen is outfitted with sleek quartz countertops, full-overlay cabinetry, and plenty of prep and storage space. Upstairs, enjoy a versatile loft area ideal for a media room or play space. Additional highlights include a spacious primary suite, attached two-car garage, and quality craftsmanship throughout. Don’t miss this opportunity to live in the Baldwin Park area.

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

Listing Agent: Robert St. Pierre

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: Under contract-accepting backup offers. Welcome to 4408 Lipton Ct. a beautifully updated single-story home in Orlando’s desirable Watermill community, offering the perfect blend of modern upgrades, functional design, and an unbeatable location. This spacious 4-bedroom, 2-bath residence features UPDATED PLUMBING (2021) and REMODELED BATHROOMS (2021), giving you peace of mind and stylish, move-in-ready comfort. Inside, you’ll love the clean, cohesive feel of WOOD LAMINATE FLOORING throughout, complemented by tile in the kitchen and baths for durability and easy maintenance.The OPEN CONCEPT LIVING & DINING area is enhanced by a VAULTED CEILING, creating a bright and airy atmosphere filled with natural light from large windows and sliding glass doors. The SPLIT BEDROOM FLOOR PLAN provides privacy and flexibility for families, guests, or a home office setup. Situated on a generous .28 ACRE LOT, this property offers ample outdoor space to relax, entertain, or play. A standout feature is the serene WATER VIEW in your backyard, perfect for enjoying peaceful mornings or unwinding at the end of the day. Additional highlights include a VOLUNTARY HOA, giving you added flexibility without sacrificing community benefits. Located in established East Orlando, you’re just minutes from UCF, Valencia College, Waterford Lakes Town Center, parks, shopping, dining, and major roadways, including SR 417 and University Blvd for easy commuting. Plus, the home is zoned for A-RATED WINTER PARK HIGH SCHOOL. Whether you’re a first-time buyer or an investor seeking a prime rental opportunity, this home checks all the boxes. Don’t miss your chance schedule your private tour of Lipton Ct today!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Frank Delesline, Iii (407-480-0157)

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)

Remarks: Under Construction. Don't miss our only Quick-delivery Vero plan with a 3-car Garage! Discover the perfect blend of comfort and functionality in this stunning home, featuring 9'4" first floor ceilings and an open-concept layout designed for modern living. With 4 spacious bedrooms, 2.5 baths, and a 3-car garage on a serene homesite with no rear neighbors, this home offers both privacy and comfort. The large Great Room flows seamlessly to a covered Lanai, ideal for entertaining or relaxing outdoors. Beautiful tile flooring enhances the 1st floor main living areas, while the well-appointed kitchen features 42" upper cabinets with crown molding, sleek quartz countertops, center island, and stainless steel appliances. Versatile Study/Den with French doors provides a perfect home office or quiet retreat. Upstairs, the Bonus Room offers flexible space for a media room or fitness area. The Primary Suite features a private sitting area, and includes a luxurious ensuite bath featuring dual sink vanity, quartz countertops, a walk-in shower, and an expansive closet. Beautifully finished exterior with brick paver driveway and attractive landscaping provides great curb appeal! Zoned for top-rated schools, Harrell Oaks also offers community parks and picnic areas, and is conveniently located near local parks, trails, and lakes, along with easy access to shopping and dining.

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

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

Remarks: Under contract-accepting backup offers. CALLING ALL DEVELOPERS! Welcome to your amazing opportunity to own 9.52 acres of prime real estate, zoned R-1A. This rectangular parcel boasts a prime location with a corner placement, offering secondary access at both Dean Rd and Nonda Lee Rd. Currently, there are two single homes on the property, but the possibilities are endless for developers or for those seeking to create a generational compound. This property offers ample space to let your imagination run wild. The zoning and Future Land Use (FLU) allow for a low-density residential development, making this an ideal location for a single-family home community. Imagine designing your own unique development, with plenty of room for outdoor amenities and green space. Alternatively, take advantage of the current structures and create a family compound with space for multiple homes, a pool, and outdoor recreation areas. The possibilities are endless, and this property provides a blank slate to create the estate of your dreams. Don't miss out on this incredible opportunity to own a piece of prime real estate in a highly desirable location. Contact us today to schedule a showing and discover the endless possibilities this property has to offer.

Listing is courtesy of: MAVREALTY (727-314-3942)

Listing Agent: Robert Kirkwood, Iv (321-297-6489)