Homes for Sale Near Winter Park High in Orlando - 96 homes

Remarks: Under contract-accepting backup offers. Imagine living, working, and earning — all in one beautifully updated space. This rare 3-in-1 live/work property offers the ultimate blend of modern comfort, flexibility, and built-in income potential in the scenic, highly desired community, Baldwin Park. The two-story townhome features 3 bedrooms and 2.5 bathrooms, thoughtfully updated with new luxury vinyl flooring, plush new carpet in all bedrooms, and fresh interior paint throughout. The spacious kitchen is designed for both function and style, showcasing updated cabinetry, new appliances, granite countertops, and a built-in workstation—perfect for today’s work-from-home lifestyle. A convenient half bath on the main level adds everyday ease. Upstairs, the primary suite is a true retreat with dual walk-in closets and a luxuriously remodeled en-suite bath. Two additional generously sized bedrooms each offer French door access to a private balcony, overlooking the charming neighborhood. A full laundry room, abundant storage, and an attached two-car garage complete the townhome’s appeal. Adding to the versatility, the separate, fully updated 1-bedroom, 1-bath apartment is located upstairs at the rear of the building—ideal for generating rental income, hosting guests, or housing extended family. This unit features new cabinetry, appliances, quartz countertops, double vanities, custom mirror, new fixtures throughout, custom walk-in closet and includes one assigned parking space. The third component is a street-accessible commercial unit with two large offices, a spacious storage room, and a half bath, accessible from both the courtyard and directly from the sidewalk. Perfect for a boutique, professional office, or service-based business, this space offers excellent visibility among the established businesses lining Lake Baldwin Lane—creating yet another income-producing opportunity. Recent upgrades provide peace of mind, including new A/C units installed in 2024. New roof installed December 2025, new exterior paint completed by HOA in 2024. Association also maintains the courtyard and landscaping, allowing you to enjoy a low-maintenance lifestyle while maximizing flexibility and earning potential. Baldwin Park isn’t just a place to live — it’s a way of life. Step outside your door and enjoy a vibrant town center filled with shops, restaurants, and everyday conveniences, all set against a beautifully walkable community. Scenic trails wind throughout the neighborhood, including a stunning 2.5-mile path along Lake Baldwin, perfect for morning jogs or evening strolls. Pet lovers will appreciate the nearby dog park with lake access, giving your furry friends space to play and cool off. Residents also enjoy an exceptional array of amenities, including multiple parks and playgrounds, three community pools, and fully equipped fitness centers, all conveniently located within the neighborhood. Whether you’re looking to live stylishly, run a business steps from home, or invest in multiple income streams, this exceptional property delivers a lifestyle that truly works for you. Don't miss this opportunity! Schedule your private showing today!

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

Listing Agent: Martina Leonard (321-202-3608)

Remarks: Under contract-accepting backup offers. Imagine living, working, and earning — all in one beautifully updated space. This rare 3-in-1 live/work property offers the ultimate blend of modern comfort, flexibility, and built-in income potential in the scenic, highly desired community, Baldwin Park. The two-story townhome features 3 bedrooms and 2.5 bathrooms, thoughtfully updated with new luxury vinyl flooring, plush new carpet in all bedrooms, and fresh interior paint throughout. The spacious kitchen is designed for both function and style, showcasing updated cabinetry, new appliances, granite countertops, and a built-in workstation—perfect for today’s work-from-home lifestyle. A convenient half bath on the main level adds everyday ease. Upstairs, the primary suite is a true retreat with dual walk-in closets and a luxuriously remodeled en-suite bath. Two additional generously sized bedrooms each offer French door access to a private balcony, overlooking the charming neighborhood. A full laundry room, abundant storage, and an attached two-car garage complete the townhome’s appeal. Adding to the versatility, the separate, fully updated 1-bedroom, 1-bath apartment is located upstairs at the rear of the building—ideal for generating rental income, hosting guests, or housing extended family. This unit features new cabinetry, appliances, quartz countertops, double vanities, custom mirror, new fixtures throughout, custom walk-in closet and includes one assigned parking space. The third component is a street-accessible commercial unit with two large offices, a spacious storage room, and a half bath, accessible from both the courtyard and directly from the sidewalk. Perfect for a boutique, professional office, or service-based business, this space offers excellent visibility among the established businesses lining Lake Baldwin Lane—creating yet another income-producing opportunity. Recent upgrades provide peace of mind, including new A/C units installed in 2024. New roof installed December 2025, new exterior paint completed by HOA in 2024. Association also maintains the courtyard and landscaping, allowing you to enjoy a low-maintenance lifestyle while maximizing flexibility and earning potential. Baldwin Park isn’t just a place to live — it’s a way of life. Step outside your door and enjoy a vibrant town center filled with shops, restaurants, and everyday conveniences, all set against a beautifully walkable community. Scenic trails wind throughout the neighborhood, including a stunning 2.5-mile path along Lake Baldwin, perfect for morning jogs or evening strolls. Pet lovers will appreciate the nearby dog park with lake access, giving your furry friends space to play and cool off. Residents also enjoy an exceptional array of amenities, including multiple parks and playgrounds, three community pools, and fully equipped fitness centers, all conveniently located within the neighborhood. Whether you’re looking to live stylishly, run a business steps from home, or invest in multiple income streams, this exceptional property delivers a lifestyle that truly works for you. Don't miss this opportunity! Schedule your private showing today!

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

Listing Agent: Martina Leonard (321-202-3608)

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: Don’t miss this exceptional opportunity to build your dream home on a high-value lot in a prime location. Ideally situated just minutes from Harry P. Leu Gardens and all that Corrine Drive has to offer—including popular dining, boutique shopping, and everyday conveniences. Zoned for highly sought-after schools, including Audubon Park School (K-8) and Winter Park High School. A rare chance to create a custom residence in one of the area’s most desirable neighborhoods. Secure your future homesite today.

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

Listing Agent: Nicole Howell (321-217-7918)

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: Spacious 4-Bedroom Home with Major Upgrades Already Completed! Welcome to 8129 Esperanza St in Orlando—an excellent opportunity for a homeowner looking to personalize a property while benefiting from major recent improvements. This 4-bedroom home offers a functional layout with great potential to create your ideal living space. Important upgrades have already been completed for peace of mind, including a NEW ROOF (2024), updated plumbing , and energy-efficient DOUBLE-PANE WINDOWS, A/C and Water Heater that help keep the home comfortable year-round. Additional features such as attic aluminum barrier insulation further enhance energy efficiency and reduce utility costs and solar roof/attic fan. Additional value high ticket items!! Enclosed sun room and newly installed gutters with warranty! The home also includes an enclosed patio and a detached shed, providing extra space for storage, hobbies, or future customization and small pond for relaxation. While the interior offers an opportunity for updates, this allows the next owner to design their kitchen and bathrooms to their exact taste and style—without the worry of major system expenses. Conveniently located near shopping, dining, major highways, and everything Orlando has to offer. Close to University of Central Florida, Full Sail, 417 Hwy, businesses, hospitals, restaurants and shopping. Priced at $265,000—an excellent value for a 4-bedroom home with key upgrades already in place. Don’t miss the chance to make it your own today!

Listing is courtesy of: REALTY LYNK INC (407-494-0803)

Listing Agent: Denise San Miguel (407-443-2070)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully refreshed home located in the desirable Bradford Cove community of East Orlando. Featuring new flooring throughout and tasteful updates to the kitchen, this home offers the perfect blend of comfort, style, and convenience. Step inside to a bright and inviting floor plan filled with natural light and spacious living areas designed for both relaxing and entertaining. The updated kitchen provides a fresh, modern feel while still offering plenty of functionality for everyday living. The home sits in a quiet, established neighborhood known for its charm and convenient location. Bradford Cove residents enjoy a peaceful residential setting while being just minutes from UCF, Winter Park, major highways, shopping, dining, and everyday conveniences. Outside, you'll find a private yard perfect for entertaining, relaxing evenings, or weekend gatherings. Whether you're a first-time buyer, growing household, or someone looking for a move-in ready home in a fantastic location, this property checks all the boxes. Homes in this area do not stay on the market long — schedule your private showing today and come see why buyers love Bradford Cove!

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: Under contract-accepting backup offers. MULTIPLE OFFERS! HIGHEST AND BEST BY FRIDAY 9PM. Ready to Move In! This beautiful home is situated on an extra large fenced lot. Roof 2023 * Ac 2023 * Water Heater 2024 * Interior Features include Eat In Kitchen with Closet Pantry, Stainless Appliances and Beautiful Artistic Lighting * Private Office with Extra Lighting * Large Open Floorplan Living Space and Split Bedroom Plan. Outdoor features include 27 x 10 Screened Patio, Work Shed, 2 Trailor Gates & Parking for riding lawn mover.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Gayle Stanley (407-579-3583)

Remarks: Space, privacy, and a pool — all on over a quarter acre in a quiet Orlando neighborhood. This 3 bedroom, 2 bathroom pool home offers the kind of room to breathe that’s becoming harder to find, with a layout that feels open, comfortable, and naturally connected to the outdoors. Inside, the main living area centers around the fireplace and flows easily into the dining space and kitchen, creating a layout that works just as well for everyday living as it does for gathering with friends. The kitchen is well-equipped with updated appliances, generous counter space, and thoughtful details like a pot filler and bottle rinser, making it practical for daily life while still feeling elevated. One of the standout features of the home is the massive screened-in back porch, a space that truly extends the living area. With room for dining, lounging, and entertaining, it’s the kind of porch that quickly becomes everyone’s favorite place to spend time. Beyond it, the private backyard opens up to the pool and expansive yard, offering plenty of green space, room to spread out, and the flexibility to create your own outdoor retreat. Major improvements have already been taken care of, including a brand new roof (2025), whole house repipe (2024), new high-wind rated windows and sliding doors (2021), hybrid water heater, and a fully updated pool system, giving the next owner peace of mind on the big-ticket items. With a large lot, a pool, and substantial upgrades already completed, this is the kind of property that rarely comes along — comfortable today, with space and potential for whatever comes next.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Shawn Layton (321-514-8055)

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 beautifully upgraded 2-bedroom, 2-bath condo in the desirable community of Baldwin Park. This rare first-floor unit offers the perfect blend of comfort, convenience, and accessibility—with true handicap access and no stairs to navigate. Step inside to discover a thoughtfully designed open floor plan featuring modern upgrades throughout. The spacious living and dining areas flow seamlessly, creating an inviting space ideal for both relaxing and entertaining. The updated kitchen features quality finishes, ample cabinetry, and sleek countertops that will impress. Both bedrooms are generously sized, with the primary suite offering a private en-suite bath and plenty of closet space. The second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Enjoy the ease of first floor living with direct access and added privacy—perfect for those seeking convenience without compromising style. Located just moments from Baldwin Park’s vibrant village center, you’ll have easy access to dining, shopping, parks, and scenic walking trails. This is a rare opportunity to own a move-in-ready, accessible 1st floor unit in one of Orlando’s most desirable communities—don’t miss it!

Listing is courtesy of: PARKSIDE PROPERTIES, LLC (407-376-6635)

Listing Agent: Kevin Spencer Pa (407-383-4827)

Remarks: Location, location, location! move-in ready, low-maintenance single-family home ideally located in Baldwin Cove near the Cady Way Trail. Built in 2014, this 4-bedroom residence offers over 2,000 square feet of living space with numerous upgrades. The bright first floor features 10-foot ceilings, brand-new tile flooring, and an open layout perfect for entertaining. The dining room includes built-ins, and the kitchen is equipped with Samsung Signature Collection stainless steel appliances. Enjoy relaxing on the spacious front patio with corner views of Lake Susannah. Upstairs, the primary suite offers partial lake views, a large walk-in closet, and a spa-style ensuite bathroom. A versatile loft provides flexible space for a home office, playroom, or second living area. The second-floor laundry room includes an LG Elite washer and dryer. Three additional bedrooms share a full bathroom with double sinks. Additional features include a two-car garage, low HOA, and no CDD. Conveniently located near Publix, downtown Baldwin Park, downtown Orlando, and Orlando International Airport. Zoned for top-rated schools: Baldwin Park Elementary, Glenridge Middle School, and Winter Park High School. Schedule your showing today! The listing agent is related to the seller.

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

Listing Agent: Toni Dolphin (407-919-9488)

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)

Remarks: LAKE VIEW!!! AT THE LUXURIOUS, AND TALLEST HIGH RISE COMMUNITY IN THE CITY BEAUTIFUL IS at THE VUE reaching 35 Floors. A few features included in this condo are: Secure/Private Parking Spot, Floor to Ceiling Sliding Glass Doors, Gourmet Kitchen with Gas Stove, Granite Counter Tops, Large Breakfast Bar and Dark Wooden Cabinets. New Carpet has been installed in Both Bedrooms, Newly Painted Walls and the Convenience of an in-home Converted Washer/Dryer System! The Master Bedroom has two Walk in Closets. The En-suite Bathroom features Double Sinks, a Separate Tub and Both Master/Guest Showers have been Upgraded with Frame less Glass Doors! The Guest Bedroom has Upgraded Custom Cabinets that can be used as an Extra Closet or Office Space! Acoustically Engineered Concrete Walls and Sealed Doors which Minimize Sound Transfers Between Units. Amenities include: Lavish Lobby staffed with 24/Hr Security, Concierge, Valet parking, Jr. Olympic size Pool, Multi-million Dollar Health Club, Tennis/Basketball Court, Private Media Room, Dog Walk and the Club Vue Lounge which is exclusively for Residents and Their Guests. There is also Resident only Bio metric Fingerprint Access which will ensure a SAFE and Private Environment. Do not miss your Opportunity to enjoy the 4th of July Lake Eola Fireworks from your Balcony!

Listing is courtesy of: JUPITER PROPERTIES, INC (386-547-6161)

Listing Agent: Marya Baqri (407-529-7200)