Homes for Sale Near Winter Park High in Orlando - 108 homes

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Pristine New Construction Home Just Minutes from Lake Baldwin & Downtown Orlando – Modern Living in a Prime Location. Welcome to this beautifully crafted new construction home offering the perfect blend of modern design, comfort, and location in one of Orlando’s most desirable pockets. Positioned just minutes from both nature and the city, this home delivers a lifestyle that’s hard to match. Just a short 15-minute walk or quick 2-minute drive to LAKE BALDWIN, where you can start your mornings with SCENIC WALKS, WATERFRONT VIEWS, or OUTDOOR WORKOUTS. Also just minutes from DOWNTOWN ORLANDO, giving you easy access to top dining, nightlife, and entertainment while still enjoying a more relaxed residential setting. Commuting is effortless with quick access to major roadways including State Road 408, State Road 417, Interstate 4, and East Colonial Drive—making it easy to navigate all of Central Florida. Built with quality and efficiency in mind, this home offers modern construction standards, energy-efficient features, and low-maintenance living—ideal for today’s buyer looking for both style and long-term value. A rare opportunity to own a pristine brand-new home in a prime location where lifestyle, convenience, and quality come together. One of the standout features is the generous lot size, providing ample space and flexibility to build an ADU or a comfortable mother-in-law suite in the backyard. Schedule your showing today.

Listing is courtesy of: FHG REALTY, LLC (407-505-7600)

Listing Agent: Kimberly Adams (407-460-1121)

Remarks: Step inside this beautifully renovated three-bedroom, two-bath home full of charm and character, perfectly situated (between Baldwin Park and Winter Park) near downtown Orlando, Florida. Every detail has been thoughtfully updated from the brand-new roof to the stylish kitchen featuring sleek quartz countertops and modern appliances. Enjoy fully renovated bathrooms, high-quality laminate flooring throughout, elegant six-inch baseboards, updated trim, contemporary light fixtures, and freshly painted interiors that create a bright, welcoming feel. New exterior doors add the perfect finishing touch. Ideally located just minutes from popular restaurants, shopping destinations, and major highways, this home offers both comfort and convenience. Whether you're starting a family, downsizing, or ready to own your first home, this inviting property is ready to welcome you.

Listing is courtesy of: INI REALTY (904-394-7125)

Listing Agent: Kp Paul (813-817-2695)

Remarks: ** PRICE IMPROVEMENT ** Come and see this beautifully maintained home in the Arbor Ridge community! Situated on nearly a quarter-acre lot, this property offers the perfect blend of comfort, space, and peace of mind with major updates already completed: Roof (2021), Plumbing (2024), HVAC (2017), Windows (2016), and Water Heater (2026). Step outside to enjoy a fully fenced backyard—ideal for pets, play, or entertaining—complete with a well-fed irrigation system to keep your landscaping lush year-round. Inside and out, pride of ownership shines throughout. Arbor Ridge is known for its well-kept surroundings, mature landscaping, and generously sized homesites, providing a welcoming neighborhood feel while still offering room to breathe. This is a rare opportunity to own a lovingly cared-for home in a sought-after community near UCF, Valencia College, and Full Sail University—schedule your showing today!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Alondra Mcintosh (407-716-1505)

Remarks: Beautifully updated and move-in ready Baldwin Park townhome ideally situated just steps from highly desirable Enders Park and its outstanding community amenities. One of the nicest updated homes to hit the market in some time, this residence showcases thoughtful renovations, timeless design choices, and a fantastic floor plan with spacious living areas and a bright, open feel throughout. The flexible front living space functions perfectly as a sitting room, home office, or additional entertaining area, while the expansive rear family room is flooded with natural light and features custom built-ins and easy access to the private courtyard, creating a seamless indoor/outdoor living experience. The beautifully renovated kitchen opens directly to the family room and offers excellent functionality, generous storage, newer appliances, and a clean, updated aesthetic. Upstairs, the spacious primary suite features a beautifully renovated bathroom, while the secondary bedrooms are comfortably sized and share an equally well-updated guest bath. The home’s renovations and design selections feel cohesive, elevated, and exceptionally well executed throughout. Additional highlights include detached garage parking with an additional dedicated parking space, NEW ROOF (2024), NEW WATER HEATER (2026), newer A/C, updated fixtures throughout, and a beautiful private courtyard with walkway. One of the standout features of this home is its exceptional location within Baldwin Park - just moments from Enders Park with its community pool, kiddie pool, clubhouse, fitness center, and playground. Baldwin Park remains one of Orlando’s most sought-after communities with picturesque lakes, walking and biking trails, excellent schools, restaurants, shopping, and vibrant neighborhood amenities throughout. Zoned for a highly desirable Baldwin Park/Winter Park school district, this is an exceptional opportunity to own one of Baldwin Park’s most best townhomes in a premier location within the community.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Robert Kurzreiter Pa (407-476-4156)

Remarks: Charming 3-Bedroom, 2-Bathroom Home in a Peaceful Cul-de-Sac Roof from 2023, A/C is 4 years old- Water heater is 2024, New windows 2024 Nestled in a quiet cul-de-sac, this lovely 3-bedroom, 2-bathroom home offers a perfect blend of comfort and convenience. Recently updated with fresh exterior paint, the property boasts a well-maintained interior and a welcoming atmosphere. Located in a highly desirable neighborhood in Orlando, you'll enjoy easy access to popular shopping centers, dining options, and recreational areas, making it an ideal spot for both relaxation and entertainment. The home is also within close proximity to A-rated schools, including Glendridge and Winter Park High, ensuring an excellent educational experience for families. Don’t miss the opportunity to make this your new home. Contact us today for a viewing! Let me know if you need to add or change anything!

Listing is courtesy of: INVESTOR'S REAL ESTATE LLC (407-688-4355)

Listing Agent: Patty Perez Renteria (407-927-4731)

Remarks: OPEN HOUSE CANCELED DUE TO PENDING STATUS. 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: Completely remodeled and truly move-in ready, this 3-bedroom home is located in the established Ivanhoe Estates neighborhood of Orlando and features new luxury vinyl plank flooring, fresh trim, exterior and interior paint, new double-pane windows, new HVAC, a fully redesigned kitchen with new cabinetry, quartz countertops, and stainless steel appliances, along with a beautifully renovated bathroom showcasing a custom tiled shower and new custom vanity. The single-story concrete block home sits on a spacious lot with no HOA and offers a functional layout ideal for everyday living, while its central location places you just minutes from Downtown Orlando, Winter Park, Baldwin Park, East Colonial Drive (SR-50), SR-408, SR-417, shopping, dining, parks, and major employment centers—making this a turnkey opportunity in a highly accessible and desirable area.

Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)

Listing Agent: James Clark (407-575-7011)

Remarks: Under Construction. Experience refined living in the stunning Newcastle - our only floorplan offering a 1st floor Guest Suite with ensuite Bath and walk-in Closet - perfect for multi-gen living! This exceptional home showcases 9'4" first-floor ceilings and a bright open-concept layout designed for both comfort and style, offering a total of 5 bedrooms and 3.5 baths, including a convenient first-floor guest suite with full bath and walk-in closet. Elegant tile flooring enhances the 1st floor main living areas, while window blinds throughout add move-in-ready appeal. The spacious Great Room leads to a Café area that flows seamlessly to an extended covered rear Lanai, ideal for entertaining and enjoying outdoor living. The deluxe kitchen is a showstopper with 42" upper cabinets topped with crown molding, quartz countertops, a stylish tile backsplash, cooktop, and built-in oven. Upstairs, an oversized secondary Family / Bonus room provides flexible space for a media room or home gym. The luxurious Primary suite features an ensuite bath with dual sinks in an adult-height vanity, quartz countertops, walk-in closet, and shower with upgraded wall tile surround and glass enclosure. Completing the home are attractive landscaping, and brick paver driveway and lead walk, adding to its exceptional 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. Want a great home for first time homeowners, or a great opportunity for investors? This property is perfect for you! This corner lot home has everything you would want. A compact cozy home with three bedrooms and two bathrooms, a kitchen with granite countertops, and an entrance with a carport. Having a new coat of paint in the inside of the house and new plumbing installed makes the property shine! The home is also zoned for fantastic schools, with several of them being A rated! Hurry, this will not last long! No HOA.

Listing is courtesy of: REMAX PREMIER PROPERTIES (407-343-4245)

Listing Agent: Blanca Armada (407-908-2846)

Remarks: Pre-Construction. To be built. Pre-construction opportunity at 1315 Georgia Blvd to secure a new custom luxury residence without the delays of the initial design phase. Offered in collaboration with the acclaimed MJS Designers Group and Deep Roots Construction, this home combines timeless architecture with modern sophistication in the heart of Colonialtown North. The exterior showcases an elegant European-inspired façade in soft neutral tones, accented with smooth stucco and light stone. Symmetrical gables, expansive windows, and a welcoming covered entry create striking curb appeal, complemented by meticulously landscaped grounds. Inside, the 3,939-square-foot residence features 4 bedrooms, 3 full baths, and a first-floor powder room easily accessible from the pool. The foyer opens to a den or study, perfect for a home office or library, while the first-floor owner’s suite offers a serene retreat with an oversized ensuite bath and a spacious walk-in closet. Designed for both everyday living and entertaining, the home includes a chef’s kitchen with a large scullery for prep and storage. Outdoor living is equally impressive, with a covered lanai, fully equipped summer kitchen, and luxury pool creating a true backyard oasis. Optional upgrades include an ADU suite and expanded patios, offering the opportunity to add additional square footage and enhanced flexibility to the home. A two-car garage completes the main level. Upstairs, a generous flex space is accompanied by one ensuite bedroom and two additional bedrooms, each with walk-in closets, along with a conveniently located second-floor laundry room. This is a rare chance to own a brand-new custom luxury home in one of Orlando’s most sought-after neighborhoods. Contact us today to explore customizing your Colonialtown North dream home!

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

Listing Agent: Vinny Lay (407-756-4255)

Remarks: LIST PRICE BELOW APPRAISAL! SELLER OFFERING $10,000 CREDIT TOWARD BUYERS CLOSING COSTS / PREPAIDS. This meticulously maintained three-story townhome is strategically situated in the core of Baldwin Park, offering convenient pedestrian access to the downtown area's restaurants and retail stores. The unit also benefits from a central location providing an easy reach to the park, pool, clubhouse, and fitness center. Baldwin Park is renowned for its resort-style amenities, the beautiful Lake Baldwin, and nearby dog park. This townhome boasts newly installed, high-grade luxury vinyl flooring and stairs, new railings, new baseboards, a fresh neutral paint throughout, updated light fixtures and ceiling fans, including refreshed switches, outlets, and plates. A very rare and notable feature of this residence is its private INDOOR ELEVATOR, which significantly simplifies the transport of groceries and other items to second and third floors. The kitchen is fully equipped with stainless steel appliances, including a newer refrigerator and a microwave featuring air fryer functionality. All bedrooms include an en-suite bathroom; furthermore, the primary bathroom offers a large garden tub and a newly installed glass shower enclosure. The HVAC unit was replaced in 2023 and incorporates a Green UV ultraviolet light system to promote superior air quality. The oversized two-car garage provides substantial additional space for storage. Additionally, the low-traffic alleyway provides convenient access to the rear-entry garage, facilitating deliveries, unloading, and vehicle washing. The private 2nd floor balcony is great for entertaining and enjoying the wonderful Florida summer nights! Baldwin Park is under an hour drive from Orlando's famous theme parks and east coast beaches. ** ACTIVE SECURITY SYSTEM AND CAMERAS ON PREMISIS **

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Flory Clark (321-228-2873)

Remarks: Welcome to the Wilshire - our largest 2-story plan available in the beautiful Harrell Oaks Community! This well-designed new home offers space, style, and versatility. The open-concept layout features a separate Living Room near the front entry—perfect for a home office or den—along with 5 bedrooms and 3 full baths, including a 1st floor Guest Bedroom with adjacent bath. The expansive Family Room overlooks an extended covered rear Lanai, ideal for entertaining and enjoying outdoor living. Tile flooring enhances the main living areas on the first floor, while the deluxe Kitchen impresses with 42" upper cabinets, quartz countertops, large corner pantry closet, and stainless steel appliances, including a cooktop and built-in oven. The split bedroom design provides privacy, with the inviting Primary Bedroom featuring an oversized walk-in closet and a spa-inspired en-suite bath complete with dual sinks in an adult-height vanity, quartz countertops, and a walk-in shower with wall tile surround and glass enclosure. Exterior includes decorative stone accents, and attractive brick paver driveway and lead walk, providing great curb appeal. Zoned for top-rated schools, Harrell Oaks also offers a community park and picnic area, 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: 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: 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: RECENTLY UPGRADED with wood look ceramic tile, quartz countertops, stainless steel appliances and wood cabinetry. NEW AC installed in 2024. Award winning community of Baldwin Park. This well maintained 3 bedroom, 2 bathroom top floor condo is located in an elevator building and includes a private one car garage with convenient guest parking nearby. Positioned in one of the most desirable locations in the community, this unit overlooks Blue Jacket Park with views of Lake Baldwin. French doors open to a private balcony that brings in beautiful natural light and creates a peaceful space to enjoy your morning coffee, unwind after a long day, or take in holiday fireworks from the comfort of home. The kitchen opens to the living area with a view of Blue Jacket Park and Lake Baldwin! The entire home features ceramic wood look tile flooring throughout, offering a seamless look with durability and easy maintenance. The spacious primary suite offers a walk in closet and an upgraded ensuite bathroom featuring double vanities and a walk in shower. Additional features include an interior laundry area with washer and dryer. Enjoy walkability to top rated schools, Lake Baldwin’s scenic jogging and biking trails, and the Village Center with restaurants, shops, and Publix. Baldwin Park residents also have access to three pools, two fitness centers, clubhouses, parks, and playgrounds, all just minutes from Winter Park and downtown Orlando. As part of ongoing community improvements, the roof for the 2315 Upper Park building is scheduled for replacement, with work anticipated to begin in late April. The garage building roof is also scheduled for replacement. These updates reflect the association’s continued investment in maintaining the quality and longevity of the community. This one won't last long. Schedule your showing today.

Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)

Listing Agent: Abby Green (321-947-4460)

Remarks: Under contract-accepting backup offers. Stunning Lakefront Home! Welcome to your dream home in the highly sought-after subdivision of The Cove. This newly renovated masterpiece offers the perfect blend of modern luxury, timeless charm, and the best of Central Florida living. Nestled on the shores of a tranquil lake, this 4-bedroom, 2-bath home boasts breathtaking water views from nearly every room. The open-concept floor plan is designed for effortless entertaining, featuring a gourmet chef’s kitchen with brand new appliances, quartz countertops, and brand-new windows throughout. The living and dining areas flow seamlessly to the spacious outdoor patio, where you can relax and soak in the serene lakefront setting. Private access to the lake- perfect for paddleboarding, kayaking, or simply enjoying peaceful sunsets from your backyard. Zoned for Winter Park schools and minutes from UCF, Rollins College, and everything in Winter Park & Orlando, including upscale shopping, fine dining, and cultural attractions. Schedule your private showing today and start your next chapter in The Cove! LEASE UNTIL AUG 2026. Roof 2023 , AC 2024, Hot Water Heater 2024

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

Listing Agent: Ashley Jacobs (407-448-6310)

Remarks: Under contract-accepting backup offers. Welcome to this charming and well-maintained 4-bedroom, 2.5-bathroom home located in a quiet, established Orlando neighborhood. Featuring a spacious and functional layout, this property offers comfortable living with plenty of natural light throughout. New roof 2025 and New Electrical 2025 . New Flooring vinyl flooring 2026 and baseboards The open living and dining areas are perfect for everyday living and entertaining, while the kitchen provides ample storage and workspace. Washer and Dryer Conveys has 2 hookups in the carport or in a bedroom. Step outside to your screened-in pool, ideal for year-round Florida natural wood throughout living, relaxing, or hosting gatherings in a private setting. The home also offers generously sized bedrooms, well-appointed bathrooms, and a backyard designed for enjoyment and comfort. Conveniently located near major highways, shopping, dining, schools, and entertainment, this property offers both comfort and accessibility. Whether you’re a growing family or looking for a great investment, This is a fantastic opportunity to own a home in the heart of Orlando. Schedule your private showing today!

Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)

Listing Agent: Antonella Martino (781-526-0211)

Remarks: Under contract-accepting backup offers. Meticulously maintained and positioned in one of Baldwin Park’s most desirable pockets, this thoughtfully cared-for two-story townhome offers an exceptional combination of location, livability, and effortless style. This property was built by the Luxury Builder ISSA and is incredibly crafted with quality construction that is hard to find! Just a short stroll from Lake Baldwin and the Village Center’s popular shops, dining, and everyday conveniences like Publix and CVS, this home places you right in the middle of it all while still providing a comforted residential feel. The property immediately stands out for its spotless condition and consistent upkeep. With a brand-new roof installed in 2025 and an updated HVAC system, new carpets and hardwoods throughout, the heavy lifting has already been done, allowing for a truly move-in-ready experience. Inside, the home feels fresh, open, and full of natural light, creating an inviting atmosphere from the moment you enter. The kitchen is both functional and stylish, designed to anchor the main living space with a large island, stainless steel appliances, granite surfaces, and warm cabinetry. Whether hosting or enjoying a quiet night in, the layout flows naturally between formal and casual living and dining areas, enhanced by classic details like crown molding. A first-floor powder room adds an extra layer of practicality. Upstairs, the primary suite offers a comfortable escape, complete with a spacious walk-in closet and a well-appointed bathroom. Additional upstairs highlights include a second and a third bedroom, full guest bath, a dedicated laundry space, and a flexible bonus space to serve as an office. RARE to find, climate controlled attic storage with a sealed room and extra decking as well. Outdoor living is equally appealing, with a private, fenced courtyard that feels like your own hidden retreat, perfect for entertaining, dining al fresco, or simply relaxing. The detached two-car garage, accessible from a rear alley, adds both convenience and extra storage capacity. With this quality construction, owners will enjoy low utility bills, the owners also have tinted the windows for more energy efficiency. High speed Fiber internet connected. Cyclists will appreciate the Baldwin Lake Bike Path being right outside your door for easy access. As a Baldwin Park resident, you’ll enjoy access to an impressive range of amenities, including two lakes, extensive green spaces, multiple pools, fitness centers, playgrounds, a dog park, and miles of scenic trails. With the Cady Way Trail just nearby, outdoor recreation is always within reach. For those seeking a home that combines a prime walkable location with a clean, well-maintained interior and meaningful updates, this property delivers a rare and compelling opportunity. Ideally located minutes to Downtown Orlando and Winter Park, this location offers prime access to great local dining and shopping. Enjoy easy access to Winter Park Hospital, Advent, Orlando Health and the Maitland Business Exchange. Enjoy the interactive walk-through video and call for your private tour. Please note taxes are non-homestead.

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

Listing Agent: Crystal Grohowski, Llc (407-462-7736)

Remarks: Welcome to the Summerlyn Homesite 20 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