Homes for Sale Near Winter Park High in Orlando - 51 homes

Remarks: ATTENTION: Builders and Investors. Exceptional redevelopment opportunity in one of Orlando's most sought after corridors. Situated on a 9992 sq ft lot, this property directly borders Lake Druid Park and Cady Way Trail, offering rate adjacency to green space and recreation - on increasingly valuable premium for new construction. Located in the heart of Orlando's urban core, this property provides unmatched connectivity-just minutes to Downtown Orlando, Winter Park, Baldwin Park and Leu Gardens. The existing 2 bedroom, 1 bath home (840 sq ft, built 1954) is ideal for teardown or full renovation. Surrounded by active redevelopment and new construction, this oversized lot offers strong upside potential for builders seeking to capitalize on location, lifestyle, and land value. Highlights: Nearly 1/4 acre (9992 sq ft) lot. High demand redevelopment pocket. Minutes to major lifestyle hubs, dining and shopping. Ideal for custom home build or investment project.

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

Listing Agent: Alan Ireton (407-310-8505)

Remarks: Charming 3-bedroom, 2-bath split-plan block home in sought-after area of Orange County! This beautifully updated home features new laminate flooring, freshly painted interior, plush new carpet, and modern fixtures throughout. French doors lead to a spacious enclosed lanai perfect for relaxing, entertaining, or enjoying Florida's beautiful weather. Home features an inside laundry room, and an oversized shed that offers plenty of storage. No HOA! Nestled in the top-rated Winter Park school district, and just minutes from parks and shopping, this home is a must-see! Don’t miss out—schedule your tour today!

Listing is courtesy of: ATKINS REALTY GROUP (407-406-1909)

Listing Agent: Larry Atkins (407-443-9812)

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: 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: One or more photo(s) has been virtually staged. Rare 70' lakefront property in the heart of Audubon Park with gazebo and dock to enjoy sunset on the lake. PROFESIONNAL INTERIOR PHOTOS COMING SOON WHEN SELLER FULLY MOVE OUT. This oversized 0.51 acre lot features an existing 1,332 sq ft home in good condition and well maintained. A/C 5 stage carrier with Hepa carrier and UV light disinfection system against viruses and bacteria new 2018, Roof permitted replacement 2022, Water Heater 2025. This property offers outstanding potential for renovation, expansion, or future redevelopment. Properties of this size with water frontage are extremely rare in this sought-after neighborhood. Prime location just minutes from East End Market, Leu Gardens, Downtown Orlando, Winter Park, Baldwin Park, and Audubon Park’s popular dining and shopping. Ideal for buyers seeking land value, a custom build, or long-term investment. Buyer to verify zoning, land use, and development potential.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Sandrine Sanchez (407-255-5292)

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 Lake Sue Drive – A Rare Gem located in Beeman Park right in the heart of the Audubon Park Garden District. Situated on an oversized 0.49 lot (21,148 sf), this property has been owned by the same family for over 80 years. This charming home offers 4 bedrooms and 2.5 bathrooms in the main residence, along with a detached guest house (704 sq ft) complete with a full kitchen and bath—perfect for guests, in-laws, or a private home office. Rich in character, the home features separate living and dining rooms with beautiful hardwood floors, plus an oversized family room with brick flooring and large windows that fill the space with natural light and overlook the serene backyard and patio. The primary suite includes Travertine flooring, generous closet space, and ample storage, while three additional bedrooms provide room for everyone. The bright kitchen offers granite countertops, double ovens, and a cozy eat-in area overlooking the backyard. A huge laundry room adds extra storage and convenience. With an expansive 162 ft frontage and 125 ft depth, you have ample space to customize and add on to this lovely and charming home to make it your own or develop something totally new. Homes in this highly sought-after area are a rare find. Renowned for its top-rated schools and prime location, you'll have easy access to Baldwin Park, Downtown Orlando, Winter Park and a variety of fantastic shopping and dining options. Take a stroll to East End Market, explore the charming local shops, or visit Palmer’s Nursery. Plus, Leu Gardens is just around the corner, offering frequent special events and a serene escape into nature. This vibrant neighborhood truly has it all! Don't miss this exceptional opportunity to own a home in one of Orlando’s most desirable neighborhoods. Truly a unique property and a must see!

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

Listing Agent: Lisa Fleming (321-228-8341)

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: Price Improvement! Luxury meets lifestyle in this exceptional Baldwin Park townhome just one block from the Village Center! Don't miss this Move-In Ready and beautifully curated living with brand new flooring, crown molding, and timeless architectural details. The entry-level bedroom with ensuite bath offers privacy for guests or a home office. The main level is perfect for entertaining with an open living area, private balcony, and a gourmet kitchen featuring soft-close cabinets, granite counters, stainless steel appliances, and custom wine storage! The third-floor primary suite is a true retreat with a large walk-in closet and spa-like bath with soaking tub and dual vanities. A versatile fourth-floor loft completes the home. Lots of natural light and and tons of space for entertaining! Neighborhood features 3 community pools, Gym, 2 event spaces and several playgrounds! Walk to dining, boutiques, Dog Park, Lake Baldwin, and top-rated schools—everything you love about Baldwin Park living is right outside your door. Schedule your showing today and experience the elegance first hand!

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Farah Bloom (407-873-5222)

Remarks: Welcome to Arbor Ridge, where comfort meets convenience! This charming 3 bedroom, 2 bathroom residence offers the perfect blend of suburban tranquility and modern accessibility. Enjoy a large walk in closet in the primary bedroom along with ample closet space throughout. Nestled on a quiet, tree-lined street, this home features a functional open-concept layout, vaulted ceilings, and a split-floorplan designed for privacy with primary bedroom on one end & additional bedrooms on the opposite end. Step outside to a VERY spacious backyard, perfect for weekend BBQs or creating your own private Florida oasis. If you are simply looking for a neighborhood that feels like home, this location delivers! Beyond the front door, you are part of a vibrant community anchored by the A-rated Arbor Ridge K-8 School, just a short stroll away. This is close to Central Florida Research Park, University of Central Florida, and Seminole Wekiva Trail! Enjoy low-traffic streets, combined with a location that puts the best of East Orlando at your fingertips.

Listing is courtesy of: GRACE REALTY, INC. (407-644-4440)

Listing Agent: Kat Harden (407-749-8165)

Remarks: Great investment opportunity near Baldwin Park! No HOA, great fixer-upper on 0.35-acre corner lot off Old Cheney/Coletta Dr in downtown Orlando! Conveniently located near SR-50, SR-436, and the 417, a short drive to shops and dining at Baldwin Park, UCF, downtown Orlando, the airport, and Altamonte Springs. This one-story home has great bones, with solid concrete block construction, hardiboard plank siding, three bedrooms, two full bathrooms, an open kitchen to the great room with a wood-burning fireplace, a den, and another bonus room. The roof and AC are only 8 years old; the house has been replumbed and the electrical panel updated; and the home is on public water and sewer. The large, fenced-in corner lot is a third of an acre, perfect for parking oversized trucks and RVs and ideal for dog lovers, with no restrictions. No HOA. Attached one-car garage and a four-car carport, a metal workshop building. This is a great starter home or rental with some new flooring, a new refrigerator, and a new range. The dishwasher is only one year old. Washer and dryer included. Great schools. Open layout, public utilities, no HOA, and oversized lot make this a GREAT home or investment.

Listing is courtesy of: Q BOUTIQUE SPECIALTY REALTY INC (407-863-7965)

Listing Agent: Laura Diss (407-388-4103)

Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 9717 Lake Douglas Pl, a spacious two story home offering 6 bedrooms and 6 bathrooms in a desirable Orlando location. Designed for both comfort and functionality, this residence provides ample space for large families, multigenerational living, or those who love to entertain. The main level features an open and inviting layout with expansive living and dining areas filled with natural light. An additional living area offers flexibility, making it ideal for a media room, home office, or playroom. The kitchen features generous counter space, abundant cabinetry, and a layout that connects seamlessly to the main living areas, perfect for both everyday living and entertaining. Each bedroom is well proportioned, with multiple ensuite bathrooms providing privacy and convenience. The primary suite serves as a private retreat with a spacious layout and a well appointed bathroom. The second floor includes two bedrooms with ensuite bathrooms, offering comfort and privacy for guests or family members. Step outside to enjoy a private patio overlooking a serene lake, creating an ideal setting for outdoor dining, relaxing evenings, or entertaining guests. Situated in a quiet residential community, this home offers easy access to local schools, shopping, dining, and major highways, making commuting throughout Orlando simple and convenient.

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

Listing Agent: Thomas Nickley, Jr (407-629-4420)

Remarks: Welcome to Baldwin Park - a desirable, centrally-located Community loaded with Amenities! Picture yourself on these tree-line streets enjoying one of three Pools, Clubhouses, Exercise Facility, Parks, Playgrounds, Bike Trails, the Gazebo and Fountain on Lake Baldwin, access to Cady Way Trail and The Town Center with it's shopping and Restaurants. Top-Rated Schools within the Community! Now, envision yourself living in your own 3 bedroom 2 1/2 Bath Townhouse, filled with natural light. Enter the Unit into a Formal Living Space and a second Cozy Living Space/Family Room off the Kitchen. Kitchen includes contrasting color Cabinets, Granite Counters and Breakfast Bar. The Living areas are accented with light-colored Laminate Flooring, Crown Moldings and Plantation Shutters. Primary Bedroom is on second Floor with Ensuite Bathroom and Double Vanity, Garden Tub and private Commode Room. Two additional Bedrooms and a Guest Bath and Laundry Area complete the Second Floor plan. The Back Yard is a relaxing combination of landscaped areas and seating area finished in Pavers. Separate Garage and additional parking space with access from the rear. Make an appointment today to see this wonderful Home!

Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)

Listing Agent: Janice Erickson (407-621-6856)

Remarks: Welcome Home to Colonialtown Charm Step into this ranch-style gem–a mid-century 2/1 located in the highly sought-after Colonialtown neighborhood directly on the Orlando Urban Trail! This home was completely renovated in 2019 including an updated electrical system, HVAC, and water heater. The kitchen is a chef’s dream that features a spacious island, quartz countertops, stainless steel appliances (including a cooktop hood and built-in microwave), a pantry, and abundant storage in the two-tone shaker style cabinets with soft close doors/drawers. Beautiful wood ceilings throughout the home carry into the two spacious bedrooms on either side of the designer bathroom. Relax from the screened in porch or on the large paver courtyard in the shaded backyard. Backyard features a large storage shed with ample interior space including two storage lofts. Single car garage has great storage options and laundry nook including washer/dryer with barn doors. Walk or bike to East End Market, Lake Druid Park, Mills Ave, and Leu Gardens. Convenient to Downtown Orlando, The Milk District, Winter Park, and other top area attractions. Schedule your private showing today! Interior photos are staged for reference only.

Listing is courtesy of: LOCAL LIVING REALTY GROUP (386-314-5458)

Listing Agent: Rob Carelli (386-801-2989)

Remarks: Your modern oasis in Orlando! Tucked away on a quiet, tree-lined street, this updated 3-bedroom, 2-bathroom charmer blends style, comfort, and convenience in one perfect package. Step inside and you’ll love the house flow — ideal for hosting friends, working from home, or just relaxing with your favorite book by the pool side, the wood-burning fireplace or the extra large back porch. The kitchen is a total win with granite counter tops, sleek stainless appliances, tons of cabinet space, with a pantry cabinet to keep everything organized. The primary suite is spacious and the bathroom features a walk-in shower and dual sink vanity. This house includes a recent roof (2018), new hot water heater (2021), energy efficient windows and sliding glass doors with blinds built inside the two panes of glass. A new driveway was put in (2023). The garage includes an extended work shop area. Inside laundry room has a sink and cabinets for extra storage.The back yard is fully fenced with a large swimming pool which is 37’ long by 15’ at it’s widest point! Location? You’re close to everything: UCF, Trinity Prep and The Masters Academy This home is zoned for highly rated Winter Park schools. Plus, you’ll have easy access to 417, Oviedo, Winter Springs, and all the best of Winter Park. Whether you're hosting a backyard BBQ or exploring the local scene, this home checks all the boxes for modern Florida living. Don’t miss your chance — come see it today and fall in love!

Listing is courtesy of: HOME SOLD REALTY LLC (833-700-2782)

Listing Agent: Camilo Perez (833-700-2782)

Remarks: BEAUTIFUL Single Story 3 Bedroom, 2 Bath, Split Floorplan Spa Home. Located in the quiet highly sought after community of Lost Lake Village. This Wonderful open floorplan home has been perfectly maintained by the owners. NEWLY installed 2026 AC SYSTEM. Remodeled Kitchen , along with a separate eat-in Nook area, features solid wood cabinets with granite counter tops and stainless appliances. Awesome natural stone fireplace in Family room. Outstanding enclosed huge screened back Patio features a built-in Spa with amazing decking. Incredible larger nicely landscaped fenced in home site. Plenty of room for family fun. Lost Lake Village is a very family and pet friendly community. It is located near everything. Major roadways, shopping and restaurants and top rated schools. This is a must see home!

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

Listing Agent: James Mccarthy (407-622-2122)

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: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Mid-Century Modern enthusiasts—this one is for you! Welcome to 3506 Pelican Lane, showcasing the signature elements of true mid-century design: floor-to-ceiling windows that flood the home with natural light, a seamless open floor plan, and original terrazzo flooring that flows throughout. Whether you choose to enhance its vintage charm or thoughtfully modernize, the possibilities here are endless. Lovingly owned since the 1950s, this 3-bedroom, 2-bath home is now ready for its next chapter. As you step inside, you’re immediately welcomed into a bright, open space that blends the living, dining, and family rooms—true to mid-century modern design. Just off to the right, the kitchen remains in its original layout, offering a nod to the home’s architectural roots. Expansive windows line the space allowing natural light to pour in , complemented by the terrazzo flooring that runs seamlessly throughout the entire home. To the left, you’ll find all three bedrooms grouped together, along with the home’s bathrooms—providing a functional layout that offers both privacy and convenience. From the main living area, you’ll enjoy direct access to the outdoor space—perfectly sized to be low maintenance but with just enough room to create your own garden, entertain, or design a private retreat that fits your lifestyle. Located in the highly sought-after Audubon Park, you’ll be in the heart of Orlando’s most vibrant and beloved communities. Just minutes from Baldwin Park and Winter Park, enjoy easy access to boutique shopping, local dining, scenic parks, and lakeside living. Spend your weekends exploring the Audubon Park Garden District, known for its charming mix of locally owned shops, farm-to-table restaurants, craft breweries, and community events that make this neighborhood truly special. If you’ve been waiting for an authentic mid-century home in a prime location at a pricepoint that is within reach—this is your opportunity. Schedule your showing today!

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

Listing Agent: Cecille Rodriguez (321-946-2102)

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 contract-accepting backup offers. BACK ON THE MARKET DUE TO FINANCING , Looking for a place to call your own in the Baldwin Park / Winter park area in Orlando? Look no further, peaceful paradise! Step into this charming, pool home and discover the ultimate oasis in Florida living. Boasting 3 bedrooms and 2 full bathrooms, this home invites you to experience privacy and quiet living at every turn. With 1,972sqft of spacious living ,dining areas and entertaining has never been easier. Take your enjoyment outdoors with a pool with a spa perfect for cooling off on those sunny summer days. And when you need a break from the sun, retreat to the tranquility of the large fenced patio for year-round enjoyment. This property offers more than just relaxation—it's practical too. With a two-car oversized garage and expanded driveway, there is ample parking. Work shop or can be an Adu or in-laws was Built with solid concrete block structure ready to be completed. . No HOA makes this property ideal for pet owners and garden enthusiasts alike. Let your furry friends roam freely in the fenced yard on .44 of an acre lot, while you take advantage of the ample outdoor space. Conveniently located in the highly sought Baldwin Park/Winter Park area in Orlando, this home puts you just minutes away from 408 , I-4 and downtown Orlando. .

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

Listing Agent: Enid Rodriguez (321-239-9517)