Homes for Sale Near Winter Park High in Winter Park - 211 homes

Remarks: GREAT HOME & GREAT VALUE — home needs some TLC and if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY which is 3 blocks away. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All rooms dimensions must be independently verified by the buyer.

Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)

Listing Agent: Donna Peebles (321-229-6085)

Remarks: Under contract-accepting backup offers. Virtually Staged. Completely renovated pool home on a large corner lot, tucked away on a quiet dead-end street in Winter Park. Solid block construction adds peace of mind, and this one has been updated top to bottom—new laminate flooring throughout, recessed lighting, popcorn ceilings removed, and a fresh, clean feel the moment you walk in. The main living area is bright and open, with natural light pouring into the living room that flows right into the dining space. The kitchen sits just off the dining area and was fully redone with soft-close cabinetry, stainless steel appliances, quartz counters, and a matching quartz backsplash. Off the dining area you’ll find a bonus family room that works perfectly as a media room, playroom, second living space—whatever fits your needs. Sliding doors open straight out to the pool, making indoor-outdoor living easy. This space also connects to a separate wing of the home featuring its own bedroom, full bathroom, and sitting area. It can be closed off from the main house and even has private access through the two-car garage, giving you flexibility for guests, extended family, or potential rental use. On the opposite side of the home are three additional generously sized bedrooms and two full bathrooms, including a bedroom with its own en-suite that can easily function as a primary depending on how you want to use the layout. Out back, you’ve got a large yard with plenty of room to make it your own, a big sparkling pool, and a covered porch area. There’s also a side gate with space to bring in a boat, trailer, or work truck straight to the backyard. A dedicated laundry setup is located off the back porch area, adding convenience for pool days and the separate suite. No HOA, roof from 2019, and a location that’s hard to beat—just minutes to 436, Downtown Winter Park, Full Sail, and UCF. Two-car garage, top rated schools, flexible floor plan, and a ton of usable space inside and out. Call today to set up a private showing!

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

Listing Agent: Ed Klein (321-377-4018)

Remarks: PRICE REDUCED, Seller motivated. Condo in Winter Park, FL Welcome to 2923 Antique Oaks Cir, Unit 39 — a beautifully updated 1,105 sq. ft. first-floor condo offering 2 bedrooms, 2 bathrooms, and modern upgrades throughout. Located in the highly sought-after Winter Park School District, this property combines comfort, style, and convenience. Property Highlights: Size & Layout: Spacious 1,105 square feet with a thoughtfully designed floor plan. Updated Interiors: Recently remodeled with modern finishes, including appliances (convection oven, refrigerator, dishwasher), and washer/dryer in the interior laundry room. Outdoor Living: Relax on your private screened patio, perfect for morning coffee or evening unwinding. Community Features: Resort-Style Amenities: Enjoy a sparkling pool, a soothing hot tub, and meticulously maintained grounds. Pet-Friendly & Welcoming: Dog-friendly and community-oriented, providing a quiet and peaceful atmosphere. Prime Location: Zoned for A-rated Winter Park schools and just 2 miles away, this condo offers unmatched convenience: Walkable access to dining, shopping, and entertainment. Minutes from Park Avenue, Baldwin Park, Winter Park Hospital, and Downtown Orlando. Close to top educational institutions: Valencia College, Rollins College, Full Sail University, and UCF. With an HOA that provides excellent management and care, this is an incredible opportunity to own in a desirable and high-quality location.

Listing is courtesy of: GLOBALWIDE REALTY LLC (352-456-9788)

Listing Agent: Michell Carrasquero (305-850-2241)

Remarks: Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated square feet of expertly crafted living space, this four-bedroom plus office, four-and-one-half-bath home blends timeless architecture, elevated finishes and effortless lakefront living. Designed with an open-concept floor plan ideal for everyday living and entertaining, the home showcases stunning European white oak hardwood flooring throughout all main living areas and bedrooms. The heart of the home is the spectacular chef’s kitchen, featuring two oversized islands, custom-designed wood cabinetry, an expansive walk-in pantry, and a premium Sub-Zero and Wolf appliance package highlighted by a 48-inch, eight-burner range. The private first-floor primary suite serves as a luxurious retreat, complete with an expansive walk-in closet and a spa-inspired bath adorned with marble tile shower walls and flooring. Also on the main level is a versatile office/den with a built-in closet. Upstairs, an expansive media/family room provides additional gathering space, accompanied by a dedicated office and three generously sized secondary bedrooms, each featuring en-suite baths and walk-in closets. The fourth bedroom offers exceptional flexibility and may easily serve as a secondary primary suite, ideal for guests or multigenerational living. Designed to embrace seamless indoor-outdoor living, expansive glass sliders extend from the gathering and dining rooms to a covered lanai overlooking the resort-style custom pool. Retractable screens create a setting for year-round enjoyment, while the fully equipped summer kitchen and generous lounge and dining areas make entertaining effortless. Expertly designed by Signature Landscape, the pool features a sun shelf, LED lighting and elegant travertine limestone decking, all surrounded by lush professional landscaping, Zoysia grass and privacy hedging for a serene outdoor setting. Additional notable features include a Brava slate tile roof and a striking custom glass front entry door, further elevating the home’s exceptional curb appeal. Ideally just minutes from the vibrant shops and dining of Park Avenue, this remarkable residence also offers convenient access to major roadways, leading area hospitals and top private schools, all within an A-rated school district. An exceptional opportunity to enjoy luxury lakefront living in one of Central Florida’s desirable settings.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood entry door, to its charming striped awnings and the flicker of gas lanterns, every detail of the exterior is carefully curated. Classic marble-paved patios frame the home, and a courtyard-style pool with fountain and sandblasted marble decking invites quiet relaxation or festive gatherings. Inside, soaring ceilings, beautiful hardwood floors and immersive color-drenched rooms create an inviting space that is luxurious but unpretentious, bold yet serene. The stunning staircase features a custom wrought-iron railing with an antique finish, offering a striking architectural focal point. The chef’s kitchen, a culinary sanctuary and social hub, is complete with graphite La Cornue range and pot filler, Monogram paneled refrigerator, custom plaster hood, quartzite countertops and backsplash, and grand center island that opens to a gathering room with a gas fireplace. This more relaxed living area flows effortlessly through French doors to the pool and patios, creating an ideal indoor-outdoor lifestyle. A butler’s pantry with a second refrigerator, cabinetry and prep space adds functionality, while the formal dining room, living room, and bar area with sink and built-in beverage cooler are ideal for entertaining. A beautiful downstairs powder bath features designer wallpaper, elegant sconces and custom cabinetry. The upstairs primary suite offers spa-like serenity, including a wet room complete with soaking tub framed by a picture window. Three additional bedrooms include one with an en-suite bath, while the other two share a hallway-accessible bath with double vanity and walk-in tiled shower. This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in an ideal location.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Bianca Khoury (407-797-1121)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained four-bedroom, two-bathroom home offering 1,677 square feet of thoughtfully designed living space nestled in a quaint neighborhood of the highly desirable Winter Park. Featuring a split-bedroom floor plan, extensive interior updates, and exceptional indoor-outdoor living spaces, this move-in-ready residence combines comfort, functionality, and convenience with access to top-rated Winter Park schools. Step inside to discover a bright and inviting interior, freshly repainted in 2026, complemented by refinished ceilings, elegant crown molding, ceiling fans throughout, and charming French doors that add character and architectural appeal. The versatile floor plan offers multiple living and gathering spaces, including a spacious den or family room ideal for entertaining, working from home, or everyday relaxation. Abundant storage throughout the home ensures there is a place for everything. At the heart of the home, the kitchen features warm honey-toned wood cabinetry, stainless steel appliances, a brand-new microwave, and a convenient dining area perfect for casual meals and family gatherings. The functional layout allows for seamless flow between the kitchen and living spaces, making entertaining effortless. Privately situated away from the secondary bedrooms, the spacious primary suite serves as a peaceful retreat. The suite includes a walk-in closet with custom organizational features, a ceiling fan, and a beautifully updated ensuite bathroom designed with spa-inspired finishes. The luxurious bath showcases floor-to-ceiling marble-look tile, a pedestal sink, a spacious tiled shower with glass enclosure, dual shower heads, a built-in bench seat, and custom linen and towel cabinetry for added convenience and storage. Three additional bedrooms and an updated hall bathroom renovated in 2022 provide comfortable accommodations for family members, guests, or flexible workspace options. One of the home's standout features is the expansive Florida room, offering an incredible extension of the living space. Filled with natural light, this inviting retreat features a vaulted ceiling, tile flooring, and large sliding windows that create the perfect setting for morning coffee, reading, entertaining, or enjoying Florida's beautiful weather year-round. Step outside to a fully fenced backyard designed for relaxation and outdoor enjoyment. Gather around the fire pit on cool evenings, enjoy weekend barbecues in the dedicated grilling area, or unwind beneath the shade of the quaint wooden swing. The private outdoor space offers endless possibilities for entertaining, gardening, pets, and play. Ideally located in Winter Park, this home offers exceptional convenience to everything Central Florida has to offer. Residents enjoy zoning for top-rated Winter Park schools, easy access to State Road 417 within five minutes, Full Sail University within five minutes, and the University of Central Florida within approximately fifteen minutes. Orlando International Airport is just twenty minutes away, while Target, Costco, grocery stores, shopping, dining, and everyday conveniences are all nearby. Combining spacious living areas, thoughtful updates, desirable schools, and an unbeatable location, this exceptional Winter Park home offers the perfect opportunity to enjoy comfortable Florida living in one of the area's most sought-after communities. ROOF - 2019 HVAC - 2022 PLUMBING - 2026 WATER HEATER - 2018

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

Listing Agent: Amy Turner (407-803-3885)

Remarks: Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

Listing is courtesy of: PARK TOWN REAL ESTATE LLC (561-801-9199)

Listing Agent: David Auerbach (407-619-5250)

Remarks: Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

Listing is courtesy of: PARK TOWN REAL ESTATE LLC (561-801-9199)

Listing Agent: David Auerbach (407-619-5250)

Remarks: Under contract-accepting backup offers. The seller has just completed a full renovation. Bathrooms have been entirely gutted and updated with new tiles, fixtures, and lighting. All lighting throughout the home has been replaced, and fresh paint has been applied throughout. Situated on a spacious double lot spanning over 1/3 acres, this home offers a private retreat, complete with an impressive 18 x 40 pool. The layout features generous common areas, including a large family room, a formal living room, a separate dining room, a kitchen with an adjacent breakfast room, a dedicated home office, a loft-style office or playroom, and a cozy home theater located above the garage. The kitchen, primary bedroom, and both the family and living rooms provide stunning views of the pool and backyard. The three-car garage offers ample space for large vehicles. Beyond the pool, you’ll find a charming gazebo and a fully equipped outdoor kitchen. Built with block and stucco construction and topped with a durable tile roof designed to last up to 100 years, this home boasts incredible durability and aesthetic appeal. Combining the feel of new construction with a rare, expansive lot in a well-established neighborhood, it provides privacy, mature landscaping, and modern elegance all in one.

Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)

Listing Agent: Teresa Chris Harralson (404-229-8737)

Remarks: LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound system, full house generator and a private elevator to all floors. The first floor has a two car garage with storage lift above, large laundry room/home office and a downstairs guest suite. The second floor features a stylish and comfortable living room with lovely custom ceiling detail and moldings, gas fireplace, a sophisticated powder bath, and a beautiful dining room that opens to an eat-in chef's kitchen with Subzero, Wolfe and Bosch appliances and light Taj Mahal quartzite countertops. The third floor offers the spacious master bedroom and bath and also has the additional guest bedroom suite. Take the elevator to the roof top for great views of the city and here find even more potential space for fun entertaining. If your dream is to own a townhome in the heart of Winter Park, here is a stunning one for you!

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

Listing Agent: Av Blalock (407-579-9056)

Remarks: Under contract-accepting backup offers. Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot, providing modern functionality, Old World charm, and an unmatched lifestyle. The main residence spans over 3,600+ SF with 4 bedrooms, 4 bathrooms, and an attached 2-car garage. Across the brick driveway is a detached, fully-equipped 700+ SF studio apartment (5th bedroom suite) located above an additional 2-car garage, and an air-conditioned outdoor bar. With two dwellings, a 4-car garage, and an expansive outdoor entertaining space on a ½ acre lot, this home is a true private compound. Notable updates include newer HVAC systems (2020 & 2025), a new tankless gas water heater (2024), a fully renovated laundry room with new LG stackable washer/dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more... Ask for the $400K list of improvements! Enter the main residence to a family room that stretches 30 feet wide, with 12-foot ceilings, a gas fireplace, and multiple French doors lining the rear wall to showcase the brick-paver pool deck and lush, fenced-in backyard oasis, and southern exposure that invites natural light all morning and afternoon. The expansive family room is open to the kitchen, making this home ideal for entertaining. The kitchen perfectly balances charm and function, with a NEW Sub-Zero refrigerator, natural gas Wolf range, 2 Miele dishwashers, a copper-topped island that offers room for prep, serving, or seating, and a spacious dinette area with pool views. Behind the kitchen sits a dining room and adjacent den (currently used as a library/office) for more living/dining flexibility. A side entrance opens to a covered side porch overlooking a generous side yard framed by tall Podocarpus hedges... ideal for pets, a fabulous garden, or future expanded parking. A 1st floor rear bedroom wing presents 3 bedrooms & 3 full baths. Privately positioned upstairs, the expansive primary suite offers a quiet retreat, highlighted by a recent luxury bathroom renovation with elegant custom finishes including a large glass shower with 3 showerheads, 2 separate vanities, a Toto washlet, and tons of cabinetry for linen storage. French doors from both the bedroom and bath open to a covered balcony overlooking the backyard and pool, while 3 custom walk-in closets create a true dressing room experience, or the perfect opportunity to turn excess space into an office or special hobby room. Designed for entertaining, the outdoor living is equally impressive, with a sprawling lawn surrounding the large saltwater pool and an expansive paver patio for lounging and dining. A covered, air-conditioned bar is designed with custom cabinetry, exquisite lighting, a copper sink, dishwasher, wine fridge, and beverage fridge...all secured by an electronic storm shutter. The extended bar seamlessly serves the adjacent tent-covered lounge area, complete with a natural gas grill, pool bath, and outdoor shower. Above the detached 2-car garage is the studio apartment with a private entry, along with a full kitchen and bath, making it ideal for extended stays or flexible living arrangements. Located just minutes from the vibrant Park Avenue, this distinctive Winter Park compound is a one-of-a-kind property!

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

Listing Agent: Marystuart Day (407-620-8683)

Remarks: Under contract-accepting backup offers. Tucked away on a quiet dead-end street in sought-after Winter Park Pines, this beautifully maintained 4-bedroom/ 2 bath pool home offers the perfect blend of privacy, updates, and location. Designed with a desirable split floor plan, the home provides separation between the primary suite and secondary bedrooms while offering comfortable spaces for everyday living and entertaining. The kitchen is positioned to overlook the backyard and pool, creating an inviting setting for both daily life and gatherings. Inside, you'll find timeless terrazzo and laminate flooring throughout, beautiful plantation shutters at the front of the home, plus a dedicated home office or flex space just outside the kitchen. Towards the back of the home you will find a versatile climate-controlled four-seasons room overlooking the backyard and pool provides even more flexibility for today's lifestyle. Whether you need a playroom, fitness area, hobby room, or additional living/dining space, this home offers room to adapt to your needs. Set on a spacious FULLY FENCED lot with mature landscaping, the property is beautiful from the moment you pull up. The private pool and expansive backyard create an ideal outdoor retreat for relaxing and entertaining year-round. Major improvements provide peace of mind, including a NEW ROOF (2021), ALL NEW WINDOWS (2025), NEW HVAC SYSTEM (2025), and EXTERIOR PAINT (2023). Additional energy-saving features include a solar-assisted hot water system helping contribute to lower monthly utility costs. Location is everything, and this home delivers. Just steps from the Cady Way Trail, you'll enjoy easy access to miles of biking, jogging, and walking paths. Nearby Cady Way Park offers tennis, pickleball, athletic fields, playgrounds, and recreation facilities. Conveniently located just minutes from Downtown Winter Park, Park Avenue, Winter Pines Golf Club, Baldwin Park, AdventHealth Winter Park, Full Sail University, shopping, dining, and SR-417. Situated in a well-established neighborhood with NO HOA, this home offers a rare opportunity to enjoy the Winter Park lifestyle with exceptional convenience and charm.

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

Listing Agent: Melissa Condrey (407-505-9339)

Remarks: Under contract-accepting backup offers. MOVE-IN READY Winter Park home on approximately 1.68 acres with NO HOA, a long private driveway, and a rare combination of usable land, privacy, and updated living space in the heart of Central Florida. Tucked away behind mature trees and set far back from the road, this one-story property offers a peaceful, secluded setting while still being conveniently located near shopping, dining, major roadways, and everyday essentials. From the moment you arrive, the extended tree-lined driveway, expansive yard, and natural surroundings create a sense of space and privacy that is difficult to find in Orange County.A welcoming covered front porch leads into a bright, open interior with updated flooring, neutral finishes, and a thoughtfully designed split-bedroom layout. Inside, the home opens into a spacious main living area filled with natural light and large sliding glass doors that frame views of the backyard and surrounding greenery. The open-concept design allows the living, dining, and kitchen spaces to flow naturally together, creating an ideal setup for both everyday living and entertaining.At the center of the home, the updated kitchen features stone countertops, stainless steel appliances, modern fixtures, recessed lighting, and an oversized island with extensive storage and seating space. The kitchen overlooks the main gathering areas, making it easy to stay connected while cooking, hosting, or spending time with family and guests. Nearby dining space offers room for larger gatherings while maintaining a warm and comfortable atmosphere.The spacious primary suite is privately positioned and offers a peaceful retreat with backyard views, a walk-in closet, and an updated en-suite bathroom complete with dual vanities, a soaking tub, and a tiled walk-in shower. Additional bedrooms are generously sized and provide flexibility for guests, home offices, fitness space, hobbies, or multi-generational living. One of the secondary rooms is currently set up as a flex space and office, highlighting the versatility of the floor plan. With 5 bedrooms and 3 full bathrooms, the layout easily adapts to changing needs and lifestyles.The large indoor laundry room adds convenience and functionality, while the attached 2-car garage provides additional storage and covered parking. Outside, the property truly stands out. The expansive 1.68-acre lot offers endless possibilities for outdoor living, gardening, recreation, pets, equipment storage, or future improvements subject to buyer verification and county regulations. The FENCED YARD and NO HOA create additional flexibility for buyers looking for space for boats, RVs, trailers, or simply more privacy and freedom than a traditional neighborhood setting can provide.Located in unincorporated Orange County with a Winter Park address, this property offers convenient access to Downtown Winter Park, Maitland, Orlando, Park Avenue shopping and dining, nearby parks, major highways, and top Central Florida destinations. This is a rare opportunity for buyers searching for Orlando homes for sale with acreage, privacy, and a MOVE-IN READY layout in a highly desirable area. Whether you're relocating, searching for additional outdoor space, or looking for a unique Central Florida real estate opportunity with room to grow, this home offers flexibility, comfort, and convenience in one exceptional setting.Contact us today for a private tour or more details on this exceptional opportunity.

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

Listing Agent: Simi Lakhani (407-408-7393)

Remarks: Under contract-accepting backup offers. BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, an opportunity priced 4-bedroom, 3.5-bath home to get into the coveted Winter Park Vias while adding your final touches to personalize this home while prioritizing location, schools, privacy and connectivity. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring a super spacious kitchen, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.

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

Listing Agent: Vincent Scarlatos (407-718-2378)

Remarks: This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a quiet complex, a perfect place to call home. It's just minutes away from the University of Central Florida, Full Sail University, & Valencia College. This location makes an excellent investment for a college (or parents of) student. The upgraded kitchen has granite countertops with a custom sink, newer stainless steel appliances, and a closet pantry. There is a separate dining room that opens onto a very private brick paver patio with a new privacy fence. This unique condo features a flexible layout, an inside utility, and includes the washer & dryer. Modern-design porcelain tile flooring. The home has a large screen porch, which is considered by many in Florida, to be extra living space. There is also a front courtyard that is perfect for a raised bed garden or ???. Highly desired Winter Park schools. A 2-car carport with an ample lockable storage closet. New roof in 2020 and an updated electric system. The complex has a private community pool

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

Listing Agent: Greg Harrison (407-276-6141)

Remarks: Under contract-accepting backup offers. Must see! This adorable three-bedroom, two-bath home is in a great location close to shopping, restaurants and freeways. A 2023 roof and no HOA! The home features gorgeous travertine flooring and a huge laundry room with extra storage. This exceptionally cared for home has character, charm and warmth. The fenced backyard and patio offer peaceful privacy. It's great outdoor space for entertaining or relaxing. The kitchen is bright and sunny with granite countertops and updated cabinets, along with a pass-through window to the patio. The bedrooms are spacious and one bedroom offers beautiful closet built-ins for maximum and stylish storage. You'll find updated baths and ample closet space (coat closet in the foyer, pantry, linen closet in the hallway). Sliding glass doors off the family room and dining room lead to the large patio for a wonderful outdoor living space. The home has lots of natural light, you can enjoy the character of the front bay window in the living room as well as the faux fireplaces. This home is a must-see with personality and has been impeccably maintained. Pride in ownership. Schedule your showing today.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)

Listing Agent: Paula Dale (407-497-3292)

Remarks: Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.

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

Listing Agent: Erin Baker (407-719-0030)

Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to this aesthetic custom luxury home in an unbeatable Winter Park location.From the moment you arrive, the custom landscaping and automated lighting make a statement, day or night.At the center of the home, the chef's kitchen is both a showpiece and a performance space. A commanding 48-inch Z-Line gas range with 8 Italian-made brass burners anchors the room, complemented by Café luxury appliances, a stainless steel refrigerator, quartz countertops, and custom cabinetry. The walk-in pantry with floating shelves and under-shelf lighting adds both beauty and function. An indoor wine bar with built-in cabinetry and wine refrigerator enhances the entertaining experience, while an upstairs beverage station keeps every level equally equipped.The primary suite is a full spa experience. The glass enclosed shower features a rain head, body jets, and handheld fixtures. A soaking tub, dual vanities with quartz counters, and a generously proportioned walk-in closet complete the retreat. Imported aged brass designer light fixtures are included in the sale. Philips Hue smart lighting synchronizes every indoor and outdoor light in one app, and a smart security camera system with fingerprint keypad entry completes the tech package. The outdoor living experience rivals the interior. A covered lanai with a fully equipped summer kitchen, including a built-in grill, dedicated refrigerator, and generous prep space, flows into a landscaped courtyard designed with an Italian villa, Mediterranean feel. As evening falls, intentional landscape lighting transforms the grounds into an intimate setting perfect for al fresco dinners, fireside gatherings, or projecting the big game under the stars. Walk to pickleball courts, athletic fields, and a premier wellness facility. Park Avenue's celebrated boutiques and dining are just minutes away. New construction of this caliber is increasingly rare in Winter Park. Schedule your private showing today. The furniture and décor, curated by a professional design team, are negotiable, making it possible to move in with the full look already in place.

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

Listing Agent: Norma Gonsalves (407-451-9533)

Remarks: Under contract-accepting backup offers. LOCATION. LOCATION. LOCATION. Heres the thing; in Winter Park, that's not a cliché. It's everything. There are homes in Central Florida that require a car for everything. This is not one of them. 641 West Lyman Avenue doesn't sit near Hannibal Square. It sits on it. This corner lot property is literally at the edge of one of Winter Park's most beloved and walkable districts — a place that draws residents and visitors alike with its brick-lined streets, acclaimed restaurants, wine bars, local boutiques, and genuine sense of community. Step outside your front door and within minutes you're at The Ravenous Pig, Prato, Chez Vincent, Park Avenue Tavern, Vinia Wine Bar, or CFS Coffee. The Saturday Farmers Market, the Hannibal Square Heritage Center, and the energy of one of Central Florida's most distinctive neighborhoods are all right here. And Park Avenue — Winter Park's crown jewel — is just a quick walk beyond that. Then there's Rollins College. Florida's oldest private university, founded in 1885, is an easy walk from your front door. Whether that matters to you as a parent, a professional, a culture enthusiast, or simply someone who values the intellectual and artistic energy a college campus brings to a neighborhood, this proximity is rare. You don't get Rollins-adjacent addresses very often — and when you do, they hold their value. And speaking of things that hold their value — the schools. This home is zoned for Winter Park High School, consistently rated one of the best public high schools in the state of Florida. Niche ranks it an A overall and among the top 5 public high schools in the entire Orlando metro area. It offers International Baccalaureate, Advanced Placement, and a college prep track that outperforms district and state averages across the board. For families, the school zone alone makes this address worth the conversation. The home itself is a clean, updated three-bedroom, two-bath bungalow — 1,120 square feet built in 2003, sitting on a corner lot enclosed by a white vinyl privacy fence. Inside, the sellers have done the work: new flooring throughout, new lighting, and all new appliances. There's nothing to fix, nothing to update, and nothing to negotiate around. You move in and you start living. That's the thing about this property. It's a turnkey home on the corner of one of Central Florida's most desirable walkable neighborhoods, in a school zone that parents actively relocate for, steps from a historic college campus and some of the best restaurants in the region. That combination, at this price point, inside the Winter Park city limits, simply does not come around often. Come see it before someone else does.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ted Moseley (352-729-1019)

Remarks: Under contract-accepting backup offers. Virtually Staged. Step into this beautifully updated home in Winter Park Pines—one of the area’s most sought-after neighborhoods—where modern upgrades, top-rated schools, and everyday convenience come together effortlessly. The front foyer showcases the home’s original mid-century planter box, a nostalgic architectural detail that some adore and others prefer to modernize. Anticipating this, the seller thoughtfully ordered extra matching flooring so you can easily update the foyer and remove the planter after closing if you choose. Beyond this space, brand-new luxury vinyl plank flooring extends through the main living areas, creating a warm, modern look that’s both stylish and durable. The kitchen has been completely transformed with sparkling quartz countertops, shaker-style cabinetry, and all-new stainless-steel appliances—offering a fresh, functional space perfect for everyday cooking and entertaining. Fresh interior and exterior paint give the home a bright, clean, move-in-ready feel from the moment you arrive. The split floor plan provides comfortable living, with the ensuite primary bedroom on one side and two additional bedrooms and the second bath on the opposite wing. The bathrooms remain in their original condition but are fully functional, allowing this home to be priced below comparable properties with recent bath renovations. With the major updates already completed—including a new roof in 2023 and new HVAC system in 2020—you can move in now and refresh the bathrooms over time to suit your style. Additional highlights include a two-car garage with an impressive 10' x 10' workshop area near the washer and dryer (both of which convey). This flexible space is ideal for hobbies, storage, or projects. An extra refrigerator in the garage also conveys. With thoughtful updates throughout, no required HOA dues, a friendly community atmosphere, and access to highly rated schools, this home offers the lifestyle buyers are searching for. It’s the perfect blend of comfort, convenience, and modern style. Schedule your showing today!

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Michelle Deleon (407-619-7056)