Homes for Sale Near Winter Park High in Winter Park - 207 homes

Remarks: Welcome to this spacious and well-maintained two-story townhome nestled in the highly desirable Four Seasons community in the heart of Winter Park. Offering 2 bedrooms, 1.5 bathrooms, and 1,219 square feet of comfortable living space, this home features a functional floor plan designed for both everyday living and entertaining. The spacious kitchen offers abundant cabinetry, generous countertop space, and stainless steel appliances replaced in 2025, creating a practical and inviting setting for meal preparation and gatherings. The dishwasher and refrigerator were replaced in 2023, adding additional value and convenience. Adjacent to the kitchen is a dedicated dining area that can easily accommodate formal dining, a home office setup, or additional living space to suit your needs. The welcoming living room opens through French glass doors to a private, fully enclosed screened porch and fenced patio surrounded by mature landscaping. Complete with a metal storage closet, this outdoor space is perfect for enjoying your morning coffee, relaxing after a long day, or entertaining guests. Upstairs, both bedrooms are generously sized, with the primary bedroom featuring dual closets and a ceiling fan for added comfort. The second floor also features new vinyl plank flooring installed in 2026, offering durability and a modern touch throughout the bedroom level. A full bathroom serves the upstairs living area, while a convenient half bath is located downstairs for guests. Additional improvements include all plumbing piping replaced approximately five years ago, an electrical panel replacement completed approximately three years ago, and all electrical outlets replaced in 2026, providing additional peace of mind for future owners. Both bathrooms feature updated lighting fixtures installed in 2026. Additional features include a full-size stackable washer and dryer, ceiling fans and blinds throughout, and fresh interior paint completed in 2026, contributing to the home's move-in-ready appeal. Residents of Four Seasons enjoy an array of community amenities including three swimming pools, a clubhouse with fitness center, tennis courts, shuffleboard courts, and beautifully maintained grounds with mature trees and walking paths. Conveniently located just minutes from Ward Park, Winter Park Pines Golf Club, the YMCA, AdventHealth Winter Park, and the Center for Health & Wellbeing. Enjoy nearby shopping and dining along Aloma Avenue, including Publix, Sprouts, and Aldi, while the shops, restaurants, and entertainment of Park Avenue are less than 10 minutes away. Easy access to SR 436, SR 417, and SR 408 makes commuting simple, and Orlando International Airport is approximately 25 minutes away. Located within the highly rated school district of Brookshire Elementary, Glenridge Middle School, and Winter Park High School. Don't miss this opportunity to own in one of Winter Park's most sought-after communities. Schedule your private showing today!

Listing is courtesy of: COMPLETE REALTY STORE, LLC (321-377-0213)

Listing Agent: Laila Nieves (407-913-0244)

Remarks: Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a well-balanced and highly functional floor plan, the home offers a seamless blend of formal and informal living spaces ideal for both everyday living and elevated entertaining. At the heart of the home, the pristine chef’s kitchen opens effortlessly to the family room and is outfitted with a built-in Thermador French door refrigerator, custom lighted cabinetry, granite countertops, a six-burner gas range with pot filler, double ovens with warming drawer, and an oversized island designed for gathering. A beautifully appointed butler’s pantry with wine fridge and wet bar creates the perfect transition to the formal dining space. Tucked away for privacy, a dedicated home office or library offers a quiet retreat for work or study. The first-floor primary suite is a true sanctuary, featuring intricate ceiling detail, expansive windows, and private French door access to the outdoor living space. The spa-inspired primary bath includes a jetted tub, dual vanities, and two oversized walk-in closets. Upstairs, three generously sized secondary bedrooms and two additional baths—including a private en suite—provide comfortable accommodations, while a charming Juliet balcony offers picturesque views of the tree-lined street below. Step outside to an exceptional outdoor living experience designed for year-round enjoyment. The covered lanai features a fully equipped summer kitchen with built-in grill, custom copper hood, and beverage fridge for the warmest Florida days. The saltwater pool creates a resort-style setting, surrounded by lush landscaping and enhanced by upgraded lighting and smart technology. This meticulously maintained home has been extensively upgraded, including new HVAC systems for both levels, on-demand water heater, whole-house surge protection, updated LED lighting with dimmer controls, smart home integrations for pool, irrigation, security, and climate, as well as complete interior and exterior repainting with premium finishes. High-end reclaimed maple and beech wood flooring has been installed and is complemented by refined architectural details such as curved archways, custom millwork, and elevated designer fixtures. Additional highlights include a newly created wine room, epoxy-coated garage flooring, central vacuum system, and enhanced exterior features with added awnings and detailed craftsmanship. Situated on a gorgeous lot with added privacy and with garage doors thoughtfully positioned away from the street, this home offers both presence and practicality. Just a short stroll to Lake Mizell and minutes from the renowned dining, shopping, and cultural experiences of Park Avenue, this exceptional property combines timeless design, modern upgrades, and an unbeatable location.

Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)

Listing Agent: Liz Jones (407-619-6345)

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 Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and an offering rarely found in Winter Park, is the underground four-car garage. Designed to discreetly accommodate an impressive vehicle collection, the garage is complemented by a striking spiral staircase that rises from the basement through the main living level and continues to the second floor. The family room is nothing short of breathtaking, featuring bespoke millwork with integrated shelving, soft architectural lighting, and a dramatic fireplace wrapped entirely in marble. The kitchen is a culinary showpiece designed for those who expect nothing less than perfection. Calcutta marble countertops cascade across the space, paired with stunning custom cabinetry, and a professional-grade Thermador appliance suite. A dedicated dirty kitchen allows for discreet preparation, while an expansive walk-in pantry ensures effortless hosting and immaculate presentation. The primary bedroom wing features a spa-inspired bathroom finished in rich marble, featuring dual vanities, a freestanding soaking tub and an enormous walk-in closet with a separate washer and dryer. Upstairs, a dedicated laundry room and a spacious secondary living area provide flexibility for family living, guests, or relaxation. The lower level extends the home’s versatility, offering a workshop, dedicated holiday and seasonal storage, and seamless elevator access to the main level of the home. Outdoor living is equally impressive. A large covered exterior lanai with a pool bath and full summer kitchen creates a seamless indoor-outdoor lifestyle, ideal for entertaining year-round. The backyard is truly resort-inspired, featuring a large swimming pool, sunken fire pit, and spa, all set within a private, beautifully secluded outdoor setting. What ultimately sets 40 Palmer apart is not just its design or finishes, but its unmatched combination of luxury and location. Just minutes from Park Ave shopping and restaurants, moments from the famous Winter Park Golf Course, yet privately tucked away, this home offers a lifestyle that is both vibrant and exclusive. A truly rare opportunity to own a part of the exceptional standard of living delivered by Vimaro Homes.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Julie Christensen (407-592-2055)

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: Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

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

Listing Agent: Brian Teach (407-923-9313)

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: Price reduced for a quick sale, creating a fantastic opportunity for the right buyer. Don’t let this one slip away. Welcome to 241 W. Lake Sue Avenue, a rare offering in Virginia Heights, one of Winter Park’s most coveted and established neighborhoods. Set along a charming oak-canopied brick street and surrounded by multimillion-dollar estates, this beautifully updated pool home sits on an oversized 12,000-square-foot lot and offers a lifestyle that is increasingly difficult to find in Olde Winter Park. Designed for effortless indoor-outdoor living, the residence showcases sun-drenched interiors, soaring ceilings, architectural wood beam accents, travertine flooring, and inviting gathering spaces that overlook a private backyard retreat. The chef’s kitchen serves as the heart of the home, seamlessly connecting the living and dining areas while offering picturesque views of the pool, spa, and lush outdoor living spaces. The spacious primary suite provides a tranquil escape, featuring vaulted ceilings, a spa-inspired bath, and generous walk-in closet. Recent improvements, including a newer roof, updated HVAC system and ductwork, and a complete replumb, offer peace of mind and modern efficiency. What truly distinguishes this property is its location within Virginia Heights, where residents enjoy deeded access to a private Lake Virginia waterfront park. Just a short stroll away, homeowners have access to a private dock, canoe and kayak storage, open green space, and breathtaking lakefront views across from Rollins College, an amenity few Winter Park neighborhoods can offer. Located moments from the boutiques and fine dining of Park Avenue, as well as nearby parks, cultural attractions, and top-rated schools, this exceptional property combines timeless charm, modern comfort, and an unparalleled Winter Park lifestyle. Opportunities to own in Virginia Heights are limited. Opportunities with private lake access, an oversized lot, and a resort-style backyard are even rarer. Priced below market value due to updates needed. Recent updates include a new A/C system (2023), new A/C ductwork (2023) and a newer roof (2021), replumbed (2026). Enhance the existing residence or build a new home from the ground up, this property presents an exceptional chance to secure a legacy worthy homesite in Winter Parks most sought-after locations.

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

Listing Agent: Ken Dalton (407-928-8587)

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. Totally traditional luxury single-story home is located in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre beautifully landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and COMPLETELY re-done. Multi-generational potential as this home has a complete attached guesthouse. Interior layout boasts formal living with bay window and tall ceilings, dining room with antiqued mirror set into extensive moldings and trim, plus a library/den with a tongue and groove wood vaulted ceiling and a wall of bookshelves and built-ins. The spacious family room with a white-washed brick, wood-burning fireplace wall and vaulted ceiling is all open to the breakfast area and kitchen. The gourmet kitchen features custom inset cabinet drawers and doors, white marble slab backsplashes, Kohler farmhouse sink and a large island with a deep prep sink. The kitchen is a chef’s delight with a 48-inch Viking gas range, Viking warming drawer, Jenn-Air refrigerator, wine refrigerator and a Bosch dishwasher. The kitchen also has amazing storage and two large pantries. There are a total of four bedrooms (the 4th is currently the living room of the in-law suite suite) and three full baths. Throughout the home are beautiful real ¾-inch-thick and 5-inch-wide plank walnut floors, beam and coffered ceilings, French doors, oversized picture windows and designer accents lighting. French doors off the family room open to seamlessly blend indoor and outdoor living, leading to a covered lanai with travertine stone tile overlooking a resort and entertaining backyard. Huge swimming pool and a 30-by-15-foot pergola with Bistro lighting, which is a wonderful spot to relax, dine and play, all on a tiny pebble surface, like an Italian driveway! French garden fountain, rose garden and synthetic turf for pets make the backyard a haven. The home’s floor plan offers a desirable layout with huge primary bedroom with a generously sized un-suite bath with dual sink counters, amazing Roman walk-in shower, jetted tub with bubblers and two large walk-in closets. Guest wing features a spacious bedroom and bath and the West Wing is a full In-law apartment, including a bedroom, handicapped bath, full kitchen and its living room (which would be easy to be converted back into the 4th bedroom - plans available). Imagine having a wonderful space for in-laws or an adult family member that needs space of their own. Just a short drive or bike ride from Park Avenue, this open and inviting home has easy access to downtown Winter Park, AdventHealth, downtown Orlando and is zoned for A-rated schools. Surround sound through most of the house and CAT 6 wiring throughout. Recent additional remodeling and updating have taken place including all new windows, paint inside and out, as well as a new roof and gutters in 2022. A detailed list of all renovations is available upon request.

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

Listing Agent: Jan Walker (407-718-9644)

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)