Homes for Sale Near Winter Park High in Winter Park - 201 homes

Remarks: This custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set apart for quiet pursuits. The chef’s kitchen opens naturally to the great room and boasts a large island, top-of-the-line Thermador appliances, complemented by the sleek quartz countertops that offer both style and functionality. Conveniently equipped with two sets of washers and dryers, this home ensures efficiency and ease for the busiest of households. Retreat to the master suite, where luxury meets serenity. A massive walk-in closet provides ample storage, while the spa-like master bath invites relaxation with its elegant design and premium features. The indoor outdoor flow is easy with the huge set of glass sliders leading to the covered porch equipped with drop down screens. Enjoy the summer kitchen and sparkling pool while entertaining family and friends. This home is a true gem that combines thoughtful details with sophisticated style.

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

Listing Agent: Matthew Burks (407-257-5347)

Remarks: One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring, recessed lighting, and all new modern fixtures. The entryway features comfortable seating, built in cabinets with an electric fireplace and wine refrigerator. The sleek, updated kitchen offers a gas range, stylish finishes and a functional layout perfect for everyday living and entertaining.  Retreat to the spacious primary bedroom with a fabulous ensuite bath, complete with a soaking tub, dual vanities, a large separate shower, and a generous walk-in closet. A split-bedroom floor plan provides added privacy and comfort. The fully fenced backyard offers plenty of room for a pool and includes private parking for a boat on the side of the home. Whether you enjoy the home as it is or choose to build your dream residence, the possibilities are endless. New roof installed in 2022.

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

Listing Agent: Cindy Kuykendall (407-718-3235)

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: Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street in one of Winter Park’s most walkable and desirable neighborhoods. The asset is being delivered with strong in-place cash flow. Current rents provide additional value-add potential, with at least one unit currently operating below market rental rates, creating an opportunity for future income growth and increased returns. The block construction property has undergone significant capital improvements, including updated electrical panels (2019), new hot water heater (2019), new windows (2017), and a new roof (2015). Two of the three units were completely renovated in 2019, offering updated interiors while maintaining the charm and character of the surrounding neighborhood. The front unit includes washer/dryer hookups, while the middle and rear units share a common exterior-access washer/dryer area. Utilities are currently included in the rent and have been factored into annual operating expenses. This is a rare opportunity to acquire a stabilized multifamily asset with strong rental demand driven by proximity to Rollins College, downtown Park Avenue, dining, shopping, and employment centers throughout Winter Park.

Listing is courtesy of: THE REAL ESTATE PRINCIPLE, INC (407-739-7209)

Listing Agent: Brian Opre (407-739-7209)

Remarks: Welcome to this thoughtfully expanded one-story home in Winter Park’s coveted “Tree Streets” neighborhood. A paved double drive and circular driveway create a gracious arrival with ample guest parking. Originally built in 1962 and expanded over time, this home offers a flexible floor plan designed for comfortable everyday living and effortless entertaining. Spacious living areas and the primary suite open to a stunning garden-like backyard, seamlessly connected by a full-length covered portico perfect for enjoying Florida’s indoor-outdoor lifestyle. The main hallway leads to the primary and guest bedrooms, along with a quiet sitting room overlooking the charming front porch. Expanded in the early 2000s, the private primary suite includes a generous bath with an oversized whirlpool tub, dual vanities, separate shower, dressing table, private water closet, and a spacious walk-in closet. At the heart of the home, the kitchen features solid wood cabinetry and solid-surface countertops, opening to the central family room with a traditional fireplace and casual dining area, all adjacent to the formal dining room. Just off the kitchen, a large flex space offers extensive built-ins, a desk area, dry bar, wine refrigerator, and integrated washer and dryer ideal for a home office, hobby room, or additional entertaining space. Located just minutes from Park Avenue, enjoy easy access to fine dining, boutique shopping, cafés, museums, and year-round community events. This one-story home offers abundant living space, exceptional entertaining areas, and a beautifully landscaped backyard complete with pool and outdoor living spaces all situated on a generous 77 x 150 lot.

Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)

Listing Agent: Anne Rogers (407-649-4141)

Remarks: Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s exclusive Chain of Lakes-Lake Virginia, Lake Mizell, Lake Osceola, Lake Maitland, Lake Nina, and Lake Minnehaha. Morning sunrises and golden afternoon sunsets create unforgettable moments to enjoy privately or share with family and friends. Built in 2008, this exceptional home welcomes you with a stunning rotunda accented by stained glass panels, setting the tone for the refined design found throughout. Vaulted recessed ceilings enhance the open floor plan, filling the home with natural light and architectural elegance. Thoughtfully curated details and custom finishes are showcased in every space. Offering approximately 5,051 square feet, the home features four spacious bedrooms, each with its own en suite bathroom. The owner’s suite is a private retreat with picturesque canal views and luxurious built-in features. The spa-inspired owner’s bath includes dual vanities, designer textiles, strategic lighting, expansive walk-in closets, a steam shower with dual stations and multiple shower heads, a Jacuzzi tub, bidet, linen storage,and a private water closet. Designed for effortless entertaining, the gourmet chef’s kitchen is both functional and beautiful. Highlights include an oversized working island, high-top bar seating,Thermador gas range,Thermadore double ovens,Thermadore refrigerator, wine cooler, hidden lighted walk-in pantry and multiple prep areas. The kitchen flows seamlessly into the formal dining room and the expansive great room, which showcases floor-to-ceiling views of the lushly landscaped backyard, paver patio and serene Venetian Canal water view. A stunning library with floor-to-ceiling canal views features a custom gas fireplace and built-in shelving, perfect for displaying books and treasured collections. The first floor features a convenient half bath adjacent to the laundry room, along with a lovely powder room ideal for guests. Upstairs, a striking staircase leads to three additional bedrooms and two bathrooms. One bedroom room has a private en-suite bathroom and the other bedrooms share an adjoining en- suite bath. There are two oversized, versatile gathering spaces complete with a built-in wet bar and beverage refrigerator. A spacious living area overlooks the canal and opens to an upper-level lanai-ideal for outdoor entertaining. This level also includes a home theater and flexible space suitable for an additional bedroom, office, or recreation room. Location is unmatched. Situated in the heart of Winter Park, this home offers easy access to both Winter Park and Maitland amenities. Enjoy Park Avenue dining, shopping, art festivals, farmers markets, outdoor concerts, scenic walking and biking trails, and beautiful green spaces. Zoned for top rated OCPS schools: Dommerich Elementary, Maitland Middle School, and Winter Park High School. This remarkable Winter Park Canal home combines timeless style, exceptional craftsmanship, private dock access, Venetian Canal frontage, and direct connection to the Winter Park Chain of Lakes-all in one of Central Florida’s most sought-after locations.

Listing is courtesy of: PALM PROPERTIES OF CF, INC. (407-467-0020)

Listing Agent: Felicia Donatelli (407-467-0020)

Remarks: Under contract-accepting backup offers. Motivated Sellers! Priced at $35,000 below recent Appraisal Price on this amazing oversized lot! Walk into this home with equity from the start! Located in one of Winter Park’s most desirable and picturesque neighborhoods, Timberlane Shores! This stunning five-bedroom residence has been recently renovated in an elegant, European style blending timeless character with modern luxury. Situated on over one-third of an acre, the property is accented by majestic oak trees and lush Florida-native landscaping that's creates a private and serene retreat where peacocks often roam freely through your yard. The heart of the home is the beautifully designed chef’s kitchen, featuring quartz countertops, a gas range with custom hood, double built-in convection ovens, stainless steel appliances, a wine refrigerator, and a well-appointed butler’s pantry—perfect for entertaining. The light-filled family room is open to the kitchen and showcases a wood-burning fireplace, custom built-ins, and an original brick accent wall that adds warmth and architectural charm. Engineered hardwood flooring and preserved original terrazzo floors run throughout the home, enhancing its quality designer choices but also an inviting feel. The flexible floor plan offers five spacious bedrooms, three full bathrooms, and two half baths, providing ample space for both everyday living and hosting guests. Expect to be impressed by the elegant owner's suite with a sizable walk-in closet and stunning ensuite bathroom featuring dual vanities, beautiful cabinetry with lots of storage and a generously sized soaking tub. Outdoor living is equally impressive, with a resort-style heated pool complete with a sun shelf, an outdoor kitchen with a built-in grill, sand volleyball court and a large deck featuring built-in seating and a fire pit—ideal for gatherings or relaxing evenings under the stars. Zoned for Winter Park’s top-rated schools, this exceptional home is just a five-minute drive to Park Avenue’s renowned shopping and dining, and walking distance to Baldwin Park’s vibrant downtown, offering shops, restaurants, and a Publix. This is a rare opportunity to own a thoughtfully renovated home in one of Winter Park’s most beautiful and sought-after settings. Experience the rare combination of European-inspired luxury, resort-style outdoor living, and an unparalleled Winter Park location. Be sure to watch the video tour and virtual property walkthrough in the attachments. Better yet, schedule a private showing today and discover a home that truly defines elevated Florida living.

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

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

Remarks: Welcome to this thoughtfully updated Winter Park home ideally on a spacious corner lot with a two-car garage offering excellent storage and everyday convenience. This home offers a flexible layout featuring two bedrooms plus an office that can function as a third bedroom, ideal for working from home or accommodating guests. Hardwood floors run throughout, adding warmth and character. Major system updates have been completed, including a 2024 metal roof and 2025 HVAC system, providing peace of mind for the next owner. Additional exterior improvements include new soffits and gutters, fresh exterior paint in 2025, a whole-home surge protector, and updated breezeway or office door and windows installed in 2024. Inside, you will find a well-equipped kitchen with Samsung appliances, including a range, microwave, dishwasher and a 2023 refrigerator, along with a 2020 Samsung washer and dryer. Comfort and efficiency have also been enhanced with replaced air ducts in 2016, an Ecobee smart thermostat and updated ceiling fans. Smart home features include a Logitech Circle View wired doorbell, smart blinds and updated smoke detectors, providing modern convenience throughout the home. The property sits toward the rear of the lot, creating a private, fenced yard space ideal for pets, outdoor enjoyment or entertaining. An irrigation system is also in place to help maintain the landscaping. In the desirable Winter Park area and zoned for highly regarded Winter Park schools, this home offers a combination of location, updates and flexibility. With major systems addressed, this home presents a move-in-ready opportunity and being sold as is.

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

Listing Agent: Audra Wilks (407-252-8582)

Remarks: Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

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

Listing Agent: John Mcdade (407-721-7275)

Remarks: Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented by a cozy fireplace, leading into the spacious formal living room with its own gas fireplace and the elegant formal dining room. Gorgeous heart-of-pine floors run throughout the first floor, adding warmth and authenticity. The kitchen has been thoughtfully updated with top-of-the-line Thermador and Sub-Zero appliances, including a 72-bottle Sub-Zero wine tower and refrigerated drawers, making it as functional as it is beautiful. Open to the family room, complete with rich woodwork and a third gas fireplace, this space is ideal for gathering and entertaining. The primary suite is conveniently located on the first floor and features an updated ensuite bath. Upstairs, three additional bedrooms and two renovated baths provide comfortable accommodations for family and guests. A charming “sleeping room,” now used as a light-filled office, overlooks picturesque New England Avenue. Adding to the property’s appeal is a detached two-story guest house offering a full bedroom, full bath, sitting area, and kitchen—perfect for extended stays or as a private retreat. Outdoor living is equally inviting, with a back porch for grilling, a separate patio for lounging and mature landscaping that enhances the home’s curb appeal. Architectural details available for adding an oversize two-car garage, if desired. Perfectly positioned on the same block as The Alfond Inn and just two short blocks from the renowned Park Avenue district, this home offers not just refined living, but a downtown walkable lifestyle that is truly unmatched. Park Avenue is the cultural heart of Winter Park—a tree-lined promenade alive with award-winning restaurants, boutique shopping, art galleries and historic landmarks. Residents enjoy a vibrant calendar of events, from the Winter Park Farmers’ Market and seasonal art festivals to beloved holiday parades and outdoor movies under the stars. Here, every day is an invitation to experience the best of Central Florida living—whether it’s sipping coffee at a charming café, strolling to or after dinner surrounded by beautiful ambience, or embracing the timeless traditions that make Winter Park so treasured.

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

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

Remarks: Under contract-accepting backup offers. New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator, that offers nearly 770 square feet of multi-use space. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...

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

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

Remarks: Under contract-accepting backup offers. Discover refined living in this stunning custom-built home located in the coveted community of Windsong. Thoughtfully designed and expertly constructed by Goehring & Morgan, this four-bedroom, 4.5 bath residence offers a perfect balance of elegance, comfort and functionality. From the moment you enter, the home impresses with its airy, open-concept design, ideal for both relaxed living and effortless entertaining. The kitchen serves as a focal point, appointed with leathered granite countertops, a generous center island with seating and a seamless connection to the inviting family room, where a gas fireplace adds warmth and charm. Walls of sliding glass doors extend the living space outdoors to a beautifully designed lanai, complete with a gas-heated pool and a fully equipped summer kitchen featuring a grill, sink, beverage refrigerator and additional seating area. The main level also includes a well-appointed guest suite with a private bath, offering comfort and privacy for visitors, along with a dedicated office or study space. Upstairs, a spacious bonus room provides flexibility for a media room, playroom or lounge, while two additional bedrooms accompany the expansive primary suite. The primary retreat is designed for relaxation, showcasing dual walk-in closets and a luxurious bath with a freestanding soaking tub, oversized shower and separate vanities. High-end finishes are showcased throughout, including travertine flooring across the main living areas and rich wood floors that continue through the bedrooms, staircase, upper hallway and bonus room. As a resident of Windsong, you’ll enjoy access to exceptional community amenities, including resort-style pools, a splash pad, playground and access to the scenic Winter Park Chain of Lakes, creating a lifestyle that is both vibrant and serene in one of Central Florida’s most desirable settings.

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

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

Remarks: Under contract-accepting backup offers. Remodeled two-bedroom, one-and-one-half-bath residence in the Mead Garden Condominium community. Spanning 908 square feet, this first-floor home features a move-in-ready interior with an open-concept layout, luxury vinyl plank flooring throughout, and in-unit washer and dryer hookups, a rare offering within the building, located in the half bath. The kitchen includes raised-panel cabinetry in a warm wood tone, a mosaic tile backsplash and black appliances, including a refrigerator, range and dishwasher. A curved island with additional storage provides space for casual dining and entertaining. The kitchen opens to the dining area and living room, highlighted by a chandelier and access to a sunroom with sliding glass doors overlooking the community pool and landscaped grounds. The primary bedroom offers natural light from a pool-facing window, a walk-in closet, and an en-suite bath with a walk-in shower featuring white subway tile and a black-and-white mosaic tile floor. The second bedroom provides flexible space for guests or a home office. A half bath includes a pedestal sink, decorative mirror and gold-tone fixtures. Additional features include crown molding, updated plumbing fixtures, new windows and a leaded-glass front entry door. Near Azalea Park, Seven Oaks Park, Mead Botanical Garden and the Orange Avenue district with dining and retail. Close to Rollins College and Park Avenue.

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

Listing Agent: Drew Henner (407-406-0662)

Remarks: Highly coveted Winter Park! 40+ Pictures! This stunning 2-story end unit offers the epitome of modern convenience and elegant living; this residence provides the ideal "lock and go" lifestyle. Step through the charming covered front porch into the inviting open living area, adorned with abundant natural light, gleaming real wood flooring, and exquisite crown molding. Hosting gatherings is effortless in the expansive kitchen featuring granite countertops, premium wood cabinetry, stainless steel appliances, and a generously sized pantry. A half bathroom and utility closet complete the ground floor, where ceilings soar to a height of 9'3". Ascend to the upper level to discover the luxurious master bedroom suite, boasting French doors leading to a balcony, a spacious walk-in closet, and a lavish ensuite bath featuring dual sinks, a glass-enclosed shower, and a relaxing garden tub. Two additional bedrooms await upstairs, both sharing access to a covered porch perfect for savoring your morning coffee. The second full bathroom and laundry closet round out the upstairs layout, with one of the bedrooms boasting its own walk-in closet. New 2026 Updates to include New Roof Feb 2026, Carpet, New main DBL pane windows, complete interior paint, light fixtures/fans. You will appreciate the convenience of an attached 2-car garage designed for SUVs, two covered entries, adorned with mature trees. Solid build quality utilizing concrete block construction on both floors. Located just a short stroll from the vibrant East End Market and various shopping, this residence also offers easy access to upscale Park Avenue, Rollins College, Baldwin Park, Florida Hospital, and the serene beauty of Leu Gardens. Zoned for Audubon and Winter Park HS, this home truly has it all!

Listing is courtesy of: NICOLE-HUDSON REALTY CORP (407-491-5488)

Listing Agent: Edward Rice, Jr (407-353-0331)

Remarks: Under contract-accepting backup offers. Beautifully updated condo in a prime Winter Park location! This move-in ready unit features a beautifully renovated kitchen, updated bathrooms, and tile flooring throughout, offering a modern and low-maintenance living space. Ideally situated on South Semoran Blvd, you’ll love the convenience of being just minutes to Baldwin Park, Full Sail University, UCF, and Downtown Winter Park, with easy access to shopping, dining, and major roadways. One of the few units in the community featuring a screened patio AND an in-unit washer and dryer, providing added convenience and everyday ease. Low HOA fees make this an excellent opportunity for both homeowners and investors alike. Whether you're looking for a primary residence or an income-producing property, this condo stands out with its upgrades, location, and unique features. NEW ROOF April 2026! Call today to schedule your private showing.

Listing is courtesy of: SHAWFIELD REALTY GROUP (407-963-7749)

Listing Agent: Carrie Sue Shawfield (407-963-7749)

Remarks: 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: Under contract-accepting backup offers. Stop the car! Develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or 15,000sq/ft. Next to the proposed Winter Park Commons project, walk to Winter Park Village, Hannibal Square, WP9 and Park Ave for top shopping, dining and entertainment. Don’t miss this unique opportunity! PROPERTY SOLD AS-IS. VALUE IS IN THE LAND. NO REPAIRS.

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

Listing Agent: Lisa Gould (407-721-7612)

Remarks: Under contract-accepting backup offers. Welcome home to the Winter Park Pines where the trees line the streets and the mailman delivers to your door. This beautifully maintained 3-bedroom, 2-bathroom home offering 1,873 square feet of comfortable living in the highly desirable and serene Winter Park Pines community. This light-filled residence features a thoughtfully designed split floor plan with high ceilings, fresh interior paint (2026), skylights, and laminate and tile flooring throughout, creating a bright and inviting atmosphere from the moment you enter. The open living and dining areas are anchored by a charming wood-burning brick fireplace, while crown molding, ceiling fans, and French doors add both style and functionality throughout the home. The well-appointed kitchen includes white and gray cabinetry, stainless steel appliances, and a convenient pantry closet, perfect for both everyday living and entertaining. It flows seamlessly into the main living areas, making it easy to gather with family and friends. The spacious primary suite offers a private retreat, thoughtfully separated from the secondary bedrooms, and features a walk-in closet with custom built-ins, ceiling fan, and French doors leading to the expansive and shaded backyard. The renovated en-suite bathroom showcases double vanities and a beautifully tiled shower with frameless glass enclosure. The secondary bedrooms are well-sized and versatile, with easy access to the renovated hall bathroom featuring a granite double vanity, navy cabinetry, and direct access to the backyard, ideal for indoor-outdoor living. Step outside to enjoy a fully fenced, landscaped backyard situated on a generous .22-acre lot. The expansive patio with terracotta tile flooring provides the perfect space for outdoor dining, entertaining, or simply relaxing in a private setting. Additional highlights include a two-car garage and a Ring home security and surveillance system for added peace of mind. Located just minutes from top-rated Winter Park schools, the Cady Way Trail, Winter Park Pines Golf Course, Advent Health Winter Park campus, Crosby Wellness Center and a variety of shopping and dining options, this home offers both tranquility and convenience. Residents also enjoy access to nearby community amenities including a pool, playground, beach volley ball courts and tennis/pickleball courts. With close proximity to major roadways, downtown Winter Park, and Orlando International Airport, this property truly combines comfort, location, and lifestyle. Don’t miss the opportunity to make this exceptional home yours in one of Winter Park’s most sought-after neighborhoods. Roof 2020, HVAC 2022, Plumbing 2014, Water Heater 2021.

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

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

Remarks: Under contract-accepting backup offers. Discover one of the sought-after communities in Winter Park, Kenilworth Shores, where mature oak trees frame the streets, spacious parks serve as gathering ground for families and peaceful walking trails weave through the neighborhood. Centrally within arm’s reach of luxury shopping on Park Avenue in Winter Park, stunning lake views and parks in Baldwin Park, and chef-driven local restaurants in Audubon Park. Kenilworth Shores isn't just a location, it's a community, and this four-bedroom, two-bath Florida ranch is your family's invitation to join. At nearly 1,600 square feet, this home provides charm, function and thoughtful design with upgraded LVP flooring flowing throughout the easy layout. Old world brick detailing gives the exterior genuine curb appeal, while a thoughtfully renovated interior delivers a ready-to-move-in home. A gorgeous brick fireplace anchors an open kitchen, family and dining room combination, with loads of natural light and function to entertain in style. The kitchen is outfitted with white shaker custom cabinetry, granite counters, a soft glass tile backsplash, stainless steel appliances and glass pendant lighting over bar seating. A desirable split-bedroom plan provides privacy for guests, while the primary suite opens to the backyard and includes a completely renovated main bath. The flexible fourth bedroom is outfitted with a custom-designed built-in Murphy bed system with flanking closets and storage. Sitting off the primary living area, this bedroom provides options to fit flexible needs such as home office, guest room, playroom or secondary family space. Go into the backyard and experience your personal Florida oasis with a screened covered porch and grand Florida pool to cool off in the heat of summer. The surrounding, spacious yard is adorned with artificial turf (beautiful, durable and effortlessly low maintenance), complete with a putting green that will make this yard the destination for every playdate, summer barbecue or birthday party. Completed upgrades include new roof (2021), resurfaced pool (2021), new irrigation and well (2022), new wood fence (2023), new dishwasher and built-in microwave (2023), HVAC (late 2023), new washer and dryer (2024), and new pool pump motor (2025). The best part of this special neighborhood is the connected community. Zoned for Brookshire Elementary, Glenridge Middle and WP High, some of the best Orange County Schools. Cady Way Park is nearby with a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and bike trails. This location checks all the boxes. Schedule your private showing today.

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

Listing Agent: Alison Mosley (407-304-6458)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 2-bedroom, 2-bathroom first-floor corner-unit condo in Winter Park, offering comfort, convenience, and peace of mind, with major updates completed in 2026. These upgrades were specifically implemented to enhance the property's aesthetic appeal and energy efficiency. The exterior updates include replacing all windows with single-hung, double-pane, low-E glass vinyl units and installing a matching vinyl sliding patio door. Interior improvements include new interior and closet doors, 5" baseboards, and fresh paint on all ceilings, walls, and trim. Additionally, all ceilings have been modernized to a smooth finish, and 2" cordless faux-wood blinds have been installed throughout. Both bathrooms have been fully renovated with new flooring, wall tiling, tubs, toilets, vanities, and updated fixtures. The kitchen has also been completely transformed with new cabinetry, granite countertops, a modern faucet, and a full suite of stainless steel appliances. Located near the University of Central Florida, Full Sail University, and SR-417, this condo offers quick access to major commuting routes, shopping, dining, and everyday essentials. Whether you're looking for a primary residence or a long-term investment opportunity, this property combines location, functionality, and value in one of Orlando's most connected areas.

Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)

Listing Agent: Reza Shirzad (407-234-1515)