Homes for Sale Near Glenridge Middle in Winter Park - 80 homes

Remarks: One of the lowest-priced homes in Winter Park with nearly 1,400 square feet, a private carport, screened balcony, community pool, and easy access to UCF, Full Sail, Rollins, Valencia East, Orlando International Airport, and downtown Orlando! The monthly HOA covers many exterior maintenance items so you can enjoy low-maintenance living.This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were professionally serviced, including roller replacement, track repairs, and installation of new locks to ensure smooth, secure operation. Deluxe vinyl fencing was installed throughout the community by the HOA replacing the older wooden fencing. The fencing was replaced with the vinyl after the listing photos were taken, please view the video to see the replacement vinyl fencing. Enjoy convenient features including an in-unit washer and dryer combo, storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens to a large screened-in balcony. Whether you’re a first-time home buyer, student, investor, or looking to make your move into Winter Park, this home offers affordability, convenience, and plenty of potential!

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

Listing Agent: Karen Salter (352-227-0451)

Remarks: Under Construction. Under Construction. A timeless expression of modern luxury, this exceptional new residence by LUIH Luxury Homes brings together thoughtful architecture, designer finishes, and refined craftsmanship in one of Winter Park’s most desirable neighborhoods. Situated on an oversized homesite along a quiet, tree-lined street, the home offers approximately 4,018 square feet of beautifully designed living space with five bedrooms, four-and-a-half bathrooms, and an open floor plan created for both everyday living and effortless entertaining. Natural light fills the interior, highlighting wide-plank wood flooring, custom millwork, curated designer lighting, and a warm, neutral palette that creates an inviting atmosphere throughout. The main living areas transition seamlessly from one space to the next, anchored by a spacious family room featuring a sleek linear electric fireplace and expansive sliding glass doors that open to the outdoor living area. Designed to be both functional and beautiful, the chef’s kitchen serves as the centerpiece of the home. Custom shaker cabinetry, waterfall-edge quartz countertops, a designer tile backsplash, and an oversized island are complemented by a premium Thermador appliance package, including a gas cooktop, built-in refrigerator, microwave and oven combination, dishwasher, wine refrigerator, and designer vent hood. A generous walk-in pantry and an adjacent wet bar further enhance the space, while the dining area offers an elegant setting for everything from casual family meals to formal entertaining. The first-floor primary suite provides a peaceful retreat with direct access to the covered lanai and pool. The adjoining bath is designed with a spa-inspired aesthetic, featuring a freestanding soaking tub, an oversized glass-enclosed shower, dual vanities with quartz countertops, designer fixtures, and a spacious custom walk-in closet. Also on the main level are a private office and an additional bedroom with an en suite bath, offering flexibility for guests, multigenerational living, or a dedicated workspace. Upstairs, a generous loft creates an ideal secondary gathering area, while three additional bedrooms and well-appointed bathrooms provide comfortable accommodations for family and visitors. Outdoor living is thoughtfully integrated into the home’s design. The covered lanai includes a fully equipped summer kitchen overlooking the resort-style pool and spa, creating an inviting setting for year-round entertaining. A spacious backyard offers additional room to relax, play, or personalize the outdoor experience. Located just minutes from the renowned shopping, dining, and cultural attractions of Park Avenue, residents can enjoy favorites including Prato, AVA Mediterranean, Boca Winter Park, Hillstone, The Ravenous Pig, Choulala Fine Pastries, and Barnie’s Coffee & Tea Co. Nearby outdoor destinations include Mead Botanical Garden, Kraft Azalea Garden, Central Park, Cady Way Park, Dinky Dock Park, and the Winter Park Golf Course. Rollins College, AdventHealth Winter Park, and Winter Park High School are also conveniently located nearby. Combining timeless architecture, thoughtfully selected finishes, and an exceptional location, this residence presents a rare opportunity to own a newly constructed luxury home in the heart of Winter Park.

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

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Welcome to Whisperwood, where space, convenience, and investment potential come together in one exceptional opportunity. This rare gem is a beautifully maintained 2-bedroom, 2.5-bath residence offering a rarely available townhome-style floor plan that combines generous living spaces, exceptional functionality, and outstanding investment potential. The spacious multi-level layout features expansive living and dining areas, a convenient guest powder bath, and two oversized dual primary-style suites, each with its own private bathroom. The thoughtfully designed floor plan delivers the privacy, flexibility, and comfort today's buyers are seeking. Natural light fills the interior, while the private balcony provides the perfect retreat for morning coffee or evening relaxation. A private fenced backyard opens to a lush green space, creating a peaceful outdoor setting rarely found in condominium living. Additional highlights include a covered carport, dedicated laundry closet, abundant storage throughout, and a large second-floor storage room. Residents enjoy a truly low-maintenance lifestyle with access to Whisperwood's sparkling community pool, clubhouse, and beautifully landscaped grounds. The HOA provides exceptional value by covering exterior building maintenance, grounds maintenance, water, sewer, trash, pest control, pool maintenance, recreational facilities, and common area upkeep. Perfectly positioned near SR-417, Goldenrod Road, and University Boulevard, this prime location offers seamless access to Downtown Orlando, Winter Park, Orlando International Airport, major employment centers, premier shopping and dining destinations, and Central Florida's world-famous attractions. For investors, this property represents a compelling income-producing opportunity. Currently tenant-occupied, offers immediate cash flow, Its strategic location near UCF, Full Sail University, Valencia College, and Seminole State College supports strong, year-round rental demand, making it an attractive move-in ready investment with enduring appeal. Whether you're searching for a primary residence, a low-maintenance lifestyle, or a strategic addition to your investment portfolio, this exceptional Whisperwood residence offers the perfect blend of space, location, convenience, and value.

Listing is courtesy of: PARKVIEW REAL ESTATE (407-312-6472)

Listing Agent: Miranda Azer (407-312-6472)

Remarks: Investor Special with Endless Potential in Winter Park! Opportunity knocks with this first-floor 2-bedroom, 2-bath condominium located in a great location in Winter Park. Whether you’re looking for your next renovation project, income-producing rental, or affordable entry into the Winter Park market, this property offers exceptional upside potential. Featuring a functional floor plan, spacious living areas, and a desirable ground-floor location, this condo is ready for your vision and updates. With the right improvements, this hidden gem can be transformed into a highly desirable residence, flip or investment property. Located just minutes from top-rated dining, shopping, major employment hubs, and a desirable school district, this property sits in a proven area for strong rental demand. SOLD AS-IS. Bring your imagination and contractor—this is the opportunity you’ve been waiting for!

Listing is courtesy of: VALENCE REALTY GROUP (407-797-5034)

Listing Agent: Cyndy Valence (407-810-3434)

Remarks: Cute as a button and move-in ready! This charming top floor 1-bedroom, 1-bath condo offers a bright, airy feel with an open-concept layout designed for comfortable living. Literally just steps away, you will enjoy peaceful views overlooking the hot tub and community pool from your private retreat above it all! The updated kitchen features beautiful white cabinetry with SOFT-CLOSE DRAWERS, providing both style and functionality. The spacious living area is enhanced by a vaulted ceiling that creates an expansive feel and allows natural light to pour in throughout the day. The primary bedroom continues the open, inviting atmosphere with vaulted ceilings and a generous walk-in closet. The bathroom offers a raised-height vanity with ample countertop space, making your daily routine both convenient and comfortable. This unit also comes with an INTERIOR LAUNDRY so you don’t have to worry about going off-site! Whether you’re relaxing at home on your SCREENED PATIO, enjoying the pool or hot tub, or taking in the view from your top floor location, this condo is the perfect blend of charm, comfort, and convenience. Come see it today!

Listing is courtesy of: VALENCE REALTY GROUP (407-797-5034)

Listing Agent: Chuck Valence (407-797-5034)

Remarks: Located in Winter Park Pines, this 4-bedroom, 2-bath home offers a warm, flexible layout with comfortable living spaces and everyday functionality throughout. With 1,596 square feet, the home provides room to gather, relax, entertain, and adapt to changing needs over time. Inside, the floor plan includes both a living room and a separate family room, creating useful separation for daily life. One of the bedrooms has been converted into a large closet and dressing room, offering generous storage while still allowing the option to easily convert the space back into a traditional fourth bedroom if desired. The backyard extends the home outdoors with a patio and cobblestone brick area that is well suited for entertaining, outdoor dining, or quiet evenings at home. Set within the established Winter Park Pines community, the home offers sidewalks for excellent walkability, with Cady Way Trail just steps from your door for morning runs, bike rides, and everything in between. Nearby, Cady Way Park adds even more to the neighborhood lifestyle with its pool, tennis and pickleball courts, playground, and beach volleyball, while Park Avenue offers boutique shopping and exceptional dining just minutes away. UCF, Rollins College, and Full Sail University are all within easy reach, along with AdventHealth Winter Park and Orlando International Airport. Zoned for top-rated Winter Park schools, this home combines comfort, convenience, and the everyday appeal that continues to make Winter Park Pines one of Winter Park’s most established neighborhoods.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Melissa Johnson (407-681-4393)

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: Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink and an expansive island designed for gathering and entertaining. The first-floor primary suite offers a private retreat with a completely reimagined spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and upgraded walk-in shower. Designed for comfort and entertaining, the home also features a dedicated office and an upstairs loft with a custom dry bar and beverage refrigerator. Outdoors, the backyard lives like a private resort-style oasis, complete with a saltwater pool and spa, sun shelf, travertine decking, electronic roll-down screens and a fully equipped outdoor kitchen designed for year-round enjoyment. Lush new backyard landscaping completed in May 2026, including enhanced privacy elements, creates an intimate outdoor setting rarely found this close to the heart of Winter Park. Additional highlights include updated irrigation supported by a private well, a new downstairs HVAC system and a home warranty provided for the buyer at closing. Move-in ready and impeccably maintained, this residence offers refined living in one of Winter Park’s desirable settings.

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

Listing Agent: Michelle Hochfelder (407-221-5073)

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: 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. 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: 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: 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: 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: A PRIVATE RESORT-STYLE SANCTUARY IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF | Saltwater Pool & Spa | Smart Home | Minutes to Park Avenue Welcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled within one of Winter Park's most desirable neighborhoods and just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom Mid-Century Modern residence delivers an extraordinary lifestyle defined by elegance, wellness, and privacy. Thoughtfully designed with a Zen-inspired aesthetic, the home seamlessly blends clean architectural lines with warm natural elements to create a living experience that feels refined and restorative. From the moment you arrive, an atmosphere of calm surrounds you, offering a peaceful escape while remaining moments from everything Winter Park has. Inside, soaring 10-foot ceilings, expansive walls of glass, and wide-plank engineered hardwood flooring create bright, open living spaces filled with natural light. A stunning semi-floating steel staircase with solid whiteoak treads serves as a dramatic architectural focal point, while designer Restoration Hardware lighting adds warmth and sophistication throughout. The main living area was designed for entertaining and everyday luxury. A sleek Dimplex fireplace anchors the great room, complemented by a custom wine bar. At the heart of the home, the chef's kitchen showcases a waterfall island, premium quartz countertops, striking marble backsplash, double-stacked cabinetry, and a custom pantry. High-end Samsung smart appliances, including a Family Hub refrigerator, WiFi-enabled convection wall oven, Flex Duo cooking system, and 36-inch Bluetooth cooktop, complete this exceptional culinary space. A first-floor guest suite and full bath provide flexibility for visitors, a private office, fitness studio, or wellness retreat. The finished two-car garage features epoxy flooring and a modern glass garage door. Upstairs, the primary suite serves as a private sanctuary. The spa-inspired bath features a freestanding soaking tub, expansive dual-entry shower wrapped in marble, semi-frameless glass enclosure, dual vanities, and a custom walk-in closet. Beyond the walls of the home lies your own private paradise. Professionally designed by Exotic Landscape Company, the resort-caliber outdoor living experience evokes the serenity of a luxury Balinese retreat. The newly constructed saltwater pool and spa showcase glass tile finishes, mini-pebble surfaces, travertine coping, LED lighting, therapy jets, a cascading waterfall, and smartphone-controlled OmniLogic automation. A custom outdoor stone shower, yoga platform, lush tropical landscaping, and curated hardscapes create an environment dedicated to relaxation and wellness. Additional features include Eufy smart lock technology, Arlo video doorbell, Google Nest thermostat, WiFi-enabled irrigation, smart garage controls, Quality Edge Vesta steel plank siding, and an expanded driveway. Located nearby highly regarded Winter Park schools and less than ten minutes from Park Avenue, this exceptional residence offers a rare opportunity to own a home that feels more like a private luxury resort. More than a home, this is a sanctuary. A place to unwind, recharge, and experience the very best of Winter Park living.

Listing is courtesy of: SIMPLICITY: A RE BROKERAGE CO (407-920-6020)

Listing Agent: Robert Sassos (407-920-6020)

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)

Remarks: Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perch, A Boutique Home Builder, offers a timeless front elevation, exquisite finishes inside and out, and unobstructed views of the beautiful outdoors from almost every room. Totaling 4,168 square feet, this five-bedroom, five-bath residence (and casita!) features a unique U-shaped floor plan ensuring natural light shines through every gathering space. Channeling the natural sands of a sunny retreat, the kitchen features white marble countertops and backsplash with blush pink undertones. A custom plaster hood, La Cornue gas range, a wall of cabinets with paneled GE Monogram appliances and a scullery with additional prep space create a kitchen ideal for entertaining. The marble island overlooks one of the main living rooms, where white oak trim highlights the precast stone surrounding the gas fireplace. A vaulted ceiling with natural wooden beams accentuates the bubble chandelier and level 5 drywall finish. Full-height sliding glass doors invite you to soak in the saltwater pool, summer kitchen, landscaped grounds and detached casita beyond. With accordion-style doors and a side entrance, the casita can serve as a pool house, personal home gym or additional bedroom with full bath. Sightlines from the main entrance lead you to the outdoors but also serve as observation points for the color-drenched first floor bedroom and primary suite with arched entry. A freestanding tub with smart glass window, zero-entry shower and extra thick Taj Mahal quartzite countertops elevate the primary bath to pure relaxation. Outside the primary suite, a concealed under-stairs laundry closet appears elegant, as impeccable millwork provides seamless transitions to the adjacent accent wall. Completing the first floor is a formal living room and dining room, a bold powder room, and a charming mudroom with custom cabinets. Follow the wrought-iron railing and engineered wood flooring to the expansive second floor. A flex room, three additional bedrooms and baths, a large laundry room, and built-in closets and benches keep everything organized and beautiful. This exceptional Winter Park home, crafted with intention and experience from award-winning local custom home builder, Urban Perch, elevates everyday living to approachable luxury.

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

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