Winter Park Homes For Sale & Real Estate - 384 homes

Remarks: Under contract-accepting backup offers. DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has been improved with raised Ceilings and expansive Wood Cabinets, Corian Sink and Countertops, Stainless Steel Appliances and expanded Pass-through Opening/Bar to Dining Room. Spacious Living and Dining Rooms with Lakeview. French Doors to Second Bedroom/Office with closets. Master Bedroom with en-suite Bath. Beautiful Cork Floors installed in all Living Areas. Tile in Kitchen and Baths. Ventless Washer and Dryer installed in Unit. Newer Double-Paned Energy-Efficient Windows. Unit has been replumbed. approximately 5 years ago. A/C and Water Heater new in 2025. Electric Panel replaced in 2019. You will love this close-in Winter Park Lakefront Community with all it's amenities, including Boat Ramp, 12 Boat Slips with Docks available for Lease to Owners, Waterfront Gazebo, Pool and. Clubhouse. Close to Shopping, Restaurants, Movie Theaters, Trader Joe's, Downtown Winter Park and Farmer's Market. Easy Access to I-4. Don't miss another Sunset! Call for a Private showing today!

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

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

Remarks: Welcome to the best of Winter Park living, where luxury meets lifestyle and every day feels like a getaway. This stunning custom home, built by Lundev, sits on a quiet, tree-lined street just a mile from Park Avenue and only steps from beautiful Lake Osceola. Imagine walking to brunch on Park Ave, then coming home to launch your paddleboard from the end of your street. From the moment you pull up, the home makes an impression from its striking architecture to the curved driveway that feels both elegant and inviting. Inside, it’s designed for the way people actually live and entertain today. The chef’s kitchen is the heart of the home, featuring a massive marble island, sleek custom cabinetry, and high-end appliances, all opening up to light-filled living spaces and three sets of French doors that flow seamlessly to the outdoors. Step outside and you’ll find your own private resort: a heated pool and spa, full summer kitchen, and a cozy cabana with a gas fireplace, all enclosed by automatic screens so you can enjoy the space year-round. Whether it’s a casual family dinner or a lively evening with friends, this backyard is one of the best in Winter Park. The first-floor primary suite feels like a spa retreat, with a soaking tub and peaceful views of the pool. Upstairs, each bedroom has its own en-suite bath, plus there’s a versatile bonus room and a large home gym that could easily flex into whatever you need, playroom, office, media space, or studio. Every detail was thoughtfully designed and beautifully executed, but what makes this home truly special is how it feels. Sophisticated yet comfortable. Private yet connected to everything that makes Winter Park so desirable. Just steps from Lake Osceola and moments from the charm of Park Avenue, this home offers a lifestyle that’s as effortless as it is exceptional.

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

Listing Agent: Brandon Geers (941-928-5152)

Remarks: Welcome home! You've found it, a spacious end unit townhome style condo with private 1 car garage with extra storage space. Open floorplan first floor, when you walk in the front door you walk into a huge living room/dining room combination room with views out the back of your private screened patio overlooking a pond. The kitchen features lots of counter space, breakfast bar on the kitchen island and all appliances included! upstairs you will find a HUGE master suite with walk-in closet and ensuite bathroom with dual vanities, separate water closet and shower. Down the hall you have your indoor laundry closet, as well as two additional bedrooms with view of the pond. Easy commute to Downtown, Baldwin Park, Winter Park with quick access to the 408 and 417!

Listing is courtesy of: COMPLETE FLORIDA REALTY LLC (407-222-7281)

Listing Agent: Greg Traub (407-222-7281)

Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome to an exceptional opportunity to own a beautifully maintained, move-in ready third-floor, water-view, corner unit studio residence in one of Winter Park’s most coveted locations—directly adjacent to Lake Osceola and just moments from iconic Park Avenue. This rare downtown setting places you within effortless reach of the Winter Park Farmers’ Market, acclaimed dining, boutique shopping, cultural venues, and a picturesque network of lakes and parks. The residence features a bright and open floor plan where the kitchen, dining, and living spaces flow seamlessly, creating an inviting atmosphere ideal for both everyday living and entertaining. Upon entry, you are welcomed by multiple storage closets and a discreet hallway that provides additional storage and convenient access to the full bathroom—an uncommon luxury for a studio-style layout. Sliding glass doors lead to a generously sized, private covered and enclosed balcony overlooking the tranquil interior courtyard, with peaceful views of the community pool and Lake Osceola beyond. This serene outdoor retreat is the perfect setting for morning coffee, evening relaxation, or quiet reflection amid lush surroundings. Residents enjoy a truly low-maintenance lifestyle, with electric, gas, water, sewer, and trash all included in the condominium fee. Building amenities include elevator access to the third floor, on-site management, a community laundry facility, and beautifully appointed common areas. The property also features expansive outdoor patios overlooking Lake Osceola, a resident club room, and immediate access to the community pool. Located within Whispering Waters, a highly desirable 55+ community, this residence is ideally suited as a primary home, seasonal retreat, or elegant in-law suite—offering timeless Winter Park living with unmatched convenience and charm.

Listing is courtesy of: TURN-KEY MOVES REALTY (407-796-2221)

Listing Agent: Mathew Kelly (407-796-2221)

Remarks: Under contract-accepting backup offers. Under Construction. A rare opportunity to own brand-new construction in desirable Brookshire Heights, this thoughtfully designed residence blends timeless finishes with modern functionality. Featuring 5 bedrooms, a dedicated office, and a spacious bonus room, the floor plan is both highly livable and exceptionally functional—ideal for everyday living and entertaining alike. All bedrooms are ensuite, offering comfort and privacy throughout, while hardwood floors run seamlessly across the entire home. Thoughtful architectural details, including custom ceiling treatments and built-ins, add depth and character throughout. The first-floor primary suite serves as a true retreat, complete with dual shower heads and a rain shower for a spa-like experience. In addition to the primary, the secondary bedrooms and office are all conveniently located on the first floor—providing a layout that lives comfortably day-to-day. Upstairs, you’ll find three spacious bedrooms, each with its own full bath, along with a generous bonus room and a large laundry room—offering flexibility for guests, family, or additional living space. Perfectly positioned within steps to Brookshire Elementary, the home is also just moments from the Cady Way Trail, Little League fields, parks with covered pavilions, and nearby medical facilities. Shopping, dining, and everyday essentials are just minutes away, with Park Avenue’s renowned restaurants and boutiques a short drive from your doorstep. A seamless blend of location, thoughtful design, and livability, this home offers an exceptional opportunity in one of Winter Park’s most established neighborhoods.

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

Listing Agent: Jennifer King (407-595-3272)

Remarks: Under contract-accepting backup offers. *Under Contract - Accepting Backup Offers* An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired foyer greets guests with precast stone-clad walls, inlaid marble flooring, and a Murano-style polyhedral chandelier. Two first-floor guest suites, each with its own bath, are adorned with rift-cut white oak millwork, curved ceilings, and crystal chandeliers. At the heart of the home lies the main salon, where oak detailing and a deco-style stone fireplace with a holographic insert create an atmosphere of understated grandeur. The two-tone oak kitchen, wrapped in natural quartzite and anchored by a curved island and custom hood, features a curated suite of professional-grade appliances: • ILVE range • Miele refrigerator, freezer, and dishwasher • Sub-Zero wine and beverage preservation systems Adjacent, a dining area glows under a custom chandelier, while the powder bath impresses with wood and marble accents, an integrated stone sink, and a Saint Louis crystal faucet by Kallista. A scullery expands the culinary capability with a chef’s sink, Samsung Bespoke laundry and refrigeration, Wolf microwave drawer, and additional Miele dishwasher—ideal for both entertaining and daily ease. The first floor primary suite, discreetly hidden behind millwork, offers a serene retreat with an opulent closet system and a marble mosaic-clad bathing suite featuring Kohler digital shower technology and MTI tub. Upstairs, two additional ensuite bedrooms, a bonus room with walk-in closet, and a secondary laundry continue the home’s standard of refined luxury. Outdoors, the residence embraces resort-style living with a natural gas summer kitchen, infinity-edge pool, and 360-degree raised glass-tile spa. A two-car garage and porte cochere, both EV-ready, provide elegant utility. Modern conveniences include Lutron HomeWorks lighting and shade prewire, built-in SONOS audio zones, pre-installed speakers, and a commercial-grade Ubiquiti WiFi network ensuring flawless connectivity throughout. A feast for the senses, The Maybourne is more than a home—it’s a statement of artistry and craftsmanship, conceived for the most discerning Winter Park resident.

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

Listing Agent: Rikhil Amin (407-792-8069)

Remarks: Under contract-accepting backup offers. *Under Contract - Accepting Backup Offers* Experience high-end luxury and effortless convenience in one of the most central locations in Winter Park. Built by Makeur Homes and thoughtfully updated by SMRS Design, this stunning Modern Mediterranean detached townhome showcases light-filled interiors and carefully curated custom finishes. Offering 3 bedrooms and 2.5 bathrooms across 1,884 square feet, the home features a desirable first-floor primary suite and elevated design details, including Level 4 drywall, engineered oak floors, Bosch appliances, LED mirrors, and a Lutron Caséta lighting and Triathlon shade system. A Calacatta Gold porcelain slab electric fireplace serves as a striking focal point in the living room. The open-concept floor plan is both functional and inviting, filled with natural light and offering views of a private paved patio and fenced backyard—ideal for relaxing or entertaining. Enjoy a low-maintenance, lock-and-leave lifestyle within an intimate four-unit community tucked along a picturesque, tree-lined brick street. Additional highlights include a private two-car garage with EV charging port, guest parking, and close proximity to premier dining, shopping, and daily conveniences, including Publix and AdventHealth. A rare opportunity to own a design-forward residence in an exceptional location.

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

Listing Agent: Rikhil Amin (407-792-8069)

Remarks: Welcome to this charming, meticulously maintained 3-bedroom, 2-bath residence in the heart of Winter Park—lovingly cared for by the same owner for over 30 years. This home reflects true pride of ownership with thoughtful updates and improvements that provide both comfort and peace of mind. Enjoy entertaining in the spacious eat in kitchen with full Stainless appliance package. Outdoor living shines with an extended paver driveway and rear patio, screened lanai, and lush, mature landscaping—creating a private, relaxing retreat perfect for entertaining or everyday enjoyment. Major upgrades include energy-efficient double-pane windows and patio door (2014), HVAC system (2020), redesigned Primary Bath Shower, updated electrical panel with new breakers including surge protection (2024), Water Heater (2024), Roof (2022). The home has also been repiped features a replaced drain field and a recently serviced septic system (2025). Additional improvements include gutters with mesh guards (2019), vinyl fencing and garage door hardware updates (2025). Designed for worry-free living, this home includes a long-standing transferable termite bond and resilient fiber cement siding for enhanced durability and protection. Ideally situated in a desirable Winter Park corridor, this home offers effortless access to both downtown Winter Park and Orlando, as well as the vibrant amenities of Baldwin Park. Surrounded by properties ranging from $600,000 to multi-million-dollar estates, the location presents an exceptional opportunity to enjoy a premier lifestyle with strong long-term value. Residents benefit from zoning to highly regarded schools and proximity to Park Avenue, Rollins College, and an array of fine dining, shopping, and cultural destinations. With convenient access to major roadways, daily commuting and connectivity are seamless. Set within an established neighborhood characterized by a blend of long-time ownership and thoughtfully updated homes, the area continues to experience ongoing growth and enhancement. A rare opportunity to own a beautifully maintained home in one of Central Florida’s most desirable communities.

Listing is courtesy of: RE/MAX SELECT GROUP (407-352-5800)

Listing Agent: Helen Thompson (407-766-7537)

Remarks: Along one of the cobblestone brick streets in the prestigious Via’s of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke finishes throughout. A circular driveway and manicured grounds designed by Signature Landscapes create a graceful approach. Inside, a dramatic curved staircase crowned by a breathtaking 1960s vintage Venini chandelier immediately sets the tone for the exceptional craftsmanship carried throughout the home. The main gathering room is striking and inviting, defined by vaulted ceilings, a Sequoia leathered stone fireplace hearth, and a wall of glass sliders that open seamlessly to the covered lanai and heated saltwater pool. The connection between indoors and out is effortless, designed for year-round entertaining and relaxed daily living, enhanced by a full outdoor audio system. A light-filled breakfast room sits just off the kitchen, offering an intimate everyday dining space. At the heart of the home, the custom kitchen is a showpiece. Naica leathered stone countertops and a waterfall island are complemented by custom cabinetry extending to the ceiling, a professional-grade appliance suite featuring Sub-Zero and Wolf, and convenience of two Miele dishwashers. Directly adjacent, the pantry mirrors the kitchen’s cabinetry and craftsmanship and features a built-in coffee station, seamlessly connecting to the laundry area and three-car side-entry garage. A beautifully appointed guest powder room with an integrated sink is thoughtfully positioned nearby. A separate lounge showcases a custom wet bar highlighted by dramatic stonework and an integrated sink, an elegant setting for conversation and evening gatherings. A dedicated office positioned just outside the primary suite features a wall of floor-to-ceiling shelving, cabinetry and file drawers. The primary suite serves as a private sanctuary, enhanced by vaulted ceilings, backyard views and a stately two-sided stone fireplace shared with the office. Two custom walk-in closets provide exceptional storage, while the spa-inspired bath showcases Taj Mahal leathered stone countertops with integrated dual sinks, a soaking tub and an oversized glass shower with dual showerheads. Upstairs, four additional bedrooms with custom closets are complemented by beautifully finished baths and a loft sitting area with hallway built-ins. Two of the bedrooms and a bath may be closed off to create a private suite, ideal for guests or multigenerational living. A secondary staircase leads to an impressive media room equipped with a 98-inch television, state-of-the-art 7.1 surround sound and extensive storage. Outdoor living is equally elevated, featuring a weathered marble pool deck, dedicated pool bath, newly installed summer kitchen with Coyote gas grill, hood vent, sink, and leathered stone counters and backsplash, plus an outdoor living room anchored by a two-sided fireplace and television. Modern systems include a Lutron lighting system on the main level, water filtration & softener, ADT alarm - security cameras throughout and a whole-home natural gas generator. Every element of this residence has been newly installed and custom-designed, resulting in a home that blends sophisticated design, advanced functionality, and exceptional spaces for intimate living and grand entertaining. From custom millwork to curated stone selections, this home reflects uncompromising quality and thoughtful design.

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

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

Remarks: Experience the art of luxury living just steps from the boutiques, cafés & celebrated dining of Park Avenue, Winter Park Village, Rollins College & the iconic Winter Park Art Festival. This beautifully crafted custom one-story pool home built in 2024 blends elegant design with an effortless, modern lifestyle. THIS HOME RECEIVED THE 2025 ARDA GRAND AWARD FOR CUSTOM HOME (built). A thoughtful quad split bedroom layout offers 4 bedrooms & 4.5 baths, including a serene primary suite with Hunter Douglas automated light filtering/light blocking shades. The primary suite includes a spectacular custom walk-in closet featuring an island, 36 drawers, built-in benches, dual hampers, a safe, locking jewelry drawers & display shelving. The ensuite bath provides a spa-like retreat. Additionally, two guest suites also enjoy private ensuite baths & large walk-in closets. The showpiece chef’s kitchen is designed for both culinary mastery & entertaining, featuring Dura Supreme cabinetry, a 60" Wolf dual fuel range with griddle, pot filler, 36" Sub Zero Designer Column refrigerator, Sub Zero freezer drawers, two Bosch dishwashers, Wolf microwave drawer, Revati dual tier 57" sink with custom inserts for colander, cutting board & strainer & dual automatic faucets. Dramatic 15-foot waterfall island with Dekton countertops & matching backsplash. A hidden scullery adds even more function with a French door refrigerator, sink, pantry shelving, Dekton counters & floating LED-lit shelves. The stylish wet bar includes white oak floating shelves with LED lighting, Dekton countertops & backsplash, a glass rinser, Scotsman gourmet ice machine & Thermador refrigerator drawers. Dining room has a climate-controlled wine cellar that holds up to 240 bottles. Enjoy picking lemons, limes & oranges from your own mature trees for juicing or garnishes. The expansive family room impresses with six LED-lit floating shelves, a 60" linear gas fireplace & an extraordinary 52 feet of 10-foot-tall sliding stacking patio doors that create seamless indoor-outdoor flow. Step outside to a resort-style outdoor kitchen & living area, complete with a Dekton waterfall countertop, Perlick refrigerator drawers & kegerator, 48" DCS grill with rotisserie & 2 side burners, pizza oven, Ruvati sink with ice chest, bar-height island seating, three 60" Minka Aire remote control fans, outdoor electric fireplace & retractable screens. The app-controlled pool features water elements, bubblers, two ledge loungers with umbrella holder/end table/ice chest & a 9-seat hot tub. Custom closets are found throughout the home, including the media room with built-in Queen Murphy bed & closet & a dedicated exercise room with closet or potential fifth bedroom. Large office filled with natural sunlight. The laundry room includes custom cabinetry with built-ins for pet bowls & bed & a fold-out ironing board. Additional features include Visual Comfort lighting, Guardian security system, Trane home automation, Quantum Fiber, built-in speakers throughout the main living areas & outdoor kitchen, living room & pool, Emtek hardware, PGT casement windows & 8" white oak hardwood floors. The sellers will also provide a one-year home warranty for added benefit. This home delivers a refined, fun & effortless luxury lifestyle in one of Winter Park’s most coveted locations—where every detail is designed to impress. Finding a one-story, almost-new home on a large lot in Winter Park is like finding a rare gem!

Listing is courtesy of: ROYALTY R E BOUTIQUE INC (407-658-0601)

Listing Agent: Domenique Lombardo (407-474-7000)

Remarks: One or more photo(s) has been virtually staged. Welcome to this inviting 2-bedroom, 2-bathroom condo located in the desirable Lancelot at Winter Park community, offering the perfect blend of comfort and convenience for investors, first-time buyers, or anyone seeking low-maintenance living. This well-appointed unit features an open and airy layout with abundant natural light, seamlessly connecting the living and dining areas to create an ideal space for both relaxing and entertaining. The modern kitchen provides a functional workspace designed for everyday ease. Residents will also enjoy access to a community pool, perfect for unwinding or hosting guests, along with professionally maintained common areas that enhance the overall appeal of the neighborhood. Ideally situated, this condo offers close proximity to UCF and Full Sail University, making it an excellent option for rental potential, as well as convenient access to major shopping centers, dining options, and key highways including I-4 for easy commuting. Whether you're searching for a primary residence, a second home, or a strong investment opportunity, this property delivers exceptional value in a prime location. The property was previously leased at $1,625 per month.

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

Listing Agent: Christina Munkberg Bianca (407-340-1308)

Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout with high ceilings, modern finishes, and tile and carpet flooring all throughout. The well-appointed kitchen flows effortlessly into the main living and dining areas, creating a seamless environment for entertaining or everyday living. All three bedrooms include generous walk-in closets, while the primary suite offers a peaceful retreat with its own private bathroom and serene ambiance. A versatile loft on the second floor adds valuable flex space that is ideal for a home office, media area, or playroom. Outside, the home offers a cozy enclosed rear patio perfect for relaxing, dining outdoors, or enjoying your morning coffee in privacy. A spacious two-car garage provides convenience and additional storage. The community surrounding Shadowland Loop is quiet, welcoming, and beautifully maintained, with tree-lined streets and easy access to the best of Winter Park. Residents enjoy proximity to top-rated schools, charming parks, boutique shopping, vibrant dining spots, and the area’s beloved lakes and recreation. With its thoughtful design, modern amenities, and exceptional location, this townhouse delivers the ideal Winter Park lifestyle.

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

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

Remarks: One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors leading to the community green space that is a tropical oasis. The adjacent dining area includes a stackable washer/dryer and flows into a modern kitchen with floor-to-ceiling cabinetry, granite countertops, and stainless steel appliances. Both spacious bedrooms sit near the entry, with the primary suite offering a walk-in closet and a sleek ensuite bath with a glass-front shower and floating vanity—mirrored in the newly updated guest bath as well. Enjoy low-maintenance living with access to resort-style community amenities including two pools, tennis courts, and a gym—all in a prime location! Schedule your private showing today!

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

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

Remarks: Charming 2-bed home in Winter Park located in the Golfview subdivision offering approximately 1,150 square feet of living space on a 6,414 square foot lot. Built in 1946, this single family residence features a functional layout with a blend of original character and updated interior finishes. The home includes original pine flooring in the main living areas, ceramic tile in the kitchen and dining spaces, and strong natural light from multiple window exposures. The kitchen has been updated with white cabinetry, granite countertops, and a mix of stainless steel and black appliances. The bathroom features updated finishes including a modern vanity and shower. Additional features include a covered front porch, one car attached garage with laundry area, central air conditioning with updated ductwork, and a fenced backyard with deck space suitable for outdoor use. The property is connected to public water and sewer and offers practical living with no HOA. Located near Dubsdread Golf Course and within close proximity to AdventHealth, College Park, and Downtown Orlando. Easy access to I-4 and surrounding roadways supports convenient travel to employment, dining, and retail centers. This property is suitable for a primary residence or investment opportunity in a well located Winter Park area.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Tyler Gibson Llc (877-366-2213)

Remarks: Experience the perfect blend of classic elegance and modern comfort in this spacious pool home. From the moment you step inside, the open spindle staircase sets a sophisticated tone that carries throughout the residence. In the Heart of the home is an upscale Kitchen equipped with solid wood cabinetry, sleek granite countertops, and a convenient breakfast bar for your morning breakfast or casual dining. Move freely from inside to outside through 3 sets of sliding glass doors in the kitchen, dining room and great room. Just walk out anytime to the massive brick paver patio and enjoy one of the two covered patio areas. The outside is Entertainment ready as the expansive brick pavers wrap around the pool, creating a seamless environment perfect for hosting summer parties or quiet evening dips. On the cool days you can retreat to the family room to enjoy the warmth of the wood-burning fireplace. The primary Suite is a true getaway featuring direct pool access via private sliders, a generous walk-in closet, and a spa-like bath. Indulge in the soaking tub or the walk-in shower with double shower heads. Includes double vanities and ample storage for a clutter-free environment. The upper level will allow family and guests to feel right at home with three spacious bedrooms and a dedicated full bathroom upstairs. You can also rest easy knowing that the Roof was installed in 2018, the Hot Water Heater was installed in 2018, and the HVAC system was installed in 2019. An oversized 2-car garage offers room for a workbench and "toys" plus an inside laundry room and convenient half-bath are located close by. This prime location is ideally situated near A/B-rated schools, UCF, and Oviedo Hospital. Enjoy easy access to the 417 and Aloma Ave with plenty of shopping, Winter Park’s nightlife and the Tuscawilla Country Club just minutes from your front door. If this sounds like YOUR Dream home, please come see it today!

Listing is courtesy of: ELLIS GROUP REALTY, LLC (407-960-4545)

Listing Agent: Jay Lacourt (386-313-5008)

Remarks: LOCATION! LOCATION! LOCATION! Beautiful 2nd floor corner condo in desirable Winter Park, featuring 1 bed/1 bath, open concept living/dining area and balcony. Move-in ready and conveniently located near UCF, Rollins College, Valencia College, Park Avenue, and Downtown Orlando. Residents enjoy resort-style amenities including two pools, tennis court, a fitness center, and clubhouse available for rental for gathering or events. The unit includes a fully equipped kitchen, stackable washer and dryer in the bedroom, and access to free community laundry. HOA covers water, trash removal, internet, pest control, exterior maintenance, and grounds care. Close to shopping, dining, and major highways for easy access across the area.

Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)

Listing Agent: Sandra Da Silva (407-840-8500)

Remarks: Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of exceptional living space, capped with a brand-new, architecturally stunning tile barrel roof that blends timeless Mediterranean elegance with lasting durability. 2614 Parkland Drive, a fully reimagined luxury residence in the heart of Winter Park. This is your chance to own a showpiece property with over 3,300 SF zoned for the coveted Audubon Park K-8 and Winter Park High School districts. Completely remodeled in late 2022, this home radiates warmth and sophistication. Solid light oak floors, custom railings, and an open-concept flow make entertaining effortless. The chef’s kitchen is a centerpiece; quartz counters, full-height designer tile, and abundant storage bring form and function together. Out back, discover your private resort. A heatable custom pool & spa finished in ultra-rare Caribbean blue tile sets the tone; elevated with two natural-gas fire pits, dramatic waterfalls, porcelain privacy walls, and a built-in grill. Every evening feels like a five-star escape.The first-floor master suite offers direct access to the outdoor oasis, while upstairs features three oversized bedrooms, a loft, and a private patio for sunset views. Brand-new tile roof, dual tankless water heaters, central vacuum, and all-natural gas appliances ensure low-maintenance, worry-free living. This is more than a home it’s a statement. A chance to live where luxury, location, and lifestyle converge.

Listing is courtesy of: JW GASTON LLC (321-239-5540)

Listing Agent: Ryan Gaston (321-239-5540)

Remarks: Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and unwind on the private back porch—an ideal outdoor sitting space. The kitchen features a pantry and cozy breakfast nook. The spacious primary suite includes a walk-in closet, updated bathroom, and direct access to the back patio. The second bedroom also offers new flooring and its own walk-in closet, making it perfect for guests or additional living space. With its inviting design and unbeatable location, this condo is a must-see—schedule your private showing today!

Listing is courtesy of: EXP REALTY LLC (407-846-0940)

Listing Agent: Jamie Bollinger (407-908-1890)

Remarks: Nestled in a peaceful setting within the serene Cedarwood Village community, this charming one-story Winter Park condo offers a quiet retreat away from traffic noise, with a rear wooden fence for no visible neighbors for added privacy. The spacious 27-foot tiled and enclosed lanai creates the perfect place to relax and enjoy the tranquil surroundings. Cedarwood Village also offers low-maintenance living, with lawn care included in the HOA, along with amenities such as rebuilt tennis courts, a recently remodeled pool, a clubhouse, dog-walking areas, and newly paved roads. Conveniently located in a highly rated school district and close to shopping, dining, and entertainment, the property is also just minutes from Full Sail University, Valencia College, and UCF. Inside, the condo is beautifully updated and shows the care of meticulous owners. The modern kitchen features granite countertops, matching cabinetry, and an eat-in area with sliding doors leading to the private patio, while the bathrooms and dining room wet bar are finished with the same stylish cabinets and granite. The split floor plan includes tile flooring throughout the main living areas and wood floors in the bedrooms. The large living and dining spaces feature vaulted ceilings with skylights for abundant natural light, along with a cozy wood-burning fireplace. French doors from the living room open to the enclosed lanai, while the primary suite also has direct lanai access, ample closet space, and a private bath with both a tub and shower. Additional features include an interior laundry closet adjacent to the kitchen, updated plumbing, a roof replaced in 2018, new ductwork installed in 2023, and a $4,500 seller credit at closing toward a new AC. Two assigned parking spaces are located directly in front of the unit. Tenants will be moving out May 31, 2026.

Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)

Listing Agent: Jeff Stewart (407-247-9762)

Remarks: "MOTIVATED SELLER" - NEED SOME CLOSING COST? RATE BUY DOWN? WE CAN HELP GET YOU INTO THIS "MOVE-IN READY", 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH "NO HOA" & LARGE PRIVATE YARD, WINTER PARK, FL 32789. The Seller has already relocated and willing to work with a "Fully Pre-Qualified" Buyer to get this home sold quickly. AWESOME LOCATION just off Corrine Drive. WALKING DISTANCE to East End Market. TOP-RATED Audubon Park (K-8) & Winter Park High (Magnet Program) Schools. The Owners completed a HOME ADDITION & UPDATE in 2020 w/over $115,000.00 of improvements, including a NEW Roof, NEW Primary Bath, EXPANDED Great Room, NEWLY Enclosed Entry way w/mudroom & pantry, along with mechanical & finishing upgrades. Enter the home through a fully ENCLOSED FOYER which allows easy access to the new MUDROOM, as well as the ENORMOUS GREATROOM, which features an open Family & Dining Room area featuring a Wood Burning Fireplace, Decorative Shiplap Niche, Vaulted Ceiling and a dual French Doors leading to the HUGE Patio & Back yard. The CHEF'S KITCHEN was redesigned to include 42" Wood Upper & Lower SHAKER CABINETS w/Soft Close Drawers, Quartz Countertops, HUGE FARM-STYLE Deep Sink, Custom Tile Backsplash, "LG" Stainless Package including a French Style Refrigerator, Flat-Top Range, Microwave, Dishwasher, Wine Refrigerator, Decorative Shelves & a Mid-Century Modern Bungalow Pendant. The Primary Suite is the perfect COUPLES RETREAT which includes a Large Bedroom, Vaulted Ceiling, and a HUGE 14' LONG WALK-IN CLOSET w/Customizable Organizers to store all your Clothes & Accessories. The Primary Bathroom includes HIS & HERS Matching Vanities with Quartz Countertops, Recessed Sinks, Dual Mirrors & Hardware. Enjoy the luxury of a custom jetted soaking tub—ideal for unwinding after a long day or for families with young children, complete with a Tile Backsplash. The "WALK-IN SHOWER" features Frameless Glass, Custom Wall & Floor Tile and an OVERHEAD RAIN SHOWER. Finally, the bathroom features oversized 24"x24" Custom Floor Tile to complete the design features. Do you ENJOY OUTDOOR SPACE & like to Entertain? Do you need a SPACIOUS KIDS AREA for them to safely play? If so, you will FALL-IN-LOVE” with the fully fenced & enclosed back yard featuring two HUGE 12'x21' and 15'x27' OPEN PAVER PATIO areas perfect for all your outdoor furniture & equipment. Also enjoy your own PRIVATE TAVERN with an 8'x12' Bar designed with Corrugated Metal Panels, a Bar Top, Shelving & Concrete Floor. The Bar is OPEN FOR YOUR FRIENDS & FAMILY. The Backyard also includes (2) Separate Gate Entrances which will accommodate & secure your Boat, Trucks, Trailers, Work Equipment, etc. In addition, there is an 8'x8' and 5'x8' Storage Rooms. Addl Features: NEW Roof (2025), NEW Interior & Exterior Paint (2025), Tankless Water heater, Carrier HVAC System (2019), Updated Electric Panel (2019), Updated PEX Plumbing (2019), Newer 8"x36" Custom Tile Flooring, Newer Double Paned Windows (2019), NEW Drain field (2024), Block Construction, HUGE Laundry & Storage Room wCustom Organizers, 6" Baseboards, Window Treatments, Ceiling Fans & Lights, Open Carport (13'x21'), Covered Carport perfect for a Golf Cart (8'x17'), Irrigation System, Gutters & Downspouts, Decorative Bamboo & much more. Just minutes to Park Avenue, Fine Dining, Leu Gardens, Downtown Orlando, Municipal & OIA Airports, Hwy 436, 408, 418, Turnpike, UCF & the Beaches. Call for more info or to schedule your private showing.

Listing is courtesy of: ROCK SPRINGS REALTY, LLC (877-333-2811)

Listing Agent: Joel Bornstein (407-252-8092)