Winter Park Homes For Sale & Real Estate - 301 homes

Remarks: This home sits at the end of a cul-de-sac with an attractive courtyard entry to the 2 car garage. The Kitchen has been updated with new cabinets and tile flooring and the baths all have been remodeled and have tile flooring. The remodeled Primary Bedroom has Luxury Vinyl Flooring. The house has had all the windows and front door replaced. The screened porch overlooks a spacious fenced backyard that includes a block building (summer cottage) with electric and plumbing that is currently being used for storage. The Roof was replaced in 2022 and the yard has a sprinkler system. Make an appointment to see today!!

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Diane Gerry Pa (407-405-5550)

Remarks: *** Seller will contribute up to $5k towards an interest rate buy down for the buyer, with an acceptable offer.*** Located within the gated community of Hawk’s Crest, one of Winter Park’s most desirable neighborhoods, this beautifully maintained two-story home is set on an oversized lot with tranquil pond views and a layout designed to live effortlessly. Light-filled, open, and thoughtfully upgraded, the home offers a balance of comfort, style, and everyday functionality. A pavered driveway and walkway create an inviting arrival, leading into a bright interior with soaring ceilings and abundant natural light. The main living space flows seamlessly, anchored by a chef’s kitchen featuring quartz countertops, stainless steel appliances, solid wood cabinetry, and a generous island with breakfast bar—perfect for casual meals, entertaining, or gathering at the end of the day. The kitchen opens naturally to the dining and family rooms, creating a connected space that feels both open and welcoming. Sliding doors lead to a covered lanai overlooking the pond, extending the living space outdoors and providing a peaceful backdrop for morning coffee or evening relaxation. Inside, upgraded luxury vinyl flooring and custom roller shades add warmth and a polished finish throughout the main living areas. The first-floor primary suite offers a private retreat with serene water views, a spacious walk-in closet, and a spa-inspired bath with dual vanities and a walk-in shower. A dedicated office on the main level adds flexibility and can easily function as a fifth bedroom if needed. Upstairs, a generous loft provides additional living space—ideal for a media room, play area, or secondary lounge—while three well-sized bedrooms offer comfort and versatility for guests, hobbies, or working from home. Energy-efficient features, ample storage, and thoughtful design make the home as practical as it is inviting. Residents of Hawk’s Crest enjoy resort-style amenities including a community pool, fitness center, clubhouse, playgrounds, and scenic walking paths, along with HOA-included lawn care for low-maintenance living. Ideally situated near shopping, dining, outdoor recreation, and major roadways, this home offers both convenience and a sense of retreat within Winter Park. Come experience the lifestyle and setting that make this home truly special—schedule your private showing today.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Beth Hobart (407-227-8192)

Remarks: Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than ¾ of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed by beautiful wood floors and versatile spaces to the left that can serve as a formal living room, dining room, office, or playroom. Continue into the impressive family room, featuring vaulted ceilings, skylights, and a wood-burning fireplace, creating a light-filled and inviting atmosphere. To the right wing of the home are four bedrooms and two bathrooms, including the primary suite. One secondary bedroom connects to the primary, making it ideal for a nursery, home office, or sitting room. The spacious primary retreat offers large walk-in closets, dual vanities, a soaking tub, separate shower, and French doors that open directly to the pool and backyard oasis. The kitchen, located just off the family room, features travertine flooring and flows seamlessly into a huge pantry, oversized laundry room, drop zone, and a second primary suite with ensuite bath—perfect for guests or multigenerational living. Outside, the home has been meticulously maintained, showcasing a new roof (2023), exterior paint (2018), pavered circular driveway, well, and lush tropical landscaping that enhances the home’s curb appeal. Additional features include a three-car side-entry garage, pool heater, designer lighting, engineered hardwood floors, and crown molding throughout. Located within the highly sought-after Winter Park School District (Audubon K-8 and Winter Park High School) and just minutes from Park Avenue, Central Park, Rollins College, SunRail, the Winter Park Farmer’s Market, and world-class shopping and dining. Schedule your private showing today—this exceptional home won’t last long!

Listing is courtesy of: VOSS REALTY INC (407-456-0777)

Listing Agent: Lindsay Kaye Voss (407-456-0777)

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)

Remarks: Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From the moment you enter, the home makes an impression. French clay tile flooring anchors the defined foyer, opening into an expansive great room where Bolivian rosewood built-ins frame a gas fireplace and oversized windows draw the eye toward the pool and lanai beyond. The living, dining and kitchen spaces connect seamlessly, designed for everyday ease and effortless entertaining. The kitchen is equipped for the serious home cook, anchored by a full Thermador appliance package and thoughtfully appointed beyond the expected. The large island integrates a sink, microwave drawer, ice maker and refrigeration drawers alongside generous seating, while a walk-in pantry, concealed outlets and a warming drawer round out a workspace as purposeful as it is refined. Outdoor living is equally deliberate. A covered lanai with fireplace and space for a mounted television flows to an open-air terrace and dedicated grilling area, all overlooking a linear pool with water feature and professionally designed landscaping with evening lighting. Upstairs, the primary suite is positioned at rear of the home for added privacy, with abundant natural light, a generous walk-in closet and an en-suite bath. Two additional bedrooms each offer their en-suite baths and built-in closets. A well-appointed laundry room, along with a linen closet and dedicated storage closet in the hall, complete the second floor. On the main level, a fourth bedroom is finished as a library with custom white oak built-ins and French doors opening to the exterior of the home, offering flexible living or professional workspace. Throughout, Panaget engineered hardwood flooring, decorative crown molding, Sierra Pacific windows and doors, cast stone accents, and integrated stair lighting reflect the home's elevated attention to detail. Additional highlights include a detached two-car garage, extensive storage throughout and an infrastructure designed for future elevator conversion. A rare opportunity to own a newer custom home in one of Winter Park's accessible and beloved neighborhoods.

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

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

Remarks: Elegant 1922 Mission Revival home, located in popular College Quarter is a registered historic place in Winter Park, FL. Lifestyle is neighborly/relaxed/pet friendly/enhanced by proximity to Lake Virginia/lakeshore sidewalks/Rollins College campus/downtown Winter Park/Central Park/museums/shops/restaurants/cultural events, most walking distance. College Quarter residents enjoy exclusive use of Park/Dock on Lake Virginia to kayak/paddleboard/motor through Chain of Lakes or meet up for holiday fireworks/once-in-a-lifetime or yearly celestial events. College Quarter is one of the oldest/most architecturally diverse neighborhoods. This 1922 home represents the Florida Mission Revival vernacular through a timeless blend of stucco exterior walls/asymmetrical façade/prominent arches above doors/large windows/a flat roof/barrel red tiles/a distinctive parapet and walled courtyard with wrought-iron gate designed by local master ironworker. True to Mission Revival style, home connects to nature and surrounding College Quarter landscape through above architectural details that embody poetics of Mission Revival style. Builder used sensitive siting, placed home at highest elevation on street & it remains responsive to prevailing lake breezes/paths of rising sun & moon 104 years later. Lake light/sunlight/moonlight take centerstage in every room. Whether through window or door, each part of house has relationship with its surroundings. Mission Revival style accomplishes what homeowners often seek—a home’s ability to surprise. Airiness/lightness, beautiful atmosphere/ambience that Mission Revival architecture creates is notable that way. Mission Revival layout is key to that effect. Home’s modified Great Room layout combines roles of several traditional rooms--family/kitchen/living/dining rooms into 1 expansive space ideal for families/entertaining guests/enjoying natural light/views. Open layout in house is conducive to spending quality time together/socializing/entertaining. Proximity of kitchen/dining/living & outdoor spaces allow for easy interaction/conversation & creates sense of togetherness. Great Room dominates first floor living/dining room areas. One interior archway frames foyer, another leads to family room. Left of fireplace in Great Room are French Doors to enclosed porch/walled courtyard/plunge pool. Ceiling is 10 ft exposed rafters, 2 large, arched windows, one on East wall, one on West, face each other across 4 interior spaces. Changing light seen through handblown windowpanes in Great Room illuminate first floor & exterior environment. When moon rises over lake's cypress trees it appears in Great Room east window, travels thru sky, peeps into 2nd floor windows before moving ever higher in the sky. Kitchen’s center island is gleaming butcher block & divides food prep area from pantry/laundry/guest bathroom/living/dining areas. Kitchen counter imported tile/oak cabinets/small eat-in breakfast nook. French Doors open to brick courtyard/garden area/plunge pool. Kitchen/Pantry/Guest Bathroom have heart of pine floors. Laundry new ceramic tile, built-in wood cabinets/shelves, new washer/dryer, stainless-steel sink. Great Room floors original oak. Staircase/second story floors original heart of pine. Bedroom 1 ensuite Bathroom/Linen Closet/Balcony. Bedroom 2 beautiful views/2 closets/built-in drawers/. Bedroom 3 best water views during day. Single-family ownership 45 years. Roof & 2 balconies 5 yrs old. Major renovations 2021- to present

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

Listing Agent: Wendy Brandon (407-435-9009)

Remarks: Located on a quiet cul-de-sac in the heart of Winter Park, this traditional two-story home offers a functional, well-designed floorplan for both everyday living and entertaining. From the moment you step inside, the home has an inviting warmth that you can immediately feel. The main level features a spacious primary suite along with connected living spaces that flow easily from room to room. The primary suite and family room both feature tall ceilings and an abundance of natural light, creating a bright and inviting wing of the home. The kitchen opens to the casual dining area and family room, creating a central gathering space. French doors from the family room lead to a peaceful, southern-inspired screened patio overlooking a spacious yard on nearly half an acre. At the front of the home, a separate living room provides a quieter setting, while the formal dining room is complemented by a butler’s kitchen for added functionality when hosting. Upstairs includes four additional bedrooms with classic charm, featuring original hardwood floors and generously sized rooms, offering flexibility for guests, family, or office space. Just steps from Park Avenue and the Winter Park 9, this home offers an ideal location with easy access to shopping, dining, and golf.

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

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

Remarks: Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors, every detail reflects a refined, cohesive aesthetic. Step inside to warm oak wood floors and a light-filled open-concept layout ideal for both everyday living and upscale entertaining. The chef’s kitchen is a true statement, featuring custom oak cabinetry, sleek quartz countertops with a dramatic waterfall island, and an expansive breakfast bar. Top-of-the-line appliances include a Sub-Zero refrigerator, Wolf 6-burner gas professional range with grill and double ovens, Wolf microwave, Miele dishwasher with PowerDisk system, and a built-in Miele coffee station. The kitchen flows effortlessly into both a breakfast nook and a separate dining area, while the designer bar serves as a stunning focal point—complete with two Sub-Zero dual zone wine refrigerators accommodating more than 200 bottles, along with additional Sub-Zero refrigerator and freezer drawers. Downstairs all blinds are motorized and have gorgeous custom drapes. Upstairs, all three bedrooms are en suite, offering a private retreat for family and guests. A versatile loft area features a custom-designed laundry space concealed behind built-in cabinetry for a clean, streamlined aesthetic. One bedroom has been thoughtfully designed as a home office with a built-in Murphy bed, providing flexibility without compromising luxury. The outdoor space is equally refined, featuring low-maintenance turf, a beautifully designed pool, and a covered lanai perfect for relaxing or entertaining. A built-in grill area and lush privacy hedging create a serene backyard oasis, with landscaping professionally designed and maintained by Signature Landscaping. Additional highlights include a 2-car garage and a Sonos sound system in the living room and lanai, enhancing the home’s elevated lifestyle experience. Most furnishings are available for purchase separately, offering a truly turnkey, designer-furnished opportunity. Ideally located just minutes from Park Avenue, top-rated schools,Rollins College, fine dining, and boutique shopping, this exceptional home represents the very best of Winter Park luxury living. Perfect lock and leave home with the perfect location!

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: Noelle Leblanc (407-491-2744)

Remarks: New listing in Winter Park! On a quiet cul-de-sac in Seminole County just off Howell Branch Road, this inviting townhouse offers comfort, flexibility and convenience in a desirable location. Inside, you’ll find a bright, spacious living room with large windows, a cozy dining nook adjacent to the kitchen with extensive cabinets, and a flexible first-floor third bedroom used as an office/gym that can easily convert to a bedroom again. Upstairs features generously sized bedrooms and a hall bath. The home has been recently painted inside and offers new laminate flooring upstairs, with tile and LVP throughout the main floor. Outside, enjoy a covered front porch, fenced backyard, storage shed and an extended driveway. The roof and air conditioner were replaced in 2018. With low monthly HOA dues of $110 that include lawn maintenance, this home offers easy, low-maintenance living. Along beautiful tree-lined streets with mature oak canopies, this neighborhood offers a peaceful, shaded setting that enhances everyday living. Conveniently just five miles from Park Avenue shopping and dining and three miles from Red Bug Lake Park, with quick access to SR 417, this home provides a balance of nearby amenities and quiet, established surroundings.

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

Listing Agent: Carrie Bantel (321-217-8750)

Remarks: Luxury Lakeview Townhome in Winter Park! Experience elevated living in this newly built 3-bedroom, 3.5-bath residence with over 2,300 sq ft and breathtaking direct views of Lake Killarney. A dramatic 17-ft foyer welcomes you into a bright, open-concept great room featuring 11-ft ceilings and floor-to-ceiling windows that capture stunning water and nature views. The designer kitchen is built for entertaining with quartz countertops, Wolf and Sub-Zero appliances, double-stacked soft-close cabinetry, a walk-in pantry, and custom lighting. Motorized window shades add comfort and convenience throughout. Step outside to the 22-ft oversized lanai surrounded by lush landscaping—perfect for outdoor living. Upstairs, a versatile loft/office space leads to a private balcony with cocktail kitchen and panoramic lake views. The luxurious primary suite features floor-to-ceiling windows, dual closets, and a spa-inspired bath with designer tile, dual vanities, private water closet, and oversized frameless glass shower. Two additional bedrooms each include private en-suite baths, with a conveniently located laundry room. Additional highlights include a two-car garage with epoxy floor, EV charging plug, and extra storage. BONUS OPTION - Impossible to find boat slip on Lake Killarney available for purchase with this unique townhome. Located in one of Central Florida’s most sought-after communities, this exceptional home combines modern luxury, scenic lake views, and an unbeatable Winter Park location. Schedule your private showing today and experience luxury lakefront living at its finest.

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 to 639 Friar Road, ideally situated on a quiet street in the highly desirable Winter Park Pines neighborhood. This extensively updated residence offers the character of a classic 1960s home with the quality and feel of a 2026 renovation. Major improvements include a new roof, new HVAC system with new ductwork, new panel box, and thoughtfully curated high-end kitchen, bath, and lighting design elements. Original terrazzo flooring has been meticulously restored and polished throughout, preserving the home’s timeless appeal. Featuring four bedrooms, three full baths, the home offers a functional open-concept layout with a desirable split floor plan. Two primary suites, each with private en-suite baths, provide flexibility for multi-generational living or guest accommodations. The property showcases strong curb appeal and continues to impress outdoors with a spacious backyard and an oversized lanai designed for entertaining. Zoned for highly rated Winter Park schools, this home delivers an exceptional blend of style, comfort, and indoor-outdoor living in one of Winter Park’s most established neighborhoods.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Dianne Moore (407-494-7575)

Remarks: Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

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

Listing Agent: Mary Colton (407-222-7388)

Remarks: 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: 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: New Construction – JUST COMPLETED! Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within walking or biking distance of premier restaurants, cafés, boutique shops, and entertainment venues. Designed for both daily comfort and elevated entertaining, the open-concept floor plan boasts thoughtful design and high-end finishes throughout. Luxury details abound, including engineered wood floors featuring an elegant herringbone pattern in the foyer, smooth finish Level 4 drywall, and a cozy electric fireplace that enhances the spacious great room, accentuated by LED mood lighting in the coffered ceiling. The expansive gourmet kitchen is a chef’s delight, equipped with ceiling-height cabinets for ample storage and premium Thermador appliances, including a 36” gas cooktop, wall oven, built-in microwave, French door refrigerator, and a wine fridge — all complemented by sleek cabinetry and contemporary details. A beautiful dry bar adjacent to the kitchen provides extra space for coffee, wine, or entertaining guests. Offering four generous bedroom suites, this home includes a luxurious primary suite on the main level, along with a versatile second suite on the first floor, ideal for use as an office or guest retreat. Upstairs, two additional suites are connected by a flexible bonus room — perfect for a home office, gym, second living area, or even a fifth bedroom. Step outside to your private outdoor oasis, featuring a covered lanai with automatic roll-down screens, a fully-equipped summer kitchen (complete with grill, sink, and refrigerator drawers), and a sparkling pool adorned with travertine decking — perfect for year-round Florida entertaining. The elegant exterior showcases outdoor lighting and lush landscaping, along with a gas generator to ensure your home is always prepared for storm season.Don’t miss your opportunity to own this exquisitely crafted home in one of Orlando’s most sought-after neighborhoods. Schedule your private showing today and experience the pinnacle of luxury living in Winter Park!

Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)

Listing Agent: Kim Griffin (407-314-5033)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to one of the most affordable opportunities to own in the highly sought-after Winter Park High School district. This well-maintained community is tucked into a beautiful setting and is extremely convenient to everything that makes Winter Park one of Central Florida's top lifestyle destinations. This end-unit two bedroom / two-and-a-half bath condo in Sandlewood Creek combines a hip retro-classic style with comfort, functionality, and peace of mind with a long list of recent improvements. Solid knotty-pine wood accent paneling is featured throughout and compliments the freshly painted walls in designer colors. The kitchen has been partially renovated and has a nice clean and modern vibe, complemented by granite countertops and updated bathrooms for a clean, modern feel. The roof was replaced in 2021. Major system upgrades include an A/C (2019) and a brand-new water heater (2026), while the entire interior has just been freshly painted, carpets professionally cleaned, and a final detailed cleaning completed—making this home truly move-in ready. Whether you're looking for a primary residence, a low-maintenance lifestyle, or a smart investment in one of Central Florida’s most consistently in-demand areas, this property checks all the boxes. Enjoy easy living in a quiet, established community just minutes from everything that makes Winter Park special—top-rated schools, dining, shopping, and parks. Pre-approved for FHA financing and recent updates that your insurance company will like - this is a rare opportunity in this market. Don't miss it!. Sellers have this priced to sell, so don't delay. Call today to make your appointment for your private viewing.

Listing is courtesy of: DERENTHAL REALTY (321-662-8014)

Listing Agent: Mike Derenthal (321-662-8014)

Remarks: One or more photo(s) has been virtually staged. Fully reimagined and COMPLETELY RENOVATED with Custom features, this stunning 4-br, 3-ba home in desirable Winter Park Pines sits proudly on a spacious corner lot and offers Modern Luxury with thoughtful, HIGH END UPGRADES throughout. The interior showcases all-new cabinetry and countertops, highlighted by a dramatic waterfall kitchen island, brand-new appliances including a built-in microwave tucked into a custom pantry cabinet. Every detail has been carefully considered, from new luxury vinyl flooring and interior doors to upgraded closet shelving, sleek bathroom mirrors, and stylish shower enclosures. Sound insulation enhancements in key areas—including the primary suite, bathrooms, and kitchen walls—provide added comfort and privacy, while smart ceiling fans, dimmable lighting, USB charging outlets, and pre-wiring for under-cabinet lighting and wall-mounted TVs bring modern convenience to everyday living. Beyond the interior, the home continues to impress with major system upgrades and durable exterior improvements designed for long-term peace of mind. Enjoy a BRAND NEW ROOF with transferable warranty, updated soffit and fascia, rot-proof siding and porch columns, and new fiberglass exterior doors with built-in blinds. The property also features a new irrigation system, vinyl fencing, and an expansive 3+ car driveway. Behind the walls, everything has been upgraded—including full electrical rewiring with a new 200-amp service, all-new plumbing from underground lines to fixtures, and a high-efficiency HVAC system with new ductwork and insulation for maximum energy savings, making this home truly MOVE-IN READY with no detail overlooked. FYI-Cool Deck texture on front and back patio and final exterior paint W/O 03/29, New Sod on 04/06, Dumpster removed and pressure washed and Install of PVC fence w/ gate at driveway on 04/08.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Kelly Butterfield (407-463-1289)

Remarks: One or more photo(s) has been virtually staged. Beautifully renovated pool home in the highly desirable Eastbrook community of Winter Park, featuring major recent upgrades including a new AC system, windows, doors, and flooring throughout the home. This move-in ready 3-bedroom, 2-bath residence sits on an oversized 0.30-acre corner lot in a quiet cul-de-sac with no HOA. The home offers a bright open-concept layout with abundant natural light and a seamless flow between the living, dining, and kitchen areas—ideal for both everyday living and entertaining. The updated kitchen features modern cabinetry, stainless steel appliances, and generous counter space. Both bathrooms have been tastefully renovated, and the spacious bedrooms provide comfort and flexibility. Step outside to a private backyard with a sparkling pool and plenty of outdoor space perfect for relaxing or hosting gatherings. Additional highlights include a 1-car garage, roof replaced in 2016, updated electrical, and a newer water heater (2021). Located within the top-rated Seminole County school district and just minutes from Park Avenue, Rollins College, shopping, dining, museums, and Winter Park Hospital. A fantastic opportunity to own a beautifully updated home in one of Central Florida’s most desirable locations.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Julimar Barreiro Pastrana (407-590-8604)

Remarks: Welcome to 647 Randy Lane in Winter Park. This is a rare opportunity to own a designer residence in one of the area's most sought-after neighborhoods, offered for the first time in over 10 years. Situated on a spacious corner lot, 0.36 acres, this meticulously maintained home showcases timeless charm paired with modern luxury. Lush, mature landscaping surrounds an oversized private pool, expansive patio and generous backyard, creating a Florida outdoor living experience ideal for entertaining or relaxing year-round. Inside, the home features an open-concept floor plan designed for both comfort and style. The chef's kitchen stands out, appointed with quartz countertops, premium Wolf double ovens and a built-in Sub-Zero refrigerator, delivering high-end performance with sophisticated design. Seamless indoor-outdoor flow enhances the living experience, leading to a resort-style backyard retreat complete with ambient lighting, perfect for evening gatherings and weekend enjoyment. Ideally situated minutes from Park Avenue's renowned dining, boutique shopping, and cultural attractions, this home offers unparalleled convenience in the heart of Winter Park. Located in one of the area’s most desired school districts, including Audubon K-8 and Winter Park High School. The home is equipped with updated features like a newer roof (2024), solar panels (2024), resurfaced pool and tile (2021), well irrigation, tankless gas water heater, oversized indoor laundry room and more. This exceptional property blends luxury, location and lifestyle-making it a standout opportunity in the Winter Park real estate market.

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

Listing Agent: Sara Cambron (321-277-8444)

Remarks: Fabulous Winter Park location. This is a 3 bedroom, 2 bath patio home with a great layout, split bedroom plan, high ceilings in the living room, and an eat in kitchen that is open to the family room. A large primary bedroom which has a walk in closet, two additional closets and french doors leading out to the back yard. There is a screened in patio off of the breakfast / dining area and an interior laundry room. Zoned for Winter Park schools, minutes from downtown Park Ave., Rollins College and Advent Health Winter Park. Property is a gem perfect for a renovation or an opportunity to build new.

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

Listing Agent: Meg Dolan (321-948-0701)