Winter Park Single Family Homes For Sale - 264 homes

Remarks: Beautifully RENOVATED and MOVE-IN READY/TURN-KEY home in the heart of Winter Park. From the moment you enter, you’re welcomed by an open, airy layout with VAULTED CEILINGS that make the home feel spacious and inviting. Beautiful TILE flooring throughout creates a seamless flow from room to room, while abundant natural light pours in through DOUBLE-PANED WINDOWS (2018) and German Velux SKYLIGHTS with remote control adjustable blinds (2021). The thoughtfully designed floor plan connects the living, dining, and kitchen areas in a natural, functional way, making the space ideal for both everyday living and entertaining. At the center of the home, the CUSTOM EUROPEAN-STYLE KITCHEN features high-end Cambria quartz countertops (2025) and upgraded appliances, including a NEW refrigerator (2025), BOSCH dishwasher (2024), and Maytag microwave (2022). Both bathrooms have been FULLY REMODELED with modern finishes, NEW VANITIES (2025), and all interior doors were replaced (2017), adding to the home’s updated feel throughout. Major system upgrades provide peace of mind, including a high-efficiency Amana AC with smart thermostat (2024) and a tankless water heater (2025). The home also features a complete PEX plumbing upgrade to the city connection (2025), modernized PVC drain in the bathrooms, laundry and kitchen (2025), new sinks and faucets (2025), and updated kitchen electrical wiring to current code (2025). Step outside to a private, fenced backyard (2018) with a screened patio (2022), perfect for relaxing or entertaining year-round. Additional exterior features include driveway pavers (2024), carport (2024), and a OVERSIZED Tuff Shed (2024) for extra storage. Modern conveniences such as electronic front door locks (2023), a smart ceiling fan (2023), and smart kitchen lighting (2025) complete this well-appointed home. Ideally located just minutes from Park Avenue and within walking distance to shopping, dining, parks, and everyday conveniences, this home offers the perfect combination of location, layout, and high-quality upgrades. SCHEDULE YOUR SHOWING TODAY!

Listing is courtesy of: ZEN LIVING HOMES LLC (407-800-2717)

Listing Agent: Nydia Marrero (407-620-6221)

Remarks: Welcome to this exceptional residence at 1550 Norfolk Ave, perfectly positioned in the highly sought-after Orwin Manor neighborhood of Winter Park. Set on a spacious corner lot, this beautifully maintained home offers 3 bedrooms and a rare 3-car garage, combining comfort, functionality, and timeless appeal. Inside, you’ll find rich hardwood floors, plantation shutters, and an extra-large family room ideal for both everyday living and entertaining. The updated kitchen features modern cabinetry with convenient pull-out drawers, balancing style and efficiency. This home also embraces modern sustainability solar panels power the entire property, providing clean energy year-round and the capability to continue powering the home for approximately 24 hours in the event of a power outage. Peace of mind comes from thoughtful updates, including new windows (2022), new garage doors (2023), a roof replaced in (2014), and new insulation installed in (2025) to enhance energy efficiency. Step outside to your private retreat a fully fenced backyard with a sparkling pool and spa, where the spa is heated using natural gas, offering comfort and relaxation at any time of year. An outstanding opportunity to own a well-appointed, energy-efficient home in one of Winter Park’s most desirable neighborhoods.

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

Listing Agent: Kevin Mcclanahan (407-491-8509)

Remarks: Discover one of the most sought-after communities in Winter Park, Kenilworth Shores, where mature oak trees frame the streets, spacious parks serve as gathering ground for families and peaceful walking trails weave through the neighborhood. Centrally located within arm’s reach of luxury shopping on Park Avenue in Winter Park, stunning lake views and parks in Baldwin Park, and chef-driven local restaurants in Audubon Park. Kenilworth Shores isn't just a location, it's a community, and this 4-bedroom, 2-bath Florida Ranch is your family's invitation to join. At nearly 1,600 square feet, this home provides charm, function, and thoughtful design with upgraded LVP flooring flowing throughout the easy layout. Old-world brick detailing gives the exterior genuine curb appeal, while a thoughtfully renovated interior delivers a ready to move-in home. A gorgeous brick fireplace anchors an open kitchen, family & dining room combination, with loads of natural light and function to entertain in style. The kitchen is outfitted with white shaker custom cabinetry, granite counters, a soft glass tile backsplash, stainless steel appliances, and glass pendant lighting over bar seating. A desirable split-bedroom plan provides privacy for guests, while the primary suite opens to the backyard and includes a completely renovated master bathroom. The flexible fourth bedroom is outfitted with a custom-designed built-in Murphy bed system with flanking closets and storage. Sitting off the primary living area, this bedroom provides options to fit flexible needs: home office, guest room, playroom, or secondary family space. Step into the back yard and experience your personal Florida oasis with a screened covered porch and grand Florida pool to cool off in the heat of summer. The surrounding, spacious yard is adorned with artificial turf (beautiful, durable, and effortlessly low-maintenance) complete with a putting green that will make this yard the destination for every playdate, summer BBQ, or birthday party. Completed Upgrades Include: New Roof (2021), Resurfaced pool (2021), New Irrigation & Well (2022), New Wood Fence (2023), New Dishwasher and Built-in Microwave (2023), HVAC (late 2023), New Washer & Dryer (2024), New Pool Pump Motor (2025). The best part of this special neighborhood is the connected community. Zoned for Brookshire Elementary, Glenridge Middle & WP High, some of the best Orange County Schools. Cady Way Park is steps away with a community pool, baseball fields, a playground, pickleball courts, and miles of walking and bike trails. This location checks all the boxes, schedule your private showing today.

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

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

Remarks: One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly positioned on a prime over-sized corner lot, the home blends transitional architecture with modern elegance. Sunlight fills the open layout through expansive sliding doors, creating effortless indoor-outdoor flow. The main living area seamlessly connects a formal living room and spacious dining area to the gourmet kitchen, complete with custom cabinetry, Carrara marble surfaces, and Sub-Zero and Wolf appliances. A cozy family room with fireplace provides a relaxed yet stylish gathering space. The private downstairs primary suite opens directly to the lanai, saltwater pool and features a spa-style bath. A secondary ground floor bedroom is perfect for guests or multigenerational living. Upstairs, enjoy a spacious loft with custom bar, leading to a versatile media room. Three additional en-suite bedrooms complete the second level. Recent enhancements include a full-house generator, a newly added semi-circular driveway that enhances curb appeal and functionality, and three newer A/C units with re-engineered, high-efficiency ductwork to ensure optimal climate control throughout the home. The outdoor living space is equally impressive, offering a saltwater heated pool and spa with cascading waterfall, elegant stone decking, ambient lighting, and a covered summer kitchen—ideal for year-round entertaining. A rare 3-car garage completes this exceptional home. All just moments from the shops, dining, and charm of downtown Winter Park.

Listing is courtesy of: SCANLON REALTY GROUP LLC (305-905-0496)

Listing Agent: Brian Scanlon (305-905-0496)

Remarks: One or more photo(s) has been virtually staged. NEW PRICE! Experience refined living in this exquisitely renovated custom home, positioned on an oversized corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. Inside, soaring 10-foot ceilings and a stately wood-burning fireplace set a welcoming tone in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools such as Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

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

Listing Agent: Kathy Summers (407-832-6986)

Remarks: A distinctive offering where design, location, and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance, and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, perfect for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with both durability and efficiency in mind. Major improvements include a commercial- grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century inspired landscaping designed for both beauty and ease of maintenance. Palms, agave, and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances both ambiance and function. Just moments from the desirable Park Avenue, this architecturally significant modern residence is ideally positioned in one of Winter Park’s most sought-after neighborhoods, near Lake Virginia, Rollins College, and the Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north- facing orientation and beautiful natural light throughout the day.

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

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

Remarks: Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights neighborhood, the location offers both prestige and convenience. From the moment you enter through the impressive double doors, you’re welcomed by a light-filled, open-concept design. Soaring 10-foot ceilings and elegant 8-foot doors create an airy, expansive feel, while abundant natural light highlights the home’s sleek, contemporary finishes. At the heart of the home, the chef-inspired kitchen truly shines. Outfitted with luxurious quartz countertops, stainless steel appliances, and a custom LED-lit wine display, it’s designed to impress. The seamless flow into the living and dining spaces—along with views of the backyard—makes it perfect for entertaining or everyday connection. The primary suite is a private sanctuary, offering a spa-like escape with dual vanities, a spacious dual-entry shower, and a freestanding soaking tub designed for relaxation. With three additional bedrooms, a dedicated office, and 3.5 beautifully appointed bathrooms, this thoughtfully designed single-story home provides nearly 2,500 square feet of flexible living space. Outdoors, your personal retreat awaits. Enjoy year-round Florida living on the covered lanai, complete with a built-in summer kitchen and a custom-designed pool—ideal for hosting or unwinding. The fully fenced yard features new vinyl fencing, fresh sod, and an automated sprinkler system for effortless maintenance. Perfectly positioned near Phelps Park, the Winter Park YMCA, Lakemont Elementary, and an array of top-tier shopping and dining destinations, this home delivers the ideal blend of privacy, craftsmanship, and everyday luxury.

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

Listing Agent: Nick Mckee (407-913-0171)

Remarks: Newly renovated 3 bedrooms 2 bath with flex room for home office or entertainment. Large lot with huge carport and storage room. Solar roof with attractive low payments to offset public utility bill. New LVP flooring throughout with tiles for bathrooms. New cabinets, appliances and relatively newer roof and AC for move-in ready home.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Mike Wang (631-748-6708)

Remarks: One or more photo(s) has been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium solar system you own outright, paying for your electricity. (Ask to see the bill.) Imagine relaxing on your private, expanded lanai, soaking in the breathtaking sunsets. Your spacious 4-bedroom, 3.5-bathroom home offers premium views of nature, and is just steps away from the community resort clubhouse. With gated access, Hawks Crest Residence enjoy an abundance of amenities, including a resort pool and fitness center, sidewalks and playgrounds throughout. And for those seeking adventure, enjoy dock access to Lake Howell, complete with a canoe/kayak launch. Daily, residents can relax and unwind while the management association takes care of all landscaping around the home, ensuring that residents can enjoy true maintenance-free living. The state-of-the-art off-grid solar system is equipped with battery backup with a warranty transferable to new owners. And this home is pre-wired for electric vehicles with room to expand. Excess power produced is sold back to the power company through the “Net Metering” program. Additionally, upgrades include heavy-duty commercial luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, along with 8-foot doors all designed for comfort, convenience and a peaceful home where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings and breathtaking views of the illuminated fountain from various rooms, creating a serene and relaxing atmosphere you’ll enjoy, even from the kitchen sink. And with a smart-winch lift, your chandelier maintenance is a breeze. (Rated up to 200lbs) Uniquely designed, this home was built to withstand extreme weather conditions, featuring concrete/granite tile roof, along with a steel reinforced, concrete-filled block walls and slab, all anchoring to the foundation that uniquely ties everything together, ensuring the utmost strength and safety for your family. Owners have meticulously maintained this home and comes with floor plans, a complete set of blueprints, along with photos of the home during the building process, and even includes documents for all equipment and appliances. The premium solar system comes with a transferable warranty, including scheduled updates like the new power panel, installing in 2026. And yes, this premium solar system is completely paid off and the warranty is transferable to new owners. This home features a split floor plan, with a primary bedroom on the first floor and a second primary bedroom upstairs. Spanning 2,589 square feet, the home also includes an additional 540 square feet of screened-in lanai (18x30), providing a private outdoor space to enjoy sunsets while overlooking the resort water features and landscaping. Schedule a showing for your buyers today!

Listing is courtesy of: BHHS FLORIDA REALTY (352-729-7325)

Listing Agent: Rod Chevalier (352-729-1818)

Remarks: Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood with the bones of new construction. Gutted to the studs and rebuilt with intention, every system is new — electrical, AC, roof, ductwork, drywall — and every finish is elevated, from the designer tile and quartz countertops to the gleaming floors and beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings.

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

Listing Agent: Olivia Maxwell (407-222-4440)

Remarks: Under contract-accepting backup offers. SWIM WHENEVER YOU LIKE! Discover a new dimension of living - Sparkling pool awaits you, so come and dip your toes here! Pool party ideas come naturally in this proud-to-show huge fenced-in backyard with lots of entertaining space. Oversized pool deck and large rock patio, plus huge screened in porch, make a great space for Florida living. This rock-solid ranch offers 4 bedrooms and 2 baths set in over 1700+ sf. Great curb appeal with cool rock trimming and freshly landscaped beds. Roomy formal living room greets you as you enter. The primary bedroom is split from the other 3 bedrooms and lies off the living room. This primary suite offers closet space galore. Plus, pretty double vanity, separated from the shower area. Terrific, updated kitchen with neat rustic tile, quartz counters, tile backsplash, stainless appliances, cool single bowl sink and faucet, shiplap wall and closet pantry round out this kitchen space. The family room is a great size, and the kitchen quartz counter/bar also serves as a gathering place flowing into the family room, which features a shiplap TV wall and blind-inside sliders to the screened in porch. The other 3 bedrooms and 2nd bath are off the family room. All are nice sized and the bath with nifty vintage tile, has an access door to outside/pool area. Pretty luxury vinyl plank flooring through living areas. All set in Winter Park on a .23 acre lot and Cul-De-Sac street. Conveniently close to schools, hospital, shopping, Costco and restaurants. Plus, easy access to highway 436 and straight shot to the Orlando International Airport. Don’t wait on this rock-solid ranch in desirable Winter Park...it’s ready for its new owners!

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Teresa Jones (407-376-2130)

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: Built in 2025 by Nautilus Homes and lightly lived in, this custom Winter Park residence offers a rare blend of new construction quality, thoughtful owner upgrades, and a highly desirable location between Orlando Avenue and Orange Avenue, just minutes from Park Avenue shopping, dining, and cultural attractions. Set behind mature landscaping and two inviting front porch seating areas, the home delivers over 3,000 square feet of living space, more than 4,000 square feet under roof, 4 bedrooms, 4 full baths, and a dedicated main-level office with a custom door package. More than $100,000 in post-build owner upgrades further enhance the home’s design, function, and everyday livability. Inside, Crème Brûlée wide-plank wood flooring runs throughout the home. Every bedroom features custom-built closets, while Arhaus lighting fixtures and plantation shutters add a refined finish across the interior. The main living area centers around a custom built-in entertainment wall with a vapor fireplace and integrated LED shelf lighting. The chef’s kitchen features ceiling-height custom cabinetry, a handcrafted wood range hood, and an adjoining butler’s pantry finished with Kit-Kat tile between the kitchen and formal dining room. A built-in wine and coffee bar sits just off the main living space, creating an easy flow for entertaining. The layout is both flexible and practical, with one en-suite bedroom and the dedicated office on the main level, plus three additional en-suite bedrooms upstairs. The primary suite includes a spa-inspired bath with soaking tub, oversized 9-foot walk-in shower, dual sprayers, frameless glass enclosure, and linear drainage. Outdoor spaces were designed for easy living, with professional front-yard landscaping, mature tree work, full gutters, and a private low-maintenance backyard retreat featuring artificial turf and decorative rock. The oversized 24x22 two-car garage has been fully built out with custom cabinetry, a full tool wall, overhead storage, and Shark Coating epoxy flooring. Zoned for Audubon Park K-8 and Winter Park High School, and located near Park Avenue, Mead Botanical Garden, and the Winter Park dining corridor. Showings by appointment. Buyer to verify school zoning, room dimensions, square footage and all property details.

Listing is courtesy of: SHAHRAM SONDI + CO. (407-718-6160)

Listing Agent: Shahram Sondi (407-718-6160)

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

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

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

Remarks: Tucked into one of Winter Park's most convenient pockets, this thoughtfully updated residence offers a seamless blend of comfort, style, and convenience. With three bedrooms and two bathrooms, the layout provides flexibility for a variety of living arrangements while maintaining a warm, welcoming feel throughout. The updated kitchen is both functional and inviting, featuring a gas stove and a dedicated coffee bar that adds a touch of everyday luxury. Living spaces flow effortlessly to the outdoors, where a large screened-in porch invites year-round enjoyment, complemented by a paved patio with a firepit that's ideal for relaxed evenings. The yard is perfectly sized for easy maintenance and enjoyment, complete with built-in swings that add a unique and playful detail. Positioned in a highly desirable location, this home is just moments from Interlachen Country Club, Full Sail University, and AdventHealth Winter Park, with everyday essentials like Costco nearby. Enjoy quick access to the shopping and dining of Park Avenue, just 15 minutes away. A rare opportunity to enjoy a move-in-ready home in one of Winter Park’s most convenient and connected areas. Recent updates include a 2021 roof, offering peace of mind and move-in ready convenience.

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

Listing Agent: Hannah True (407-923-9330)

Remarks: Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools. Schedule your showing today!

Listing is courtesy of: SOTERA LIVING (407-725-9660)

Listing Agent: Lianna Dangelo (321-446-3509)

Remarks: Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample space for your morning routine. The fenced-in backyard provides a private outdoor space for relaxation and entertainment. The home has been recently updated with fresh interior and exterior paint, giving it a clean, refreshed look. New flooring throughout the home adds a touch of sophistication and durability. The new appliances ensure efficiency and convenience. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV - creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.

Listing is courtesy of: KGV REALTY GROUP (407-474-0844)

Listing Agent: Kristin Vogt Pllc (407-417-7206)

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

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

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

Remarks: Pre-Construction. To be built. On a prominent corner lot in the evolving Killarney neighborhood, this offering presents a rare chance to create a custom residence in the heart of the 32789 zip code. Set among a mix of established homes and new construction, the setting reflects the ongoing transformation of the area while remaining close to the amenities that define Winter Park living. The proposed plan features over 3,700 square feet of living space with a layout designed for both everyday comfort and entertaining. Current plans accommodate five bedrooms, five and a half baths, and a dedicated office, with flexibility to tailor the design or incorporate an accessory dwelling unit (ADU) depending on buyer preferences and final approvals. The building process is structured to allow selections to be made through a private showroom experience, offering an opportunity to personalize finishes and design elements throughout. Inside, the home is envisioned with clean architectural lines and a focus on natural light. The kitchen is designed as a central gathering space with quartz countertops, custom cabinetry, and an oversized. The primary suite is planned as a private retreat with a spacious bath, dual vanities, a glass-enclosed shower, and curated tile finishes. Flooring is specified as wide-plank luxury vinyl throughout the main areas, combining durability with a warm, cohesive aesthetic. The lot size and configuration provide the option to design an outdoor living environment, including space for a future pool, subject to final plans. The location offers convenient access to Park Avenue, the Winter Park Chain of Lakes, I-4, and nearby medical facilities, with dining options such as Hillstone within close proximity. Offered at a starting price of $1,360,000, this to-be-built opportunity combines location, flexibility, and a structured customization process for buyers seeking new construction in a well-located, established area. Buyers should verify all specifications, plans, pricing, and timelines with the builder.

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

Listing Agent: Leighton Hope (407-619-7897)