Winter Park Homes For Sale & Real Estate - 446 homes

Remarks: A fully renovated property is situated in the heart of Kenilworth Shores, Winter Park and nestled among tree-canopied streets. This home is a rare find, completely reimagined in 2005, adding square footage and function, creating a floor plan that is unique to this home. The layout includes four bedrooms with four full baths and one half bath; three are ensuites and stretch across 2,638 square feet with generous living spaces in this Florida ranch-style home. Gorgeous Brazilian cherry wood flooring in living spaces adds to the luxury of this home. The formal living room opens to the dining room and kitchen combined, adding back family space, which features vaulted ceilings and French doors to the back patio. There is a dedicated office or flex space to accommodate your family. The backyard includes a covered porch with an insulated roof and remote-controlled screens that overlook the saltwater pool, recently refinished and tiled, all ideal for entertaining. The pool also includes a water feature and solar heating for year-round use. Expansive patio surrounds with paver decking are the ideal setting to lounge and soak up the sun. Plenty of green space for play and property secured by a 6-foot vinyl fence with two gates and solar lantern lighting, adding to the beauty. A timeless kitchen awaits with solid cherry wood, clean-lined cabinetry with under-mount lighting, Silestone counters, stainless appliances and loads of counter space. Additional recessed task lighting makes cooking a breeze and a generous pantry space with solid wood cabinetry combined with laundry provides great storage. Imported Italian ceramic floors with neutral tones beautifully ground the kitchen and dining rooms. The primary suite is spacious and was expanded with renovation to allow for a spacious bath with a walk-in shower with a frameless glass enclosure, double sinks and tons of storage. Fresh carpet in all bedrooms was installed in 2023 and two of the additional bedrooms are en suites with an added study or flex room to each suite. This home has been meticulously updated and maintained and additional upgrades include a new roof (2022), electrical panels replaced (2005), exterior paint and trim (2022), an owned security system with all windows and doors, two touch panels and remote control with an app, an EcoBee Thermostat, programmable and remote control with an app, updated LED recessed lighting in select rooms, an indoor laundry room with pantry storage, large standup attic space, a full-yard zoned sprinkler system and fresh groundwater well, two water heaters, a 6 by 10-foot backyard storage shed and so much more. This home is zoned for some of the best Orange County schools: Brookshire Elementary, Glenridge Middle School and Winter Park High School, which offers a globally recognized International Baccalaureate program. Close to every convenience with two Publix grocers less than two miles away, Winter Park Pines Golf Course, a short drive to Park Avenue and Baldwin Park Town Center with world-class restaurants, shopping, parks and museums. Cady Way public park is a short walk and features a new community swimming pool, a home for youth sports, a children's playground and fantastic recreational and bike trails. This home provides all the Winter Park lifestyle that makes our city so special. Kenilworth Shores is an established community with much to offer.

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

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

Remarks: One or more photo(s) has been virtually staged. Set apart from the ordinary, this historic Winter Park residence offers a rare opportunity to own a home rich in character and authenticity. Homes like this, with timeless architectural detail and enduring charm, rarely come to market, especially in such a premier location just steps from the shores of Lake Virginia. Surrounded by multi million dollar estates, this 4 bedroom, 2 bath home blends classic warmth with everyday livability. Original wood floors, a wood burning fireplace, and thoughtfully designed living spaces reflect a level of craftsmanship and character that simply cannot be replicated. The spacious dining room is perfect for hosting memorable family gatherings, while the updated kitchen with wood cabinetry offers both function and charm. Upstairs, a versatile loft space provides flexibility for a media room, office, or play area, complete with peekaboo views of Lake Virginia that create a subtle connection to the surrounding landscape. Adding to the home’s appeal is a detached 20 x 20 studio flooded with natural light and offering endless possibilities, ideal for an artist’s retreat, home office, gym, or guest space.This is more than a home, it is an opportunity to own a piece of Winter Park’s character and history. Set among some of Winter Park’s most distinguished homes, this property delivers an unbeatable lifestyle, walkable to all that Park Avenue has to offer, surrounded by luxury, and full of potential to enjoy, enhance, or reimagine.

Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)

Listing Agent: Elizabeth Nordquist (407-694-0996)

Remarks: Rare opportunity to own a beautifully upgraded lakefront property on half acre in one of Winter Park's most desirable locations. This homesite offers the perfect setting to enjoy the current residence or build your future dream home! When you step inside you'll find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes. The home boasts new windows that fill the space with natural light and frame serene lake views, as well as a brand new roof and AC offering peace of mind for years to come. Split floor plan with 3 large bedrooms and each has a walk-in closet. Step outside and take in the beautifully landscaped yard, complete with mature trees and plenty of space and privacy. Whether you’re sipping coffee by the water or hosting friends for a sunset BBQ, this home is made for living the good life! Zoned for A rated schools. Situated on a quiet street yet just minutes from Winter Park and Baldwin Park dining, shopping, parks and culture. Call today before it's gone!

Listing is courtesy of: TAL BUSIDAN PA (407-227-3001)

Listing Agent: Tal Busidan (407-227-3001)

Remarks: Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lane. This meticulously reimagined estate represents the pinnacle of refined living in one of Winter Park's most prestigious neighborhoods, offering an effortless blend of classic architecture and contemporary luxury. From the moment you step through the elegant foyer, you're greeted by sun-drenched interiors showcasing gleaming hardwood floors, soaring coffered ceilings, and designer details at every turn. The thoughtful floor plan reveals a private home office with custom built-ins and fireplace to the right, and a gracious formal dining room to the left—perfect for hosting memorable gatherings. The heart of this home is the spectacular kitchen, a true chef's masterpiece featuring custom cabinetry, pristine marble countertops, statement pendant lighting, and top-tier appliances. This culinary haven flows seamlessly into the light-filled family room, where expansive windows frame views of your private outdoor sanctuary. The first-floor primary retreat is a haven of tranquility, featuring an expansive walk-in dressing room with exceptional storage and a spa-inspired ensuite bath. Luxuriate in the freestanding soaking tub, refresh in the walk-in shower, or prepare for your day at the generous double vanity—all appointed with elegant finishes befitting this caliber of home. Three generously proportioned guest bedrooms upstairs offer optimal comfort and privacy, complemented by a Jack-and-Jill bath and additional hall bath. A spacious bonus room with backyard views provides versatility for a media room, playroom, or home gym. Above the garage, an additional 260-square-foot bonus room with wet bar and wine fridge creates the ideal entertainer's lounge or game room. Step through French doors to your private resort-style backyard—a meticulously landscaped oasis featuring a sparkling pool and spa surrounded by lush greenery, stately palms, and thoughtful lighting. Whether gathering around the firepit, lounging poolside, or dining alfresco under the stars, this outdoor retreat elevates everyday living to an art form. No detail has been overlooked in this complete renovation: designer light fixtures and custom window treatments throughout, first-floor laundry convenience, elevated trim and baseboard, fresh paint, recessed lighting, and three HVAC units ensuring year-round comfort. The location is simply unparalleled—a leisurely stroll to the Winter Park Racquet Club, zoned for A-rated public schools, and just moments from the world-renowned shops and restaurants of Park Avenue. This is more than a home; it's a lifestyle of distinction in Central Florida's most desirable address.

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

Listing Agent: Kelly Price (407-645-4321)

Remarks: NEW PRICE!!! Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an ideal setting for both everyday life and elegant entertaining. The chef's kitchen is a true showpiece, featuring top-of-the-line Monogram appliances, a sleek Ruvati sink, built-in oven and microwave, and a professional gas range. Gorgeous Taj Mahal Quartzite countertops provide both beauty and durability, while thoughtful design elements include the option for a full-height wine refrigerator or additional cabinetry to suit your lifestyle. The living room offers a modern ambiance with an electric fireplace and expansive glass sliders that open to a covered lanai overlooking your private pool—perfect for Florida's indoor-outdoor lifestyle. For those who love to entertain, the home has been pre-stubbed for an optional outdoor kitchen. The luxurious first-floor primary suite provides a private retreat with a spa-inspired en suite bath featuring a double sink vanity, walk-in shower, soaking tub, and an oversized walk-in closet complete with custom built-ins and convenient washer and dryer hookups. Upstairs, the home continues to impress with a generous bonus room, a sophisticated loft with glass walls, three additional bedrooms, two full baths, and a second laundry area for ultimate convenience. A dedicated pool bath adds another layer of functionality for poolside enjoyment. Nestled in the desirable Lake Killarney Shores community, this home offers the perfect blend of tranquility and accessibility. Residents enjoy a low HOA, private boat launch access to Lake Killarney, and the convenience of being within walking distance to Winter Park's renowned restaurants, boutiques, and cultural attractions. This is move-in ready modern luxury at its finest.

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

Listing Agent: Kelly Price (407-645-4321)

Remarks: In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered at a newly adjusted price, the home presents a compelling opportunity to experience design-forward new construction in the Vias neighborhood. Developed and designed by Steve & Jodie Warrick Konold of Scout & Co., the 3,850-sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway & garden courtyard—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer introduces a tongue-and-groove ceiling & woven rattan chandelier, sourced & designed in London, leading to a sculptural stairwell positioned just off the main living spaces. The great room features soaring ceilings, a sleek fireplace & walls of glass windows & doors that blur the boundary between inside & out. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. In the kitchen, materials w/ function are elevated w/ a Thermadore dual-fuel range, custom plaster hood, full refrigerator & freezer columns & a large island topped in honed black quartzite. The surrounding cabinetry is crafted from hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces run along the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balance the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The primary suite occupies a private wing on the main floor accessed via antique gallery doors that lead to the rear courtyard. Vaulted ceilings, a custom walk-in closet w/ a spa-like bath provide a luxurious retreat. Features include a long double vanity, matte black Kohler fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink w/ handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby guest suite is marked by an antique door entry. The en-suite bath features a hand-painted tile threshold & suede-framed mirror. Two upstairs bedroom suites feature en-suite baths, designer lighting, distinctive mirrors & continuous European oak flooring. Positioned at the front of the home, the rooftop terrace is accessible via the upper hallway. The detached casita opens to the pool courtyard through accordion glass doors & features micro-crete floors, a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Outdoor spaces include two garden courtyards, a fully fenced backyard, a heated saltwater pool & a rooftop terrace, all enclosed by masonry walls & a board-on-board privacy fence. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core interior doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle tucked within one of Winter Park’s most exclusive enclaves.

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

Listing Agent: Padgett Mccormick (407-645-4321)

Remarks: Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Brian Hyser (407-951-2472)

Remarks: Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-home innovation, and effortless indoor-outdoor living across three thoughtfully designed levels. From the moment you arrive, the striking foyer makes a memorable first impression with its bold geometric detailing, designer finishes, and contemporary ambiance that immediately sets the tone for the home. Beyond the entry, the main living spaces unfold into an open-concept kitchen, dining, and living area designed for both everyday comfort and elevated entertaining. The chef’s kitchen is beautifully appointed with custom cabinetry, a Wolf stove, Bosch dishwasher, a premium side-by-side True Residential refrigerator and wine column combination, and a separate under-island beverage refrigerator designed for effortless entertaining. Expansive PGT sliding doors connect the interior spaces seamlessly to the lanai and outdoor retreat, while the Klipsch 5.1 surround sound system, electric fireplace, Anderson windows, ceiling fans, and integrated Elon smart-home system enhance the experience throughout the home. The outdoor living area was designed as a private modern zen-inspired escape, featuring a fully air-conditioned and heated lanai with cedar-lined ceilings, rolled screens, and direct access to the serene backyard retreat complete with a four-person sauna. Thoughtfully integrated technology and upgrades include Jellyfish lighting, Nest cameras, power-over-Ethernet shades, leak protection system, water filtration systems including Aqua Sauna Water Filter and Kohler Connect Water Minder, as well as two separate AC units serving each floor independently. The first floor also offers a private guest suite, ideal for visitors or multigenerational living. Upstairs, the second level features a spacious laundry room, two additional en-suite bedrooms, and an impressive primary suite designed as a true retreat. The luxurious primary bathroom showcases a standing shower with digital water controls, dual sinks with custom storage cabinetry, and an expansive custom walk-in closet. Additional highlights throughout the home include engineered wood flooring, electric blinds, and refined designer details at every turn. Crowning the residence is a spacious third-floor bonus area offering endless flexibility for a media room, fitness studio, office, or additional lounge space, all fully air-conditioned for year-round comfort. Combining exceptional craftsmanship, advanced smart-home functionality, and an unbeatable Winter Park location with exceptional proximity to both Park Avenue and Winter Park Village, this extraordinary residence places premier dining, boutique shopping, cafés, entertainment, and everyday conveniences just moments from home while delivering a truly elevated lifestyle experience.

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

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

Remarks: Welcome to 340 Killarney Bay, a beautifully maintained residence located within one of Winter Park’s most charming and sought-after communities. With access to Lake Killarney, residents enjoy a waterfront community pool, dock, and a peaceful setting that perfectly complements the relaxed Winter Park lifestyle. This home offers a spacious and inviting layout with both bedrooms located upstairs for added privacy, as well as a balcony off one of the upstairs bedrooms. Recent updates include newer appliances, newer water heater (2022), and fresh interior paint downstairs and in bathrooms. Ideally located just minutes from Winter Park Village, Park Avenue, Trader Joe’s, top dining, shopping, and major roadways, this home delivers the perfect blend of convenience, lifestyle, and serene community living. Schedule your showing today!

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

Listing Agent: Blaike Gill (407-545-6430)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully renovated home tucked away on a quiet cul-de-sac in Winter Park. Thoughtfully redesigned with a modern open-concept layout, this home offers an expansive single-story layout with over 1,500 square feet of inviting living space designed for both everyday living and effortless entertaining. From the moment you enter, you’re greeted by a welcoming foyer with new flooring running throughout the home, complemented by fresh interior and exterior paint and updated lighting that creates a bright, contemporary feel. The spacious living room flows effortlessly into a new kitchen, featuring updated cabinetry, sleek countertops, and a large breakfast bar, creating an ideal space for gathering with family and friends. The private primary suite serves as a relaxing retreat, featuring generous proportions, abundant natural light, and a well-appointed en-suite bath. Two additional bedrooms are thoughtfully positioned, each offering spacious closets and flexibility for family, guests, or a home office setup. With two full bathrooms, comfort and convenience are built into every corner. A large enclosed patio extends the living space outdoors, creating the perfect spot for morning coffee and year-round entertaining while overlooking the backyard, ready to create your own outdoor retreat. A large detached workshop is perfect for additional storage or to convert into a dedicated workshop for your creative projects. Major upgrades include the replacement of aluminum wiring with copper, providing long-term reliability and added buyer confidence. Additional highlights include updated finishes throughout, recessed lighting, new flooring throughout, fresh neutral interiors, and ample storage. Located in an established neighborhood just minutes from shopping, dining, and major roadways, this move-in-ready home is a rare opportunity to own a fully updated property in Winter Park without the wait or hassle of renovations. Schedule your showing today, homes like this don’t last. Save Big: 1% lender credit (based on loan amount) toward closing costs or rate buy-down with seller’s preferred lender. Ask for details!

Listing is courtesy of: EXP REALTY LLC (407-305-4300)

Listing Agent: Kristin Mcintosh, Pa (407-492-5666)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath pool home nestled in one of the desirable neighborhoods of Winter Park within Seminole County. Offering the perfect blend of comfort, space, and Florida living, this home is designed for both everyday enjoyment and effortless entertaining. Step inside to discover a spacious, light-filled floor plan featuring generous living areas, well-sized bedrooms, and a thoughtfully designed layout ideal for families or guests. Out back, you’ll find your own private oasis. The freshly resurfaced sparkling pool and expansive backyard provide the perfect setting for weekend barbecues, gatherings with friends, or simply relaxing under the Florida sunshine. With plenty of room to entertain, play, or unwind, this outdoor space truly sets the home apart. The property also features a metered irrigation system, helping maintain the lush landscaping efficiently and economically. Conveniently located near top-rated schools, shopping, dining, and major roadways, this exceptional property combines comfort, convenience, and the charm that makes Winter Park such a wonderful place to call home. Recent updates include: Pool resurfaced – April 2026 Roof replaced – 2022 New electrical panel – 2025

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Nancy Morales (321-747-7448)

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: Under Construction. This modern farmhouse designed home is under construction proposed completion March 2027. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping.  Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool.  Spacious layouts, refined detailing, and quality construction create an elevated yet livable environment, all set within a beautifully landscaped and private setting. Please inquire for details and customization options.

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

Listing Agent: Laura Earl (443-994-9441)

Remarks: **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s most sought-after communities. Designed for both everyday comfort and effortless entertaining, the first floor features an open-concept kitchen and living area filled with abundant natural light, along with a convenient half bath—ideal for hosting guests. Upstairs, the spacious primary suite boasts a private ensuite bathroom, walk-in closet, and a newly refinished balcony—perfect for morning coffee or evening cocktails. Two additional bedrooms provide generous space and share access to a second balcony, creating a seamless indoor-outdoor living experience. Recent upgrades include a new dishwasher and smart refrigerator (2022), new water heater (2025), refinished front balcony (2025), new roof, and new carpet upstairs (2026). Updated light fixtures and primary bedroom flooring within the last five years add a modern touch throughout. The $400 monthly HOA fee includes landscaping and insurance, offering low-maintenance living and added peace of mind. Zoned for some of Orlando’s top-rated schools and walking distance from the new Audubon Park K-8 School, this home presents a rare opportunity to enjoy the very best of Winter Park living. Don’t miss your chance to call this exceptional property home.

Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)

Listing Agent: Courtney Dietch (407-952-3779)

Remarks: 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: Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

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

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

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

Remarks: Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.

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

Listing Agent: Cathy Sawruk Williams (407-489-3921)

Remarks: Welcome to this beautifully updated four-bedroom, two-bathroom pool home offering 1,813 square feet of thoughtfully designed living space in one of Winter Park’s most desirable locations. Perfectly positioned on a spacious lot backing up to the scenic Cady Way Trail, this residence seamlessly blends modern updates, timeless charm, and exceptional outdoor living. Inside, the versatile floor plan includes a dedicated den, office, or playroom, ideal for today’s flexible lifestyle needs. Engineered hardwood flooring flows throughout the home and is complemented by recessed lighting, crown molding, plantation shutters, ceiling fans, and elegant French doors that add warmth and character to every space. A spacious laundry/utility room offers additional storage and convenience, complete with a washer and dryer replaced in 2024. The beautifully remodeled kitchen, updated in 2020, serves as the heart of the home and showcases white shaker-style cabinetry, sleek black granite countertops, matte grey stainless steel appliances, a striking herringbone tile backsplash, and a charming exposed wood beam feature that adds architectural interest. A breakfast bar with seating for three creates the perfect gathering space for casual dining and entertaining, while the spacious dining room easily accommodates sit-down meals and larger gatherings. The private primary suite offers a relaxing retreat featuring a shiplap accent wall, ceiling fan, and an updated ensuite bathroom remodeled in 2020 with a single vanity and beautifully tiled shower with a glass partition. The secondary bedrooms are generously sized and share an updated hall bathroom featuring a tiled tub and shower combination along with a contemporary single vanity. Step outside into your own backyard oasis where a screened, heated, salt-generated pool installed in 2022 creates the ultimate setting for year-round enjoyment. The fully fenced backyard, updated in 2022, offers privacy and plenty of room for pets, play, and entertaining while overlooking the picturesque Cady Way Trail. A private gate provides direct access to the trail, allowing for convenient access to Brookshire Elementary and nearby community amenities. Additional exterior highlights include a spacious two-car carport, whole-house generator hookup, and two included storage sheds providing excellent functionality and additional storage space. This exceptional location places you just minutes from some of Central Florida’s most sought-after amenities including the Winter Park Pines Golf Course, the Cady Way Trail, and the popular Cady Way recreational amenities featuring a community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Conveniently located near University of Central Florida, Rollins College, and Full Sail University, this home also offers quick access to AdventHealth Winter Park and the Crosby Wellness Center, both less than five minutes away, while Orlando International Airport is approximately 25 minutes from home. Zoned for top-rated Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this property offers an incredible opportunity to enjoy the very best of Winter Park living. ROOF - 2014 HVAC - 2023 ELECTRICAL - 2021(new panel)

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

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

Remarks: One or more photo(s) has been virtually staged. Completely renovated pool home on a large corner lot, tucked away on a quiet dead-end street in Winter Park. Solid block construction adds peace of mind, and this one has been updated top to bottom—new laminate flooring throughout, recessed lighting, popcorn ceilings removed, and a fresh, clean feel the moment you walk in. The main living area is bright and open, with natural light pouring into the living room that flows right into the dining space. The kitchen sits just off the dining area and was fully redone with soft-close cabinetry, stainless steel appliances, quartz counters, and a matching quartz backsplash. Off the dining area you’ll find a bonus family room that works perfectly as a media room, playroom, second living space—whatever fits your needs. Sliding doors open straight out to the pool, making indoor-outdoor living easy. This space also connects to a separate wing of the home featuring its own bedroom, full bathroom, and sitting area. It can be closed off from the main house and even has private access through the two-car garage, giving you flexibility for guests, extended family, or potential rental use. On the opposite side of the home are three additional generously sized bedrooms and two full bathrooms, including a bedroom with its own en-suite that can easily function as a primary depending on how you want to use the layout. Out back, you’ve got a large yard with plenty of room to make it your own, a big sparkling pool, and a covered porch area. There’s also a side gate with space to bring in a boat, trailer, or work truck straight to the backyard. A dedicated laundry setup is located off the back porch area, adding convenience for pool days and the separate suite. No HOA, roof from 2019, and a location that’s hard to beat—just minutes to 436, Downtown Winter Park, Full Sail, and UCF. Two-car garage, top rated schools, flexible floor plan, and a ton of usable space inside and out. Call today to set up a private showing!

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

Listing Agent: Ed Klein (321-377-4018)