Winter Park Single Family Homes For Sale - 313 homes

Remarks: Charming Pool Home in Prime Winter Park Location Welcome to 2758 Banchory Road — a true gem nestled in the heart of the desirable Winter Park Pines community. This beautifully maintained 3-bedroom, 2-bath ranch-style home offers the ideal combination of comfort, privacy, and location. With a private swimming pool, lush landscaping, and no direct front neighbors on a quiet cul-de-sac street, this home is perfect for families or anyone seeking tranquility just minutes from city conveniences. Property Highlights Spacious backyard featuring a private pool—perfect for Florida living and entertaining. Fully fenced yard with a storage shed and dedicated area for pets or gardening. Open-concept layout with natural light, mature trees, and charming curb appeal. Located steps from the Cady Way Trail, ideal for biking, jogging, or weekend strolls. Unbeatable Location Just minutes to Downtown Winter Park with boutiques, restaurants, Rollins College, and Park Avenue. Close to Winter Pines Golf Club, Cady Way Park, and public tennis courts. Easy access to Baldwin Park, Full Sail University, Advent Health Winter Park, and the 417 expressway. Top-Rated School Zone Located within the Orange County Public Schools district, this home is zoned for: Aloma Elementary School (PK–5) ~ 0.7 miles Glenridge Middle School (6–8) ~ 1.6 miles Winter Park High School (9–12) ~ 0.6 miles Highly rated with International Baccalaureate (IB) and Advanced Placement (AP) programs Private schools nearby include Trinity Prep, Geneva School, Chesterton Academy, and St. Margaret Mary K–8. Why You’ll Love It Relax and entertain year-round with your private pool and covered patio. Walkable to trails and parks, bikeable to schools, and 10 minutes to Park Avenue. Family-friendly neighborhood with strong community feel and no HOA. A rare combination of location, schools, and lifestyle opportunities. “Solar panels are negotiable. Terms to be agreed upon between Buyer and Seller and reflected in the purchase contract.” Whether you’re relocating, downsizing, or looking for the perfect place to raise a family, this Winter Park beauty has it all. Schedule your private tour today!

Listing is courtesy of: MR VARGAS PROPERTY MANAGEMENT LLC (407-557-2150)

Listing Agent: Erwin Vargas (407-557-2150)

Remarks: Short Sale. Short Sale – Subject to Lender Approval. Exceptional investment opportunity in the desirable Winter Park area. This property offers strong potential for value-add through renovation or repositioning. Located in an established community with no HOA, the home sits on a generously sized lot, providing flexibility for improvements and long-term upside. The current layout presents a solid starting point for updates, making it suitable for rental income, resale, or portfolio expansion. Conveniently positioned near shopping, dining, parks, and major roadways, with access to highly regarded schools and surrounding amenities. Winter Park continues to experience steady demand, supporting long-term investment potential. Property is being sold as-is. Buyer to verify all measurements, condition, and intended use. Don’t miss this opportunity to secure a property with upside in a sought-after Central Florida location. Highest and Best due April 17th

Listing is courtesy of: DREAM HOME REALTY GROUP AND ASSOCIATES LLC (407-504-7282)

Listing Agent: Latisha Smith (407-504-7282)

Remarks: Graceful and timeless, this classic Southern-inspired residence by esteemed builder Charles Clayton sits on a generous lot in Winter Park’s coveted Park Grove neighborhood and makes a striking first impression with beautifully composed architecture, charming dormer windows, a sweeping front porch with historic reclaimed Detroit brick flooring, and curated landscaping. Inside, the foyer unfolds with rich wood floors, raised-panel wainscoting, layered crown molding and detailed millwork which sets the tone for depth and quiet sophistication throughout the home. Just off the entry, a beautifully appointed office with finely crafted built-in shelving thoughtfully designed for both display and function. The same refined trim details carry through, while generous windows introduce soft natural light—an ideal setting for work or a quiet reading. Across, the dining room is both elegant and inviting—bathed in natural light from large windows and enhanced by more detailed millwork that adds character and creates a polished backdrop for dining and entertaining. Continue through wide detailed trim opening to an expansive great room anchored by a classic fireplace with custom built-ins, while a wall of French doors invites in natural light and extends the living space seamlessly to the covered verandah with more reclaimed Detroit brick flooring and the pool, creating perfect space to gather, lounge or entertain. Open to the Great room, the beautifully designed kitchen stands out with a coffered ceiling, marble countertops, and crisp white cabinetry, featuring illuminated upper cabinets and open shelving for thoughtful displays. A central island is complimented by an integrated breakfast table—perfect for casual dining or morning coffee. Professional-grade appliances, including a Wolf gas range and Sub-Zero refrigerator, are paired with a thoughtfully tucked-away walk-in pantry offering abundant storage and effortless organization—bringing both refined style and everyday function to the kitchen. Positioned between the kitchen and living area, this adaptable space creates a natural gathering point—ideal for casual dining, relaxed conversation, or a cozy sitting area thoughtfully suited to your lifestyle. The 1st floor primary suite offers a true retreat, with an elegant, coffered ceiling, private verandah access and dual walk-in closets. The marble bath includes a generous glass-enclosed shower with double shower heads, pedestal soaking tub, a pair of vanities, and water closet. Completing the 1st floor is a large mud room with custom built-in bench seating and integrated storage, an oversized laundry room that blends utility and style with generous storage and marble counters, and a well-appointed guest bath accented with herringbone wainscoting. Upstairs, a versatile loft area is laid out to easily accommodate multiple uses—lounge area, work-from-home space, or media retreat. The 2nd floor split-bedroom plan features a separate guest suite, with vaulted tongue & groove ceilings, a private living area and en-suite bath, a 3rd bedroom with an en-suite bath and walk-in closet, and two additional bedrooms are connected by a bath, plus an air-conditioned storage room. Outdoor living is elevated, with a covered veranda and built-in gas grill, overlooking a sleek, resort-style pool, marble decking, and a beautifully landscaped backyard. Every element of this home reflects livable elegance, all just a stone’s throw from renowned downtown Park Avenue.

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

Listing Agent: Marystuart Day (407-620-8683)

Remarks: Set on an approximately one-quarter-acre homesite in a desirable Winter Park location, this property presents an exceptional opportunity to build a custom residence in one of Central Florida’s most sought-after communities. The existing property features a one-story pool home offering approximately 2,723 heated square feet with four bedrooms and three baths; however, the value is primarily in the land. A brick-paver circular driveway enhances the property’s curb appeal, while the generous lot size provides ample space to create a beautifully tailored new construction home. Ideally located just minutes from the vibrant shopping, dining and community events of downtown Winter Park and Park Avenue, the property also offers convenient access to downtown Orlando, major area hospitals, Orlando Executive Airport and Orlando International Airport. Zoned for highly regarded Audubon K-8 and Winter Park High School.

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

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

Remarks: Under contract-accepting backup offers. 3 bedrooms PLUS an office (or 4th bedroom) AND a "flex space". Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll find a bonus space (perfect for an office or home gym) as well as a large indoor laundry room/mudroom, and the converted garage which is ideal for a playroom or secondary living space. On the other side of the home, 2 secondary bedrooms, an oversized hall bathroom, and a primary with en suite bath. There are additional touches that go a long way, too, including the custom plantation shutters throughout the home and updated countertops in the kitchen. Much of your time will be spent in the backyard, enjoying a fenced in pool, screened porch, new custom shed (2025), and fully fenced yard with turf play area. Systems in the home have been well maintained: roof (2017), HVAC (2017), tankless gas water heater (2018), and brand new electrical updates (2026). The home was also re-plumbed in 2008.

Listing is courtesy of: MILLER GRANT AND COMPANY (407-399-6031)

Listing Agent: Courtney Pelfrey (407-454-0538)

Remarks: On a picturesque brick street in Winter Park, this beautifully designed modern traditional pool home blends timeless architecture with thoughtful, high-end finishes throughout. Built in 2015 and offering over 3,100 square feet, the home features four bedrooms, three full baths, and a flexible three-story layout designed for everyday living and effortless entertaining. A welcoming front porch leads into a bright foyer highlighted by custom millwork and warm wood flooring, setting the tone for the home’s clean, curated style. The open-concept main living space flows seamlessly from the dining area into a spacious family room and a chef’s kitchen designed to impress. Anchored by a generous marble island with seating, the kitchen features Viking stainless steel appliances, a gas cooktop, honed granite perimeter countertops, custom cabinetry with upper and under-cabinet lighting, and stylish tile backsplash. A wet bar with wine refrigerator adds to the home’s entertaining appeal. The first floor also includes a versatile office or playroom with custom built-ins, a functional mudroom/drop zone and abundant storage throughout. Upstairs, the primary suite offers a peaceful retreat with natural light and a spa-inspired bath featuring dual vanities, a soaking tub and a glass-enclosed shower. Secondary bedrooms are well-sized and thoughtfully designed, while the third-floor bonus suite with full bath provides ideal space for guests, a home office or additional living. Outdoor living is equally inviting, with a covered back porch equipped with remote-controlled phantom screens overlooking a private, professionally landscaped yard with artificial turf and a low-maintenance pool, ideal for year-round enjoyment. Additional features include two HVAC systems with Nest thermostats, hardwood flooring on the main level, and designer finishes throughout. Zoned for sought-after schools including Dommerich Elementary, Maitland Middle and Winter Park High. This is a rare opportunity to own a move-in ready home that balances style, function and location in one of Winter Park’s desirable settings.

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

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

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: 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: Rare lakefront opportunity on the beautiful pristine Lake Killarney in the heart of Winter Park! Build your dream home on this coveted corner lot graced by original brick streets. Lake Killarney is a crystal-clear, spring-fed private lake — motorized boats welcome, yet no public boat ramp ensures a peaceful, exclusive experience. Enjoy sweeping 1-mile sunset views from one of only three homes on a quiet dead-end street. Walk to Hillstone, Trader Joe's, and 20+ world-class restaurants. An additional 30 X 65 ft from rear lot line is available to purchase to extend the footprint of your dream home. This is Florida lakefront living at its finest — don't miss it!

Listing is courtesy of: PROMAX PROPERTY SOLUTIONS (407-647-3377)

Listing Agent: David Murray (407-647-3377)

Remarks: Welcome to this beautifully maintained Winter Park home in coveted 32789, offering over 2,600 square feet, peekaboo Lake Killarney views, and a peaceful setting on a quiet private lakefront street. From the moment you enter, pride of ownership shines through, with custom built-ins throughout creating stylish and functional living spaces. The heart of the home is the updated kitchen and dining area, featuring high-end bamboo floors, stainless steel appliances, real wood custom cabinetry, and a large island overlooking a versatile flex space perfect for a formal living room, den, or office. The spacious great room is warm and inviting with a wood-burning fireplace and a dramatic wall of four French doors that fill the space with natural light. The elegant primary suite offers a walk-in closet and a spacious bath with dual vanities, a soaking tub, and separate shower. Step outside to a covered patio and expansive backyard with plenty of room to entertain, garden, or unwind. Just minutes from Park Avenue, premier shopping, dining, and Winter Park’s beloved parks and amenities, this is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods on .33 acres. Brand new roof and newer AC for total peace of mind. Schedule a private tour today.

Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)

Listing Agent: Jacob Johnson (407-353-0106)

Remarks: Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character and functionality in mind, this unique residence features abundant natural light, clean architectural lines, and a striking pass-through fireplace that creates the perfect ambiance between living spaces. Enjoy true Florida living with a private backyard pool, ideal for relaxing or entertaining year-round. The home also includes deeded access to a private dock and boat ramp, making boating on beautiful Lake Killarney just steps from your door. Perfectly positioned for convenience and lifestyle, this property is just a 6-minute drive to the upscale shopping and dining of Park Avenue, only 10 minutes from Downtown Orlando and Camping World Stadium, and approximately 35 minutes from Walt Disney World. Whether you're seeking a stylish primary residence or a one-of-a-kind Central Florida retreat, this home delivers the perfect blend of location, design, and lifestyle. Call to schedule your showing today!

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Samuel Kingsford (407-808-6633)

Remarks: This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.

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

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

Remarks: PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated everyday living, this exceptional 5-bedroom, 3.5-bath residence (currently configured as 4 bedrooms + dedicated office) offers a level of quality that simply cannot be replicated at this price point. Just minutes from Park Avenue, Audubon Park, dining, shopping, and top Winter Park amenities, the location is as compelling as the home itself. This residence delivers the rare combination of TIMELESS ARCHITECTURE + MODERN CONSTRUCTION. Built using INSULATED CONCRETE FORM (ICF) CONSTRUCTION, the home offers exceptional durability, energy efficiency, and a remarkably quiet interior—creating a true retreat from outside noise and Florida heat. Average summer utility bills are approximately $185/month. The exterior was freshly repainted in 2023, further enhancing the home’s curb appeal and long-term maintenance appeal. The floor plan was intentionally designed for real life. The FIRST-FLOOR PRIMARY SUITE serves as a private retreat with an attached office, custom walk-in closet with hidden under-stair storage, and a spa-like bath featuring dual sinks, marble vanity, freestanding cast iron soaking tub, marble floors, and an oversized walk-in shower with dual shower heads. A separate downstairs office easily functions as a fifth bedroom if desired. At the center of the home, the chef’s kitchen was built to perform as beautifully as it looks with MARBLE COUNTERTOPS, WALNUT ISLAND, GE CAFÉ GAS RANGE, BOSCH DISHWASHER, BRAND-NEW SAMSUNG REFRIGERATOR, and an oversized walk-in pantry/butler’s pantry. The adjacent living room is equally impressive with extensive custom built-ins, gas fireplace, library shelving, surround sound wiring, and French doors opening seamlessly to outdoor entertaining spaces. Designed with entertaining in mind, the outdoor spaces feel like an extension of the home with a spacious river rock patio, covered breezeway with tongue-and-groove ceiling, natural gas hookup for grilling, detached rear-entry two-car garage, circular front drive, and additional rear parking—an uncommon luxury in this highly sought-after location. Upstairs, soaring ceilings frame a large bonus/playroom alongside three additional bedrooms and two baths, including a Jack-and-Jill layout. A climate-controlled attic space under AC offers valuable bonus storage not included in the home’s stated square footage. Additional upgrades include NATURAL GAS (range, fireplace, dryer & grill), TANKLESS WATER HEATERS, CAT 6 ETHERNET WIRING, QUANTUM FIBER READINESS, and LOW-E DOUBLE PANE WINDOWS. Every inch of this home was intentionally designed with longevity, comfort, and function in mind. Try building this level of fully custom home in Winter Park today—on this timeline, with these finishes, this infrastructure, and this location—at this price point. It’s nearly impossible. Homes of this caliber rarely become available, especially PRICED BELOW APPRAISAL. Schedule your private showing and experience firsthand what makes this Winter Park home so exceptional.

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

Listing Agent: Jill Healey (407-797-1420)

Remarks: This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.

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

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

Remarks: Under Construction. Welcome to 2228 Howard, a designer home that complements the irreplaceable natural beauty surrounding it with a one-of-a-kind façade. This curved street-front home winds around century-old oaks while overlooking Lake Howard, creating the kind of property you will love coming home to. Many rooms inside the home are designed to incorporate the outdoor spaces. These artfully designed exterior areas feel like an extension of the interior, making the home feel even larger and more luxurious. The first floor welcomes you and your guests through the 5’ wide steel pivot door near the private office. The extra-large kitchen, open pantry, and breakfast nook are framed by warm natural oak floor-to-ceiling cabinetry and Thermador appliances while overlooking the exterior raised garden bed. This beautiful kitchen flows seamlessly into the living room, which features a modern floating-hearth fireplace. The living room opens to the outdoor living space, summer kitchen, pool, and hot tub. The primary bathroom has a modern natural feel, featuring a glass sauna room that opens to a private outdoor spa with hot and cold plunge tub. The first-floor laundry room is located just off the two-car garage and includes a drop zone for additional organization. Another bonus feature is the inclusion of two laundry rooms—one on each floor. Upstairs, the kids’ lounge is surrounded by three bedrooms and a secret media room. One bedroom is en-suite, while the other two bedrooms share a common bathroom with dual vanity areas. The exterior of the home utilizes every area like a thoughtfully designed park, creating usable space around every corner. The driveway accommodates several vehicles and includes a side drive for additional parking and storage behind the gate and garage. When you do leave your beautiful home, you are surrounded by the best that Winter Park and Orlando have to offer. This neighborhood is zoned for top-rated schools, where kids walk and ride their bikes to school daily, and is surrounded by amazing parks, restaurants, shops, and nature. Your home can feel like a perfect balance of natural and modern architecture, both inside and out. Call us to see how this home delivers that truly unique feeling.

Listing is courtesy of: COLEDEV REAL ESTATE LLC (407-915-0456)

Listing Agent: Ryan Feely (321-663-1433)

Remarks: Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blending refined luxury with modern comfort. Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stacked crown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen is thoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island, and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining. The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, a jetted soaking tub, and exceptional custom closet space. Additional features include a private elevator, Control4 automation, integrated audio/video/security systems, five HVAC systems, a central vacuum system, and a Generac whole-home generator. A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s living and entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a full beverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna and steam room, an additional laundry room, a creative storage center, and a private 4K theater with seating for multiple guests. Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood, an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creating exceptional beauty and privacy. The property also features a dog run with artificial turf. Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiance throughout the home. This home also features a whole-house water softener system. Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools include Park Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake Highland Preparatory School, and Bishop Moore Catholic High School. Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes from the Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own an exceptional custom estate in one of Central Florida’s most sought-after communities.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Vonda Fields (321-438-6906)

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

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

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

Remarks: Repositioned at $2,850,000, 151 Oakwood Way is one of the strongest newer luxury opportunities under $3M in Winter Park. Built by LunDev Custom Homes in 2023, this 4,129-square-foot residence sits on a quiet brick street in Charmont and offers a private pool, spa, covered lanai, summer kitchen, automatic screens, and a rare under-$700/sf position for newer luxury construction in 32789. Inside, the home features wide-plank wood flooring, high ceilings, quartz surfaces, Thermador appliances, custom built-ins, a wet bar, walk-in closets, and an open kitchen, dining, and living layout filled with natural light. The main living areas connect directly to the outdoor entertaining space, creating the indoor-outdoor flow buyers want in Winter Park. The floor plan includes 4 bedrooms, 4.5 baths, a main-level primary suite, generous secondary spaces, and a large flex room that can function as an office, family room, media room, game room, or future guest suite, with plumbing already in place. Set on a landscaped 0.26-acre lot with no HOA shown publicly, 151 Oakwood offers a compelling combination in 32789: newer LunDev construction, private pool, outdoor kitchen, brick-street setting, and a sub-$3M position close to Winter Park, Baldwin Park, Audubon Park, and Park Avenue.

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

Listing Agent: Matthew Burks (407-257-5347)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bath home with a 2-car garage, perfectly situated on a quaint, low-traffic street. This thoughtfully designed split floor plan offers both privacy and functionality, while soaring vaulted ceilings create an open, spacious feel throughout. The updated kitchen serves as the heart of the home, offering modern touches and great flow for everyday living or entertaining. Enjoy peace of mind with a newer A/C, adding comfort and value for years to come. Step outside to a fully fenced backyard overlooking a tranquil pond—perfect for relaxing, entertaining, or enjoying Florida’s beautiful weather. Whether you’re a first-time buyer, downsizing, or looking for a smart investment property, this home offers the ideal combination of comfort, charm, and opportunity in Florida.

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

Listing Agent: Dominick Florio (321-377-4045)

Remarks: Under contract-accepting backup offers. Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main house has a flexible floor plan that includes four bedrooms and four and one half baths, a sunroom ideal for home office, formal dining room, oversized family room and charming sitting area with fireplace. The kitchen is a chef's delight with six burner gas range, large center island, plentiful l space for gatherings and a separate breakfast room. Other notable features include gleaming wood floors, double pane windows offering abundant natural light, adorable laundry room/mud room. French doors from many rooms open to a classic front porch that is a perfect place for relaxing and enjoying picturesque grounds with towering oaks. Step outside to a private heated pool. Detached garage includes Tesla charging station. This gated compound situated on .42 acres is one block from Lake Osceola and a easy walk to Park Avenue.

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

Listing Agent: Nicole Seybold (407-808-9374)