Homes for Sale Near Winter Park High in Winter Park - 205 homes

Remarks: Winter Park lakefront home! A rare opportunity to own a thoughtfully renovated mid century lakefront residence in Winter Park. This three bedroom four bath home offers stunning views, high ceilings and abundant natural light. The open layout flows effortlessly for everyday living and gatherings with friends and family. As you walk through the front door, you will be drawn to the large living area and a wall of windows and doors leading to the lake. The island kitchen is a cook's dream with abundant workspace and welcoming island seating. Imagine waking up every morning to yet another amazing view- The primary suite is spacious and private with newer bath and large walk- in closet. Nicely appointed secondary bedrooms and updated baths. In addition to the main living area, there is a separate oversized family room with a full bath adjacent. This home was completely renovated and expanded in 2013 creating a perfect blend of timeless architecture and carefully designed updates. Other features include two car garage with "glass" overhead doors and mini-split HVAC, metal roof, generous closets & storage throughout and recently installed sod. What makes this house truly special is the setting on Lake Spier- a ski lake tucked away in a secluded part of Old Winter Park . There are no homes across the lake- so spending time on the patio and dock offers an expansive view of water and trees and a remarkable sense of privacy. Inside and out, every space feels connected to the natural beauty. Great location to enjoy Winter Park living. Ideally situated near top rated schools - Baldwin Park, Glenridge and Winter Park High School. Enjoy close proximity to walking trails, restaurants and shopping. This home is truly special!

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

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

Remarks: Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and an offering rarely found in Winter Park, is the underground four-car garage. Designed to discreetly accommodate an impressive vehicle collection, the garage is complemented by a striking spiral staircase that rises from the basement through the main living level and continues to the second floor. The family room is nothing short of breathtaking, featuring bespoke millwork with integrated shelving, soft architectural lighting, and a dramatic fireplace wrapped entirely in marble. The kitchen is a culinary showpiece designed for those who expect nothing less than perfection. Calcutta marble countertops cascade across the space, paired with stunning custom cabinetry, and a professional-grade Thermador appliance suite. A dedicated dirty kitchen allows for discreet preparation, while an expansive walk-in pantry ensures effortless hosting and immaculate presentation. The primary bedroom wing features a spa-inspired bathroom finished in rich marble, featuring dual vanities, a freestanding soaking tub and an enormous walk-in closet with a separate washer and dryer. Upstairs, a dedicated laundry room and a spacious secondary living area provide flexibility for family living, guests, or relaxation. The lower level extends the home’s versatility, offering a workshop, dedicated holiday and seasonal storage, and seamless elevator access to the main level of the home. Outdoor living is equally impressive. A large covered exterior lanai with a pool bath and full summer kitchen creates a seamless indoor-outdoor lifestyle, ideal for entertaining year-round. The backyard is truly resort-inspired, featuring a large swimming pool, sunken fire pit, and spa, all set within a private, beautifully secluded outdoor setting. What ultimately sets 40 Palmer apart is not just its design or finishes, but its unmatched combination of luxury and location. Just minutes from Park Ave shopping and restaurants, moments from the famous Winter Park Golf Course, yet privately tucked away, this home offers a lifestyle that is both vibrant and exclusive. A truly rare opportunity to own a part of the exceptional standard of living delivered by Vimaro Homes.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Julie Christensen (407-592-2055)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained four-bedroom, two-bathroom home offering 1,677 square feet of thoughtfully designed living space nestled in a quaint neighborhood of the highly desirable Winter Park. Featuring a split-bedroom floor plan, extensive interior updates, and exceptional indoor-outdoor living spaces, this move-in-ready residence combines comfort, functionality, and convenience with access to top-rated Winter Park schools. Step inside to discover a bright and inviting interior, freshly repainted in 2026, complemented by refinished ceilings, elegant crown molding, ceiling fans throughout, and charming French doors that add character and architectural appeal. The versatile floor plan offers multiple living and gathering spaces, including a spacious den or family room ideal for entertaining, working from home, or everyday relaxation. Abundant storage throughout the home ensures there is a place for everything. At the heart of the home, the kitchen features warm honey-toned wood cabinetry, stainless steel appliances, a brand-new microwave, and a convenient dining area perfect for casual meals and family gatherings. The functional layout allows for seamless flow between the kitchen and living spaces, making entertaining effortless. Privately situated away from the secondary bedrooms, the spacious primary suite serves as a peaceful retreat. The suite includes a walk-in closet with custom organizational features, a ceiling fan, and a beautifully updated ensuite bathroom designed with spa-inspired finishes. The luxurious bath showcases floor-to-ceiling marble-look tile, a pedestal sink, a spacious tiled shower with glass enclosure, dual shower heads, a built-in bench seat, and custom linen and towel cabinetry for added convenience and storage. Three additional bedrooms and an updated hall bathroom renovated in 2022 provide comfortable accommodations for family members, guests, or flexible workspace options. One of the home's standout features is the expansive Florida room, offering an incredible extension of the living space. Filled with natural light, this inviting retreat features a vaulted ceiling, tile flooring, and large sliding windows that create the perfect setting for morning coffee, reading, entertaining, or enjoying Florida's beautiful weather year-round. Step outside to a fully fenced backyard designed for relaxation and outdoor enjoyment. Gather around the fire pit on cool evenings, enjoy weekend barbecues in the dedicated grilling area, or unwind beneath the shade of the quaint wooden swing. The private outdoor space offers endless possibilities for entertaining, gardening, pets, and play. Ideally located in Winter Park, this home offers exceptional convenience to everything Central Florida has to offer. Residents enjoy zoning for top-rated Winter Park schools, easy access to State Road 417 within five minutes, Full Sail University within five minutes, and the University of Central Florida within approximately fifteen minutes. Orlando International Airport is just twenty minutes away, while Target, Costco, grocery stores, shopping, dining, and everyday conveniences are all nearby. Combining spacious living areas, thoughtful updates, desirable schools, and an unbeatable location, this exceptional Winter Park home offers the perfect opportunity to enjoy comfortable Florida living in one of the area's most sought-after communities. ROOF - 2019 HVAC - 2022 PLUMBING - 2026 WATER HEATER - 2018

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

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

Remarks: Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

Listing is courtesy of: PARK TOWN REAL ESTATE LLC (561-801-9199)

Listing Agent: David Auerbach (407-619-5250)

Remarks: Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

Listing is courtesy of: PARK TOWN REAL ESTATE LLC (561-801-9199)

Listing Agent: David Auerbach (407-619-5250)

Remarks: Welcome to Whisperwood, where space, convenience, and investment potential come together in one exceptional opportunity. This rare gem is a beautifully maintained 2-bedroom, 2.5-bath residence offering a rarely available townhome-style floor plan that combines generous living spaces, exceptional functionality, and outstanding investment potential. The spacious multi-level layout features expansive living and dining areas, a convenient guest powder bath, and two oversized dual primary-style suites, each with its own private bathroom. The thoughtfully designed floor plan delivers the privacy, flexibility, and comfort today's buyers are seeking. Natural light fills the interior, while the private balcony provides the perfect retreat for morning coffee or evening relaxation. A private fenced backyard opens to a lush green space, creating a peaceful outdoor setting rarely found in condominium living. Additional highlights include a covered carport, dedicated laundry closet, abundant storage throughout, and a large second-floor storage room. Residents enjoy a truly low-maintenance lifestyle with access to Whisperwood's sparkling community pool, clubhouse, and beautifully landscaped grounds. The HOA provides exceptional value by covering exterior building maintenance, grounds maintenance, water, sewer, trash, pest control, pool maintenance, recreational facilities, and common area upkeep. Perfectly positioned near SR-417, Goldenrod Road, and University Boulevard, this prime location offers seamless access to Downtown Orlando, Winter Park, Orlando International Airport, major employment centers, premier shopping and dining destinations, and Central Florida's world-famous attractions. For investors, this property represents a compelling income-producing opportunity. Currently tenant-occupied, offers immediate cash flow, Its strategic location near UCF, Full Sail University, Valencia College, and Seminole State College supports strong, year-round rental demand, making it an attractive move-in ready investment with enduring appeal. Whether you're searching for a primary residence, a low-maintenance lifestyle, or a strategic addition to your investment portfolio, this exceptional Whisperwood residence offers the perfect blend of space, location, convenience, and value.

Listing is courtesy of: PARKVIEW REAL ESTATE (407-312-6472)

Listing Agent: Miranda Azer (407-312-6472)

Remarks: Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

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

Listing Agent: Brian Teach (407-923-9313)

Remarks: Under contract-accepting backup offers. The seller has just completed a full renovation. Bathrooms have been entirely gutted and updated with new tiles, fixtures, and lighting. All lighting throughout the home has been replaced, and fresh paint has been applied throughout. Situated on a spacious double lot spanning over 1/3 acres, this home offers a private retreat, complete with an impressive 18 x 40 pool. The layout features generous common areas, including a large family room, a formal living room, a separate dining room, a kitchen with an adjacent breakfast room, a dedicated home office, a loft-style office or playroom, and a cozy home theater located above the garage. The kitchen, primary bedroom, and both the family and living rooms provide stunning views of the pool and backyard. The three-car garage offers ample space for large vehicles. Beyond the pool, you’ll find a charming gazebo and a fully equipped outdoor kitchen. Built with block and stucco construction and topped with a durable tile roof designed to last up to 100 years, this home boasts incredible durability and aesthetic appeal. Combining the feel of new construction with a rare, expansive lot in a well-established neighborhood, it provides privacy, mature landscaping, and modern elegance all in one.

Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)

Listing Agent: Teresa Chris Harralson (404-229-8737)

Remarks: 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: Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus a private backyard oasis complete with a full summer kitchen, covered rear lanai, and saltwater pool with a heated spa. The large, covered front porch welcomes guests into a foyer that opens to a spacious and well-orchestrated floorplan. Just off the entry sits a versatile office/flex space, providing the perfect setting for a private workspace or playroom, while a conveniently located powder bath serves visitors with ease. The foyer unfolds with effortless flow into the heart of the home, where an expansive living room is designed for both everyday living and entertaining. The open-concept kitchen is both functional and refined, featuring a natural gas cooktop, built-in double ovens, and adjacent sunny dinette that overlooks the backyard and pool, creating a casual dining space filled with natural light. On the opposite end of the kitchen, a large walk-in pantry offers tons of storage, and a butler’s pantry/dry bar seamlessly adjoins the large dining room—ideal for hosting gatherings with a polished, intentional flow. At the rear of the living space, expansive stacking glass sliders open to the rear covered lanai, extending the living space outdoors. Enjoy space for dining, lounging, and entertaining with a full summer kitchen that includes a large gas grill, double gas burners, a sink, beverage fridge, and storage cabinets. The backyard beyond creates a true retreat that embodies the Florida lifestyle, where a heated spa overflows into a beautifully designed saltwater pool complete with a sun shelf, all wrapped in travertine decking, tropical landscaping, and a masonry wall for enhanced privacy. Situated at the rear of the home, the well-appointed primary suite offers a quiet escape with generous proportions, dual walk-in closets, and a sensible primary bath with split vanities, a soaking tub, separate shower, and private water closet. The main level continues with exceptional functionality, including a spacious laundry room lined with built-in cabinets for storage, and a 2-car garage with direct access to the side yard and overhead racks for additional storage capacity. Upstairs, a thoughtfully designed 2nd level provides incredible flexibility, featuring a central loft for a reading or study area, a large bonus room that's perfect for a game room or secondary living area, three additional bedrooms - each with walk-in closets, two full bathrooms, and a linen closet, plus an additional storage/media closet. This home is not just a residence—it’s a lifestyle. Windsong residents enjoy access to premier amenities, including multiple community pools, a splash pad, playgrounds, a clubhouse, and 2 community docks providing access to the Winter Park Chain of Lakes via Lake Berry & Lake Mizell. Ideally located just minutes from Park Avenue, Baldwin Park, and the vibrant Corrine Drive corridor, this property offers tranquility and convenience in one of Winter Park’s most desirable neighborhoods.

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

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

Remarks: LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound system, full house generator and a private elevator to all floors. The first floor has a two car garage with storage lift above, large laundry room/home office and a downstairs guest suite. The second floor features a stylish and comfortable living room with lovely custom ceiling detail and moldings, gas fireplace, a sophisticated powder bath, and a beautiful dining room that opens to an eat-in chef's kitchen with Subzero, Wolfe and Bosch appliances and light Taj Mahal quartzite countertops. The third floor offers the spacious master bedroom and bath and also has the additional guest bedroom suite. Take the elevator to the roof top for great views of the city and here find even more potential space for fun entertaining. If your dream is to own a townhome in the heart of Winter Park, here is a stunning one for you!

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

Listing Agent: Av Blalock (407-579-9056)

Remarks: Pre-Construction. To be built. 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. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.

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

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

Remarks: One or more photos was virtually staged. Tucked away on a quiet circle in one of Winter Park's most sought-after neighborhoods, this distinctive pool home offers a rare opportunity. Set on an approximately .26-acre lot, the home features striking architectural lines, soaring wood ceilings with exposed beams, polished concrete flooring, and an abundance of natural light throughout. This is the only home currently for sale in Quail Hollow. Access to top rated schools. The exterior has been comprehensively updated: both the metal and flat roof sections (2022) and dual A/C units (2022) are already behind you, along with fresh interior and exterior paint, refinished ceilings, and new carpet. The backyard is a genuine retreat — the pool deck and fencing were both redone in 2026 — with a fully fenced yard and expansive deck ready for patio furniture, a barbecue, and effortless entertaining. Inside, a flexible and spacious layout offers room to put your own stamp on a truly special property. Practical upgrades round out the package: a Level 2 EV charger in the garage, a second Level 2 EV circuit wired to the driveway, fiber optic internet connectivity, and a recent refrigerator and dishwasher replacement. Conveniently located near Winter Park's best shopping, dining, parks, and major roadways, this home combines an unbeatable location with a strong foundation of recent improvements — and real upside for the buyer ready to make it their own.

Listing is courtesy of: BREC PROPERTIES INC (407-374-9408)

Listing Agent: Caroline Borling (407-694-3871)

Remarks: Under contract-accepting backup offers. Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot, providing modern functionality, Old World charm, and an unmatched lifestyle. The main residence spans over 3,600+ SF with 4 bedrooms, 4 bathrooms, and an attached 2-car garage. Across the brick driveway is a detached, fully-equipped 700+ SF studio apartment (5th bedroom suite) located above an additional 2-car garage, and an air-conditioned outdoor bar. With two dwellings, a 4-car garage, and an expansive outdoor entertaining space on a ½ acre lot, this home is a true private compound. Notable updates include newer HVAC systems (2020 & 2025), a new tankless gas water heater (2024), a fully renovated laundry room with new LG stackable washer/dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more... Ask for the $400K list of improvements! Enter the main residence to a family room that stretches 30 feet wide, with 12-foot ceilings, a gas fireplace, and multiple French doors lining the rear wall to showcase the brick-paver pool deck and lush, fenced-in backyard oasis, and southern exposure that invites natural light all morning and afternoon. The expansive family room is open to the kitchen, making this home ideal for entertaining. The kitchen perfectly balances charm and function, with a NEW Sub-Zero refrigerator, natural gas Wolf range, 2 Miele dishwashers, a copper-topped island that offers room for prep, serving, or seating, and a spacious dinette area with pool views. Behind the kitchen sits a dining room and adjacent den (currently used as a library/office) for more living/dining flexibility. A side entrance opens to a covered side porch overlooking a generous side yard framed by tall Podocarpus hedges... ideal for pets, a fabulous garden, or future expanded parking. A 1st floor rear bedroom wing presents 3 bedrooms & 3 full baths. Privately positioned upstairs, the expansive primary suite offers a quiet retreat, highlighted by a recent luxury bathroom renovation with elegant custom finishes including a large glass shower with 3 showerheads, 2 separate vanities, a Toto washlet, and tons of cabinetry for linen storage. French doors from both the bedroom and bath open to a covered balcony overlooking the backyard and pool, while 3 custom walk-in closets create a true dressing room experience, or the perfect opportunity to turn excess space into an office or special hobby room. Designed for entertaining, the outdoor living is equally impressive, with a sprawling lawn surrounding the large saltwater pool and an expansive paver patio for lounging and dining. A covered, air-conditioned bar is designed with custom cabinetry, exquisite lighting, a copper sink, dishwasher, wine fridge, and beverage fridge...all secured by an electronic storm shutter. The extended bar seamlessly serves the adjacent tent-covered lounge area, complete with a natural gas grill, pool bath, and outdoor shower. Above the detached 2-car garage is the studio apartment with a private entry, along with a full kitchen and bath, making it ideal for extended stays or flexible living arrangements. Located just minutes from the vibrant Park Avenue, this distinctive Winter Park compound is a one-of-a-kind property!

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

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

Remarks: Under contract-accepting backup offers. Tucked away on a quiet dead-end street in sought-after Winter Park Pines, this beautifully maintained 4-bedroom/ 2 bath pool home offers the perfect blend of privacy, updates, and location. Designed with a desirable split floor plan, the home provides separation between the primary suite and secondary bedrooms while offering comfortable spaces for everyday living and entertaining. The kitchen is positioned to overlook the backyard and pool, creating an inviting setting for both daily life and gatherings. Inside, you'll find timeless terrazzo and laminate flooring throughout, beautiful plantation shutters at the front of the home, plus a dedicated home office or flex space just outside the kitchen. Towards the back of the home you will find a versatile climate-controlled four-seasons room overlooking the backyard and pool provides even more flexibility for today's lifestyle. Whether you need a playroom, fitness area, hobby room, or additional living/dining space, this home offers room to adapt to your needs. Set on a spacious FULLY FENCED lot with mature landscaping, the property is beautiful from the moment you pull up. The private pool and expansive backyard create an ideal outdoor retreat for relaxing and entertaining year-round. Major improvements provide peace of mind, including a NEW ROOF (2021), ALL NEW WINDOWS (2025), NEW HVAC SYSTEM (2025), and EXTERIOR PAINT (2023). Additional energy-saving features include a solar-assisted hot water system helping contribute to lower monthly utility costs. Location is everything, and this home delivers. Just steps from the Cady Way Trail, you'll enjoy easy access to miles of biking, jogging, and walking paths. Nearby Cady Way Park offers tennis, pickleball, athletic fields, playgrounds, and recreation facilities. Conveniently located just minutes from Downtown Winter Park, Park Avenue, Winter Pines Golf Club, Baldwin Park, AdventHealth Winter Park, Full Sail University, shopping, dining, and SR-417. Situated in a well-established neighborhood with NO HOA, this home offers a rare opportunity to enjoy the Winter Park lifestyle with exceptional convenience and charm.

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

Listing Agent: Melissa Condrey (407-505-9339)

Remarks: Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’ Market, and the Chain of Lakes, all just moments from your front door. Built in 2017 by David Weekley, this thoughtfully designed home combines modern luxury with effortless everyday living. Soaring ceilings, oversized windows, and an open-concept floor plan fill the home with natural light and create an inviting atmosphere throughout. The first-floor primary suite offers a private retreat complete with a spa-inspired bath and spacious walk-in closet, while two additional bedrooms, a full bath, and a dedicated laundry room provide flexibility and convenience. Upstairs, the expansive living and entertaining space serves as the heart of the home. The chef’s kitchen is outfitted with custom cabinetry, granite countertops, premium stainless-steel appliances, a large center island, and a natural gas cooktop—perfect for everything from weeknight dinners to hosting friends and family. Sliding glass doors lead to a spacious balcony with new Trex decking, creating the ideal setting for morning coffee, outdoor dining, or evening cocktails overlooking the neighborhood. With professional landscaping maintained by the HOA, this home offers the ultimate low-maintenance, lock-and-leave lifestyle without sacrificing location or luxury. Opportunities to own in such a highly walkable, centrally located Winter Park setting are exceptionally rare. Experience the convenience, charm, and energy of Park Avenue living while enjoying the privacy and comfort of a beautifully appointed residence. This is Winter Park at its finest.

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

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

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: A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.

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

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

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)

Remarks: Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighborhoods! Situated on nearly a quarter-acre lot, this beautifully maintained home with fresh interior paint combines modern updates, everyday comfort, and an unbeatable location. The stunning recently updated kitchen serves as the heart of the home, featuring stylish finishes and an inviting space for cooking, entertaining, and gathering. Throughout the home, you'll find attractive flooring with no carpet, offering both a clean, modern look and easy maintenance. Major improvements provide peace of mind, including a new roof and complete re-plumbing completed in 2023. The spacious lot offers plenty of room to enjoy outdoor living, gardening, pets, or future possibilities. Location is everything, and this home delivers. Just steps from Cady Way Pool and the popular Cady Way Trail, you'll enjoy easy access to recreation, fitness, and outdoor activities. Residents also love the convenient proximity to restaurants, shopping, parks, golf, and the charm of Downtown Winter Park. Best of all, there is no HOA, providing added flexibility and freedom. With significant recent updates, a generous lot, and a prime location in highly sought-after Winter Park Pines, this move-in-ready home is a wonderful opportunity to enjoy the very best of Winter Park living.

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

Listing Agent: Jonathan Cole (407-928-9516)