Winter Park Single Family Homes For Sale - 312 homes

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

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

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

Remarks: Welcome to this thoughtfully updated Winter Park home ideally on a spacious corner lot with a two-car garage offering excellent storage and everyday convenience. This home offers a flexible layout featuring two bedrooms plus an office that can function as a third bedroom, ideal for working from home or accommodating guests. Hardwood floors run throughout, adding warmth and character. Major system updates have been completed, including a 2024 metal roof and 2025 HVAC system, providing peace of mind for the next owner. Additional exterior improvements include new soffits and gutters, fresh exterior paint in 2025, a whole-home surge protector, and updated breezeway or office door and windows installed in 2024. Inside, you will find a well-equipped kitchen with Samsung appliances, including a range, microwave, dishwasher and a 2023 refrigerator, along with a 2020 Samsung washer and dryer. Comfort and efficiency have also been enhanced with replaced air ducts in 2016, an Ecobee smart thermostat and updated ceiling fans. Smart home features include a Logitech Circle View wired doorbell, smart blinds and updated smoke detectors, providing modern convenience throughout the home. The property sits toward the rear of the lot, creating a private, fenced yard space ideal for pets, outdoor enjoyment or entertaining. An irrigation system is also in place to help maintain the landscaping. In the desirable Winter Park area and zoned for highly regarded Winter Park schools, this home offers a combination of location, updates and flexibility. With major systems addressed, this home presents a move-in-ready opportunity and being sold as is.

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

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

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

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

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

Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately wood-burning fireplace which sets a welcoming feeling in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage, irrigation system and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools such as Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

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

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

Remarks: 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: (HUGE PRICE REDUCTION & NEWLY ENHANCED REAR LANDSCAPING ADDED FOR EXCEPTIONAL PRIVACY AND MORE SECLUDED OUTDOOR LIVING EXPERIENCE) Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the City of Winter Park. This five-bedroom seven-bath home that includes a private in-law suite offers plenty of exquisite interior features. The home welcomes you with a beautifully designed 16 ft wide circular driveway wrapped in upgraded pavers, offering both elegance and functionality. A very rare 4-car garage in Winter Park with two in the rear and two in the front of the home. Starting with entering through massive 10 ft. double iron doors flowing into the foyer with 11ft high ceiling beginning with the flex/office room and formal dining to your left and right. Followed by entering the gallery that leads to the great room. The Chef’s Kitchen, a culinary dream featuring an oversized center island, quartz countertops throughout, custom 42"+15" wood cabinetry, a custom walk-in pantry, and top-of-the-line Thermador professional series. That Includes a 48' refrigerator, 48" gas cooktop, custom hood, dishwasher, built-in microwave, double convection ovens and built in coffee station. On your way to the formal dining, you pass by the show-stopping, Tempered glass wine room. Its crystal-clear glass enclosure offers a striking view of your curated collection, while the built-in wine chiller ensures each bottle is perfectly preserved. This elegant transition creates a seamless blend of function and sophistication, setting the tone for unforgettable dining experiences just steps away. The primary suite offers tranquility peace of mind, and the primary bath has a spa-like oasis with a spacious shower stand-alone tub. Followed by a custom closet thoughtfully design with plenty of room and storage. The guest retreat area has a huge bedroom, access to a full bath including private access to the Lania and pool. Tucked away with its own private entrance attached to the rear garage, the in-law suite above the garage offers the perfect blend of comfort and independence. This thoughtfully designed space includes a full bath, a cozy living area, and a convenient space with a kitchenette—ideal for extended stays or multi-generational living. Make your way to the second floor that has 11ft ceilings as well. As you reach the top the space opens into a massive game room with a wet bar, perfect for entertainment retreat with a balcony. All second-floor bedrooms have a thoughtfully design with a full bath for privacy. As you make your way back downstairs to outside, step through the oversized sliding glass doors and into your private outdoor oasis. Effortlessly extending your living space into the open air. Just beyond, the sparkling gas heated/saltwater pool and spa framed by lush landscaping and designed for both relaxation and recreation. Also, the fully equipped summer kitchen features gas grille, beverage refrigerator and ample counter space—perfect for alfresco dining and effortless entertaining. This masterpiece is equipped with a full irrigation system around the home, exterior lighting, exterior cameras for security. Smart home system ready for lighting, music and security controlled by Control 4 system for your convenience. Interlachen Golf community less than 5 min, Phelps Park walking distance, Park Ave 10 min and restaurant and retail minutes away.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Prentice Williams (321-438-8955)

Remarks: Exquisite new construction in the heart of Winter Park, this LUIH Luxury Homes residence distinguishes itself through refined design, thoughtful efficiency, and an elevated level of craftsmanship. From the moment you enter, the home reveals itself with deliberate intention, clean architectural lines and a light-filled, open-concept layout create an effortless flow throughout. The main living space is both sophisticated and inviting, anchored by a sleek electric fireplace and expansive pocketing glass doors that gracefully blur the line between indoor and outdoor living. At the heart of the home, the chef’s kitchen is as striking as it is functional. Adorned with Calacatta quartz countertops and a full suite of premium Thermador appliances, it is designed to accommodate both everyday living and elegant entertaining. The kitchen transitions seamlessly into the dining area, while a walk-in pantry, generously sized mudroom / laundry space, and wine cellar add layers of convenience and luxury rarely found in homes at this price point. The primary bedroom suite offers a true sanctuary with direct access to a secluded outdoor patio that provides a serene extension of the space. The spa-inspired bath showcases a freestanding soaking tub, dual vanities, and an expansive walk-in shower. Upstairs, four additional bedrooms offer generous proportions and versatility, ideal for guests, family, or tailored uses such as a home office or fitness studio. Designed for year-round enjoyment, the outdoor living experience is equally captivating. A sprawling covered lanai features a fully equipped summer kitchen with grill, sink, and beverage refrigerator, overlooking a meticulously designed backyard complete with a resort-style pool and spa, perfect for both intimate evenings and grand entertaining. All of this is ideally located just moments from the boutiques and dining of Park Avenue, with convenient access to Phelps Park and the Winter Park YMCA, placing you at the center of one of Central Florida’s most desirable lifestyles.

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

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Introducing a standout new construction in Winter Park’s coveted Tree Streets! As you arrive the home’s modern façade is complemented by a charming front porch, creating a warm yet striking introduction that feels both inviting and intentional. Inside, the home unfolds with a highly functional floor plan designed to enhance everyday living while still accommodating entertaining with ease. Clean lines, curated finishes, and natural light define the main living spaces, where the kitchen, dining, and living areas flow seamlessly together. The kitchen serves as a true focal point, featuring Calacatta Gioia quartz countertops, custom cabinetry with ample storage, a paneled refrigerator, and a full suite of Thermador appliances. The space transitions naturally into the dining area and living room, where a built-in wet bar with a wine fridge adds an elevated layer of functionality and style. The living room is designed to feel both open and connected, anchored by expansive pocketing sliders that completely open to the outdoor living area. The primary suite is thoughtfully positioned on the main level, serving as a calming retreat, featuring a spa-inspired bathroom with dual vanities, a freestanding soaking tub, and a spacious walk-in shower. Upstairs, three additional bedrooms are generously sized and well laid out, providing flexibility for guests, family, or a secondary living setup. The outdoor living experience is equally impressive, centered around a large covered lanai that offers ample space for al fresco dining and lounging. The spacious pool area is designed to complement the home’s indoor-outdoor lifestyle, creating a private setting that feels both relaxed and elevated. Beyond the home itself, the location is what truly sets this home apart. Situated in the heart of the Tree Streets, you are just a short walk to Phelps Park and the YMCA, minutes from Interlachen Country Club, and only a quick golf cart ride to the shops, dining, and energy of Park Avenue. Homes of this caliber and location are few and far between, making this a standout opportunity in today’s market.

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

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Positioned as one of the best values currently available in Winter Park, this exceptional residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking facade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chefs kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry, sleek quartz countertops, a paneled refrigerator, and a premium induction range, reflect the builders uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.

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

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

Remarks: Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansive 0.30-acre lot, this residence captures attention from the moment you arrive, with its striking architectural details, a sweeping driveway, and detached garage that together set a tone of timeless sophistication. Inside, soaring 20-foot ceilings welcome you into a grand foyer framed by curved archways and exceptional millwork. The living room is a true showpiece, centered around a statement fireplace with built-in shelving and subtle LED underlighting that accentuates every detail. The chef’s kitchen is a work of art, showcasing quartz countertops, exquisite custom cabinetry, integrated LED lighting, a Wolf appliance suite, and a charming breakfast nook. The formal dining room captivates, with stunning coffered ceilings floor to ceiling windows, and an atmosphere perfectly suited for elegant entertainment. The primary suite is a private sanctuary, offering dual vanities with floating mirrors, a freestanding soaking tub, a walk-in rain shower, and a spacious custom closet. Each additional bedroom has been thoughtfully designed with generous proportions and its own en-suite bath, blending comfort with sophistication. Upstairs, a loft and secondary laundry area provide convenience and versatility, while the main level includes a full mudroom and butler’s pantry with an additional washer and dryer, tailored for effortless living. The outdoor living space rivals the most luxurious resorts. A covered lanai with retractable screens seamlessly extends the interior’s sophistication outdoors, offering a year-round retreat for dining or lounging. The expansive pool deck unfolds around a sparkling pool and integrated spa, complemented by a dedicated pool bath connected to the detached garage. From the curved archways to the meticulous millwork and layered LED lighting throughout, every inch of this home reflects the builder’s attention to detail and commitment to craftsmanship. It is more than a home, it is a statement of style, presence, and precision in the heart of Winter Park’s most coveted location.

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

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

Remarks: Welcome to your dream Home! This stunning and elegant single-story home, built by Meritage Homes in the gated community of Hawk's Crest in Winter Park, includes numerous upgrades. This is the Pomelo model, equipped with an upgraded kitchen package that includes built-in double ovens and a stainless steel range hood. Beautiful quartz countertops feature an oversized kitchen island with excellent space for family gatherings. Other features include a walk-in pantry and fantastic lighting. The luxurious kitchen integrates with the dining and living areas. The dining area is enhanced by a screened-in deck overlooking a pond. The backyard features a new, large, extended patio for entertaining. The master bedroom has an ensuite bathroom with a double vanity, a small closet, and a large walk-in closet that can be customized for a future owner. The home also comes with new gutters. Other amenities in the Hawk's Crest community include a resort-style pool with a clubhouse, a splash pad, a fitness center, barbecue grills, playgrounds, a dog park, and a community fishing pier with views and access to beautiful Lake Howell. Nearby, you'll find shops, restaurants, and specialty physicians such as Kelly's Ice Cream, Foxtail Coffee, Sobol, Winter Park Pediatric Dentistry, and the Park Maitland Preschool Campus, along with excellent schools in the area. Enjoy a short drive to Downtown Winter Park, with its extensive dining and shopping options. Hawk's Crest is also very close to Rollins College and UCF. Schedule your private tour today!

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Carmen Molina (321-331-5679)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 3167 Ash Park Loop, a beautifully maintained 4 bedroom, 2.5 bathroom home tucked inside the Hyde Park community of Winter Park. Set on one of the largest lots in the neighborhood, this two-story brick front home combines character, functionality, and major system updates that make everyday living feel easy. Inside, the home immediately stands out with vaulted ceilings, a dramatic floor-to-ceiling brick wood-burning fireplace, and a fully updated staircase that gives the space a fresh, custom feel. The layout offers flexibility in all the right places, including an additional flex room off the kitchen that works perfectly as a home office, playroom, second living area, or creative space depending on your needs. The current owners have taken exceptional care of the home, with recent improvements including a new roof, gutters, and gutter guards in 2021, HVAC replacement in 2020, and a classic vinyl fence installed in 2022. Out back is where this property really opens up. With one of the larger homesites in Hyde Park, there’s room to garden, entertain, relax around the fire pit, or simply enjoy the privacy and outdoor space that’s hard to find in this area. Hyde Park residents enjoy access to community amenities including a private fishing dock on Lake Florence, basketball and tennis courts, and a playground, all contributing to the neighborhood’s welcoming, connected atmosphere. This is the kind of home that feels lived in for all the right reasons: cared for, updated thoughtfully over time, and designed for real day-to-day living.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: Built in 2018, this beautifully designed 4-bedroom, 3.5-bath home offers 2,843 square feet of refined living in a prime Winter Park location, walking distance to Park Avenue and the renowned Winter Park 9 golf course. Thoughtful architectural details set it apart, including shiplap ceilings in the living room and kitchen, decorative ceiling finishes in the bedrooms, and a striking tile staircase wall enhanced by natural light. The open-concept layout centers around a chef’s kitchen with Wolf and Sub-Zero appliances, custom cabinetry, and Kohler fixtures—perfect for everyday living and entertaining. The primary suite features a spa-inspired bath with a marble shower, while secondary baths include Kohler and Rohl fixtures. An upstairs bonus room adds flexible living space. Enjoy a private pool, oversized two-car garage with storage, and an extended driveway for ample guest parking. Additional features include dual Carrier HVAC systems, custom window treatments, and elegant Bevolo gas lanterns that create a warm, upscale presence at night. This home offers a rare combination of style, comfort, and walkable convenience in one of Winter Park’s most desirable areas.

Listing is courtesy of: FLORIDA CAPITAL REALTY (786-953-5870)

Listing Agent: Jacob Theisen (407-908-1735)

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)

Remarks: Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute. From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right, a spacious step-down living room offers abundant natural light and lovely views of the front yard. To the left, the formal dining room flows effortlessly into the heart of the home—a stunning, fully renovated kitchen and inviting family room overlooking the private pool and patio. The kitchen is designed to impress, featuring solid wood cabinetry, stainless steel appliances, sleek modern lighting, ample counter space, and a center island perfect for gathering. The adjoining family room is anchored by a stylish electric fireplace, creating a cozy ambiance while offering serene views of the outdoor living area. This home features a desirable split-bedroom floor plan, providing privacy and flexibility. The primary suite is tucked away on one side, while two additional bedrooms and a full bathroom are located on the opposite wing—ideal for family or guests. Extensive upgrades provide peace of mind and modern appeal, including a newer roof (2021), a newer AC (2019) fully renovated kitchen and bathrooms, 5-inch baseboards, knockdown ceiling texture, textured walls, luxury vinyl plank flooring throughout, fresh interior and exterior paint, and updated electrical and plumbing fixtures. Step outside to your private oasis—a fully fenced backyard with a screened-in pool enclosure and lanai, perfect for relaxing or entertaining year-round in true Florida style. This move-in-ready gem truly has it all. Don’t miss your opportunity—schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)

Listing Agent: Tony Nicolas (630-514-9342)

Remarks: 330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and designer finishes—including a farmhouse sink and gold hardware/fixtures that add a high-end touch. The bedrooms offer comfortable space with updated finishes throughout, while the oversized backyard provides plenty of room to relax, entertain, garden, or create your ideal outdoor setup. Conveniently located near shopping, dining, parks, and major roadways—and zoned for top-rated schools including Winter Park High School—this home is a standout opportunity in one of the area’s most sought-after neighborhoods.

Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)

Listing Agent: Neil Chetram (407-752-1597)

Remarks: MOVE-IN READY Winter Park home on approximately 1.68 acres with NO HOA, a long private driveway, and a rare combination of usable land, privacy, and updated living space in the heart of Central Florida. Tucked away behind mature trees and set far back from the road, this one-story property offers a peaceful, secluded setting while still being conveniently located near shopping, dining, major roadways, and everyday essentials. From the moment you arrive, the extended tree-lined driveway, expansive yard, and natural surroundings create a sense of space and privacy that is difficult to find in Orange County.A welcoming covered front porch leads into a bright, open interior with updated flooring, neutral finishes, crown molding, and a thoughtfully designed split-bedroom layout. Inside, the home opens into a spacious main living area filled with natural light and large sliding glass doors that frame views of the backyard and surrounding greenery. The open-concept design allows the living, dining, and kitchen spaces to flow naturally together, creating an ideal setup for both everyday living and entertaining.At the center of the home, the updated kitchen features stone countertops, stainless steel appliances, modern fixtures, recessed lighting, and an oversized island with extensive storage and seating space. The kitchen overlooks the main gathering areas, making it easy to stay connected while cooking, hosting, or spending time with family and guests. Nearby dining space offers room for larger gatherings while maintaining a warm and comfortable atmosphere.The spacious primary suite is privately positioned and offers a peaceful retreat with backyard views, a walk-in closet, and an updated en-suite bathroom complete with dual vanities, a soaking tub, and a tiled walk-in shower. Additional bedrooms are generously sized and provide flexibility for guests, home offices, fitness space, hobbies, or multi-generational living. One of the secondary rooms is currently set up as a flex space and office, highlighting the versatility of the floor plan. With 5 bedrooms and 3 full bathrooms, the layout easily adapts to changing needs and lifestyles.The large indoor laundry room adds convenience and functionality, while the attached 2-car garage provides additional storage and covered parking. Outside, the property truly stands out. The expansive 1.68-acre lot offers endless possibilities for outdoor living, gardening, recreation, pets, equipment storage, or future improvements subject to buyer verification and county regulations. The FENCED YARD and NO HOA create additional flexibility for buyers looking for space for boats, RVs, trailers, or simply more privacy and freedom than a traditional neighborhood setting can provide.Located in unincorporated Orange County with a Winter Park address, this property offers convenient access to Downtown Winter Park, Maitland, Orlando, Park Avenue shopping and dining, nearby parks, major highways, and top Central Florida destinations. This is a rare opportunity for buyers searching for Orlando homes for sale with acreage, privacy, and a MOVE-IN READY layout in a highly desirable area. Whether you're relocating, searching for additional outdoor space, or looking for a unique Central Florida real estate opportunity with room to grow, this home offers flexibility, comfort, and convenience in one exceptional setting.Contact us today for a private tour or more details on this exceptional opportunity.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Simi Lakhani (407-408-7393)

Remarks: 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: Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, offering a bright, open floor plan with modern finishes designed for both comfort and functionality. A standout feature of this property is its commitment to sustainable living and energy efficiency. Highlights include: - Newer Roof: Installed in 2023 - Radiant Barrier & Blown-In Attic Insulation: Keeps the Florida heat out and significantly lowers cooling costs. - High-Efficiency HVAC: Energy Star rated AC unit ensuring consistent temperatures and peak savings. Step outside to an expansive backyard featuring a private pool, perfect for relaxing or entertaining. This large outdoor space offers endless possibilities for customization, such as a garden or an outdoor kitchen. Located in a quiet, established neighborhood within an A+ rated school zone, this home provides convenient access to top shopping, dining, parks, and major highways. Don't miss this incredible opportunity to own a fully updated turnkey property in one of the most desirable areas of Winter Park.

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

Listing Agent: Bernardo Carrasquel (407-920-4973)