Winter Park Homes For Sale & Real Estate - 441 homes

Remarks: Rare opportunity to own on one of the most desirable streets in Audubon Park with a coveted Winter Park address. Just a few blocks from East End Market and surrounded by many of Orlando’s Michelin-recognized restaurants, this location offers an unbeatable combination of walkability, lifestyle, and top-rated schools. Zoned for Audubon Park K-8 and Winter Park High School, you’ll enjoy the best of both worlds: the character and community of Audubon Park with the prestige and convenience of Winter Park. This thoughtfully updated home features a 2024 roof, tankless water heater, new carpet, fresh interior and exterior paint, newer insulation, solid-core interior doors, Rain Bird irrigation with well, Vivint security system with cameras, and an Ecobee smart thermostat. The sunken living room creates a unique space for entertaining (it can provide stadium seating or be a conversation pit), while the detached mother-in-law suite adds flexibility for guests, multigenerational living, or rental income. Tucked away from the noise of Corrine Drive yet only blocks from East End Market, neighborhood parks, coffee shops, and dining, this is a rare chance to own in one of Orlando’s most sought-after neighborhoods. Front door does not convey and will be replaced with a similar refinished wood door prior to closing.

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Patrick Arenson (305-951-6054)

Remarks: Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completely transformed in 2005. The redesign added substantial square footage and created a completely unique, functional floor plan that separates it from any other home in the area. Spanning 2,638 square feet of seamless indoor-outdoor living, the property features four bedrooms, 4.5 baths, including three complete en-suite setups that offer maximum privacy for family or guests, plus a dedicated 130-square-foot office. Key property features include elegant design. Go onto gorgeous, rich Brazilian cherry wood flooring that flows beautifully through the open living spaces. Work from home where a dedicated, quiet office space provides an environment for remote work, study or creative projects. Spacious kitchen allows you to enjoy an open-concept floor plan, an eating space in the kitchen, solid wood cabinetry, Silestone countertops and coordinating GE Profile appliances, including a convection oven microwave, giving the kitchen dual oven capacity. Indoor laundry room is a convenient, separate indoor laundry room that keeps household chores organized, quiet and out of sight. Private saltwater oasis allows you to relax in your fully fenced, private backyard featuring an in-ground saltwater pool with spa jets and solar heat. Turnkey infrastructure where peace of mind comes built-in with a new roof (2022), fresh exterior paint and trim (2022), and an updated 200-amp electrical panel. Smart home and systems, equipped with an app-controlled smart security system covering all doors and windows, an EcoBee thermostat and energy-efficient LED recessed lighting. Location and lifestyle benefits include top-tier education, zoned for premier Orange County schools, including Brookshire Elementary, Glenridge Middle School and Winter Park High School (home to a globally recognized International Baccalaureate program). Active recreation to Cady Way Park to enjoy the community pool, playground, sports fields and extensive bike trails. Unbeatable convenience just minutes away from Winter Park Pines Golf Course, two Publix grocery stores, and the upscale dining, boutique shopping, and museums of Park Avenue and Baldwin Park Town Center. This exceptional property blends classic Winter Park lifestyle with the modern infrastructure you demand.

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

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

Remarks: 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: 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: Welcome to this charming and well-maintained condominium located in the desirable Winter Park area, offering the perfect blend of comfort, convenience, and low-maintenance living. This inviting residence features a spacious and functional layout filled with natural light, creating a warm and welcoming atmosphere ideal for everyday living or entertaining. Enjoy an open living and dining area that flows seamlessly to a private screened porch with additional storage space, perfect for relaxing and enjoying the peaceful surroundings. The home offers generous room sizes, ample storage throughout, and a comfortable living environment within a quiet and established community. Residents enjoy access to community amenities including a sparkling swimming pool, fitness center, clubhouse/conference room, beautifully maintained grounds, and ample parking. HOA benefits may include exterior maintenance, landscaping, water, trash service, and roof maintenance, providing added convenience and value. Ideally situated in East Winter Park, this property offers exceptional access to everything Central Florida has to offer. Conveniently located just minutes from Full Sail University, the University of Central Florida (UCF), Rollins College, Downtown Winter Park, Baldwin Park, and Downtown Orlando. Enjoy nearby shopping, dining, entertainment, golf courses, parks, grocery stores, and everyday conveniences all within close proximity. Commuters will appreciate the easy access to major highways including SR-417 and SR-408, while Orlando International Airport is only a short drive away. Whether you are a first-time homebuyer, downsizing, investing, or searching for a centrally located primary residence, this home presents an outstanding opportunity to enjoy the Winter Park lifestyle in a peaceful and well-connected community.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Vincenza Di Cesare De Vieira, Pa (407-680-8118)

Remarks: Been looking for a 4 bedroom home? Well, you have found it!!! This one owner home definitely shows pride of ownership! The attention to detail is obvious! Some of the upgrades include a 10 KW solar panel system, double pane gas insulated windows throughout the house and the enclosed lanai. The kitchen has LG appliances and granite countertops. Both bathrooms have updates as well. The house has ceramic tile throughout and bamboo flooring in the master bedroom. More updates include Trane A/C system, newer water heater, roof in 2021, and electrical panel in 2017. Also included are a garage door opener that has battery backup for power outages, ring door sensors on all main windows and doors, motion activated lights at night on all 4 sides of home, a water softener, and an I-Flo system on the A/C. All that, and a desirable neighborhood with highly rated schools! You don't want to miss this one! Make your appointment today!!!

Listing is courtesy of: OPTIMA REAL ESTATE (407-366-4500)

Listing Agent: Deborah Morgan (407-314-8610)

Remarks: Under contract-accepting backup offers. Welcome to Winter Park. VIEW VIRTUAL TOUR! The Original Owner has meticulously cared for this home and the pride of ownership shines through. The real showstopper is your private outdoor oasis! Enjoy Florida’s endless sunshine in the expansive, screened-in back porch and pool area—perfect for year-round gatherings, pool parties, and quiet weekends at home. Have your morning coffee or afternoon cocktails sitting out back on the porch enjoying the birds. This large, fenced 120 x 80-foot yard provides plenty of room for little ones and pets to play, gardening, or simply unwinding. for comfortable Florida living! Perfectly situated in a desirable, close-in location and zoned for award-winning Seminole County schools, this remodeled, one-story home offers the ideal setting for all family households. Step inside and discover an inviting split floor plan featuring 3 spacious bedrooms and 2 modern bathrooms. The formal living and dining rooms create an elegant atmosphere for entertaining, while the stunning remodeled kitchen is light and bright, complete with contemporary finishes and new appliances. Relax in the cozy family room, where a charming brick wood-burning fireplace adds warmth and ambiance on cool evenings. You do have formal areas that have a multitude of options for space where YOU Need it. Once you get to the kitchen you will be amazed with the sleek white brand new cabinets with trendy quart counters and a gorgeous back splash. WOW! You can enjoy yourself while you are at the sink and watch whatever is going on in the backyard. No expense spared with banks of drawers too. Additional highlights include a 2-car garage, newer windows for energy efficiency, and NO HOA—giving you the freedom to truly make this home your own. Bring your camper, toys because you have loads of room in the backyard to work on multiple projects. Roof and A/C are 2021 adding to peace of mind with your insurance 4 point inspection. Garage is even 24x21. With ample parking, an amazing outdoor space, and proximity to top-rated schools, shopping, dining, and major highways, 3641 Oak Vista Lane delivers the ultimate Florida lifestyle for your family inside the home and outside. You deserve your own Backyard paradise. Don’t miss the opportunity to make this move-in ready Winter Park gem your forever home. Seminole County schools complete the package. Schedule your private tour today!

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

Listing Agent: Laurie Cain (407-484-9944)

Remarks: Virtually Staged. *** JUST REDUCED TO $625,000 | 1830 Edwin Blvd, Winter Park, FL 32789*** This is your moment. One of Winter Park's most beautifully RENOVATED and MOVE-IN READY homes has just been repriced, and at $625,000, it will not last long. From the moment you step inside, you are welcomed by an open, airy layout with soaring VAULTED CEILINGS that make the home feel expansive and inviting. Gorgeous TILE FLOORING flows seamlessly throughout every room, while natural light floods the space through DOUBLE-PANED WINDOWS (2018) and remote-controlled German Velux SKYLIGHTS (2021), creating an atmosphere that simply feels good to be in. The thoughtfully designed floor plan connects the living, dining, and kitchen areas in a way that is as functional as it is beautiful, making it ideal for everyday living and effortless entertaining. At the heart of the home, the stunning CUSTOM EUROPEAN-STYLE KITCHEN is a true showpiece, featuring premium Cambria quartz countertops (2025) and top-of-the-line appliances including a NEW refrigerator (2025), BOSCH dishwasher (2024), and Maytag microwave (2022). This kitchen was designed to impress and built to perform. Both bathrooms have been FULLY REMODELED with sleek modern finishes and NEW VANITIES (2025). All interior doors were replaced (2017), and every detail has been carefully considered to deliver a home that feels truly turnkey from top to bottom. For peace of mind, major systems have all been upgraded. A high-efficiency Amana AC with smart thermostat (2024), a tankless water heater (2025), a complete PEX plumbing upgrade to the city connection (2025), modernized PVC drain lines in the bathrooms, laundry and kitchen (2025), new sinks and faucets (2025), and updated kitchen electrical wiring to current code (2025) mean you can move in with complete confidence. Step outside to your own private retreat. A fenced backyard (2018) and screened patio (2022) create the perfect space for relaxing or entertaining year-round. Driveway pavers (2024), a carport (2024), and an OVERSIZED Tuff Shed (2024) round out an exterior that is just as polished as the interior. Smart home features including electronic front door locks (2023), a smart ceiling fan (2023), and smart kitchen lighting (2025) add a layer of modern convenience that ties it all together beautifully. And the location? Simply unbeatable. Just minutes from the legendary Park Avenue, and within walking distance to premier shopping, dining, parks, and everyday conveniences, this home places you right in the heart of everything Winter Park has to offer. Location. Layout. Quality. This home has it all, and now at a price that reflects real value in today's market. Opportunities like this do not come around often. *** SCHEDULE YOUR SHOWING TODAY BEFORE IT IS GONE! ***

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

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

Remarks: Under contract-accepting backup offers. Beautifully renovated and thoughtfully designed, this exceptional residence is nestled in the heart of Winter Park’s sought-after Tree Streets neighborhood. Privately behind entry gates, the home welcomes you with a picturesque front courtyard highlighted by a tranquil water feature, setting the tone for the sophisticated living experience that awaits. Expansive walls of glass and disappearing sliders flood the interiors with natural light while creating a seamless connection between indoor and outdoor living spaces, all while maintaining a remarkable sense of privacy. Designed for both everyday living and effortless entertaining, the open-concept floor plan showcases a spectacular custom entertainment bar featuring a stunning stone countertop, handcrafted cabinetry, an ice maker, a wine tower and a beverage cooler. The great room, dining area and kitchen flow together in one expansive space, framed by pocketing glass doors on both sides that open completely to the front courtyard and the rear lanai, pool and backyard beyond. The chef’s kitchen is a true centerpiece, outfitted with an impressive suite of Wi-Fi-enabled Thermador appliances, including a six-burner gas range with a steam oven and warming drawer and an integrated refrigerator with freezer drawers and additional refrigerated storage drawers. Thoughtfully designed for both functionality and style, the kitchen also features an appliance garage, a dedicated coffee bar, custom cabinetry and a large pass-through window that pockets into the wall, providing convenient service access to the covered lanai. A fully equipped secondary kitchen and butler’s pantry offers abundant storage, a built-in oven, a microwave and an additional refrigerator, making entertaining on any scale effortless. Privately situated on the first floor, the luxurious primary suite serves as a peaceful retreat with direct access to the lanai and outdoor living areas. The spa-inspired primary bath features a sculptural stone soaking tub, an oversized shower with multiple rain shower heads and a secluded outdoor patio complete with an open-air shower. A beautifully customized walk-in closet completes the suite. Additional first-floor amenities include a dedicated office, an elegant powder bath, and a unique dog room. A versatile flex space currently utilized as a spa room with laundry offers endless possibilities as a fitness room, expansive mudroom, storage area or wellness retreat, with direct access to one of the garage bays. The second level features a spacious family room along with two generously sized bedroom suites, each offering walk-in closets and private ensuite baths. One of the home's most remarkable features is the expansive rooftop balcony, complete with a gas fireplace and panoramic views overlooking both the front courtyard and backyard. Whether hosting guests or enjoying a quiet evening sunset, this elevated outdoor living space provides an unforgettable setting. Situated on a sprawling half-acre lot, the property offers exceptional outdoor space with room for future expansion or simply enjoying the privacy and beauty of the backyard, pool and lanai. Ideally located just minutes from vibrant Park Avenue, residents enjoy convenient access to Winter Park’s renowned dining, shopping, parks and cultural amenities, while major roadways provide easy commutes to downtown Orlando, Orlando Executive Airport and Orlando International Airport.

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

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

Remarks: What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real estate in the heart of Winter Park, Florida. This beautifully appointed condo apartment is located within a vibrant, amenity-rich HOA community offering a perfect blend of convenience and value. Whether you're a first-time buyer, a savvy investor seeking strong rental return, a student prioritizing location and community or a loving and supportive parent wanting to be closer to your excelling child, this unit checks every box, all at an exceptional, reasonable price point. The very best luxury boutiques, fine dining, sidewalk cafes, and vibrant art festivals. Instant access to top tier schools and hospitals. Directly across from Full Sail University, minutes to Rollins College, UCF, Valencia College and major medical centers like AdventHealth and Orlando Health facilities, making it ideal for any resident, and or faculty. Transportation is easily accessible to Downtown Orlando where the famous Lake Eola Park is, Winter Springs, Oviedo, The Orlando International Airport, Cady Way Trail, biking, hiking, swimming, volleyball, pickleball, tennis and painting at The Crealde School of Art. There's just so much within reach. Explore local gatherings, social events and community connections. For all investors, strong rental income potential and appreciation value. There's low maintenance and worry-free ownership opportunities. Let's build a portfolio together or get you owning immediately. Let's get your private tour scheduled.

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Cassandra Kelly Flores (347-723-4649)

Remarks: Welcome to this charming ground-floor condo, nestled in the highly sought-after 55+ community of Winter Park Gardens. This TWO-bedroom, TWO-bathroom condo offers a perfect blend of comfort, and stunning picturesque views. The open layout seamlessly connects the kitchen to the living area, and into to the sunroom/Florida room. This space is perfect for enjoying the tranquil views, offering a peaceful ambiance year-round. The spacious bedroom is filled with natural light, creating a bright and inviting atmosphere. This condo is located in a vibrant 55+ community that offers beautifully landscaped grounds with lush landscaping, lighted paths, and scenic pond, a sparkling community pool, and a clubhouse where residents can gather and enjoy social activities. The prime location provides easy access to a variety of amenities and attractions. Just minutes away, you'll find the historic Winter Park district, home to the renowned Park Avenue with its boutique shops, restaurants, and cultural events. The nearby Azalea Tennis Center, Mead Botanical Gardens, and Rollins College offer further enriching experiences. Embrace the serene and active lifestyle this community provides, with the added convenience of being close to Downtown Orlando, Baldwin Park, major highways like 408 and I-4, and the MCO Airport. The assigned parking space is just steps away from your front door with plenty of additional parking for guests. Don't miss the chance to make this delightful condo your own.

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

Listing Agent: Rob Rallo (407-448-2427)

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

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

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

Remarks: *Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental income potential. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. The primary bedroom and bathroom offer the opportunity to be expanded, allowing a future owner to customize and enhance the suite to their needs. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. This ADU has the ability to be separately metered from the main house and can have its own independent address if desired. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.

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

Listing Agent: Ryan Leitter (321-684-9699)

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: Welcome to 1220 Woodmere Drive, where timeless elegance and modern luxury come together in one of Winter Park’s most coveted neighborhoods. This exceptional 4-bedroom, 3.5-bath residence offers 2,815 square feet of thoughtfully designed living space, blending classic charm with today’s most desirable comforts. The spacious first-floor primary suite serves as a private retreat, complete with dual walk-in closets and a spa-inspired bath designed for relaxation. Rich solid hardwood floors flow throughout the main downstairs living areas, creating warmth and sophistication at every turn. Upstairs, a smart split-bedroom layout provides three additional bedrooms and two full baths, offering privacy and flexibility for family and guests alike. A detached two-car garage adds even more versatility, featuring an expansive bonus room above—perfect as a home office, fitness studio, creative space, or hobby room. Ideally positioned on one of Winter Park’s most sought-after streets, this home places you just moments from the Winter Park Racquet Club, the scenic Chain of Lakes, and the vibrant shops and dining of downtown Winter Park. With top-rated public schools nearby and an unbeatable location, this is a rare opportunity to enjoy the very best of Winter Park living. 1220 Woodmere Drive isn't just a home—it's a lifestyle.

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

Listing Agent: John Mcdade (407-721-7275)

Remarks: No-HOA home with NEW ROOF 2022 and dedicated HOME OFFICE/FLEX SPACE! This move-in-ready 3-bedroom, 2-bathroom residence offers 1,366 sq ft of smart living plus an bonus room perfect for remote work, creative studio, or guests—functionality of four spaces without the 4-bedroom price premium.Enjoy zero HOA restrictions, significant monthly savings, and peace of mind with a 3-year-old roof (transferable documentation included). Features include updated flooring throughout (no carpet), fully fenced backyard, and 2-car garage. Zoned for desirable Seminole County schools (Eastbrook Elementary/Lake Howell High) with quick access to SR-436, shopping, and downtown Winter Park. Ideal for remote professionals, small families, or savvy buyers seeking low-maintenance ownership with room to work and grow. Quick closing available. Schedule today!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Fernando Perez De Armas (407-837-7144)

Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.

Listing is courtesy of: EQUITYPRO LLC (407-203-6860)

Listing Agent: Navid Rokh (321-900-5977)

Remarks: Nestled in a peaceful setting within the serene Cedarwood Village community, this charming one-story Winter Park condo offers a quiet retreat away from traffic noise, with a rear wooden fence for no visible neighbors for added privacy. The spacious 27-foot tiled and enclosed lanai creates the perfect place to relax and enjoy the tranquil surroundings. Cedarwood Village also offers low-maintenance living, with lawn care included in the HOA, along with amenities such as rebuilt tennis courts, a recently remodeled pool, a clubhouse, dog-walking areas, and newly paved roads. Conveniently located in a highly rated school district and close to shopping, dining, and entertainment, the property is also just minutes from Full Sail University, Valencia College, and UCF. Inside, the condo is beautifully updated and shows the care of meticulous owners. The modern kitchen features granite countertops, matching cabinetry, and an eat-in area with sliding doors leading to the private patio, while the bathrooms and dining room wet bar are finished with the same stylish cabinets and granite. The split floor plan includes tile flooring throughout the main living areas and wood floors in the bedrooms. The large living and dining spaces feature vaulted ceilings with skylights for abundant natural light, along with a cozy wood-burning fireplace. French doors from the living room open to the enclosed lanai, while the primary suite also has direct lanai access, ample closet space, and a private bath with both a tub and shower. Additional features include an interior laundry closet adjacent to the kitchen, updated plumbing, a roof replaced in 2018, and new ductwork installed in 2023. AC 2008. Seller providing a $4,500 Buyer credit at closing toward a new AC. Two assigned parking spaces are located directly in front of the unit.

Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)

Listing Agent: Jeff Stewart (407-247-9762)

Remarks: BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, an opportunity priced 4-bedroom, 3.5-bath home to get into the coveted Winter Park Vias while adding your final touches to personalize this home while prioritizing location, schools, privacy and connectivity. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring a super spacious kitchen, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.

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

Listing Agent: Vincent Scarlatos (407-718-2378)