Courtesy: 4 ACRE REALTY LLC
407-963-7850
Discover timeless charm and modern comfort in this beautifully maintained 4-bedroom, 3-bath home built in 1957, located in one of the most highly desirable areas of Winter Park. Nestled along picturesque, tree-lined streets, this property offers the perfect blend of classic character and thoughtful updates. Step inside to find a recently remodeled kitchen featuring top-of-the-line appliances, ideal for both everyday living and entertaining. The spacious layout provides generous living areas and comfortable bedrooms, making the home perfect for families or anyone seeking extra space. Major updates provide peace of mind, including a newer AC system, roof replaced in 2010, and updated plumbing. Outside, the private backyard retreat is designed for relaxation and gatherings, complete with a cozy fire pit and a versatile accessory unit—perfect for guests, a home office, or rental potential. Located within an excellent school district and just minutes from popular restaurants, boutiques, and shopping, this home offers the best of Winter Park living—charming neighborhood appeal with convenient access to everything you need. A rare opportunity to own a classic home in one of Central Florida’s most sought-after communities.
Courtesy: KELLER WILLIAMS WINTER PARK
407-545-6430
Offering the comfort and feel of a single-family home with the convenience of townhome living, this beautifully maintained two-story residence features 3 bedrooms, 2.5 baths, and a private courtyard conveniently located in Winter Park. Sliding glass doors throughout the home fill the interior with natural light and create a seamless connection to your private outdoor courtyard. Inside, the spacious layout is complemented by low-maintenance tile flooring throughout and a cozy wood-burning fireplace, adding warmth and character to the main living area. The kitchen is well-appointed with granite countertops, stainless steel appliances, and a newer refrigerator, while the generously sized bedrooms provide comfortable retreats. The primary suite features two closets and an ensuite bath with dual sinks. Major system updates provide exceptional peace of mind, including a brand-new roof and HVAC system installed in January 2026, along with fresh exterior paint, newer gutters (approximately three years old), and a newer fence. The washer and dryer convey, making this home truly move-in ready. The community offers an exceptionally low HOA fee of under $200 per month, adding to the home’s overall value. Ideally located with easy access to Winter Park, Maitland, Full Sail University, UCF, Rollins College, and Valencia College, as well as nearby shopping, dining, and major roadways. With its spacious design, private outdoor space, and proven rental history, this property presents an outstanding opportunity as either a primary residence or investment. Reach out to schedule your private showing now!
Courtesy: AGILE GROUP REALTY
813-569-6294
Welcome to this beautifully remodeled home in the heart of Winter Park, offering the perfect blend of charm, privacy, and convenience. Situated at the end of a quiet street, this unique property provides exceptional privacy while showcasing peaceful views of nearby Lake Wilderness. The main residence features 3 bedrooms and 2 bathrooms, complemented by an attached mother-in-law suite with a full bath and private entrance, making it ideal for multigenerational living, guests, a home office, or potential rental income. Inside, the home has been thoughtfully updated with a fully remodeled kitchen and bathrooms, real hardwood flooring throughout, and a bright open-concept layout designed for comfortable everyday living and entertaining. Additional upgrades include plantation shutters, double-pane windows (2021), and added attic insulation (2023) for improved energy efficiency. Major system updates provide peace of mind with HVAC replaced in 2022 and roof installed in 2018. Step outside to enjoy a screened-in back porch overlooking a spacious fully fenced yard with plenty of room to garden, relax, or entertain. The property is enhanced by maturing fruit trees in both the front and back yard, creating a private and serene outdoor setting. Location is another major highlight. The home offers quick access to Interstate 4, making commuting throughout Central Florida easy. It’s also just 10 minutes from Winter Park Village, where residents enjoy some of the area’s best restaurants, shopping, and a movie theater. Additionally, Winter Park is known for its charming tree-lined streets, beautiful lakes, parks, golf courses, and vibrant cultural scene, including the renowned Park Avenue district, museums, and top-rated dining. This rare property offers privacy, flexibility, and modern updates in one of Central Florida’s most desirable communities.
Courtesy: KELLER WILLIAMS ADVANTAGE REALTY
407-977-7600
Hidden gem in the heart of Winter Park! This beautifully updated 2-bedroom, 2-bath single-story townhouse offers a private fenced backyard, additional storge closet on back patio and a low HOA. The home features granite countertops, new cabinetry, and stainless steel appliances, along with tastefully renovated bathrooms and fresh interior paint throughout. Major upgrades include 2022 pavers, a whole-house repipe, and a newer roof. Enjoy community amenities such as a resort-style pool, basketball courts, and a clubhouse—perfect for entertaining. Centrally located near shopping, dining, major travel routes, Altamonte Springs Mall, Downtown Winter Park, Full Sail University, and UCF. Zoned for top-rated Seminole County schools. A fantastic single-level townhome in a prime location with very reasonable HOA fees.
Courtesy: CHARLES RUTENBERG REALTY ORLANDO
407-622-2122
One or more photo(s) has been virtually staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle. The beautifully renovated interior features a modern kitchen, quartz countertops, soft-close shaker cabinets overlooking the dining room & family room. The updated bathrooms and fresh finishes throughout create a move-in ready home that feels brand new! The spacious layout flows seamlessly into the outdoor living area where you’ll find a large fenced-in backyard with a pavered patio and a cozy fireplace perfect for entertaining, relaxing or enjoying Florida evenings. Located just minutes from shopping, dining, parks, and top Winter Park amenities this property is an excellent opportunity for first-time homebuyers or investors looking for a turnkey home in a prime location. A rare opportunity to own a fully updated home with modern style and a spacious backyard in the heart of Winter Park!
Courtesy: PREMIER SOTHEBY'S INTL. REALTY
407-644-3295
Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a highly functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park Avenue. Inside, rich hardwood floors run throughout the living spaces, complemented by Restoration Hardware lighting that brings a refined, cohesive feel to every room. The welcoming foyer opens to a gracious formal living room with a gas fireplace and custom built-ins—an elegant yet comfortable space for entertaining or relaxing. Just beyond, the formal dining room is well proportioned for hosting holiday gatherings and dinner parties with ease. The heart of the home is the expansive chef’s kitchen, thoughtfully designed for both everyday living and effortless entertaining. An oversized island anchors the space, topped with Carrara marble counters and offering generous seating. A dual Wolf oven with six-burner range plus French cook top, custom cabinetry, walk-in pantry, and a butler’s pantry complete with under-counter wine refrigerator provide both beauty and functionality. A spacious breakfast room filled with natural light overlooks the backyard and flows seamlessly into the family room. Here, a gas fireplace, custom built-ins, and three sets of French doors create a warm focal point while inviting the outdoors in. The first-floor primary suite serves as a private retreat, featuring large windows with tranquil views of the pool and direct access to the covered lanai. Dual walk-in closets provide ample storage, and the spa-like primary bath is finished in Carrara marble, offering a large soaking tub and an expansive glass-enclosed shower with dual shower heads. Two powder baths—one thoughtfully designed as a pool bath—along with one of two laundry rooms complete the main level. Upstairs, four additional bedrooms and a dedicated office provide generous space for family and guests. Two of the bedrooms feature private ensuite baths, while the remaining two share a well-appointed Jack & Jill bathroom. One of these rooms is currently arranged as a bonus lounge, offering flexibility to serve as a fifth bedroom, media room, or additional gathering space if desired. The thoughtful second-floor layout easily adapts to a variety of lifestyle needs, whether accommodating guests, growing families, or multi-generational living. A secondary laundry room upstairs adds an added layer of everyday convenience. Outdoor living is equally impressive. The spacious covered lanai with summer kitchen overlooks the saltwater, heated pool and spa, creating a true extension of the interior living space. Brick paver flooring continues from the lanai to the open patio, offering multiple areas for lounging, dining, and entertaining beneath the Florida sky. Ideally positioned in a highly desirable location and zoned for sought-after Audubon Park K-8, 2040 Randall Circle offers timeless style, thoughtful design, and seamless indoor-outdoor living in one of the area’s most charming neighborhoods.
Courtesy: KELLER WILLIAMS WINTER PARK
407-545-6430
A masterfully crafted custom residence in the heart of Winter Park, this 2014 Barefoot Brothers home blends timeless architecture with modern functionality just moments from Park Avenue and the Audubon Park Garden District. Designed for both refined entertaining and active everyday living, this 5-bedroom + office home offers a flexible, family-focused floor plan plus an expansive second floor bonus room, ideal for recreation, media, or study. A formal dining room and oversized great room with 11.5’ ceilings create the perfect balance of comfort and sophistication. The first-floor primary suite features a private, attached office space and a spa-inspired ensuite with marble floors, marble-topped double vanity, freestanding cast iron soaking tub with gooseneck filler, double walk-in shower, Kohler fixtures, and a statement chandelier over the tub. The chef’s kitchen showcases marble countertops, a walnut center island, a large walk-in pantry, 10’ ceilings, GE gas range, new Samsung refrigerator, and Bosch dishwasher — all opening seamlessly to the living area anchored by a gas fireplace with custom built-ins and double French doors leading outside. Designed with connection in mind, the breezeway links the main home to the detached garage and opens to a charming river rock paved patio — perfect for gatherings and outdoor dining. A recently repainted timber-framed front porch welcomes guests with timeless curb appeal, complemented by a circular driveway, irrigation system, and landscape lighting. Built with longevity and energy efficiency in mind, this home features insulated concrete form (ICF) construction, vinyl double-pane Low-E windows, two tankless water heaters, natural gas connections (fireplace, range, dryer, outdoor grill), Cat 6 ethernet wiring, surround sound, and ceiling fans throughout. Spend your mornings biking to coffee on Park Avenue and your evenings enjoying dinner in the Audubon Park Garden District — all while coming home to a thoughtfully constructed retreat designed for modern family living. With roof, electrical, and plumbing completed in 2013, this home offers peace of mind, architectural character, and an exceptional lifestyle in one of Winter Park’s most desirable corridors. Schedule your private showing today!
Courtesy: EQUITYPRO LLC
407-203-6860
Welcome to 2407 Lion Heart, Winter Park — where timeless elegance meets modern comfort. Nestled in one of Winter Park’s most desirable communities, this fully renovated 3-bedroom, 2-bath residence offers the perfect blend of sophistication, functionality, and peaceful living. Step inside and experience 1,785 square feet of thoughtfully designed open-concept living space, highlighted by wide-plank luxury vinyl flooring and designer finishes throughout. Every detail has been carefully curated to create a home that feels both elevated and inviting. At the center of the home is the chef-inspired kitchen, designed to impress and built for everyday living. This stunning space features 42” soft-close solid wood cabinetry, quartz countertops, a custom coffee bar/work nook, and Energy Star stainless steel appliances. Whether you're preparing a quiet morning coffee or hosting guests, the kitchen serves as both a functional workspace and a beautiful gathering place. What truly sets this property apart are its private pool and outdoor living spaces. Enjoy your morning coffee in the peaceful courtyard, or entertain guests on the spacious screened-in patio, ideal for relaxing evenings and indoor-outdoor living. Situated in the back of the neighborhood, with the deepest setback on the street, this property offers a rare combination of privacy, space, and exceptional curb appeal. Conveniently located just minutes from top-rated A-schools, shopping, dining, and all that Winter Park has to offer, this home presents an incredible opportunity to enjoy modern luxury in a prime location.
Courtesy: COLDWELL BANKER REALTY
407-647-1211
Discover this completely renovated 4-bedroom pool home plus office with custom built-ins (could be a 5th bedroom) tucked away in the quiet, highly sought-after Winter Woods neighborhood. Backing up directly to the gorgeous Interlachen Golf Course, this property offers no rear neighbors—a rare opportunity in such a prime location. Extensively updated in 2018, this home features a new roof (2018), flooring, 16 SEER A/C with new ductwork, full electrical and plumbing updates, water heater, and a solar-heated (solar paid /not a lease!) pool with new pool deck, along with numerous additional improvements (see attached list for full details). The open-concept kitchen and living area center around a spacious island. The primary bedroom is generously sized, while the 2.5 bathrooms are thoughtfully updated with stylish finishes that blend comfort and functionality. A two-car garage and interior laundry room provide convenience. Step outside to your private retreat—featuring a screen-enclosed, sparkling solar-heated pool and a backyard to enjoy. Whether it’s morning coffee poolside or relaxing evenings under the stars, this outdoor setting truly shines. Ideally located just minutes from the charm of Park Avenue and vibrant downtown Winter Park, you’ll enjoy easy access to top dining, shopping,
Courtesy: UNITED REALTY GROUP INC
954-450-2000
Lovely 2 bedroom, 2 bath condo with formal dining room. The building exterior features Brick, Colonial Style with Brick Paver Walkway and Beautifully Landscaped Grounds. Community Amenities include 2 Swimming Pools, Lighted Tennis Courts, Fitness Center, Car care facilities and a Clubhouse. WATER INCLUDED IN HOA FEE! Check out the Large Living Room next to the HUGE Porch overlooking the SCENIC COURTYARD. This upstairs unit has an inside stairwell leading to the entrance to the unit. The Living Room also has GREAT VIEWS of the COURTYARD beyond the Sliding glass doors! BEAUTIFUL LAMINATE FLOORING THROUGHOUT, except TILED Bathrooms and Foyer. ENJOY your coffee or favorite beverage on your Over-sized BALCONY while inhaling Fresh Air and Absorbing the PEACEFUL AND TRANQUIL VIEWS! WALK TO THE SHOPPING MALL! CLOSE to 436, bus route. GREAT SEMINOLE COUNTY SCHOOLS!! GREAT CENTRALIZED LOCATION!! WELCOME HOME!!
Courtesy: CORCORAN PREMIER REALTY
407-965-1155
Welcome to 2814 Sheriff Way, an exceptional residence nestled in the vibrant neighborhood of Winter Park Pines. This remarkable home combines comfort and elegance, offering a tranquil lifestyle with unparalleled convenience. Spanning 1,948 square feet, this property boasts four generously sized bedrooms and two bathrooms (both showers renovated 5/25) perfect for family living or entertaining guests. As you step inside, you'll be welcomed by a spacious living area that effortlessly transitions into the dining space, creating a warm and inviting setting for gatherings and family meals. The kitchen is thoughtfully designed for both functionality and efficiency, ready to cater to all your culinary needs. Additional living areas include a sunroom back porch and a screened-in carport, providing versatile spaces for relaxation or entertainment. The home is perfect for entertaining, with a rear sunroom/porch, pool, offering a personal oasis for unwinding or hosting friends and family. This outdoor retreat is destined to become a favorite spot for relaxation and enjoyment. The 2-car carport with a screen creates another space to entertain. Located just minutes from Cady Way Trail, Ward Park, Cady Way Community Pool, Lake Baldwin Dog Park, Winter Park Pines Golf Club, and the iconic Park Avenue, this home is perfectly positioned for both convenience and leisure.
Courtesy: 1% LISTS CENTRAL FLORIDA
727-967-9779
Welcome home to a well-maintained 3-bedroom, 2 full bath, and 1 half bath home tucked away on a quiet cul-de-sac. This home offers a comfortable layout with just the right amount of space for everyday living and entertaining. The main living areas feel open and inviting, with plenty of natural light flowing throughout. The kitchen features granite countertops, ample cabinet and counter space, and connects easily to the dining and living areas, making it perfect for gatherings or casual nights at home. The bathrooms also include granite countertops, adding a clean and updated touch throughout. Upstairs, the primary bedroom offers a peaceful retreat with its own private bath, while the additional bedrooms provide flexibility for guests, a home office, or hobbies. The half bath downstairs adds extra convenience for visitors. Conveniently located near great schools, shopping, dining, and everything Orlando has to offer, this home combines comfort with a great location. Also close to the University of Central Florida and Oviedo. Schedule your private showing and come see it for yourself.
Courtesy: DAILLAND REAL ESTATE
407-666-7860
Welcome to 1760 Alabama Drive, an architectural standout in Winter Park’s coveted Golden Triangle, known locally as The Vias. Positioned just houses away from some of the most valuable real estate in 32789 and steps from Kraft Azalea Park, this 2,841 sqft mid-century residence sits in one of Winter Park’s most exclusive and tightly held enclaves. Lakefront sunsets, shaded walking paths, and the serenity of the Chain of Lakes lifestyle are at your doorstep with a respected local racquet club just minutes away for those who value both community and an active lifestyle. This is authentic mid-century architecture, thoughtfully modernized without compromising its soul. Clean lines. Intentional geometry. Expansive walls of glass. Natural light floods nearly every room through oversized windows, while dramatic 20 foot hedges on both sides create an extraordinary sense of privacy. You experience openness without exposure a rare and highly desirable balance. At the heart of the home is a true chef’s kitchen featuring completely custom cabinetry and restaurant quality appliances. This is a serious culinary space built for performance and designed with craftsmanship in mind. It flows seamlessly into the main living areas, supporting both elevated entertaining and everyday living. The home offers (4) four bedrooms and (2.5) two and a half baths, including an impressively scaled primary suite that feels like a private retreat. A massive great room anchored by a functional fireplace provides architectural presence and flexibility currently styled as a study or office, but equally suited as a dramatic living space. Step outside and the lifestyle expands. The backyard is designed for gathering, centered around a fully realized outdoor gourmet kitchen and expansive entertaining area made for long evenings and effortless hosting. There remains generous room for a future pool without compromising the integrity of the space, a rare blend of finished outdoor luxury and future optionality in this neighborhood. A private rear driveway and (2) two-car garage add convenience and discretion rarely found in this pocket of Winter Park. In this market, location drives value. This address is not just a location, it’s a strategic position. Architectural distinction, immediate park access, privacy, and proximity to the very best of Winter Park define its enduring appeal.
Courtesy: KELLY PRICE & COMPANY LLC
407-645-4321
Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.
Courtesy: THE REALTY MEDICS
321-947-7653
This well-maintained 3 bedroom, 2.5 bath home is located in the quaint, charming city of Winter Park. Step inside to a split-bedroom floor plan featuring a spacious living and dining area with high ceilings and beautiful natural lighting. The kitchen is equipped with ample cabinetry in excellent condition, spacious countertops with breakfast bar seating, and a large pantry. The primary bedroom suite is on the first floor and boasts a walk-in closet and an updated bathroom with a dual sink vanity and walk-in shower. The two remaining bedrooms are on the second floor and share a guest bathroom with a large vanity and bathtub. Upgrades include ceiling fans in all rooms, a laundry space with a washer and dryer included, and a 1-car garage. This home also features a private patio and backyard with no rear neighbors, perfect for an outdoor dining set, grilling station, lounge area, or garden. The Villas of Casselberry offers low HOA fees and a community swimming pool. Conveniently located near highly rated K-12 schools, Full Sail University, UCF, and Rollins College. Approximately 15 minutes away from Park Ave and Orlando Ave offering a variety of shopping, dining, and entertainment. The roof, A/C, and water heater are all less than 10 years old. Schedule a showing today!
Courtesy: REAL BROKER, LLC
855-450-0442
Welcome to 188 Lewfield Cir — a beautifully designed 1-bedroom, 1-bath condo located in the highly desirable The Stratford at Winter Park Condominium community. This unit features an open floor plan that creates a bright, spacious feel, perfect for comfortable everyday living or entertaining guests. The layout maximizes functionality while maintaining a modern, low-maintenance lifestyle. Residents of The Stratford enjoy resort-style amenities including two outdoor swimming pools, a clubhouse, a fully equipped fitness center, and beautifully maintained grounds; offering both relaxation and convenience right outside your door. Located in the heart of Winter Park, you’re just minutes from premier shopping, top-rated restaurants, entertainment, and major roadways. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this location places you in one of Central Florida’s most sought-after areas. Comfort. Convenience. Winter Park lifestyle. 188 Lewfield Cir is ready to welcome you home.
Courtesy: PRESTIGE PROPERTY SHOP LLC
407-331-8000
Spacious 2-bedroom unit offering 1,008 sq ft plus a 16x8 enclosed Florida room and a one-car garage, presenting a great opportunity for an investor or buyer ready to add value. The unit has been professionally cleaned, and following a water heater failure, ServPro inspected and addressed the area—no severe damage reported. As a result, baseboards have been removed throughout, and carpet has been removed from both bedrooms, leaving bare concrete and a blank slate for new flooring. The home features vaulted ceilings in the living and dining areas, a large welcoming foyer, and a functional kitchen with pantry and dual lazy Susan cabinets. Major components include a 2023 roof, 2025 water heater,2010 A/C, poly piping, and a Gould-brand electrical panel. HOA covers roof, exterior maintenance, termite bond, and pest control; buyer approval is required. Recent comparable sales support strong potential—bring your vision and make this one your own.
Courtesy: FANNIE HILLMAN & ASSOCIATES
407-644-1234
Discover a rare opportunity to own a beautifully maintained home that perfectly blends comfort, style, and location. Nestled in a desirable neighborhood, this property welcomes you with inviting curb appeal and a thoughtfully designed layout ideal for both everyday living and entertaining. Inside, you’ll find spacious living areas filled with natural light, a modern kitchen featuring quality finishes and ample storage, and generously sized bedrooms that offer the perfect retreat at the end of the day. This home has been thoughtfully updated with major improvements already completed for peace of mind, including a new AC system, all new ductwork, and new insulation installed in 2020 for enhanced energy efficiency and comfort. The exterior was freshly painted in 2020, the roof was replaced in 2021, and the pool was resurfaced in 2021—perfect for enjoying warm days in your own backyard oasis. Electrical panels were updated in 2018, and the water heater was replaced in 2024, offering added reliability and value. Ideally located just minutes from Baldwin Park and the prestigious Park Avenue district, you’ll enjoy easy access to boutique shopping, dining, and community events. This home is also a short drive to Rollins College, Full Sail University, and the University of Central Florida (UCF), making it a convenient choice for professionals, faculty, and students alike. Step outside to a private backyard ideal for relaxing evenings or entertaining guests. Conveniently located near parks, schools, and everyday amenities, this move-in-ready home offers both tranquility and accessibility. if you're on the market this exceptional property is ready to welcome you home.
Courtesy: URBANISTA BROKERS
407-619-7272
Great opportunity to own this 3 bedrooms, 2 bathrooms single-story, ground level, end unit condo located in the quaint community of Cedarwood Village with a desirable Winter Park address! This light and bright home features vaulted ceilings in the living room, creating an open and airy feel. The kitchen offers an eat-in space, stainless steel appliances, a convenient pass through to the living room, and a laundry closet with washer and dryer included. Enjoy seamless indoor-outdoor living with sliding glass doors leading to a private rear screened-in lanai, plus an additional front patio just off the kitchen. Recent upgrades include new luxury vinyl flooring, a new roof (2023), new A/C ducts and insulation (2023), and full re-plumbing (2021), providing peace of mind for years to come. Two reserved parking spaces are located directly in front of the condo for added convenience. Community amenities include a pool, tennis court, and clubhouse. Ideally located near shopping and dining, as well as Rollins College, Full Sail University, UCF, and major thoroughfares for easy commuting. This move-in ready condo offers comfort, convenience, and value in an unbeatable location!
Courtesy: CLASSIC HOMES
407-493-8553
Newly built in the heart of Winter Park, this warm modern-industrial residence offers 4 bedrooms, 3.5 baths and 3,031 heated square feet of thoughtfully designed living space (3,674 total including a two-car garage). Soaring 12’8” ceilings downstairs and 10’ ceilings upstairs create volume and light throughout. Oversized black grid windows flood the home with natural light and offer water views from the second level. Designer LED ambient lighting is integrated throughout — including illuminated floating stair treads and custom feature shelving — creating a dramatic yet inviting atmosphere. The kitchen is both refined and functional, featuring an oversized island, premium appliances, expansive prep space, and a generous walk-in pantry. The open layout flows seamlessly into the living and dining areas, anchored by a striking fireplace feature wall and wide-plank wood flooring. The primary suite offers a spa-level retreat with a dedicated wet area and freestanding soaking tub, delivering a luxurious, architectural bathroom experience. Designed for entertaining, the outdoor living space includes a private pool and a fully equipped summer kitchen — ideal for Florida living year-round. Additional features include: • Spray foam insulation for superior efficiency • Deeded access to a private boat ramp on Lake Killarney • No HOA dues Located in one of Central Florida’s most desirable neighborhoods, this home is just a short walk or drive to Park Avenue dining, shopping, and entertainment. A rare opportunity to own new construction with architectural character in Winter Park.
Courtesy: WINTER PARK REAL ESTATE CO LLC
407-405-6612
This isn’t your average condo. It’s professionally updated with large rooms and more closet space than you’ll know what to do with. There’s even a washer and dryer right in the unit (no more laundry runs!), newer appliances, and parking right outside your door. On a scale from 1 to 10, this place is easily a TWENTY! Seriously, no expense was spared to make it super comfortable. You’ll love the bright living room that opens into a dining area and cozy kitchen that has been remodel and replace for today's lifestyle. There’s no carpeting flooring anywhere, making clean up easy! They even thought of the little things and replaced the following items: doors, bigger baseboards, oversize crown molding, shiplap ceilings, fancier trim work on doors, locks and knobs, updated electrical outlets and switches, brand new vanity cabinet in the bathroom, toilet and all around newer light fixtures—it’s all been done for you. The full-size washer/dryer is cleverly tucked away in the primary closet for convenience. The location? Perfect! At Four Seasons you’re just minutes from Winter Park shops and restaurants—and downtown Orlando is just a short trip away when you want some excitement. If you’re looking for comfort AND style in an unbeatable location—this is it!
Courtesy: PINEAPPLE PLACE REALTY, LLC
407-497-8563
Welcome home to this updated 1-bedroom 1-bathroom GROUND FLOOR condo, ideally positioned toward the desirable rear of the sought-after Lakeside Manor community. The move-in-ready residence features a spacious, open floor plan enhanced by ceramic tile throughout, elegant crown molding and a thoughtfully updated kitchen complete with modern countertops, soft-close cabinetry, and newer stainless-steel appliances. Additional value-added improvements include newer windows and updated plumbing (re-piped and newer water heater) offering peace of mind to the next owner. Lakeside Manor is a highly desirable lakefront community offering private access to Lake Killarney a 239-acre spring fed lake. Residents enjoy premium amenities including a private boat ramp, community dock, access to boat slips (subject to availability, a monthly fee applies). The community also features a swimming pool, guest parking, extra parking (subject to availability, additional fee applies), community laundry facilities (nominal usage fee), storage cabinets, outdoor grill and picnic tables. Condo fees conveniently include monthly internet and water service. Ideally located just minutes from Winter Park and Park Avenue’s renowned shopping and dining, with quick access to I-4 and Downtown Orlando, this property offers the perfect combination of comfort, convenience, and lifestyle.
Courtesy: FANNIE HILLMAN & ASSOCIATES
407-644-1234
FURNISHINGS INCLUDED! Experience high-end luxury and effortless convenience in one of the most central locations in Winter Park. Built by Makeur Homes and thoughtfully updated and furnished by SMRS Design, this stunning Modern Mediterranean detached townhome showcases light-filled interiors and carefully curated custom finishes. Offering 3 bedrooms and 2.5 bathrooms across 1,884 square feet, the home features a desirable first-floor primary suite and elevated design details, including Level 4 drywall, engineered oak floors, Bosch appliances, LED mirrors, and a Lutron Caséta lighting and Triathlon shade system. A Calacatta Gold porcelain slab electric fireplace serves as a striking focal point in the living room. All major designer furnishings are included—featuring pieces from renowned design houses such as Restoration Hardware, Caracole, Eichholtz, and Jonathan Charles—creating a truly turnkey opportunity. The open-concept floor plan is both functional and inviting, filled with natural light and offering views of a private paved patio and fenced backyard—ideal for relaxing or entertaining. Enjoy a low-maintenance, lock-and-leave lifestyle within an intimate four-unit community tucked along a picturesque, tree-lined brick street. Additional highlights include a private two-car garage with EV charging port, guest parking, and close proximity to premier dining, shopping, and daily conveniences, including Publix and AdventHealth. A rare opportunity to own a fully furnished, design-forward residence in an exceptional location.
Courtesy: FANNIE HILLMAN & ASSOCIATES
407-644-1234
One or more photo(s) has been virtually staged. Experience the FLAGSHIP LIFESTYLE of Winter Park, where COASTAL INSPIRATION MEETS TIMELESS CHARM. This beautiful 3-bedroom, 3-bath residence offers a thoughtfully designed floor plan with inviting living spaces downstairs and all bedrooms upstairs for added privacy. Built in 2004 with solid concrete block construction and a metal roof, this home perfectly balances durability with style. The LOCATION IS TRULY EXCEPTIONAL. Just 1 1/2 BLOCKS FROM FAMED PARK AVENUE, you can stroll along brick-lined sidewalks and explore vibrant boutiques, charming cafés, and cultural venues that define this beloved destination. Minutes away, Hannibal Square offers its own eclectic mix of dining and shopping. Weekends can be spent enjoying local favorites such as the Winter Park Farmers’ Market, scenic cruises aboard the Winter Park Boat Tour, or a relaxing round at the Winter Park Golf Course. Nearby Winter Park Station, including Amtrak service, keeps you conveniently connected throughout the state and beyond. From the moment you arrive at 456 Carolina Ave, you are welcomed by a brick-paved walkway and charming front sitting porch. Inside, a warm and inviting living and dining area awaits. The kitchen overlooks the main living space and features granite countertops, newer cabinetry, and a newer refrigerator. Plantation shutters, French doors, crown moulding and surround sound add character and sophistication throughout. Upstairs, the primary suite offers a spacious CUSTOM WALK-IN CLOSET and an ensuite bath complete with dual sinks, a soaking tub, and a walk-in shower. UPSTAIRS SITTING PORCHES provide the perfect spot to unwind at the end of the day. Out back, enjoy a screened patio that can accomodate casual outdoor seating and a dining table. The SUMMER KITCHEN comes equipped with a propane grill, sink, and refrigerator, making this whole space ideal for effortless entertaining. A PRIVATE ELECTRIC ENTRY GATE leads from the front of the home to the detached garage, and the property is FULLY FENCED for added privacy. Above the garage, you’ll find an AIR-CONDITIONED BONUS SPACE perfect for a home office, game room or creative retreat. A comfortable, connected lifestyle awaits in the heart of Winter Park. Schedule your private showing today. Video here:
Courtesy: WATSON REALTY CORP
407-323-3200
Welcome to the highly desirable Garden Grove community of Winter Park. This 3-bedroom, 2-bath home offers comfort, functionality, and exceptional outdoor space on a generously sized lot with room to add a pool. Inside, you’ll find a well-designed split floor plan with ceramic tile flooring throughout. The family and dining room combination creates an inviting space for everyday living and entertaining, complete with a charming wood-burning fireplace. The updated kitchen opens to the dining area and features granite countertops, new cabinetry, and a convenient breakfast bar for casual meals. Sliding glass doors lead directly to the expansive fenced backyard, blending indoor and outdoor living. The oversized backyard is a standout feature—perfect for gatherings, pets, gardening, or storing RVs, boats, and other recreational vehicles. Major updates include a roof replacement in 2019, offering added peace of mind. Conveniently located near shopping, dining, and major roadways, this home delivers space, flexibility, and value in one of Winter Park’s most established neighborhoods.
Winter Park is located in Florida. Winter Park, Florida has a population of 29,672. Winter Park is less family-centric than the surrounding county with 27.95% of the households containing married families with children. The county average for households married with children is 31.51%.
The median household income in Winter Park, Florida is $88,688. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Winter Park is 45.3 years.
The average high temperature in July is 92 degrees, with an average low temperature in January of 49.4 degrees. The average rainfall is approximately 51.9 inches per year, with 0 inches of snow per year.
