One or more photo(s) has been virtually staged. Pre-Construction. To be built. Customize the finishes-to-suit on your new home located on one of the most sought-after streets in Winter Park. Lincoln Circle is a quiet street next to Park Avenue restaurants and shopping. Easily walk to your favorite shops, restaurants, and the Winter Park Golf Course. Presented by an established, award winning luxury home builder, this bespoke home includes premium features, appliances, fixtures and finishes as follows: ELEVATOR, WOLF/SUB ZERO appliances, wine cooler tower, built-in coffee maker, trash compactor, AUTOMATED LIGHTING and window treatments, full house SOUND SYSTEM, first floor primary bedroom wi
Don’t miss out on this stunning 4-bedroom, 3 full and 2 half bath, corner lot home in the heart of Winter Park’s sought-after Via’s neighborhood. Fully updated with high-end finishes, hardwood flooring, crown molding, stainless steel appliances, granite countertops and much more. The first floor features a library/den with a gas fireplace, a formal dining room with coffered ceiling, and 2 large bedrooms that share a full bathroom. The gourmet kitchen includes an induction top, stainless appliances, a large closet pantry and spacious eat in area. The cozy family room and kitchen overlook a lush, private fenced back yard and beautiful pool. A large private primary suite is u
Welcome to 160 Trismen Terrace. This brilliant home has much to offer. Spotlighting an inviting formal living room, formal dining room with built in cabinetry and side board, a luminous family room with french doors to the pool deck, expansive kitchen with stainless steel appliances, prep sink, numerous cabinets, and vaulted ceilings complete with breakfast area. The generous primary en-suite bedroom features his and hers custom closets, newly remodeled primary contemporary bath with a stand alone tub, walk-in shower, dual vanities and water closet. Guest en-suite bedroom with new modern updated bath, 3rd bedroom can be used for the perfect office featuring views of the pool, and 4th bedr
Step through the door, take a deep breath, and know that you are finally where you are supposed to be in this delightful Winter Park home! This 3 bedroom, 2 bath with open-concept floor plan is situated in the desired EASTBROOK community. The open family/kitchen/dinette exudes a sense of spaciousness as you enter through the front door. The kitchen features GRANITE countertops, STAINLESS STEEL APPLIANCES and a kitchen island offering additional cabinet space. When you prefer a more private place to relax, the separate living room with BRICK FIREPLACE and additional mini split offers that tranquillity year-round with a door leading to your own large PATIO with an outdoor shower. As you walk
Welcome to 1563 Lakehurst, a stunning 5-bedroom, 5-and-a-half-bathroom pool home that epitomizes luxury living and has been meticulously remodeled to perfection. This residence won the prestigious Orlando Parade of Homes 2021 First Place and Grand Award and is a masterpiece of design and craftsmanship. Initially conceived by the local architect Gary Hancock, this home was reimagined by the renowned Ted Maines and Hardwick General Contractors, resulting in a comfortably elegant living space deserving of accolades and awards. Located on an oversized lot on a charming brick-lined street in one of the most desirable neighborhoods of Central Florida, this home boasts an enviable address just mom
Step into luxury living at its finest in this exquisite two-story condominium in the Douglas Grand of downtown Winter Park. Boasting sophistication and elegance, and offering unparalleled comfort and convenience. Spanning across two levels on the north side of the building which is more energy efficient, this residence features three bedrooms, two owner suites one on the main level and one up, 3.5 baths, and a private interior elevator, ensuring effortless access and seamless transitions between spaces. The bright open floor plan is ideal for entertaining and everyday living, highlighted by a spacious kitchen equipped with top-of-the-line Sub-Zero, Bosch and Wolf appliances, complemented by
Welcome to your dream home in the heart of Winter Park's Glencoe subdivision, where luxury meets convenience with NO HOA fees! This meticulously renovated and updated 4-bedroom, 3-bathroom residence sits majestically on over a quarter-acre lot, offering a sanctuary of modern comfort and style. From the moment you arrive, the curb appeal beckons with its custom pavers driveway and a detached 1-car garage, providing both parking convenience and additional storage space. Step inside to discover a harmonious blend of contemporary design and functionality, highlighted by brand-new AC, roof, water heater, appliances & septic tank. The interior welcomes you with matching vinyl flooring that
One or more photo(s) has been virtually staged. Welcome to your dream home in Winter Park! This completely renovated gem showcases a spacious layout with a modern farmhouse style, nestled in a classic, sought-after Central Florida neighborhood. As you step onto the covered front porch, you'll immediately feel the inviting atmosphere, perfect for unwinding and soaking in the tranquil neighborhood vibe. Inside, the open floorplan offers versatility to configure living spaces to your heart's desire. The kitchen is a chef's delight, boasting beautiful butcher block counters, a farmhouse sink, and a stylish tile backsplash. Equipped with stainless steel appliances, including a 6 burner gas stove
Welcome to easy living in Winter Park! Step into this charming townhouse nestled in the Villas of Aragon. With just 4 townhouses in the neighborhood, connected solely by the garage, you'll enjoy a secluded setting. On the first floor, discover a delightful kitchen boasting timeless white cabinets, granite countertops, stainless-steel appliances, a large breakfast bar, and a charming tongue and groove ceiling which adds a touch of character to this heart of the home. Enjoy meals in the spacious dining room, illuminated by natural light streaming through French doors leading to the courtyard. The dining room seamlessly flows into the inviting living room, adorned with a stunning white brick w
One or more photo(s) has been virtually staged. Welcome home to this well maintained 3-bedroom 2-bathroom home right in the heart of Winter Park. The location is phenomenal - walking distance to East End Market, a short bike ride to Baldwin Park, Ivanhoe Village, or esteemed Park Avenue. While the area boasts an endless list of places to visit you will also enjoy the quiet, oak tree lined streets of his highly sought after Eastern Parkway address as you are welcomed with lush landscaping surrounding the bungalow style home. This home boasts a separate dining area off the living room, with a breakfast nook located off the kitchen. The stunning wood floors lead you back to a primary suite tha
LOCATION, LOCATION, LOCATION in UPSCALE Winter Park ! This MODERN RENOVATED TOWNHOME is perfectly located where you can walk to PARK AVE, MEAD GARDENS, Azalea TENNIS Courts & ROLLINS COLLEGE & ORANGE AVE area with coffee shops & bakeries enjoy some of the best shopping & restaurants in Winter Park with over 2,000 SF of living space & lots of natural light this townhome offers it all to those seeking a peaceful oasis The property sits on a private quiet cobblestone street Once inside the home has a Mediterranean courtyard with BBQ a? great outdoor space for entertaining. The EUROPEAN KITCHEN with modern quartz countertops, new cabinets & appliances opening
Welcome home to the Winter Park Pines Community, with its beautiful tree-lined streets and close proximity to all the wonderful aspects of living in Winter Park. This meticulously kept pool home was custom-built for the original owner, offering an abundance of closet space and a thoughtful floor plan. One of the standout features of this home is the oversized kitchen space, back screened covered patio, and the enormous indoor laundry room. Outside, the home boasts an enormous fenced backyard with an oversized pool, creating the perfect oasis for relaxing under the sun or hosting memorable poolside gatherings. The location of this home is incredibly convenient, with easy access to Park Ave.
Welcome to your new home in the charming Eastbrook Community of Winter Park, offering the best in location and lifestyle! This 3-bedroom, 1.5-bathroom home is light and airy with plenty of windows for natural lighting. Step into the spacious living room, perfect for entertaining guests or enjoying quiet time. The kitchen is light and bright with a wall of floor-to-ceiling windows. Cooking is a pleasure with matching GE appliances, lots of counter space including an island for prep and seating, plenty of storage, and an eating nook. Moving on, you'll find the large family room with a brick, wood-burning fireplace and high ceilings. The bedrooms are roomy, and there is no lack of storage in t
Welcome home to Winter Park Woods! Charming renovated second-floor unit is a 2 bed 2 bath condo with all stainless steel appliances, dishwasher, microwave, refrigerator, and stove! Newer A/C! Winter Park Woods offers residents two community pools, a tennis court, and a playground. Conveniently located near Full Sail, UCF, Valencia College, and Downtown Orlando.
Experience the epitome of lakeside living in beautiful Park Lake Grove with this remarkable Maitland condo. Discover the perfect fusion of urban convenience and serene comfort within this meticulously maintained, rare 3-bedroom, 3-full bath townhouse, boasting not one, but two master suites. Nestled in the heart of picturesque Maitland, FL, this cozy abode offers 1,328 square feet of carefully crafted space, blending functionality with style seamlessly. The community covers essential maintenance services including pool, roof, exterior, and landscape upkeep, ensuring a worry-free lifestyle. Plus, with lake access to the dock included, you'll have the luxury of enjoying the tranquility of the
Welcome to a charming dwelling place featuring a cozy fireplace to uplift the ambiance of your living space. The dwelling place benefits from a tasteful neutral color paint scheme throughout, providing a welcoming canvas for your interior design aspirations. The kitchen is a cook's paradise, complete with a stunning accent backsplash that truly makes the room pop. Enjoy the luxury of a generous walk-in closet in the primary bedroom, perfect for all your storage needs. The primary bathroom offers the convenience of double sinks, making morning routines smooth and efficient. A separate tub and shower in the primary bathroom add an opulent touch to your personal spa-like retreat. Relax or ente
Condo in the heart of Winter Park! Recently renovated with new bathroom fixtures and fresh paint. Clean and efficiently updated with lots of room, and lots of storage and cabinets! Best screened back porch Garden views offer privacy & shade - The perfect place to enjoy your coffee, or share a meal! Mount on wall remains for big screen TV easy-mount in large living room! Interior laundry room (Washer/Dryer included!) PLEASE NOTE: This is one of only a few units that is allowed to have in-unit washer and dryer!! Stainless Streel Appliances, hard surface counters, extended kitchen counters and storage area--- Beautiful & Convenient (within a block or so) to the new Down Town W
Welcome to paradise! This home boasts four bedrooms, two bathrooms, and 1800 square feet of living space nestled on a picturesque . 58 acre lot! The dining room showcases elegant laminate hardwood floors and seamlessly flows into the spacious kitchen, complete with main floor laundry closet. In the living room, master bedroom, and guest bedrooms, you'll find exquisite wood laminate flooring. The master suite is generously sized, enhanced by French doors leading to a bath with a garden tub and a sizable walk-in closet. Additionally, the three guest bedrooms are spacious and share a beautifully appointed second bath. Other highlights include a well system equipped with an iron filter and chlo
Walk to Winter Park Village for movies, shopping & restaurants! Close to Trader Joe's and Park Avenue! Boat ramp access and fishing pier on Lake Killarney for skiing and water sports. Community pool and clubhouse with expansive lake views. Move-in Ready 2 bedroom 2 bath second-floor unit with updated a/c unit and hot water heater. Updated kitchen with granite countertops and appliances. Upgraded fixtures and vanities in both bathrooms. Laundry facilities provided on-site at clubhouse/pool area. Enjoy a maintenance-free lifestyle close to everything you could ever need!
Will not last long. Located in the in one of the highly sought after communities in Winter Park, Oakcrest, No HOA or CDD, 3 bedroom 2 bathroom, 2 car garage, 1524 heated square feet, over 2000 sq ft under roof, nice sized lot with big back yard, needs TLC, new roof installed 11/2021, A/C replace 2017. re-pipe 01/22 close to shopping and transportation, Zoned for Eastbrook Elementary, Tuskawilla Middle and Lake Howell High School, . Property is currently tenant occupied please do not disturb tenant.
Introducing a stunning, spacious four bedroom /four bathroom sanctuary boasting hardwood flooring in all main areas, complemented by designer porcelain tile in bathrooms and laundry. Custom by Native Homes. Expansive kitchen showcases beautiful exotic, neutral granite island, large breakfast room overlooking pool and tiled backsplash. There is a separate dining room on the first floor, as well as a second bedroom or private study with a bathroom and closet. Primary suite plus another bedroom suite conveniently located on first floor. Master suite is a dream! The dual sinks in the oversized bathroom offer convenience, while the 66-inch Jacuzzi brand stand-alone soaking tub adds a touch of lu
Welcome to a great street in Winter Park where you can build the home of your dreams or simply remodel the existing home. This property is surrounded by Multi Million Dollar homes Enjoy yourself in the Winter Park lifestyle on this beautiful street while having the luxury of just being minutes from downtown Winter Park and Orlando. This home is near Lake Sue, Leu Gardens, Mead Botanical Gardens and many more gems of Winter Park.
"Location is paramount! The property stands in immaculate condition. " Discover your dream home in Winter Park, fully renovated with a fenced-in yard. This exquisite single-story 4 bedroom/2 bathroom residence is set in a coveted community. Be delighted by the expansive open floor plan that seamlessly blends sophistication with practicality, which is ideal for family life and hosting gatherings. Renovations encompass a new roof, AC system, doors, double-pane windows, fresh paint inside and out, fixtures, cabinets, granite countertops, stainless steel appliances, an updated bathroom, and ceramic tiles across living and sleeping quarters. Additionally, the home features a new 32.5 x
Welcome to your dream home in the coveted Waterbridge neighborhood! This stunning one-story pool home boasts everything you've been searching for and more, including a three-car garage. Situated on a spacious corner lot, this residence offers both elegance and comfort. Step inside to discover a welcoming ambiance, highlighted by a gathering living room featuring a double-sided gas fireplace, perfect for cozy evenings or entertaining guests. The dining room is conveniently located off the kitchen, complete with double built-in ovens and overlooking the inviting family room. A sunny Florida room extends off the family room, offering picturesque views of the lush backyard oasis and sparkling p
Welcome to this RARE find on Dana Way on the corner of Dana Way and Winter Park Road. This 1/4 acre lot is ready for you to remodel the current home or build your dream home. This home is near Lake Sue, Leu Gardens, Mead Botanical Gardens and many more gems of Winter Park. Immerse yourself in the Winter Park lifestyle on this brick street while having the luxury of just being minutes from downtown Winter Park and Orlando. The last time a house sold on this street was four years ago.
A Testament to Timeless Elegance: Your Dream Home Awaits in Winter Park. Step into a piece of history with this beautifully restored 1927 Florida Bungalow, situated in the cherished and serene neighborhood of Orwin Manor. This exquisite home seamlessly blends the charm of its original architecture with modern luxury and conveniences, offering a unique sanctuary for those who value both tradition and contemporary living. As you enter through the inviting foyer, you are welcomed by new tile flooring and vertical shiplap walls, creating an atmosphere of fresh sophistication. Custom transitions draw you into a living room where the warmth of original hardwood floors meets the convenience of sma
Welcome to your new home at 3047 George Mason Ave in Winter Park, Florida! This charming condo offers convenience, comfort, and endless possibilities. Nestled on the first floor, this 1-bedroom, 1-bathroom unit boasts easy accessibility and a cozy ambiance. Step inside to discover sleek tile flooring throughout, providing both durability and style. Families will delight in knowing that this property is zoned for Winter Park's top-rated schools, ensuring an excellent education. Relaxation and recreation are just steps away with access to the community pool, perfect for enjoying sunny Florida days. Located in the heart of Winter Park, this condo offers unparalleled convenience. Enjoy plenty o
Luxurious lakefront living with unparalleled view of Lake Maitland, part of the famed Winter Park chain of lakes with 180 feet of water frontage. Enjoy tranquil views from the lake from almost every room. This custom home is located in the Via's of Winter Park and is close distance to downtown Park Ave and the Winter Park Racquet Club. This home was built by Gallimore and features five bedroom, five & one half bath. As you enter the foyer, you are immediately greeted by high ceilings, open floor plan and panoramic views of the lake. The family room is a fantastic place for entertaining, featuring a gas fireplace, wet bar with refrigerator and opens to the screened pool and gorgeous la
Welcome to 2731 Tierra Circle. A charming Winter Park pool home located within the Casa Aloma Community. Boasting 4 bedrooms and 2 bathrooms, this residence sits gracefully on a corner lot. As you step through the front entryway, you'll be greeted by a generously sized living area. The formal dining area provides an elegant setting for special occasions, while an oversized front great room offers additional space for versatile living. The heart of the home lies in the large kitchen, featuring updated appliances and ample counter space and cabinets. Inside the garage offers a bonus space that can be easily transformed into an office or gym. The space has been set up with a split a/c unit tha
This home is a work of art ready to be enjoyed by those who appreciate attention to detail. It was completely renovated in 2011/2012 including all walls, kitchen, bathrooms, roof, electrical and plumbing - with the most elegant and timeless of modern touches. From the moment you arrive you will notice the double french doors that welcomes you into the home! The foyer is grand and draws you into the formal living and formal dining rooms. Floor to ceiling windows throughout this home provide lots of natural light. The floors throughout the home are either elegant marble or wood. The formal living room and the great room share a double sided fireplace with elegant touches of marble. The vault
Nestled in the heart of Winter Park, FL, this charming 3-bedroom, 2-bathroom home offers the perfect blend of comfort and convenience. With its spacious design, luxurious master suite, and versatile bedrooms, this property ensures a welcoming retreat for family and guests alike. Located just minutes from I-4 and downtown Orlando, this home ensures easy access to amenities and attractions. Plus, with no HOA fees or restrictions, you'll enjoy the freedom to personalize and enhance your space. Don't miss the opportunity to make this Winter Park oasis your own! Schedule a viewing today and start envisioning your dream lifestyle.
COMPLETELY RENOVATED 5 Bedroom 3 bathroom home on a cul-de-sac in beautiful Lake Waunatta Woods. This stunning home offers a wide open great room/kitchen floor plan, perfect for entertaining. The beautiful updated, bright kitchen features a large island, stainless steel appliances, and quartz countertops. The entire home has been meticulously designed to blend a new chic look with the homes original beauty. Glass double doors lead from the great room to an office (5th bedroom). The Primary bedroom has floor to ceiling windows overlooking the lush green front yard. The primary bath includes zero entry shower with handheld and rain shower heads. Two Sliding glass doors off the kitchen/great
Explore this newly renovated 2 bedroom, 2 bathroom condo in Winter Park, Florida, at 107 Lewfield Circle. Totaling 953 square feet, this unit features a versatile bonus room, perfect for an office or extra living space, and boasts new stainless steel appliances and in-unit laundry. The interior's fresh update complements the covered patio and community amenities like a pool and ample parking. With recent improvements like a new roof and exterior paint, the building is as inviting as the condo itself. Located in a sought-after area, the condo provides easy access to highways, shops, and restaurants, offering a convenient and attractive lifestyle in Winter Park.
A new opportunity for homeownership is located behind the gates of the highly sought-after Seminole County community of Waters Edge at Hawk’s Crest. This energy efficient Kerrville plan, built by Meritage Homes, features space, function & flexibility to accommodate today's evolving lifestyle needs. As you enter the foyer you are welcomed by defined living and dining to either side, which can also be multipurpose usage. The dining room is ample in size, flowing directly to the kitchen through the butlers pantry. The large, open kitchen design will impress the cook of the house with quartz countertops, stainless steel appliances, double oven, single level island with eating space,
Downtown Winter Park!Walk one block to Park Avenue's restaurants & shops, Rollins College, and Sunrail. Gorgeous garden views from your balcony. Fully Gated community. Cathedral ceilings in family room and master bedroom. Huge walk-in closet, washer/dryer and fireplace. Complex has clubhouse with billiard table, pool, outside grill and tennis/pickleball courts. Once a 2 bedroom but converted to a one bedroom to allow for extra large living spaces. Wall for 2nd bedroom has been removed but could easily be added to convert back to a two bedroom. Inside laundry & plenty of storage.
Beautifully Renovated and Move-In Ready home in sought after Winter Park! Features 3 Bedroom, 2 baths, NEW ROOF, Vinyl Flooring Throughout, No Carpet! Upgraded gorgeous kitchen with Quartz Countertop, oversize island, recess lighting and fully equipped with new stainless steel appliances. Upgraded bathrooms with Quartz Countertops. Fresh new landscaping front and back. Enjoy and relax in your own private pool along your covered lanai with new screens and privacy fence. Brand new water heater installed. NO HOA and NO CDD! Conveniently located minutes to UCF, Full Sail, Barry University, Valencia, multiple grocery stores and pharmacies, Winter Park’s scenic Park Avenue, Downtown Orlando
For sale. Step into the inviting embrace of this remarkable ground floor unit nestled within the heart of Winter Park. Boasting a generous layout with 2 bedrooms and 2 bathrooms, this residence offers an ideal blend of comfort and convenience. With its tile flooring spanning throughout, the unit exudes a sense of modern elegance, further accentuated by the granite countertops adorning the kitchen. Residents will delight in the amenities provided by the community, including access to a refreshing pool, perfect for relaxation and recreation. Beyond the comforts of home, this property is strategically located within close proximity to an array of shopping destinations, diverse culinary offerin
Move-In Ready condo with a Winter Park address! Close to UCF & Full Sale University! Not far from downtown Winter Park and downtown Orlando. 2022 ROOF. Lots of storage. This 2 bedroom condo offers low maintenance living. Remodeled Kitchen features cabinets with genie drawers and a closet pantry. The Spacious interior offers a large Great Room, well designed half bath downstairs, and 2 generous sized bedrooms with walk-in closets. Enjoy the lush landscape from your screened porch over-looking a large green space. Indoor laundry. Well-maintained neighborhood. The low HOA fee includes building maintenance, grounds maintenance, Water/Sewer service, community POOL, and clubhouse. Call to s
Presenting an exquisite property at 1251 Palmer Avenue, Winter Park, FL 32789. Built in the year 1948 and completely re-built/remodeled in mid-1990’s. Close to the vibrant Park Ave shopping and dining district, the location offers convenience and lifestyle. The four spacious bedrooms and three full bathrooms, along with a fireplace, are ideal for family gatherings, and the screened, heated pool offers year-round enjoyment. The property also boasts a 3-car garage with an easy access circle driveway and ample parking for residents and guests alike. From its well-planned layout to its prime location, this property offers a perfect blend of comfort and convenience. Experience the best of
Based on information submitted to the MLS GRID as of Sat Apr 20 2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
School data is provided by GreatSchools, a nonprofit organization. Redfin recommends buyers and renters use GreatSchools information and ratings as a first step, and conduct their own investigation to determine their desired schools or school districts, including by contacting and visiting the schools themselves.Redfin does not endorse or guarantee this information. School service boundaries are intended to be used as a reference only; they may change and are not guaranteed to be accurate. To verify school enrollment eligibility, contact the school district directly.
Homes for sale in Winter Park have a median listing price of $825K. Some of these homes are Hot Homes, meaning they're likely to sell quickly.
What are some of the most popular neighborhoods in Winter Park?
Popular neighborhoods include Virginia Heights, Garden Acres, Winter Park Downtown Historic District, College Park, Winter Park Pines, Windsong, Baldwin Park, and Orwin Manor.
Winter Park, Florida boasts a well-structured transportation system, with several options for residents. The city experiences moderate traffic levels, making driving a car a feasible option for commuting. Public transportation is also available, with a reliable bus service catering to the needs of the community. Additionally, Winter Park is conveniently located near major highways, providing easy access for longer distance travels. Learn more on our Winter Park city guide.
What types of properties are available in Winter Park?
Winter Park, Florida offers a variety of single-family home types, including ranch-style homes, contemporary homes, and Mediterranean-style homes, among others, with options ranging from 2 to 6 bedrooms and varying year built. To explore different property types for sale in Winter Park, Florida, use the 'Home type' filter located above the active listings. Customize your search by selecting options like single-family homes, condos, townhomes, and more.
What is life like in Winter Park?
Winter Park, Florida offers a serene and picturesque living experience with its charming landscape characterized by lush greenery, shimmering lakes, and tree-lined streets. The region enjoys a mild and pleasant climate throughout the year, with warm summers and mild winters. The area provides a variety of job opportunities across sectors, including healthcare, education, technology, and hospitality. Residents can engage in a range of recreational activities, such as exploring the numerous parks and trails, indulging in water sports on the lakes, and enjoying the vibrant arts and culture scene with events and festivals held regularly.
What are the schools and amenities like in Winter Park?
Winter Park, Florida, is a vibrant community with a variety of public amenities for its residents. The city boasts a multitude of restaurants, offering a wide range of cuisines to satisfy any palate. For those who enjoy outdoor activities, Winter Park has numerous parks for leisure and recreation. Grocery stores are conveniently located throughout the city, making shopping for daily necessities easy and convenient. Additionally, the city provides other amenities such as libraries, fitness centers, and community centers, catering to a wide range of interests and needs.
In the past month, 52 homes have been sold in Winter Park. In addition to houses in Winter Park, there were also 64 condos, 17 townhouses, and 2 multi-family units for sale in Winter Park last month. Winter Park is a minimally walkable city in Orange County with a Walk Score of 44. Winter Park is home to approximately 27,958 people and 25,253 jobs. Find your dream home in Winter Park using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Park are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Park. Our Winter Park real estate stats and trends will give you more information about home buying and selling trends in Winter Park. If you're looking to sell your home in the Winter Park area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Park with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.