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Winter Park is quite a charming city, filled with an abundance of open parks, affluent neighborhoods, a popular shopping district known as Park Ave, and a plethora of museums and galleries. It offers great schools for its over 29,500 population, like Eastbrook Elementary School and Winter Park High School. Located just 30 minutes from the Orlando Airport and less than 10 minutes away from downtown Orlando, it makes a great home for city commuters. There is also a convenient SunRail train station for those traveling to neighboring cities as well as easy access to I4.  

Downtown Winter Park 

This delightful area of Winter Park is located in the heart of the well-known shopping district of Park Ave. Local eateries and quaint shops line the beautiful brick streets. This is a popular destination for locals enjoying the beautiful art, parks, and shops surrounding the downtown district. On Saturday morning, head over to the well-known farmers market that was voted #1 in produce and plant market for Central Florida. It is held every Saturday from 7 a.m. to 1 p.m. Many popular museums, art galleries, and gardens are very close by for locals to enjoy as well. 

See more Winter Park Events on their website!

Brand New Winter Park Listings

$535,000
4 Beds 2 Baths Autumn Glen Ph 2 SubDv. 32792 Zip Code
Welcome to your dream home in Winter Park's beautiful Autumn Glen community! This immaculate 4-bedroom, 2.5-bathroom residence boasts a wealth of features designed to enhance comfort, convenience, and luxury living. As you step through the front door, you're greeted by the warmth of beautiful wood, laminate, and tile flooring that flows seamlessly throughout the home. Natural sunlight floods the space, creating a bright and inviting atmosphere that invites you to unwind and relax. The heart of this home is the stunning kitchen, which is sure to delight any chef. Complete with granite counters, wood cabinets, stainless steel appliances, and an eat-in area, it's the perfect place to gather with loved ones or enjoy a quiet meal. Entertaining is effortless thanks to the expansive lanai area and screened pool, where you can soak up the Florida sunshine or host gatherings with friends and family. The fenced yard offers privacy and security, while the vinyl shed provides additional storage space for all your outdoor essentials. This home has been meticulously maintained, with numerous upgrades completed within the last 7 years. From the new roof and air conditioning system to the rescreened pool and laminate flooring throughout, every detail has been thoughtfully considered. Additional features include an irrigation meter, termite bond, and annual air conditioning maintenance contract for peace of mind. Hurricane-rated windows offer added protection during storm season, while a whole-house water filter and softener ensure clean, pure water throughout the home. Conveniently located in the highly sought-after Autumn Glen community, this home offers easy access to top-rated schools, shopping, dining, and entertainment options. Don't miss your chance to make this Winter Park oasis your own – schedule a showing today!

4160 Waterview Loop, Winter Park

$750,000
3 Beds 2 Baths Lawndale SubDv. 32789 Zip Code
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 smart lighting and a cozy fireplace, perfect for both lively gatherings and quiet evenings at home. The dining room, capable of hosting eight, dazzles under a stylish Serena and Lilly chandelier, setting the scene for memorable dinners. Adjacent lies the heart of the home: a chef’s paradise kitchen. Renovated in 2020, this culinary haven boasts striking Calacatta countertops, a grand island, top-of-the-line Samsung appliances, and chic West Elm lighting. The adjoining eat-in area offers a relaxed dining experience and opens to a beautifully paved backyard, ideal for alfresco dining and entertainment. Accommodation is generous and refined, featuring a lovely master suite with dual closets and a sleek bathroom equipped with matte finishes. Additional rooms include a versatile rec room and a guest bedroom, each meticulously designed for comfort and style. The home also includes a secluded attic for extra storage. Special attention has been given to both aesthetics and functionality, from smart exterior lighting and a durable new vinyl fence to minimal maintenance landscaping designed to flourish in Florida's climate. The updated HVAC system features a Carrier unit and smart thermostat, ensuring year-round comfort. This home is not just a place to live but a piece of history to cherish. Original woodwork, including baseboards and casings, pay homage to the home’s heritage, while the curated paint choices and Trex exterior staircases ensure its beauty endures. Located just minutes from Park Ave, College Park, and major thoroughfares, this home offers an unparalleled blend of tranquility, community, and convenience. Do not miss the chance to own a legacy of luxury in Orwin Man. Every corner of this home tells a story, and every detail invites you to make it your own. Welcome to your dream home, where history and modernity live in perfect harmony.

1707 Harmon Avenue, Winter Park

$6,995,000
5 Beds 5.5 Baths Sicilian Shores SubDv. 32789 Zip Code
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 lakefront. The gourmet kitchen is a chef’s dream featuring a large center island, custom cabinetry, quartz surfaces, top of the line Thermador appliances, and walk-in pantry. The spacious master bedroom is a retreat of its own with amazing views of the lake and a sitting area. The master bathroom has custom cabinets with dual sinks, makeup vanity, modern stand alone tub, walk-in shower and a large walk around closet. There is a guest suite on the first floor with en suite bathroom and walk in closet. Two additional bedrooms upstairs with en suite bathrooms and a huge bonus room or fifth bedroom. This home also features a 3 car garage, a home office, laundry room and walk-in storage room with a large wine refrigerator. Step outside to the backyard paradise, where the pool, heated spa and sun shelf beckons you to relax and unwind. The large covered boat dock is a perfect place to watch the colorful sunset at night and has a separate enclosed storage room. Bring your boat and all your toys and enjoy lakefront living at its best!

1761 Pinetree Road, Winter Park

$1,495,000
3 Beds 3.5 Baths Winter Park Residential SubDv. 32789 Zip Code
Come live the Winter Park lifestyle in this Douglas Grand brownstone in the heart of Winter Park. This townhome style condo is located one block in between the shops and restaurants of Park Ave. & Hannibal Square. Live in the middle of it all with the privacy of being tucked away on a quiet street. Ideally situated so guests will enter through the front door located at street level on Welbourne Avenue. This unit is one of only 8 units with a PRIVATE two car garage located in the secured parking garage! Fully renovated in 2023, the work has been done for you in this 2,734 square foot, three bedroom and three and one half bathroom property. Large scale windows and high ceilings on both floors enhance the natural light and spacious feeling of the interior. The gourmet kitchen has been redesigned with an island and open shelving added to extend the space. Enjoy new wood floors throughout the first floor which also includes a second master suite with huge full bath and large closet (currently used as a home office). The powder bath on the main level has been renovated with new floors, new commode & vanity. Two additional bedroom suites, including the master, are located on the second-floor and new carpeting was replaced in 2023 throughout the second level. The luxe master suite features a spacious bedroom with two well designed custom walk-in closets, two sizable vanities with new quartz counters, a separate walk-in shower with glass enclosure, oversized garden bathtub, water closet and linen space. The second upstairs bedroom with en-suite bathroom is ideally separated from the master though still located at the front of the property allowing for incredible city views. Completing the second floor is a laundry room with washer, dryer, custom cabinetry for storage and a utility sink. Finishes and appointments throughout the home include; Pella® windows and doors, Kohler® fixtures, counter depth Sub-Zero® refrigerator, Wolf®, and Bosch® appliances, new quartz countertops, walk-in customized closets, wood floors, natural stone, two AC units (new in 2023 & 2016) and a new hot water heater (2023). Additional updates include new light fixtures throughout, new blinds (master is motorized), garage storage system, video door bells on front and back of the home, new alarm system, wifi enabled thermostats, to name a few. The Douglas Grand is a newer, quality-built community with the character of a historically charming building. Enjoy the low maintenance lifestyle of this townhome style condo with all of the comforts of a custom home in an unparalleled location. This home is available with the option to purchase fully furnished. This exceptional location is centrally located in Downtown Winter Park and just steps away from all the restaurants, shopping, Sun Rail and train station, WP Farmer’s Market and all things that make Winter Park so special!

345 W Welbourne Avenue Unit 104, Winter Park

$750,000
4 Beds 3.5 Baths Lake Waunatta Woods SubDv. 32792 Zip Code
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 vaulted ceilings provide plenty of space to showcase your art collection or photos of your family. As you enter the heart of this home the kitchen draws your attention to the large entertaining island with classic pendant lighting. The kitchen features stainless steel appliances, Quartz counters, built in pantry, double oven/microwave oven, warming drawer, and beautiful glass tile making this a chef's delight and a wonderful space to enjoy making many gourmet meals. The kitchen opens to the Florida Room and the office - and provides unobstructed views of the pool and patio area. This home features 2 master bedrooms each with its own en-suite. All of the bathrooms have been meticulously updated featuring modern touches with a classic use of marble and glass tile. Finally the backyard is an Oasis - the pool is surrounded by a glass enclosure providing an elegant way to secure the area. The pergola is covered giving you a wonderful space to enjoy dining al fresco - even during a light summer shower. You will love enjoying and entertaining your friends and loved ones in this one of a kind masterpiece. (Foyer, Dining Room and Great Room Chandeliers along with Washer and Dryer do not convey.)

4046 Quenita Drive, Winter Park

$995,000
5 Beds 4.5 Baths Waters Edge At Hawks Crest SubDv. 32792 Zip Code
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, and separate café area. The kitchen is open to the family room, with plenty of space to entertain and relax, with triple wide sliding doors for seamless transition to an ample sized backyard. The first level is accessible to all, with a half-bath for day to day living & guests, as well as a complete primary or in-law/guest suite with an ADA compliant private bath, equipped with a double sink vanity, standing shower, and private water closet. This bathroom can double as a cabana bath when entertaining outdoors! The second level of the home features an expansive open gathering room with wet bar, office/media room, laundry room, 3 secondary bedrooms, and 2 secondary bathrooms. The primary retreat finishes off the space upstairs, with ample wall space for furnishings, a bathroom boasting separate vanities, a standalone soaking tub, shower, private water closet & spacious walk-in closet. Take your entertainment outdoors to enjoy coffee, cocktails, cornhole, bbq's & dining under the cover of an expansive porch and open yard. Waters Edge at Hawk’s Crest Community offers something for everyone, with dedicated green space, clubhouse, community pool, gym, dog park, 2 playgrounds, and dock access to Lake Howell. Conveniently located along the southern shores of beautiful Lake Howell, Hawk’s Crest provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including the renowned Park Avenue. This home is also located just a short drive from Downtown Orlando, UCF, and major highways I-4 and SR-436, making traveling Central Florida a breeze! Schedule your private tour today.

1113 Wading Waters Circle, Winter Park

$1,495,000
5 Beds 4 Baths V H Musselwhites Sub SubDv. 32789 Zip Code
Presenting a distinguished European Modern residence, the "Ponte Vedra" home epitomizes refined living with its meticulous upkeep and sophisticated design. Boasting 5 bedrooms, 4 baths, and encompassing 3,067 square feet of impeccably maintained open living space. Upon entry, a grand foyer sets the tone, leading seamlessly into the combined living room and dining room, characterized by clean lines and an abundance of natural light. To the left, the gourmet kitchen beckons with its array of upscale features, including Stainless Steel appliances, Stone tile backsplash, and Quartz Counters adorning a spacious breakfast island. A Butler's pantry and Walk-in pantry provide ample storage, ensuring both functionality and style. The gathering room beckons with triple sliders opening onto a captivating covered patio, complete with a roll-away screen and a stunning Tongue and Groove ceiling. Outside, an impressive 47' long market light, paver walkway, and Custom Water Fountain feature create an enchanting outdoor oasis, ideal for entertainment and relaxation. The first floor hosts a generously sized bedroom and full bathroom, catering to guests or multi-generational living needs. Upstairs, a versatile bonus loft space awaits, while the Owner's suite offers luxurious touches such as elegant tray ceilings, recessed lighting, and crown molding. The en-suite bathroom features walk-in closets, split vanities, and an oversized Floor to Ceiling tiled frameless shower with both a rain head and hand-held, accompanied by an iconic floating tub. Additional accommodations include three bedrooms, two full bathrooms, and a well-appointed laundry room with a sink and ample storage. This residence has been meticulously maintained, freshly painted inside and out, and boasts the added convenience of plantation shutters and custom drapery, ensuring a move-in ready experience. Ideally situated near Lakemont Elementary, Publix, Advent Health, and mere minutes from Park Avenue.

1880 Windsor Drive, Winter Park

$350,000
3 Beds 2 Baths Park Green SubDv. 32789 Zip Code
Welcome to your future home at 1244 Park Green Place, nestled in the vibrant heart of Winter Park, FL. This move-in-ready townhouse offers a seamless blend of comfort and convenience, making it the perfect setting for both new beginnings and cherished memories. Step inside this inviting residence and be greeted by an expansive living space, bathed in natural light, thanks to the high, vaulted ceilings that create an airy and open feel. The hard flooring throughout the home is not only elegant but also promises easy maintenance and durability. This townhouse features three cozy bedrooms and two well-appointed bathrooms, providing ample space for family, guests, or a home office. A/C was recently replaced and roof was replaced within the last 5 years. At the heart of this home is a modern kitchen, boasting luscious granite countertops that offer both beauty and practicality. Whether you're a seasoned chef or a culinary novice, this kitchen is designed to inspire delightful dining experiences. Entertaining is a breeze with the enclosed back porch, providing a perfect backdrop for gatherings or a peaceful retreat after a long day. The fenced-in yard adds an extra layer of privacy and security, making it a safe haven for both relaxation and play. Located conveniently close to shopping centers, appetizing restaurants, world-famous theme parks, and major roads, 1244 Park Green Place ensures that you're never far from where you need to be. Embrace the opportunity to live in a home that combines practicality with endless possibilities for leisure and enjoyment. This townhouse is not just a dwelling; it's a foundation for a life filled with ease, accessibility, and joy. Don't miss the chance to make 1244 Park Green Place your own — a place where every day feels like a breath of fresh air. Welcome home.

1244 Park Green Place, Winter Park

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