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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

4 Beds 3 Baths Preserve At Hawks Crest SubDv. 32792 Zip Code
Unique opportunity to own this updated, 4-bedroom and 3 bathroom, 5-year-old, one-story home with newly-added sunroom overlooking pond and fenced garden. Located in the desirable, gated community of HAWK'S CREST AT WINTER PARK. Engineered wood plank flooring in foyer, hallways, great room, kitchen, and dining room. Freshly painted interior. Brand-new carpeting in primary bedroom and walk-in closet. New porcelain tile flooring in Bedroom 4 ensuite. All bathrooms have TOTO energy-efficient, comfort-height toilets. Beautifully landscaped front and back yards. Paver and slate walkways lead from the front of house to the fenced, landscaped garden area and the newly built sunroom. Expanded paver driveway. Adjacent pond also wraps around the rear of the property. Great room, open to dining room and kitchen, has wood plank flooring, decorative 72-inch ceiling fan with light, and large windows overlooking the pond and fenced backyard. Gourmet kitchen has wood-plank flooring, recessed lighting, large center island with quartz counters, stainless-steel undermount sink, KitchenAid dishwasher, disposal, and decorative pendant lighting. The kitchen features white Shaker wood 42-inch upper cabinets with undercabinet lighting, ceiling-height custom glass & granite tile backsplash surrounding upper cabinets, quartz counters, banks of white Shaker wood lower cabinets with dovetailed drawers, vented decorative stainless-steel and glass range hood, Bosch knob-less cooktop, KitchenAid built-in wall ovens (microwave/convection combination oven and large conventional/convection combination oven) and LG side-by-side refrigerator with glass easy-access door feature. Large laundry room has shelving and utility sink; LG washer and dryer are included! HAWK'S CREST AT WINTER PARK, a sought-after gated community, has numerous amenities including community clubhouse, fitness center, and large community pool area with barbeque grills, cabanas, lounge chairs, and splash pad. Also available to residents are playgrounds, park areas, and gazebo overlooking Lake Howell. Central Parc at Howell Branch is located at the front of the neighborhood and has retail shops, offices, and Park Maitland Preschool. HAWK’S CREST AT WINTER PARK is easily accessible to employment centers, Park Ave shops and restaurants, SunRail station, Rollins College, University of Central Florida, tourist attractions, entertainment venues, hospitals, and highways. THIS IS A MUST SEE HOME!

2091 Laurelwood Way, Winter Park

2 Beds 1 Baths Lake Killarney Condo SubDv. 32789 Zip Code
Amazing location in Winter Park! Full LAKEFRONT view, fully renovated end unit condo on spring fed, navigable, & private Lake Killarney. Sunset views every evening from your living, kitchen, dining, and master bedroom! . Lakefront pool and private boat dock with ~14 slips (see management for availability). Assigned parking space, community storage & mail just outside the back door. Walk to Trader Joe's, Hillstone's, Winter Park Village, Publix, movies, restaurants, shopping, etc. Bike or walk to Downtown Winter Park and Sunrail. Fully renovated unit with extra care to space planning. o Highest ceilings in the community. Solid bamboo wood flooring. Recessed lights. Surround sound & TV mount . Textured walls & ceiling . Custom trim . 4 panel sliding glass and transom windows looking over lakeview & lawn . Large renovated kitchen with glass tower cabinets . Drink bar and large island . Granite counters . Stainless steel appliances. Downlighting, under & over cabinet lighting o stainless steel appliances. End your day enjoy the lake views while making dinner. Shower cubbies & candle cubbie for baths . Italian space enhancing vanity . Upgraded fixtures . Frame mirrored medicine cabinet for hidden extra storage o Custom expanded master closet system. Community amenities include o Lakefront dock with boat slips o Private boat ramp o Lakeside pool & large lawn with Adirondacks o Grills & picnic tables o Paddle board / canoe / kayak racks o Bass fishing . Bike racks, shuffleboard . Assigned Parking space just outside the door . Storage Space o Gym, laundry rooms, community storage, and recycling.

151 N Orlando Avenue Unit 131, Winter Park

3 Beds 2 Baths Timberlane SubDv. 32789 Zip Code
GLORY OF A SUMMER NIGHT…experience it under the stars by the beautiful pool that comes with this innovatively styled & remodeled 3bed/2bath home, nestled in the desirable Timberlane neighborhood of Winter Park. This terrific layout features a completely updated (2020) & tastefully designed gourmet kitchen, with gorgeous cabinetry, quartz counters and large island perfect for entertaining…this opens to the living and dining room that feature large windows with views to the giant backyard and huge pool. Enjoy chilly nights with a wood burning fireplace in the family room. Additionally, there is a nice sized flex space off the living/dining area that has lots of uses: office, guest bedroom, exercise room, additional living space... French sliding doors here lead out to the covered deck, pool and backyard. Why do we love Florida? enjoy outdoor living of course…enjoy your new outdoor space with lots of updated pavered spaces & pool deck and newly sodded grassy areas…and of course, your huge pool that has been recently resurfaced. Inside, the bedrooms are conveniently located on the other wing of the home, all rooms are generously sized with large closet spaces. Additionally there are multiple closet storage spaces in the hall. The primary ensuite has been reconfigured and includes a large walk-in closet and updated sleek bathroom with double vanities and glass enclosed shower. This bedroom also has access to the yard/pool. Home features a 2 car garage with ample storage spaces and nice sized laundry and storage areas. Gorgeous engineered hardwood floors, plantation shutters and designer touches throughout, including a new front door to greet your guests-done in 2024. The garage also has access to the flex space and kitchen. All new windows too, done in 2020. Don’t forget about the location, currently zoned for coveted Audubon K-8 & Winter Park High School. Close to all things Winter Park…walk or bike to all the stores and restaurants on trendy Corrine Drive and Baldwin Park downtown is also just a minute away. Access to highways, hospitals and shopping are super convenient. No HOA. This is a one-of-a-kind opportunity to turn the key and enter into this desirable area of Winter Park, don’t miss your chance…Please see Virtual Tour 1 for views of home/lot/location & Virtual Tour 2 for Matterport spatial layout and walk-thru.

2217 Howard Drive, Winter Park

3 Beds 2.5 Baths Amberwood SubDv. 32792 Zip Code
This two-story, beautiful multi-level home is nestled in the Amberwood subdivision of Winter Springs. Lake Howell High School is located right around the corner. This home sits on .49 acre of property. So, there is plenty of room in the backyard to entertain family and friends, and room for pets too. Lush green front yard and well-manicured beds welcome you home with a long, curved driveway and two-car side entry garage space for everyone’s parking needs. This newly painted home boasts soring front-facing windows and skylights that flood the space with natural light. Upon entering the home, the two-story vaulted ceiling invites you into the formal living room and dining spaces. The living room has a stone-faced wood-burning fireplace, a huge skylight and ceiling fan, and beautiful engineered hard wood floors. Sliding glass doors showcase the view of the screened lanai and inviting pool area. The formal dining area is raised with a modern chandelier and tile flooring. The eat-in kitchen is a cook’s delight with updated light wood cabinets, granite tops and backsplash, and Maytag stainless steel appliance package. The breakfast bar overlooks the spacious family room and oversized glass doors leading out to the pool and yard. Upstairs, there are two spacious bedrooms and a full bath, as well as a bonus space currently used as a home office that could be a fourth bedroom. The roomy master retreat is located on the ground floor and has a huge walk-in closet and a third set of sliding glass doors. The master bathroom has one sink, two vanity areas, a skylight, and a large shower. A half bath is located just outside the master bedroom. The pool is large and has been resurfaced with a pebble-tech finish. The covered patio extends the length of the home with a large bar area that can be moved, three ceiling fans, and additional attached cabinetry for storage. A screened enclosure surrounds the porch and pool area. Mature trees, landscaping, and large side yards on both sides of the home. The right-hand side yard has a double-gated fence with a parking pad behind the fencing for parking a boat or another vehicle. Large work shed with power and light for a workshop. The side garage door entry and work area have a second fence to isolate pets from the yard. The entire back yard is enclosed with a privacy fence. Upgrades include a roof (2021), A/C (2016), windows, electrical panel (2024), surge protector with transfer switch (2024), Water Heater (2023), bath and kitchen renovations, re-piping, mini split A/C addition (2019), laundry valve replacement, and a new garage side door. This property has been very well maintained and has a long list of upgrades; please see attachments. Convenient location to Red Bug Lake Park, shopping, and 15 min. drive to UCF.

1514 Sugarwood Circle, Winter Park

4 Beds 3.5 Baths Lawndale SubDv. 32789 Zip Code
Welcome home to 1245 Wisconsin Avenue in beautiful Winter Park! If you are dreaming of a move-in ready newer home on a quiet, tree-lined street, close to shopping and cafes, this 4-bedroom, 3.5-bath charmer in the sought-after Orwin Manor neighborhood is for you! From the moment you walk in the front door, you will fall in love with this open-concept home with high ceilings and over-sized windows, drenching the home with natural light. The spacious living area leads to an amazing kitchen, boasting solid hardwood cabinets, stainless steel appliances, custom granite countertops, and a huge granite island. Add in the bar/buffet area with two wine & beverage fridges, a large dining space, and a huge screened-in patio with electricity and ceiling fans, and you have the perfect setting for entertaining family and friends. Also on the main floor is the spacious master suite, featuring a double-door entrance, vaulted ceilings, a custom walk-in closet and a master bathroom with double sinks, a large walk-in shower, and a private commode area. A wide staircase to the second floor leads to three additional bedrooms and a huge bonus room/flex space. The first bedroom is very private – perfect for guests – with a private bathroom and walk-in closet. The second and third bedrooms share a full Jack & Jill bath, and each has its own oversized closet. The expansive bonus room would make a great playroom, gym, or both! It’s so large that you would still have room for an office! Outdoors, you will love the privacy of your vinyl fenced-in backyard with no-maintenance artificial turf and a private putting green! The paver driveway and walkways add a special touch of quality, as does the the 2-car garage with sparkling clean epoxy flooring. This home is in a quiet neighborhood, located just minutes from Park Avenue and all it has to offer. Call for your private showing today to make this your very own home sweet home!

1245 Wisconsin Avenue, Winter Park

3 Beds 2.5 Baths Coronado Twnhms SubDv. 32792 Zip Code
Situated near the vibrant and desirable community of Winter Park, FL, this stunning townhome at 3226 Crown Jewel Ct offers a perfect blend of modern luxury and convenient living. Step inside to discover an open and spacious layout that is filled with natural light, creating a warm and inviting atmosphere. The heart of the home is the gourmet kitchen, featuring gleaming granite countertops, sleek stainless steel appliances, and rich dark wood cabinetry that provide ample storage and style. The large living area is perfect for both entertaining guests and enjoying quiet family evenings, while the adjacent dining area offers a seamless flow for meals and gatherings. Upstairs, the home boasts generously sized bedrooms, each designed for comfort and relaxation. The master suite is a true retreat, complete with an ensuite bathroom featuring dual sinks and a walk-in shower. Additional highlights of the home include a convenient laundry area equipped with modern appliances, ensuring household chores are a breeze, and a private backyard that is perfect for outdoor relaxation or hosting barbecues. The property also includes a garage and additional parking space, providing ample room for vehicles and storage. This townhome is part of a great community that offers a peaceful and secure living environment. Energy-efficient appliances and systems are incorporated throughout the home, helping to save on utility bills and reduce your carbon footprint. With easy access to Full Sail University, the University of Central Florida, Valencia College, and major employers, this home is ideally located for both students and professionals. The area is surrounded by great shopping and a variety of restaurants, ensuring you have plenty of options for dining and entertainment. Additionally, a short commute to the renowned downtown Winter Park allows you to enjoy its charming shops, cultural venues, and vibrant community events. Don’t miss the opportunity to own this exceptional property, schedule your showing today!

3226 Crown Jewel Court, Winter Park

Timberlane SubDv. 32789 Zip Code
Discover the perfect canvas for your dream home at 674 Randy Lane in Timberlane, the address where your aspirations meet reality. Spanning 0.41 acres (almost 18,000 SF), a fabulous lot and ideal location invite you to build your dream home with all the bells and whistles! This exceptional parcel offers a prime interior corner location on Randy Lane and Fosgate Drive, where the back property line expands 200 feet wide and captures 35 feet on General Rees, creating the perfect space to add your multi-car garage or workshop. With underground utilities and sewer connected, this pad is primed and ready to go. The existing 1950’s single-family home has graced Timberlane’s charming community for decades, and is now ready to join the newer construction homes already peppered throughout the neighborhood. This property is in the heartbeat of everything! Head out the back gate and cross General Rees to Blue Jacket Park, which leads to downtown Baldwin Park. Stroll through the neighborhood to the East End market or Kelly’s Homemade Ice Cream, among other shops and restaurants along the Corrine Drive corridor. Venture North just 2.5 miles to the cultural delights of Park Avenue and downtown Winter Park. Looking to land just a few minutes from Downtown Orlando with easy access to I-4?...This is the location for you! Embrace the convenience of urban amenities in this fabulous neighborhood, enriched by top-rated schools, including the acclaimed Audubon K-8 School. *HOME IS OCCUPIED; do NOT walk the property without permission and approval.

674 Randy Lane, Winter Park

3 Beds 2 Baths Georgeann Homes SubDv. 32792 Zip Code
WINTER PARK LAKEFRONT HOME! Schedule your showing today for this Beautiful 3/2/2 Pool home with an office! NO HOA! It is situated on Lake Waunatta and part of a chain of lakes. As you enter the home, your eyes are automatically drawn to the Gorgeous views of Lake Waunatta! Wide Open Floorplan with large dining, living and family rooms and a cozy den. 2 tiled bedrooms located downstairs and the entire upstairs is the Primary Suite and large office space. There are 2 spacious closets with lots of storage space! The Primary bath is huge! Soaker tub and a newly remodeled shower! Enjoy your morning coffee or glass of wine on the private balcony outside the Primary bedroom overlooking the lake. and soaking in the sunrise or sunset. The spacious brick paved pool deck and surface was completely redone in 2021. Enjoy the evening sunsets from your covered 30' x 10' mahogany patio with teak ceilings, hard wired stereo system and outdoor lighting- just Gorgeous! Perfect home for entertaining! Private covered area over the 2021 hot tub and take a boat ride from your mahogany dock. There is plenty of room to park your boat or RV in the long driveway. The lake fed irrigation system helps to lower your water bill. 2019 ROOF, HVAC is well-maintained with service every 6 months. This home is zoned for all the top Winter Park schools! A little piece of paradise that is conveniently located to shopping, restaurants and SR 417!

7801 Georgeann Street, Winter Park

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