Winter Park Real Estate

Winter Park Real Estate

Nestled in the sunshine state of Florida, Winter Park is a charming city known for its picturesque parks, upscale shopping, and cultural experiences. Located in Orange County, Winter Park offers a mix of historic architecture, tree-lined brick streets, and a thriving arts scene.

One of the city's highlights is Park Avenue, a popular shopping district featuring boutique stores, sidewalk cafes, and art galleries. Residents and visitors alike can enjoy leisurely strolls, gourmet dining, and unique finds in this vibrant area.

Nature lovers will appreciate the city's numerous parks and lakes, providing opportunities for outdoor activities such as boating, picnicking, and scenic walks. The annual Winter Park Sidewalk Art Festival attracts artists and art enthusiasts from around the country, showcasing a wide range of creative talents.

With top-rated schools, a strong sense of community, and proximity to Orlando's attractions, Winter Park offers a high quality of life for its residents. Whether you're exploring the Morse Museum's collection of Tiffany glass or enjoying a boat tour on the Winter Park Chain of Lakes, this city has something for everyone to enjoy.

Newest Listings in Winter Park

LOCATION - LOCATION - LOCATION!!! The most coveted area of town has an EXCEPTIONAL BUSINESS OPPORTUNITY!!! An upscale - highly successful salon, known for its extraordinary customer service and top-notch beauty treatments is waiting for you. Ratings on Google and Yelp are solid 4.9 stars This turnkey operation has an established clientele. From Day One - you will be making money without having to invest in startup or development fees. Phenomenal walk-in traffic, especially going into the Winter season in the most coveted high end part of town - providing a village-like atmosphere, wonderful restaurants and a beautiful park in the center. The sale includes not only the good will, but also furniture, fixtures and equipment. The cost to build-out, furniture, fixtures and inventory was in excess of $50,000. The current owner is willing to remain and work part-time. The salon also has 5 stylists. Please call the listing agent to view this property. Additional services such as eyebrow threading, facials and make up can be added. It is fully operational which guarantees you income. This salon has a reputation of high volume clientele. Schedule your visit now. Do not miss this opportunity. Come and bring your offer right away. DOES NOT INCLUDE THE REAL ESTATE ***PLEASE do NOT approach any of the Employees or Clients of this Business. This Sale is Strictly Confidential.***

Winter Park

3 Beds ⋅ 3.5 Baths ⋅ Lake Spier Crossing SubDv. ⋅ 32792 Zip Code

2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! Don't miss your opportunity to win this extraordinary move-in ready new residence situated amidst the tranquil shores of Lake Spier and Lake Compton, within the exclusive Lake Spier Crossing community centrally located in Winter Park. Consisting of 10 impeccably designed two-story townhomes, this enclave of contemporary living is brought to you by Meridian Homes, Winter Park's premier builder. Anticipate modern architectural brilliance and carefully planned floor layouts that prioritize stylish, hassle-free living. Meticulous attention to detail is evident both indoors and outdoors. Your kitchen boasts state-of-the-art stainless steel appliances and elegant stone countertops, complemented by luxurious hardwood flooring throughout. Convenience is key, with in-unit laundry facilities and a two-car garage ensuring seamless daily routines. Residents of Lake Spier Crossing relish exclusive access to three private docks, ideal for launching paddleboards, kayaks, or enjoying a spot of fishing. This exceptional locale offers proximity to Lake Baldwin Dog Park and the picturesque Cady Way Trail, catering to an active outdoor lifestyle. Enjoy the convenience of strolling to Downtown Baldwin Park for dining, shopping, and lively entertainment, or embark on a leisurely 10-minute bike ride to the iconic Park Avenue. Benefit from access to Winter Park's esteemed school district, enhancing the allure of this exceptional community.

1919 S Lakemont Avenue, Winter Park

2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 1 SubDv. ⋅ 32792 Zip Code

Welcome home to this 2 bedroom 2 bath single story townhouse within close to shopping, restaurants. banks, etc. Priced to sell quickly. Floor plan offers a Living-Dining combo, tile floors with a pass-through to kitchen. Sliding glass doors lead to your own privacy fenced back yard with a large concrete patio. This must-see home has the following updates: Roof replaced, A/C replaced in 2016, re-piped in 2018 , exterior painted all within the last 2-8 years for worry free living. Investors are welcome. Could be updated or lived in as is. Enjoy the sparkling community pool year round, play tennis within this wonderful community with LOW HOA dues. This must see home won't last long so schedule your private showing today.

2403 Dominica Run, Winter Park

5 Beds ⋅ 5.5 Baths ⋅ Tuscany Terrace SubDv. ⋅ 32789 Zip Code

PROUDLY PRESENTING THE WINTER PARK VIA's NEWEST ADDITION TO THE LUXURY HOME MARKET ...BUILT BY M. LAHR HOMES! Prominently sited on a fantastic lot, this custom home has come together perfectly as a unique, awe-inspiring estate offering an unparalleled combination of function, elegance, and aesthetics. The home boasts a very well thought out design with finishes and features that showcase professional design planning at a very high level. There is even more detail, function, and quality than what is typically available in the Winter Park New Construction market. Offering a great combination of an expansive living area, large bedrooms, and unique spaces accented by three (3) feature fireplaces, the house feels nothing less than a resort. Expansive glass from the oversized doors and windows flood the home with natural light and create a dramatic exterior evening presentation. The entire main floor living area opens perfectly out to the large covered patio, back yard, and the pool/spa area making this entire area a beautiful four (4) season extension of the interior living space. The floor plan features a private ground floor primary suite, four (4) additional large bedrooms (all with private baths and walk-in closets), and numerous sitting areas/loft/dining spaces that can be utilized to suit multiple needs! Please see floor plans attached and CLICK ON TOUR LINK FOR A COMPREHENSIVE VIDEO WALK THROUGH . You will not find a better opportunity to secure a highly detailed, unique, luxury home in the WP area that offers the feel, presentation, and function of 1229 Via Del Mar. Located in the desirable Winter Park Via's location in top rated Dommerich/Winter Park School District and minutes to WP Raquet Club, Park Ave. Shopping, Winter Park Village, DT Orlando, Advent Health, ORMC and more. An exquisite Luxury Estate in one of Central Florida's most dynamic areas!

1229 Via Del Mar, Winter Park

1 Beds ⋅ 1 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code

Welcome to 227 Scottsdale Square #227, a cozy and well-maintained 1-bedroom, 1-bath condo located in the desirable Winter Park Woods community. This second-floor unit offers a spacious living area with an open floor plan, perfect for relaxing or entertaining guests. The updated kitchen features modern appliances and plenty of cabinet space. The master bedroom is generously sized with ample closet space, while the second bedroom is perfect for guests or a home office. Enjoy the convenience of in-unit laundry, private balcony, and assigned parking. The community offers fantastic amenities, including a pool, tennis courts, and playground. With easy access to shopping, dining, and major highways, you’re just minutes from downtown Orlando, UCF, Full Sail University, and Winter Park’s best attractions. Perfect for first-time homebuyers, or investors looking for a great rental property! Don’t miss out on this incredible opportunity—schedule your showing today!

227 Scottsdale Square Unit 227, Winter Park

Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Hard to find frontage on Fairbanks Avenue in desirable Winter Park. This lot and business offer a prime location being on a corner lot just one mile from Park Avenue and Rollins College. 34,000 plus vehicles pass by this location daily! Building features concrete block construction and stucco exteiror. It has 2 service bays with energy efficient doors and automatic openers. The roof was replaced in 2017 with energy efficient 6-inch roof laminate. Interior is fully air conditioned by 2 units. There is a large storage room in the rear, separate from the office. Property has a top of the line video surveillance system inside and out. Property is fenced with a 4 foot metal fence and 2 rolling gates.

1931 W Fairbanks Avenue, Winter Park

3 Beds ⋅ 2.5 Baths ⋅ Winter Park Pines Condo SubDv. ⋅ 32792 Zip Code

Welcome to your dream home! This elegant two-story villa-style condominium combines sophistication and comfort. The convenient downstairs primary bedroom ensures privacy, while the single-car garage and guest parking cater to your needs. Enjoy the serene courtyard, cozy brick corner fireplace, and spacious kitchen with stainless steel appliances. The open great room features high ceilings and tile floors, with natural light flowing through large windows. A bonus room and storage closet overlook the fenced-in rear patio, perfect for displaying potted plants. Impeccably maintained and move-in ready, this unit must be owner-occupied as rentals are not allowed. Located near Full-Sail University, Rollins College, the University of Central Florida, and Downtown Winter Park’s Park Avenue, you’ll have easy access to top-notch educational institutions and vibrant shopping and dining options. Don’t miss out—schedule your viewing today and experience the blend of modern features and inviting ambiance this home offers!

543 Warrenton Road Unit 543, Winter Park

4 Beds ⋅ 2.5 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Welcome to this stunning 4-bedroom, 2.5-bathroom POOL home with a NEW ROOF, offering a perfect blend of modern luxury and functionality, located in the desirable Sylvan Lake Shores neighborhood of Winter Park. The property boasts a thoughtfully designed open floor plan with dark oak wood floors and recessed lighting throughout, creating a bright and inviting atmosphere. The gourmet kitchen is a standout feature, equipped with a gas stainless steel range, pot filler, stainless steel hood, quartz countertops, a farmhouse-style sink, and a large island with seating—perfect for casual dining or entertaining guests. French doors open from the kitchen and living areas to a covered, paver lanai, where you’ll find an outdoor summer kitchen complete with a fridge, gas cooktop, grill with rotisserie feature, and vented hood. The outdoor living space also includes a TV, offering the ideal setup for year-round entertaining. Step into your private backyard oasis, fully fenced and surrounded by lush vegetation, a waterfall, and a water feature. The paver, heated pool provides a relaxing escape, while the expansive lanai runs the width of the home and features seating, dining, and lounge areas. Whether hosting a poolside gathering or enjoying a quiet evening, this backyard offers unparalleled privacy and tranquility. The home’s split floor plan ensures privacy for all, with the primary bedroom and two secondary bedrooms featuring French doors that open to their own private retreats. The primary suite has been fully remodeled and includes a spacious walk-in closet with built-ins and a safe, as well as private access to the pool deck. The luxurious en-suite bathroom boasts a dual-sink vanity, a throne room, and a large shower with a wand feature, creating a spa-like experience. Additional features include a Nest thermostat, Ring security system, a laundry room with a utility sink, and a 2-car garage. The office, which can be used as a fourth bedroom, offers built-in cabinets, shelves, and a closet, providing ample storage. The home also comes with a gas hot water heater and a new metal roof, ensuring energy efficiency and durability. Located just minutes from Winter Park's vibrant shopping, dining, and top-rated schools, this home offers a rare opportunity to enjoy modern living in one of Central Florida’s most sought-after areas. Schedule your private showing today and discover the perfect blend of comfort, luxury, and outdoor living!

345 Sylvan Boulevard, Winter Park

3 Beds ⋅ 2 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Timeless Elegance in the Heart of Winter Park! Discover the perfect blend of charm and modern luxury in this stunning 3-bedroom, 2-bathroom POOL home, located in the highly sought-after “Tree Streets” neighborhood of Winter Park. From the moment you step inside, you'll be welcomed by an open-concept kitchen, dining, and living area designed for both style and functionality. The beautifully updated kitchen features TOP-Of-THE-LINE GE Café stainless steel appliances, including an induction cooktop, double oven, and a Bosch ultra-quiet dishwasher, all installed in 2023. Complemented by professionally painted cabinetry with pull-out shelving, a spacious island extension, quartzite countertops and backsplash, and premium Kohler fixtures, this space is a chef’s dream. The primary bedroom exudes tranquility with its serene ambiance and custom-designed walk-in closet. Adjacent to this private retreat, an office overlooks the sparkling pool, offering a peaceful workspace. Both bathrooms have been meticulously remodeled to deliver a luxurious, spa-inspired experience. The EXPANSIVE FAMILY ROOM is ideal for entertaining or unwinding, featuring new French doors that open to the pool area. The entire interior has been professionally painted. Outdoors, you'll find a sprawling deck perfect for lounging or hosting, alongside the shimmering SALTWATER POOL, newly added in 2022. Lush tropical landscaping surrounds the space, providing privacy and a resort-like atmosphere. This home is packed with upgrades, including designer light fixtures, dimmable recessed lighting, and a state-of-the-art HVAC system with a 22 SEER variable speed unit and humidity control (installed in 2023). The back living room also boasts a 20.5 SEER mini-split system, both covered by a 10-year warranty. Owned solar panels and Roof (both new in 2019) provide energy savings. Double-paned windows with plantation shutters, a full-home re-pipe and rewire have been completed in recent years ensuring value and efficiency. Additional outdoor improvements include a new sprinkler system, fresh sod, landscaped garden beds, a paver pathway, a retaining wall, and new gutters. Nestled on a quiet, tree-lined street, this neighborhood offers easy walkability to Phelps Park (with tennis and pickleball courts) and the serene Kraft Azalea Garden. Downtown Winter Park and the Winter Park Village are both less than two miles away. Take moment to visualize yourself in this beautiful property and then make an appointment to see it in person, you won't be disappointed!

1762 Chestnut Avenue, Winter Park

4 Beds ⋅ 2 Baths ⋅ Lake Waunatta Woods SubDv. ⋅ 32792 Zip Code

Nestled within the desirable family community of Lake Waunatta Woods, this home is beautifully updated and meticulously maintained. The fenced back yard is spacious with a patio and gazebo that is perfect for relaxing, BBQ's and entertaining. Enjoy the benefits of top rated Winter Park schools and the convenience of nearby amenities. State Road 417, the University of Central Florida, Full Sail University, downtown Winter Park, and Downtown Orlando! NEW ROOF! NEW AC! NEW KITCHEN APPLIANCES! NEW WASHER AND DRYER! NEW FENCE! NEW GAZEBO AND LANDSCAPING! Preferred lender offering appraisal credit! Bring all offers as homes in this neighborhood rarely go on the market and don't last long! All rooms sizes should be confirmed by buyer.

4025 Quenita Drive, Winter Park

Winter Park SubDv. ⋅ 32789 Zip Code

Build your dream home a few steps away from beautiful Park Ave in Winter Park.

443 Carolina Avenue, Winter Park

3 Beds ⋅ 3.5 Baths ⋅ Lake Spier Crossing SubDv. ⋅ 32792 Zip Code

Special financing or closing cost credits available to qualified buyers. 2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! Don't miss your opportunity to win this extraordinary move-in ready new residence located between the tranquil shores of Lake Spier and Lake Compton, within the exclusive Lake Spier Crossing community in Winter Park. Featuring 10 impeccably designed two-story townhomes, this enclave of contemporary living is crafted by Meridian Homes, Winter Park's premier builder. Expect modern architectural brilliance and thoughtfully planned floor layouts for stylish, hassle-free living. Meticulous attention to detail is evident indoors and outdoors. The kitchen includes state-of-the-art stainless steel appliances and elegant stone countertops, complemented by luxurious hardwood flooring throughout. Convenience is prioritized with in-unit laundry facilities and a two-car garage. Residents of Lake Spier Crossing enjoy exclusive access to three private docks, perfect for paddleboarding, kayaking, or fishing. This exceptional location offers proximity to Lake Baldwin Dog Park and the picturesque Cady Way Trail, ideal for an active outdoor lifestyle. Enjoy the convenience of walking to Downtown Baldwin Park for dining, shopping, and entertainment, or taking a leisurely 10-minute bike ride to the iconic Park Avenue. Access to Winter Park's esteemed school district enhances the allure of this exceptional community.

1915 S Lakemont Avenue, Winter Park

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