Winter Park FL Real Estate & Homes for Sale

Elegant, timeless home located on one of the most desirable streets in Winter Park. This exceptional 5 bedroom, 5 ½ bathroom French chateau designed by Nasrallah Architectural Group is a rare find! Thoughtfully planned, this home is ideal for a family with a layout that flows seamlessly for entertaining. Whether it's cocktails at the wet bar in the living room, fine dining in the grand dining room, movies in the bonus/media room, or an outdoor pool party this house can accommodate all types of social engagements from large crowds to intimate gatherings. The heart of the home is a beautiful kitchen that opens to the great room highlighted by vaulted ceilings with cypress beams, a stone fireplace, and custom French doors overlooking the beautiful backyard. The primary suite is intentionally situated in a private wing on the first floor and boasts a fireplace, dual walk-in cedar closets and a grand bathroom. Just off the primary suite is the richly appointed study with Busby cabinetry, floor to ceiling wainscoting, and a fireplace. The quality of design and finishes is maintained on the second floor where there are 4 bedrooms, 3 full bathrooms, a loft, custom built-ins, and lots of closet space. The bonus/media room is accessible from a secondary staircase and can easily be used as an additional bedroom. Outside there are several areas to enjoy spending time. Just off the breakfast room is a patio perfect for morning coffee. All the rooms on the back side of the house have access to and views of the picturesque pool. In addition to the covered porch there is a detached loggia that provides a large outdoor living space with a dual sided fireplace, TV and a refrigerator. This home is equipped with a whole house generator. Via Salerno is a brick, tree-lined street in the heart of the Vias with close proximity to Park Avenue, Kraft Azalea Gardens, the Winter Park Golf Course, the Racquet Club, and Interlachen Country Club.

Spacious 2 bedroom condo in Winter Park. Association has 2 pools, playground and tennis courts. Tenant occupied. Great investment opportunity with great stable tenant. There is a dining area, living room and a storage-laundry room off of the patio. To be SOLD AS-IS with the right to inspect, the Roof was completed in 2021. This Condo is zoned for some of the best schools in Florida. Convenient location, close to UCF, Full Sail University, Advent Health, Downtown and the International Airport! Buyer is to assume code enforcement liens, as the Association is working to correct them.

Perfect for the investor that wants to generate income immediately! Experience no vacancy or up front out of pocket expenses for renovations. This property is close to shopping and restaurants, and public transportation. It is a close drive to the airport, downtown Orlando, and many of the local theme parks.

Welcome home! This beautiful 2 story 3 bed 2.5 baths is located one block form Dubsdread Golf Course in Winter Park. The home has been lovingly cared for inside and out. You are greeted with lush tropical landscaping and an inviting cobblestone pavered, covered front porch. Inside you will find a bright and open floorplan with tons of windows and 3 sets of French doors leading you to the back yard. As you enter the home you will find the perfect space for a formal dining room with plenty of natural light and a fabulous light fixture. Next you will find the open great room and kitchen area perfect for entertaining with gas fireplace, high-top bar seating, and French doors leading outside- one that enters the enclosed screened porch perfect for relaxing on a warm central Florida evening. The kitchen features upgraded granite countertops, stainless steel appliances including a gas range, and plenty of storage space with 42" cabinets. Through the kitchen you will find an oversized laundry room with extra storage space. Downstairs also features a spacious half bath with a new countertop. All bedrooms are upstairs, secondary bedrooms feature a Jack and Jill bathroom with separate sink areas, both with new countertops. Both bedrooms have ample closet space. The master suite features 10' ceilings, crown molding and plenty of natural light, the master bathroom includes a huge walk in closet with built-ins, garden tub, and separate walk in shower, dual sinks with new countertop, and a separate water closet. Downstairs through the French doors you will find a backyard oasis with covered patio with cobblestone pavers, gas hookup for your grill, lush landscaping featuring many flowering plants to attract butterflies. Wrought iron fencing in back yard, and oversized 2 car detached garage. Designer features and attention to detail can be found throughout the home including 10 foot ceilings, crown molding, 8" doors, upgraded tile in kitchen, bathrooms, and laundry room. Fresh paint inside and out and all carpet has been replaced. Dubsdread Heights is a well established community with no HOA and conveniently located just off of Fairbanks from I-4. Winter Park is a wonderful city filled with arts and culture. Nearby is Rollins College, the Charles Hosmer Morse Museum of American Art, Mead Botanical Garden, Albin Polasek Museum and Sculpture Gardens, the Enzian Theater, and so much more. Winter Park is also home to over 70 parks, all home to various events, festivals and celebrations throughout the year. A quick ride to almost anywhere in central Florida, minutes to Downtown Orlando, Winter Park Village, College Park, and Park Ave, 20 min to Disney World, and plenty of shopping and award-winning restaurants just minutes away! Put this home at the top of your list and schedule a showing today!

Located in Winter Park close to major universities, Full Sail, UCF, and Valencia. Convenient location, just minutes to downtown Orlando, close to public transit, walking trail in the area and shopping. Ground floor end unit with 2 bedroom 2 bath, patio and loads of community amenities. Tenant occupied with 30 day notice to move.

One or more photo(s) has been virtually staged. This charming 3 bedroom, 2 bathroom, 1 car garage home is now on the market! The kitchen boasts generous counter space and a breakfast bar, making cooking and entertaining a delight. Entertaining is a breeze with this great floor plan complete with a cozy fireplace. The main bedroom boasts a private ensuite and walk-in closet. Other bedrooms offer plush carpet, ceiling fans, and sizable closets. Relax with your favorite drink in the fenced in backyard with a covered patio, lush grass, and great opportunity for adding personal touches. Don't miss this incredible opportunity.

This townhouse is a jewel in Winter Park near shopping and on Lake Killarney for the ultimate Florida living. The home has been updated with stainless steel appliances and new wood cabinets and granite countertops. It has a wood burning fireplace in the living room and a large screened in porch. There are two master bedrooms upstairs both with en suite bathrooms and walk in closets. One bedroom has a covered porch with an outside closet. This unit has tons of storage. Your covered carport parking space is just steps from the front door of your townhouse. There is a beautiful pool with a large dock and a gazebo overlooking Lake Killarney. The sunsets are magical. Very quiet and relaxing complex. Close to everything. You must see to appreciate!!!!

A custom masterpiece! 4 bedrooms, 5 full baths, and 3 half baths. The prestigious Windsong community has a lakefront clubhouse, playground / splashpad area for families, boardwalk to lake for fishing or boating and plenty of walking paths along the lakes. The home has a large Master suite which features vaulted ceilings, separate his and her vanities, spa tub with travertine and glass tile. Master shower has 3 separate water options w/ rainfall head, regular, and handheld option. Split his/her custom closet w/ hidden safe bolted to foundation of home. There is another bedroom downstairs with full bath which was used mainly for guests. The living areas are open and perfect for entertaining. The open-plan kitchen has an oversized granite island that can seat up to 8, with under-counter lighting and stone covered dimmable halogen "art light", plus oversized cabinets with under-cabinet lighting, a Bosch dishwasher and a Wolf commercial range, Wolf steam oven & Wolf warming drawer, a Subzero refrigerator-freezer, and a custom tiled oven hood. Off the kitchen is a Butler's Pantry and Walk-In Pantry with floor-to-ceiling custom shelving. Adjacent to the kitchen is a "sitting room" with a remote controlled natural gas log fireplace with floor-to-ceiling stone veneer, and built-in seating with under-seat hidden storage cabinets and dimmable halogen "art light" above the wood beam mantle. Past the laundry room, stairs lead to the second-floor man cave / game room / media room w/ drop down projector screen and surround sound system, full bath with shower, and hewn log bar with kegerator, plumbed and wired to be able to be easily converted to mother-in-law apartment. It also has a finished, oversized storage room. Across from the living room is a grand staircase leading to the loft area upstairs and two bedrooms w/ a full bath in each bedroom. This loft area space was helpful "homework" quiet space, also good for friends gathering after school or could be another game room. Off from the loft is a large, finished, air-conditioned storage room. The impressive outdoor space features a fully enclosable patio w/ remote-control drop-down screen system, al fresco natural gas grill, custom wood cabinetry, and a wood-burning hand-laid stone fireplace w/ natural gas starter system. Outdoor TV, and wired for a second TV. The pool/hot tub is natural gas heated, custom lighting system in both pool and hot tub, pool has swim resistor system for "lap in place" swimming and a brand new (May 2022) Hayward heater. Finished 3-car garage with stucco, molding and Loewen windows, plus a long paver driveway that can park up to 8 cars. Just a few more details: Nest climate control, 3 separate air handlers and zones, whole-house EWS water filtration system (rated at 10 years or 2.5 million gallons), second water filter system at kitchen sink for double-filtered drinking and cooking water, blown foam Icynene insulation, wood floors throughout, ceiling fans throughout. Alarm system with motion sensors, Loewen windows throughout house, 10-year warranty, wood beams and coffered ceilings on main floor and master bedroom, Rheem dual tankless natural gas, "continuous on" hot water system, tongue and groove ceilings on front porch and back covered summer kitchen/fireplace area, M & S intercom system throughout, Hidden storage room at entry (currently storing wine), keyless Schlage entry system. One-owner custom home - Cahill Builders.

Come see this 3 bedroom, 2 bathroom, end-unit condo nestled in the community of Winter Park Villas. Great layout. Inside you will find a spacious living room/dining room with vaulted ceilings. Complete with a wood burning fireplace and wet bar gives this living space a cozy at home feeling. Kitchen has updated cabinets, built in pantry and breakfast bar. All appliances included. First level, large primary bedroom with ensuite bathroom. Full sized washer/dryer tucked neatly into hallway closet. On the second level, you will find two nicely sized bedrooms and one full-sized bathroom. PRICED TO SELL AS_IS. HVAC 2018, Water Heater 2011. Security system. Fenced backyard with patio and outside storage/utility closet. Association updated roof 2020. Enjoy the wonderful community amenities which includes Pool, Fitness, Clubhouse, Tennis, Basketball Court, Playground, Grilling and Car Wash area. INVESTORS WELCOME! EASY TO RENT---near universities. Walking distance to Full Sail University. Close to UCF, Seminole Trail and a quick 10 minute drive to the esteemed Park Avenue.

New Construction, to be built. This Cape Cod inspired home provides a rare pre-construction opportunity in highly coveted Winter Park, FL. Make this modern marvel your forever home and take advantage of the initial planning stages by adding your personal touches and finish options. Designed by Ben McCoy, known for engineering/building custom homes in Winter Park for over 15yrs; this home features: solar panels with EV charger & back up battery, both smart home capabilities & appliances throughout home, 10ft ceilings, & an open floor plan for all shared living spaces (laundry facilities on both floors). Home is centrally located next to award winning schools, lush gardens/museums, & just minutes from downtown Orlando. Plans subject to change. Call today and schedule your consultation.

Incredible Opportunity to own in an ideal Winter Park location for under $500,000. This charming Ranch is steps from the Winter Park YMCA, located in the sought after school district of Lakemont Elementary, Maitland Middle and WP High, has NO HOA, close proximity to Winnie Palmer Hospital, Interlachen Country Club, Rollins College, and Park Avenue to name a few things! The home offers an Open feel Kitchen/Dining area with tons of natural light pouring over the Living Room. Off the Living Room you'll find a flex space currently being used as an office and workout space hidden behind a beautiful Large Barn Door. Down the hallway you'll find the guest rooms and guest bath. The cozy Master bedroom leads into an oversized Master bath with direct access out to the Pool. There is also a large Bonus room at the back of the house leading out to the spacious fenced backyard and inground pool. New Roof in 2020! Electrical Updated 08/2022! The AC, Hot Water Heater, Dishwasher and Fence were all done in the last 5 years. Move right in without any worries!

Totally renovated, "like-new" home on beautiful Henkel Circle, nestled between Lake Virginia and Like Mizell, easy walking to Park Avenue. The first floor was designed by Tom Lamar, gutted and rebuilt in 2015, the second story was added in 2018 including new roof. Light, bright and looks like a catalogue with features like crown molding, plantation shutters, wood floors, and whitewashed brick accents throughout. Excellent curb appeal with winding brick walkway to covered front porch with swing, tongue & groove wood ceiling, copper window boxes, and all new landscaping. Gourmet kitchen with Cambria quartz counters, stainless appliances, large island, gas range, and dining space opens to family room. Adjacent sunroom with French doors overlooks backyard. Downstairs master suite has vaulted ceiling and designer brick accent wall; master bathroom with double vanity with Carrara marble, free standing soaking tub, separate shower, and walk-in closet. Two additional bedrooms downstairs are great for guests, nursery, or office. The 2nd story opens to a bonus room with large storage closet plus two additional bedrooms with shared bathroom artfully decorated with Serena & Lily wallpaper, tall ceilings with high windows, and double vanity. Lake views from upstairs! All systems new since 2015 and numerous updates. Recent extensive exterior redesign includes custom shed to match home, 2-hole putting green, landscape lighting, Zoysia grass, pergola, and fire pit.

Welcome to this beautiful, move-in-ready, Winter Park home! The home's location is prime - just one block from the Dubsdread Golf course, and within minutes to College Park, Winter Park Village, Downtown Orlando, Park Ave, Rollins College, and major roadways. There is NO HOA! As you walk into this 3-bedroom, 2-bath home, you will notice updates throughout, along with charm and character. The floor plan is open and has a split bedroom layout. The living room features a wood burning fireplace and updated flooring that flows through the dining room into the family room. The kitchen includes granite countertops, breakfast bar, separate eat in area, and large closet pantry. The home's outdoor space is perfect for entertaining with an oversized fenced-in yard, and large 440 sq. ft. deck. The fence even has an extra wide opening on the east side of the property providing room to park a boat or R/V, if you so choose. A true hidden gem! Call to schedule a private showing today!

LOCATION LOCATION LOCATION! It is located on a LARGE CORNER LOT in Kenilworth Shores. Kenilworth Shores Section 7 has deeded access to skiable Lake Berry. Zoned for Winter Park High, Glenridge Middle and Brookshire Elementary. Situated in close proximity to Cady Way Trail, Cady Way Pool and Courts, Winter Pines Golf Club, Showalter & Ward Park Fields, Baldwin Park, Park Avenue, Advent Health, YMCA, Center for Health and Wellbeing, Rollins College and Full Sail University. Roll up your sleeves and bring your paintbrush to this wonderful 4 bed/2 bath SPLIT PLAN home. This home needs a little TLC and a cosmetic refresh but has great bones and could be a stunning home! Walk through the front door and you are greeted by a cozy spacious living room. To the left is a master bedroom fashioned in a SPLIT FLOOR PLAN offering privacy. This master bedroom offers an ENSUITE BATHROOM and HIS-AND-HERS CLOSETS. As you head out of the master bedroom you will find the laundry room and continue into the kitchen with WOOD CABINETS, NEWER REFRIGERATOR, GAS OVEN, and DUAL SINKS. Alongside the kitchen is the cozy dinette. Head through the dinette into the spacious dining room with lots of natural light and direct access to the back yard. Across the living room are the remaining 3 generous sized bedrooms and hall bathroom. NEW VINYL FLOORING (2021) runs through the main part of the house. This is a perfect starter home or add it to your rental portfolio and start renting it soon! DON'T let this opportunity pass you by! NEW modified bitumen ROOF (2021), Exterior electrical panel replaced (2019), Plumbing: Poly

One or more photo(s) has been virtually staged. This magnificent estate was originally built in 1938 with a major addition in 1999. The estate is nestled on nearly 2 acres of prime property on Lake Maitland on the Winter Park Chain of Lakes and walking distance to all the shops and restaurants on Park Avenue. As you drive up to the estate, you will be impressed by the entry gate that leads to the huge circular paved driveway complete with a fountain. For the car enthusiast, there are 2 separate garages totaling 7 spaces. There is plenty of additional parking as this house was built for luxury living and entertaining! The home spans 19,304 square feet under air and 25,124 square feet under the roof. There are two separate grand foyers to welcome you, with high ceilings, gorgeous staircases, and magnificent lake views. This home was built to showcase the stunning lake views from almost every room. There are multiple patios and balconies to offer the perfect spots to take in the incredible views. With a total of 8 bedrooms, 3 of which are master suites with ensuite bathrooms and massive walk-in closets there is no shortage of space in this home. In total, there are 9 full baths and 5 half baths making sure everyone has plenty of space in this Park Avenue Estate. Plus, there is a caregiver's suite with private entries for live-in help. This home is equipped with 3 kitchens making any large gathering a breeze to accommodate! As well as 3 elevators so everyone can move about the estate with ease. The expansive estate is perfect for a multi-generational family, with plenty of bedrooms and bathrooms for everyone to comfortably live together. The grounds are simply beautiful, with mature landscaping and expansive lake views there is truly nothing like it. The possibilities are endless with this home! If you are looking for a one-of-a-kind property, this is it! The grandeur of this estate and its prime location makes it a truly unique find. Don't miss your chance to own a piece of Winter Park history!

Amazing Winter Park/Lake Killarney Location! Sit on your front porch swing and enjoy the beautifully landscaped yard with Magnolia trees and Almond trees that are in bloom and smell heavenly right now! Walk into your open and bright living areas with trendy concrete floors, lots of architectural features and a wood burning fire place. The charming kitchen opens up to the dining area with views of the large fenced backyard. Upstairs you will find three huge bedrooms with wood floors and a separate area that could be used as an office, playroom or fourth bedroom. All drapes, washer/dryer and furniture stay! Roof replaced 2018. View Lake Killarney from your front yard! Easy access to I-4 for commute time.

Winter Park Lakefront living on Lake Killarney can be yours to enjoy. NEW PRICE!!! This ground floor 2BR 2BA Condo offers newer deluxe renovations in this solid built building for maximum neighbor quietness! Two entryways - one convenient to utilize your assigned parking spot and the rear door for access to the visitor parking lot. Abundant natural light comes from the covered patio with privacy offered by plantation shutters. This open floor plan combines the living room, dining room and kitchen. The modern opened/updated kitchen offers quartz countertops, stainless steel appliances and eat-in dining countertop. Master BR includes new laminate flooring and Master BA offers separate bath/toliet area from vanity/wash area. Lots of closet space and nice storage in hallway. All tile or laminate flooring - no carpets! HOA monthly fee includes sewer/trash/water. Chateaux Du Lac Community features a private boat ramp for skiable/fishable Lake Killarney access and lakefront clubhouse with pool for natural enjoyment. Or walk across the street to shop, dine and enjoy a movie at Winter Park Village! Convenient to Rollins College, Advent Health University, Park Ave., Trader Joes, Downtown and I-4. Fabulous location and move-in ready!!!

Charming 3 bedroom 2 bathroom home in Winter Park. This lakefront community with neighboring million dollar plus homes. Prime location in Winter Park with easy access to I-4, Winter Park Village, shopping and 17/92's restaurant row. Minutes from the beautiful Park Avenue shopping and dining district. The one third acre lot has plenty of room to add additional square footage. The roof is 7 years old and the drain field was replaced in 2018. The great room has hardwood floors. Solar panels are owned. The laundry room is inside and off the kitchen. The Florida room overlooking a picturesque backyard. The expansive covered porch and large private fenced yard with swimming pool is great for entertaining. This won't last long!

Pre-Construction. To be built. Preparing to break ground on this newest Winter Park opportunity with F.G. Schaub Custom Homes. This Timeless Modern elevation offers a grand entrance with Anderson double doors, oversized windows, and a 3 car garage. The interior will offer 4,905sqft, including 5 beds, and 7 baths, a sprawling open floor plan and of course an outside entertainment oasis. Adding to the grandeur of the home is a homesite with nearly 1/2 acre of land, creating private destination within town limits. Zoned for Audubon School District. Call Today for more information

YOUR SEARCH STOPS HERE!! LOCATION, LOCATION, LOCATION!!! This COMPLETELY UPGRADED AND FULLY RENOVATED end unit, townhome style condo is situated in the HIGHLY DESIRABLE Four Season's community. As you enter the home, you'll see the updated kitchen with beautiful countertops and backsplash with ample cabinet space, leading straight into your spacious dining room. The dining room opens to the living room, with plenty of room for seating, and the sliding glass doors lead out to the serene, private screened in patio space. Downstairs you'll also find a charming half bath, tucked under the stairs. Heading upstairs, you'll instantly love the two very sizeable bedrooms with double closets and a completely remodeled full bath. Close to shopping, restaurants, Cady Way Trail and more, with beautiful amenities, including tennis, shuffleboard, pools, clubhouse, and fitness center, this home and location lacks nothing. Call today to schedule your private showing.

The first thing you will notice is how grandly this Colonial inspired home is situated on a gently arcing lot within the tree-lined streets of Quail Hollow. With nearly 4000 square feet of living space, 5 full bedrooms and 3 and a half baths, the warmth of the hardwood floors and sense of the open spaces makes this an amazing home your your enjoyment and entertaining. Complete with formal living and dining areas, the kitchen opens to a spacious family room with wood-burning fireplace with Sumpter rock façade AND a bright and cheerful dining nook which overlooks the screen enclosed pool and covered patio. There are generous en-suite bedrooms on both the lower and upper levels (with a wood-burning fireplace enhancing the oversized downstairs suite). The functional kitchen is complete with an abundance of wood cabinets, stainless appliances and a convenient island. The detached oversized side-entry garage is situated to the rear of the property for the most logical safety and convenience. Zoned for some of the best schools in the county (and walkable/bike-able to them as well) this is one of very few Winter Park neighborhoods which is appointed with sidewalks throughout! No mandatory homeowner association dues, fees or restrictions and easy access to Rollins College, Baldwin Park's shopping, dining, activities and entertainment, Blue Jacket Park, Orlando's Fashion Square and Winter Park's world famous PARK Avenue. Place this amazing home at the TOP of your list.

Location, location, this amazing opportunity to build your DREAM HOME is here for you in prime location of Winter Park. The key and main value here is in the LAND!!!!. This home is close to I-4, the Florida Sun rail and Winter Park Village. This is a 3 Bedroom 1 Bath and also adorable, with a wood floors and on an oversized lot, This home is only minutes from 1-4 and restaurants. Come remodel this home to your taste or build your dream home.

This Central Winter Park location, one mile from the Winter Park Mall provides a rare opportunity for investors.

Don't miss out on this beautiful home in the heart of Winter Park! Just one block from your entrance to Lake Virginia, kayaking or paddle boarding has never been easier. Located a golf cart ride from amazing shopping and dining at the famous Park Ave and zoned for the highly desired Audubon K-8. A truly incredible location! A mid-century modern masterpiece, fully remodeled in 2019. The kitchen cabinetry extends nearly 35 ft in length, gas cooking, Italian granite counters & waterfall island. Custom wood cabinetry with soft close. Spacious, open floor plan ideal for entertaining. The kitchen flows into casual, informal dining and a family room. Off the kitchen and dining area is a flex space, perfect for an office, a playroom, game room, or more. The luxurious main suite is located on the first level, with an elegant owner's soaking tub and steam shower. 2 spacious bedrooms upstairs with full bath and natural hardwood floors. An oversized 2 car garage was newly built with space for a future mother-in-law suite. Beautiful backyard courtyard- plumbed and gas-ready for your outdoor kitchen. Complete redesign and remodel boasts over 2100 square feet of living area and approximately 2800 square feet under-roof. Includes a new lifetime metal roof, new 100% vinyl double pane windows, doors, electrical, plumbing, elegant strand-woven bamboo, and more. Don't miss out on this rare opportunity! Call today to schedule your personal visit.

It is all about LOCATION, LOCATION, LOCATION!! This beautiful spacious Winter Park home is located in the Lost Creek subdivision, a very private community with no rear neighbors, backing up to a lush conservation area that offers trails leading to Howell Creek. The house has an enormous screened patio overlooking this conservation land which allows for total privacy and tranquility. Upon walking inside this two-story property you notice the very high cathedral ceilings and open floor plan, with lots of natural light being let in through the windows and sliding doors. Enjoy the outside views, bug-free, in the screened enclosed back porch spa area. What a wonderful site to enjoy your morning coffee or evening relaxation. The kitchen has stainless steel appliances and plenty of storage, under the island and around the fridge. The flooring are wood planks from Composer Collection Vivaldi, giving the home a one-of-a-kind look. The master bedroom has a large walk-in closet with an amazing bathroom that includes a garden tub, separate shower, dual sinks, and a linen closet. Upstairs has bedrooms, a secondary bathroom, and a loft. New hot water heater. roof 2016. Oversized two-car garage!