Winter Park Real Estate Search

Winter Park Homes for Sale

In Orange County, Florida, in the Orlando Metro Area, the charming community of Winter Park has much to offer prospective homebuyers. Winter Park has roughly thirty thousand residents and is well-known for its glistening lakes, lush mature trees, and quaint brick-lined streets. This well-established community also boasts a rich heritage and long history, initially chartered in 1887. Today it sits just north of Orlando, thereby offering proximity to a long list of big-city attractions, amenities, and services. Simultaneously, Winter Park offers a relaxed, laid-back lifestyle and a variety of local high-end restaurants, boutique shopping, and other upscale amenities, particularly along Park Avenue but also in smaller pockets of the area. 

Winter Park is the ideal destination for an afternoon promenade with an extensive collection of award-winning restaurants and frequent festivals and events. Among the most popular Winter Park festivities are the Florida Film Festival, Winter Park Sidewalk Art Festival, the Bach Festival Society of Winter Park, and the Winter Park Autumn Art Festival. Additionally, the community is home to the Winter Park Historical Museum and the second oldest golf club in Central Florida. 

Homes for sale in Winter Park are equally desirable and diverse and are located in appealing neighborhoods and subdivisions like Orwin Manor, Northwood Circle, College Quarter, Windsong, Hannibal Square, Green Oaks, and Plymouth Apartments. Real estate in Winter Park consists of an array of semi-detached, attached, and detached homes of many ages, architectural styles, sizes, and floor plans. If you would like specific details about available properties in Winter Park, Florida, please connect with us today, and we will happily help you with your Winter Park home search.

Our website features the best Winter Park real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in the Winter Park real estate market? Sign up for a Winter Park Real Estate Market Report to see what’s active, under contract, and sold!

today to find out how we can be of assistance to you!

Newest Winter Park Homes and Condos for Sale

$7,250,000
4 Beds 4.5 Baths Winter Park SubDv. 32789 Zip Code
**500 N. INTERLACHEN AVENUE, WINTER PARK, FL 32789** INCREDIBLE OPPORTUNITY – HISTORIC LAKEFRONT ESTATE ON THE SHORES OF LAKE OSCEOLA – ONE BLOCK FROM PARK AVENUE! Absolutely stunning and timeless, this historically designated home sits on an oversized 0.74 acre lot and features a private boathouse with approximately 50’ of waterfrontage. Originally built in 1934 the 4 bedroom, 4.5 bath home embraces Spanish-revival style through its elegant use of sun-kissed terracotta floors, arched entries, ironwork details, dark wood accents, and imported chandeliers. Formal living spaces are complimented by hand-painted ceilings, custom moldings, marble fireplaces, and handcrafted built-ins. The gourmet kitchen features professional grade appliances, custom cabinetry, emerald green granite countertops, and a large island. Laid out extremely well, the interior floorplan offers a first-floor primary bedroom with walkouts to the terrace and an en suite bath with dressing room. Upstairs are three guest rooms, each with a private bath, and generously sized closets. Unlike many homes in the area, this residence offers a lower level, or finished basement, that showcases a several hundred bottle wine room and additional storage area. Inspired by its Spanish-Mediterranean roots the home relies on several outdoor courtyards, patios, terraces, and balconies to extend living space outdoors, creating the ideal setting for large gatherings with friends and family. With it’s resort-like setting, this home provides year-round opportunity to enjoy the Florida weather along with a private salt-water pool and expansive rolling green space down to the shores of Lake Osceola. Located in charming Winter Park, FL, this magnificent estate is just a short walk to award-winning dining and boutique shops as well as the Alfond Inn, Rollins College, and many other nearby historic sites and attractions.

500 N Interlachen Avenue, Winter Park

$299,900
2 Beds 2 Baths Winter Park Pines Patio Homes SubDv. 32792 Zip Code
MOVE RIGHT IN! This well maintained 1233sf, 2 BEDROOM/2 BATH VILLA on a CORNER LOT in the beautiful WINTER PARK PINES neighborhood is ready for a new owner! Centrally located, this GOLF COURSE COMMUNITY boasts gorgeous OAK LINED STREETS and is just minutes to UCF, downtown Orlando, the Airport, Cady Way Park, Baldwin Park and the VA Hospital, Full Sail University and so much more…definitely a COMMUTER’S DELIGHT! The KITCHEN has a CLOSET PANTRY, SOLID MAPLE CABINETRY, a PASS THRU TO THE GREAT ROOM, sliders to an OUTDOOR COURTYARD and includes ALL APPLIANCES, even the WASHER & DRYER. A CATHEDRAL CEILING with WOOD BEAMS and a rustic BRICK and WOOD FIREPLACE with a hearth enhance the spacious GREAT ROOM. Oversized sliders in the Great Room lead to a 30x12 PATIO enclosed with a WOOD FENCE which is the perfect spot for private relaxation with your favorite beverage at the end of the day. DOUBLE DOORS lead to the16x12 MASTER SUITE which has a CATHEDRAL CEILING and a WALK-IN CLOSET. The EN SUITE MASTER BATH has SOLID WOOD CABINETRY and a SOLID SURFACE VANITY area which is separate from the shower and toilet area. Additional INTERIOR FEATURES of this home include a NEW HVAC SYSTEM (currently in the permitting stage and will be installed during MAY 2024), TILE and LAMINATE FLOORING throughout, WOOD FAUX BLINDS in the bedrooms, CEILING FANS in all above grade rooms and an abundance of NATURAL LIGHT. EXTERIOR FEATURES include a TILE ROOF, GUTTERS and DOWNSPOUTS, a SINGLE CAR GARAGE with PULL DOWN ATTIC ACCESS, BUILT IN SHELVING and a WORKSHOP AREA. The HOA FEE is LOW and INCLUDES FRONT & REAR LAWN MAINTENANCE (mowing and edging) and IRRIGATION. Don’t miss your opportunity to own this lovely home…Call us today for a private showing!!

603 Warrenton Road, Winter Park

$2,795,000
5 Beds 6.5 Baths Winter Park Village SubDv. 32789 Zip Code
Welcome to the sophistication and contemporary masterpiece by Parkland Homes. This exceptional residence features five spacious bedrooms, six and a half bathrooms, and 4,500 square feet of meticulously designed living space. Nestled within the exclusive enclave of Winter Park, this new construction opportunity redefines opulent living. The architectural marvel boasts a unique contemporary design, seamlessly integrating form and function. From the moment you arrive, the striking facade captivates with sleek lines and 10 foot ceilings on both levels of the home. Inside, natural light floods the open-concept living spaces, creating an inviting atmosphere that is both luxurious and welcoming. Entertain with ease in the gourmet kitchen, equipped with top-of-the-line appliances, Sub Zero, Wolf and Miele, custom cabinetry, a spacious island, and a wine cooler. The adjacent living and dining areas provide the perfect backdrop for gatherings, both large and small. The lavish primary suite, located on the first level, offers a private sanctuary of comfort and style. Indulge in the spa-like en-suite bath, featuring a soaking tub, oversized shower with dual shower rain shower heads , and dual vanities, creating the ultimate haven for relaxation. Escape to your outdoor oasis directly from the primary suite. An additional bedroom on the first level adds convenience, featuring a walk in closet and ensuite bathroom and currently staged as the home office. Retreat to the upper level to find a spacious loft that features a wrap around balcony, this space is ideal for relaxation and entertainment. Adjacent to the loft are three generously sized bedrooms, each offering a unique blend of comfort and style. Whether for family members, guests, or a home office, these bedrooms provide versatile spaces that adapt to your lifestyle needs. Outside, discover your personal paradise that sits on the largest lot on the street, featuring a sparkling pool, expansive patio, and outdoor kitchen, perfect for alfresco dining and year-round entertaining thanks to the retractable screens enclosing the lanai when needed. Additional features include a three-car garage with an EV car connection, leading to a mudroom and laundry area with ample storage, ensuring every aspect of this residence exceeds the expectations of the most discerning homeowner. Nestled in a highly sought-after location, this residence enjoys an enviable address surrounded by top-rated schools and is moments from renowned attractions such as Park Avenue, that promises unique shopping and upscale dining. Experience the pinnacle of luxury living with this exceptional new construction home.

2412 Chantilly Avenue, Winter Park

$850,000
4 Beds 3 Baths Kenilworth Shores Sec 03 SubDv. 32792 Zip Code
Welcome to this beautifully cared for family home, 4 bedrooms, 3 full baths, plus an office. Located in the highly desirable Kenilworth Shores neighborhood in the heart of Winter Park. The inviting entry with a cozy front porch and a brick paver walkway and driveway are bordered by colorful garden beds containing a lovely variety of shapes, colors, and textures of foliage and flowers. A seamlessly open floor plan connects the living room, dining room and kitchen area, surrounded by large windows and French doors offering natural light and scenery. The fabulous expansive kitchen has an abundance of cabinets, drawers, and counter space, a floor to ceiling cabinet pantry with pull out shelves, 2 separate sinks, pretty granite countertop, stainless steel appliances and a breakfast bar that seats 8. Huge master bedroom has plenty of room for a sitting area, vaulted ceiling and 2 walk-in closets. The master bath offers a dual sink vanity and a spacious walk-in shower with dual shower heads. The master suite has its own 2024 HVAC. Additional features – re-pipe 2024, roof 2012, updated windows, beautiful engineered wood floors, newer carpet, recessed lighting, and no shortage of closets - plenty of storage, jack and jill bath between bedrooms 2 & 3, a new water heater, added hurricane straps, and a freshly painted exterior. Mature towering trees shade the backyard and the 17 x 13 open brick paver patio from summer heat. Pathways wind through an array of native plants and flowers in this wildly naturalistic style garden. Walking distance to the Phillips Crosby Wellness Center and Ward Park – one of the most diverse parks in the city, from the athletic facilities to the playground to the walking and biking trails. A short drive or bike ride to Rollins College and to shops and restaurants on Park Ave. Don’t miss out on this gem, book your showing appointment today.

2013 Kimbrace Place, Winter Park

$2,150,000
3 Beds 3.5 Baths Virginia & Morse Brownstones SubDv. 32789 Zip Code
Welcome to Luxury Townhome Living in Winter Park. Indulge in sophisticated urban living with this meticulously designed 3-bedroom, 3.5-bathroom townhome by renowned architect Phil Kean. Spanning over 3,000 square feet, this residence seamlessly blends privacy, convenience, and luxury. Every detail has been thoughtfully curated, from the custom wood cabinetry to the exquisite Carrara marble primary bath. Upon entering, you'll find a spacious office and a bedroom with an en-suite bath on the ground floor. The private elevator provides effortless access to all three stories, as well as the rooftop terrace. The second floor unveils an open-concept living area, perfect for entertaining, featuring a gourmet kitchen equipped with top-of-the-line Wolf and Sub-Zero appliances, a 36" gas range, quartz countertops, and a dry bar with wine refrigerator. The third-floor primary suite is a sanctuary with two walk-in closets, a private balcony, and a spa-like bathroom featuring a soaking tub within a large glass and marble shower. An additional bedroom on this level also includes a private balcony and an en-suite bath, along with a walk-in closet. Outdoor living reaches new heights on the rooftop terrace, complete with an outdoor television, ideal for gatherings and enjoying breathtaking Florida sunsets. The home is adorned with custom built-ins, designer fixtures, California closets, and a Control 4 security system for peace of mind. Enjoy the ease of the lock-and-leave lifestyle and explore all Winter Park has to offer, just steps from fine dining, boutique shops on Park Avenue, Hannibal Square, and the Winter Park Farmers' Market. This residence is the epitome of sophisticated living, where every detail embodies elegance and comfort.

419 W Morse Boulevard, Winter Park

$1,895,000
5 Beds 3.5 Baths Lake Knowles Terrace Add 02 SubDv. 32789 Zip Code
Stunning SINGLE STORY, four-way split plan masterpiece. Inspired by California's award-winning "House of Windsor" (architect Windsor Smith) design and purchased by Gwyneth Paltrow. Home is located in one of Winter Park's most cherished neighborhoods. Completed in November 2014, this property stands out with five bedrooms plus an office, all nestled on a spacious 1/3 acre lot along a picturesque brick street. Upon entering, you're greeted by an inviting open floor plan adorned with striking marble foyer and white oak engineered flooring. The family room serves as the centerpiece, boasting a modern fireplace, while the adjacent dining area features a tray ceiling and grasscloth wallpaper. The kitchen is a culinary haven, showcasing Quartzite waterfall countertops, white cabinetry, complemented by high-end appliances including a Verona 36-inch Dual Fuel gas range, Bosch dishwasher, and a GE French Door refrigerator. Whether entertaining guests or preparing family meals, this kitchen is sure to impress. Retreat to the private large primary suite, where luxury abounds with Carrera marble counters, a marble-tiled shower, and a claw foot tub in the primary bathroom. Primary closet caters to the most extensive wardrobes. Ample storage and organizational features. The four additional bedrooms offer comfort and privacy, with one serving as a quiet guest suite, ideal for accommodating visitors. Step outside to discover a resort-like oasis, featuring a saltwater pool surrounded by travertine paving and a beautiful screened porch, providing the perfect setting for outdoor relaxation and entertaining. Recent improvements include two enlarged bedrooms, one with built-in custom bunk beds, built-out closets, completely renovated bathroom, custom locker built-ins in laundry room. Home updated with "smart" technology Lutron lighting system to control and schedule lights, dimmers added throughout controlled by mobile device, Alexa or Google Home. Security System with touch screen keypad and points on all windows and doors. Black metal gate entrance, remote controlled for cars and detached 2 car garage. Side entry for grocery and package drop off. Gravel driveway sets the tone as you arrive. Ideally situated in one of Winter Park's most coveted neighborhoods, this home offers easy access to Park Avenue, Phelps Park, and Rollins College. Excellent Schools- Lakemont Elementary, Maitland Middle School and Winter Park High School. Experience this Winter Park masterpiece, where every detail has been thoughtfully considered. Original Windsor Home-http://www.nicolegibbonsstyle.com/2012/07/magnificent-house-windsor-gwyneth-paltrow.html <div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=um1jfojVRWw&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

1540 Palm Avenue, Winter Park

$650,000
3 Beds 3 Baths Golfside Sec 03 SubDv. 32792 Zip Code
Welcome to the Golfside Community with its stunning canopy of trees which line the streets and spectacular golf course views! This home features breathtaking views of the 9th hole on the adjacent Winter Park Pines 18 hole Golf Club. This spacious 3-bedroom, 3-bathroom abode offers an unparalleled living experience with access to top-tier schools and amazing neighborhood amenities. As you step into this meticulously designed home, you're greeted by an expansive living space, bathed in natural light streaming through large windows that frame the verdant greens of the golf course. The open floor plan seamlessly connects the living, dining, and kitchen areas, providing an ideal setting for both intimate gatherings and lively entertaining. A double-sided fireplace connects the 21’ x 12’ living room to the sunken family room that is off of the kitchen. The heart of this home is undoubtedly its updated kitchen, boasting sleek granite countertops, modern stainless appliances, and ample cabinet space. Whether you're a culinary enthusiast or simply enjoy preparing meals for loved ones, you can prepare meals while gazing across the green. Retreat to the spacious master suite, where tranquility awaits after a long day. Complete with a luxurious ensuite bathroom and generous closet space, this private oasis offers the perfect retreat. Two additional bedrooms each have their own ensuite baths providing privacy for guests and ensuring everyone has their own space to unwind and recharge. Step outside to discover your own slice of paradise in the backyard oasis. With direct access to the golf course, you can enjoy leisurely strolls or simply soak in the panoramic views from the comfort of your own patio. Whether you're savoring your morning coffee or hosting al fresco dinners under the stars, this outdoor haven is destined to be your favorite retreat. Located in highly sought-after Winter Park proper and zoned for A rated schools in the area including Winter Park High School and Brookshire Elementary, this home offers not just a place to live, but a lifestyle to be cherished. Quick access to the Cady Way Trail provides a beautiful pedestrian path on which to exercise or walk the pets. Additional neighborhood amenities include the nearby Cady Way Pool, tennis and pickle ball courts, playground, Ward Park sports fields and MORE! The Wellness Center and Advent Health sit just outside of this community along with a plethora of grocery stores, restaurants, and shopping. Area colleges including Full Sail, Valencia, Rollins and UCF are all just minutes away. Don't miss your chance to make this exquisite property your forever home. Schedule a showing today and prepare to be captivated by all that this stunning residence has to offer! ROOF - 2023, HVAC - 2018, ELECTRIC - 2011.

1037 Fairway Drive, Winter Park

$639,000
4 Beds 3 Baths Lawndale SubDv. 32789 Zip Code
Welcome to this immaculately remodeled 4-bedroom, 3-bathroom home, ideally situated just minutes from Downtown Winter Park, showcasing exquisite attention to detail and a blend of elegant, luxurious, and modern architectural elements. Upon arrival, you're greeted by an extended paver driveway, ensuring effortless parking. Step through the double door entryway onto gleaming wood flooring that flows seamlessly throughout the home. To your left, discover a sophisticated formal dining room adorned with a captivating chandelier. The heart of the home is the stunning kitchen, boasting quartz countertops, a spacious center island, a farmhouse sink, stainless steel appliances including a 5-burner stove, and ample cabinet and counter space. The kitchen seamlessly transitions into the family room, creating an ideal space for entertaining and everyday living. Adjacent to the family room is a versatile flex room, perfect for a theater room, office, home gym, or any other desired use. The property features two ensuite bedrooms, one on the main floor and a sprawling one on the second floor with a charming balcony, expansive walk-in closet, and abundant space for relaxation and privacy. Outdoors, the entire property is fenced, providing a sense of security and seclusion. Recent updates include a new roof, AC system, tankless water heater, septic tank, drainage, plumbing, and electrical—all completed in 2022-2023, ensuring modern comfort and peace of mind for years to come. Nestled in one of Winter Park's most coveted neighborhoods, this home is conveniently situated near Dubsdread Golf Course, the vibrant Mills/50 district, Fairbanks Ave, and College Park. Enjoy a plethora of walkable dining and shopping options, with easy access to Orlando's premier regions and restaurants and the charming Park Ave. Additionally, its proximity to I-4 and other major roads ensures convenient connectivity to the greater Orlando area. Don't miss this opportunity to own a sophisticated and impeccably updated home in a prime Winter Park location, offering both luxury and convenience at your doorstep. Schedule your showing today!

1546 Minnesota Avenue, Winter Park

Start Your Search