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. 

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Newest Winter Park Homes and Condos for Sale

$295,000
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 1 SubDv. ⋅ 32792 Zip Code
This charming townhouse offers a comfortable and inviting living space with three bedrooms, two bathrooms, one being an en-suite bathroom in the main bedroom, and a bonus room, making it the perfect place for a family or individuals seeking a spacious and comfortable living environment. NEW roof and NEW A/C units (both in September 2023) add to the property’s value and ensures durability for years to come, coffee nook adjacent to the kitchen, and three parking spaces in front of the property. The spacious living room contains a solarium that can be used as a winter garden or small office. One standout feature of this property is the bonus room with a walk-in storage. This versatile space can serve as a home office, a playroom, or even a guest room, offering endless possibilities to suit your lifestyle. The backyard features lush greenery and a manicured lawn, creating a space for relaxing and fun (belongs to the HOA).

2452 Harbour Way, Winter Park
$549,995
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code
Come see this beautifully maintained home in the heart of Winter Parks Kenilworth Shores. Situated just a short walk from Ward Park, Cady Way Trail, Advent Health Wellness Center, Brookshire Elementary and Winter Park Highschool, this 3/2 home offers sought-after functionality both inside and out. The kitchen/family room combo allows you to entertain indoors, while the Florida room and newly built stone patio will offer the chance to impress your guest's out back. The Primary suite boasts a walk-in closet, updated en-suite and French Doors leading out to a private outdoor patio for your morning coffee. The 2nd and 3rd bedrooms with walk-in closets share a second updated bath. Double-pained windows allow for an abundance of natural light throughout living, dining and family rooms. Improvements include new plumbing, a new roof, windows, back patio, and fresh paint throughout. The attached two car garage, and additional shed in the rear offer plenty of extra storage. Minutes from downtown Park Ave, Baldwin Park, the YMCA, I-4 and shopping/dining, this Winter Park gem is not to be missed. Schedule your private showing today.

381 Perth Lane, Winter Park
$629,900
3 Beds ⋅ 2 Baths ⋅ Dommerich Hills Fourth Add SubDv. ⋅ 32789 Zip Code
Nestled in the beautiful city of Winter Park, this delightful 3 bedroom, 2 bathroom POOL home is Florida living at its finest. Boasting a spacious layout, lush landscaping, and convenient location, this property offers a truly inviting and relaxing lifestyle. Best of all, zoned for Orange County schools and NO HOA! Stepping inside, you are greeted with an open and airy living space, perfect for family gatherings and entertaining friends. An abundance of natural light floods through the updated windows, highlighting the warm, neutral color palette throughout the home. Entering the living room you will find an updated and oversized sliding glass door that encompasses the beauty of the outdoor oasis. The spacious kitchen features ample counter space and a convenient breakfast bar for early mornings with your family and friends. The primary bedroom features an en-suite bathroom and a renovated stand up shower. Two additional bedrooms offer comfort and space for family members or guests. These rooms can also be flexibly used as a home office, fitness room, or a nursery. A screened lanai and sparkling 22,000 gallon pool create the perfect backdrop for outdoor entertaining. Enjoy a refreshing dip on a warm Florida day while you listen to the custom waterfall. New vinyl fencing surrounds the backyard providing privacy and security. Located in the desirable Winter Park community, you're just moments away from top-rated schools, parks, shopping, and dining. Enjoy easy access to downtown Orlando, major highways, and all the cultural attractions the area has to offer. Don't miss the opportunity to make this Winter Park gem your forever home. Interior/Exterior Paint 2021

2524 Sweetwater Trail, Winter Park
$2,749,000
4 Beds ⋅ 4.5 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code
A thoughtfully reimagined Winter Park custom home with transitional style & Mediterranean architectural influences awaits. Built by renowned Bates Driscoll Homes & designed by Gary Hancock, no detail has been overlooked. Located in one of the most sought-after areas in 32789, on a cobblestone street with walkability to lifestyle that makes this town unique. A streamlined design blends warm surfaces & modern appointments with volume ceilings that welcome you. Gentle view lines were carefully considered to emit abundant light. Living & dining spaces combine travertine marble floors, Georgian wood windows, smooth finish level 5 museum quality walls, add to the carefully selected Designer finishes. Function was at the forefront when designed with 4,692 sf featuring a 3-way split bedroom plan, with a main-floor owner’s retreat & upstairs 3-bed ensuites, one could be a second master, a large multi-purpose space. Main floor foyer French doors welcome you into a dedicated entry to office or library, living & dining rooms combine, open kitchen & family concept overlooks covered porches & courtyard with pool, ultimate privacy. A chef’s kitchen is expansive with stainless Wolf Pro Range/Subzero appliances, 42” Kitchen wood cabinetry, granite counters task lighting, alabaster pendants & luxurious alabaster backlit backsplash behind range. A side entry door opens to a family drop-zone for backpacks & shoes and easy access for deliveries to “back of the house” function. Center Island, casual bar seating & additional dining allow for any size gathering. The family room enjoys cypress beamed ceiling, stone fireplace, oversized chandelier with Agate disks sparkles above. Unobstructed views through 4 sets of French doors across gathering space & open to courtyard, so green & filled with afternoon light. The veranda features wood ceilings, a stone gas fireplace, breezy ramada porches with lantern lights that reflect in the pool. Travertine deck surrounds the pool and leads out to greenspace at the back. It’s about bringing the outside in as views abound and emphasize the beauty of the professional landscape. First-floor primary retreat is tucked away with doors to veranda & a spacious seating area for peace & quiet as you wind down the day. The owner’s bath showcases mother of pearl in-sets in floor, in walk in shower, & accented in custom-made dual vanity doors & fixtures. Main closet is expansive with a space for a peloton, intimate yoga retreat or for a newborn to snuggle in. Upstairs flex space is oversized with great possibilities for a variety of uses. New wood floors throughout second floor & all bedrooms have a dedicated bath with generous closet. Juliette balcony with windows to the floor capture the beauty of the views & add to the charm of the spaces. The back balcony adjoins 2 bedrooms with views of the treetops & captivating sunsets. Other features: opened spaces – walls removed, smooth walls, new interior/exterior paint, spectacular barrel tile roof, plantation shutters, utility closet added, all baths, lighting, fixtures & hardware updated, solid doors, professionally landscaped, artificial turf in back, 2 staircases include a service stair from laundry for easy housekeeping, add a chair lift for those in need & a front grand stair with iron details. A short walk to Lake Chelton, Sue & Virginia, Park Avenue, Rollins College, Corrine Dr & downtown. Zoned for Audubon K-8, WP High & step from the 9th grade Center.

1741 Glencoe Road, Winter Park
$589,000
4 Beds ⋅ 2 Baths ⋅ Arrowhead Cove SubDv. ⋅ 32792 Zip Code
This completely renovated home is located on a large corner lot, in the popular Arrowhead community in Winter Park with the sought-after school district of Lakemont Elementary, Maitland Middle, and Winter Park High. Roof is 2018. A/C is 2014. Underground utilities. Having 4 bedrooms, 2 bathrooms with a split bedroom plan makes it a wonderful family home. Multiple entertaining spaces to choose from with two family rooms, formal dining, and an open and updated kitchen will give you 1,936 square feet of perfectly move in condition for you! The Florida room overlooking the sparkling blue pool is amazing and could also serve as a game room for family gatherings. The north-facing backyard provides perfect all-day sun for pool fun days with friends/family with still plenty of yard for dog ball tossing or relaxing gardening. This amazing home is just minutes to local shopping, restaurants, the WP YMCA, and Park Ave, and only 20 minutes to the center of Orlando.

7551 Bent Bow Trail, Winter Park
$1,349,000
5 Beds ⋅ 3 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
This custom 5-bedroom, 3-bath home just steps from Winter Park's exclusive Vias neighborhood features interior architectural accents throughout, including hardwood floors, architectural ceilings, and custom closets and shelving in each bedroom. Enjoy the 2,577 sq. ft. home's professionally designed lush landscaping, trees and backyard privacy from a heated saltwater pool and spa and covered lanai with stained tongue and groove ceiling. A gourmet kitchen with quartz counter tops includes an oversized island with seating for four, Miele and subzero appliances, white shaker style cabinets and a kitchen tile backsplash. The elegant master suite includes spacious closets, a soaking tub, large European sport showers, designer porcelain tile, and Moen faucets. Designed as a smart home perfect for entertainment and working from home, it includes high-speed WIFI with professional CAT 6 wiring, an upgraded alarm system with five cameras, and programmable Nest thermostats controlling the zoned air conditioning system. Other interior features include upgraded crown molding throughout, motorized blinds, 4-panel shaker solid core doors, 6-inch baseboards, and a tankless water heater. A covered front porch includes Old Chicago brick pavers, a tongue and groove ceiling, and metal roof. Other exterior accents include sand finish smooth stucco, Shaker siding on the front, a front covered porch , a sand set paver driveway and walkway, low voltage landscape lighting and a privacy fence. The garage was upgraded with epoxy flooring. This great location is zoned for top-rated schools including Dommerich Elementary, Maitland Middle, and Winter Park High School.

1320 Bessmor Road, Winter Park
$849,900
4 Beds ⋅ 3 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code
Welcome to this gorgeous remodeled home with a huge fenced in backyard in highly sought after Winter Park! This open concept, split-plan home boasts four bedrooms, three full bathrooms, a large living room, an eat-in kitchen area, a huge dining room, plus an extra room with beautiful French doors. Natural light fills every corner of this contemporary space. Within the past five years countless upgrades have been made; exterior and interior freshly painted, kitchen renovation including new wood cabinetry, quartz countertops and new stainless steel appliances, bamboo flooring installed, and all three bathrooms freshened up with granite countertops and new vanities. More recently, in 2019, new washer and dryer replaced in the inside laundry room, new modern blinds installed on all of the big windows for privacy, new side gate built into the white vinyl fencing, and new heavy duty insulation added in the attic. In 2020, a new garage door was installed, a new exterior back door leading to the patio was created, and BOTH Air Conditioning systems were replaced. (One in 2019, the other in 2020.) In 2023, a brand new garbage disposal and dishwasher were installed. For extra peace of mind, a complimentary complete 1-year Home Warranty is provided! Also, this move-in ready home with its huge backyard has plenty of room for a pool, it's zoned for the top-rated school district, is close to prestigious Rollins College and minutes away from beautiful downtown Winter Park. Don't miss out on this dream home. Schedule your private showing today!

350 N Phelps Avenue, Winter Park
$3,950,000
4 Beds ⋅ 4.5 Baths ⋅ Morse & Pennsylvania Twnhms SubDv. ⋅ 32789 Zip Code
This stunning DETACHED ELEVATOR CITY home, meticulously crafted by the renowned Phil Kean Design Group, presents itself as an opulent haven in the heart of Downtown Winter Park, FL. With innovative modern architecture & state-of-the-art technology, this magnificent residence has been classified as a Net Zero/-16HRZ energy rating, producing more power than it uses, making it one of the most eco-friendly homes on the market. Designated as a showcase home for the National Association of Home Builders & International Builders Showcase, the interior spanning across three levels, boasts elegance coupled with unsurpassed luxury. The grand entrance on the FIRST level welcomes you with an exquisite gallery, adorned with conversational spaces, an en-suite bedroom, an office or bedroom, a mud room with doggie door and fenced dog run, and a spacious oversized 3 car garage equipped with an electric car charger and overhead storage system. Ascend to the SECOND level and discover the primary owner's suite, an absolute masterpiece, with a spa-like bath fitted with a steam shower, a lavish & posh walk-in closet with showcase lighted storage, a storage island & a large balcony perfect for unwinding in supreme comfort. A workout room (additional bedroom) with a full-sized sauna adds to the retreat-like atmosphere of this floor. In addition, there is a large loft area perfect for an additional lounge or office and a beautiful laundry room with double LG washer & dryer sets and a phenomenal dry-cleaning closet, the next must have appliance! The TOP level of this home is a showstopper. With an open-concept design and breathtaking views from every angle, this luxurious and expansive area will be the perfect place to entertain guests or unwind after a long day. This level features a well-lit dining area, a stunning wet bar, a warm and cozy fireplace, 2 outdoor balconies ideal for basking in beautiful views and enjoying Florida’s outdoor living. The exquisite kitchen, hailed as the "Best Kitchen in Country 2020," will be a chef’s dream and is fitted with state-of-the-art Wolf & Signature appliances, including a 48-inch dual fuel range and 4 Wi-Fi-enabled smart ovens & a sous vide cooking system for perfectly cooked meals every time. The kitchen also features a built in Espresso Maker for a perfect coffee to compliment the beautiful surroundings. Lighted, Temperature-controlled wine towers built to impress any wine connoisseur and boast ample space for up to 600 bottles of your favorite vintage. The home is unique in every sense of the word. With its 14-foot ceilings, 12-foot external doors, symphony of natural light, and awe-inspiring views, the home is a haven of unparalleled sophistication. The floating walnut staircase with unique underlighting will surely captivate your attention & add a touch of class to the space. The elevator with leather walls and brass flooring provides easy access to all three floors and adds to the home's elegance. Additional features, such as a whole-home generator, state of the art home security system, Panasonic air filtration system, 2 tankless, gas water heaters, Control4 Home automation system, outdoor terraces, summer kitchen, and automated louvered porch roofing system, solar panels on roof, & remote-controlled balcony screens will deliver convenience and peace of mind to all. 674 W Morse is located in Hannibal Square and is only a short three city-block walk to Park Avenue’s restaurants, galleries, shops and entertainment.

674 W Morse Boulevard, Winter Park
$475,000
3 Beds ⋅ 2.5 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to the Enclave at Hawks Crest, a newly built GATED luxury townhome community in sought-after Winter Park! Delivering this largest floor plan in the community this 3BD/2.5BA home has a bright OPEN CONCEPT, nice finishes throughout, HIGH CEILINGS, formal/flex space and a spacious COVERED LANAI with no immediate rear neighbors! Conveniently located to all that Winter Park and the surrounding communities have to offer including easy access to local schools, shopping, dining, parks and more! WOOD LOOK TILE FLOORS and styled light fixtures give this home a fresh modern vibe. The family chef will appreciate the spacious kitchen delivering plenty of cabinet space, STAINLESS STEEL APPLIANCES, closet pantry, QUARTZ COUNTERS and large ISLAND with breakfast bar seating! Your bedrooms are all on the second floor, all three a great size, including the primary suite - a tranquil retreat under a decorative tray ceiling and complete with a WALK-IN CLOSET and private en-suite bath. On the other side of the large BONUS/LOFT space are two more bedrooms both with their own walk-in closets that share a second full bath. Residents of Enclave at Hawks Crest will enjoy access to the wonderful amenities; a BBQ/picnic area, playground and COMMUNITY POOL. Built in 2018 but with a new construction feel, low maintenance and in the perfect location just off Howell Branch Rd - call today for your private showing!

2469 Firstlight Way, Winter Park
$560,000
3 Beds ⋅ 2 Baths ⋅ Blk C Pt Rep 02 SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. Drawing inspiration from the sophistication of the mid-century modern era, 1319 Orchid Ave is more than just a home; it's a statement piece nestled in the heart of Winter Park, Florida. Every room and every corner of this meticulously renovated masterpiece speaks of elegance and class, reminiscent of the tonality you’d expect from the finest homes. With a single-story layout sprawling over a generous 1,668 sq ft, this residence boasts three beautifully appointed bedrooms and two pristine bathrooms, completely renovated in 2021. The split-level bedrooms offer an exquisite balance between privacy and connectivity. Walk on light ceramic wood tiles that flow seamlessly through each room, only to be met by the refined touch of slate flooring in the bathrooms—a detail that exemplifies pure luxury. The heart of the home? The immaculately renovated kitchen (2021). Outfitted with gleaming granite countertops, complemented by top-tier stainless steel appliances, this kitchen is both a chef's dream and an entertainer's paradise. And then there's the centerpiece—the fireplace. A nod to timeless elegance, this feature beckons for intimate gatherings or quiet, reflective evenings. Step outside, and you’re greeted by a spacious, private backyard—a canvas ready for your landscaping dreams. But what’s design without function? New homeowners can enjoy peace of mind knowing that this gem offers a newer HVAC system (2021), newly painted interiors throughout (2022), and a complete electrical rewiring (2022). Oh, and for those tired of pesky HOA fees? Breathe a sigh of relief—there's no HOA to contend with here. Now, let's talk location. Zoned for the coveted Audubon K-8 school, this home is also a stone's throw away from Mead Gardens, Seven Oaks Park Project, the Winter Park Tennis Center, and the alluring Orlando Urban Trail. Want to explore the local scene? Rollins College, Winter Park Library, Winter Park Village, and other attractions are just a brisk bike ride away. Not to mention, convenience is redefined with over 70 restaurants, high-end shopping destinations, barbershops, and essential amenities all within a mile. Imagine living in a home where every feature and detail elevates your lifestyle while being close to the best Winter Park offers. 1319 Orchid Ave isn't just a home—it's a lifestyle. And it awaits the discerning buyer ready to embrace it. Welcome to Winter Park Luxury. Welcome home.

1319 Orchid Avenue, Winter Park
$699,000
4 Beds ⋅ 4 Baths ⋅ Parklando #3 SubDv. ⋅ 32789 Zip Code
Look no further, bring your own builder and build your dream home on this a quiet Cul-De-Sac in Winter Park! Over 1/3 acre homesite on private street and walking distance to the nearby Audubon Park K-8 School. Enjoy local shopping & dining in the Audubon Park District, East End Market & close by Downtown Baldwin Park. Plus you can play all day at Blue Jacket Park, the perfect place to picnic or participate in its many year-round outdoor activities. This could be the one you have been waiting for if you have been looking for land to build.

2619 Winter Park Road, Winter Park
$1,275,000
Maitland Shores Second Add SubDv. ⋅ 32789 Zip Code
Welcome home to 1000 Howell Branch Road, the opportunity awaits for you to come build your dream home. This recently cleared lot is located on an oversized half acre+ lot with a recently dredged fresh water canal frontage, with access to the Winter Park Chain of lakes. The possibilities are endless on this lot. The incredible backyard has views of the conservation area across the canal. This lot has an incredible feel, you can be minutes from the hustle and bustle but step onto the lot and you will feel like you are in your own private oasis. This lot is zoned for top rated schools and the premium location makes this a must see opportunity. Enjoy the close proximity to Kings Row park. The home is Conveniently located to downtown Park Avenue’s shops and restaurants, with easy access to Maitland City Centre and downtown Orlando, what else could you want? Come see this one today before it’s gone.

1000 Howell Branch Road, Winter Park
$159,900
1 Beds ⋅ 1 Baths ⋅ Winter Park Villas Condo SubDv. ⋅ 32792 Zip Code
This charming one-bedroom Winter Park Villas corner unit condominium with a wood-burning fireplace. Light and bright with plenty of windows. This condo has a fantastic layout with a very efficient use of space and design. It offers a spacious 759-square-foot floorplan with a soaring ceiling. The features include a large master bedroom with a walk-in closet, a bathroom with dual vanity, a kitchen complete with all appliances, ample cabinet space, and vaulted ceilings. You will surely enjoy the private, fenced backyard! The HOA includes a sparkling community pool, clubhouse with fitness center, tennis courts, car wash station, charcoal grill areas, exterior maintenance and lawn service. An ideal location adds to this home's appeal: within walking distance to Full Sail University, close proximity to UCF, shopping, dining.

614 Grenadine Court Unit S, Winter Park
$185,000
1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code
Tenant has a lease until end of JAN 2024. Community does not allow rentals at this time. Must be a PRIMARY BUYER! This unit was one of approved units but it does not transfer to the new owner. Excellent location. Walk to grocery stores, pharmacies, coffee shops, retail near by. Short drive to Farmer's Market in Winter Park, Full Sail, Park ave with many restaurants and retail.

178 Lewfield Circle Unit 178, Winter Park
$875,000
3 Beds ⋅ 2.5 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Don't miss this exquisite ORWIN MANOR residence, nestled in the heart of a historic neighborhood. With 3 bedrooms, 2 baths, and an additional half bath by the poolside retreat. This home spans 2,114 sq ft and features beautiful WOOD FLOORING throughout. The one-car garage blends seamlessly with the classic design. Enter a refined and upscale ambiance adorned with VAULTED CEILINGS that create an expansive sense of space, complemented by the gentle glow of RECESSED LIGHTING, and enriched with luxurious high-end finishes. A GAS FIREPLACE sets a cozy atmosphere in the formal living area, while the adjacent dining room is perfect for intimate dinners. The spacious family room with CUSTOM NANYA DOORS opens to the enchanting backyard oasis. The impeccably outfitted kitchen showcases stunning quartz countertops, gleaming STAINLESS-STEEL APPLIANCES, and a NATURAL GAS RANGE complete with a convenient pot filler. The master suite is a private sanctuary with DUAL SINKS, a WALK-IN CLOSET, and a luxurious bath with a separate shower and soaking tub. Two additional guest bedrooms share a beautiful bath with a REFRESHING RAIN SHOWER. The backyard boasts meticulously designed landscaping reminiscent of a LUSH TROPICAL PARADISE, an elegantly appointed patio space, and an inviting round SALTWATER POOL that's comfortably HEATED. Conveniently located close to Winter Park's Park Avenue, Downtown Orlando, AdventHealth, and I-4, this home is both beautiful and convenient. Additional practical upgrades include a gas-heated TANKLESS WATER HEATER and a WHOLE-HOUSE GENERATOR. Don't miss out on the opportunity to embrace the elegance, convenience, and comfort of Orwin Manor living at its finest.

1714 Westchester Avenue, Winter Park
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