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

$1,479,000
4 Beds ⋅ 2 Baths ⋅ Tuscany Place First Add SubDv. ⋅ 32789 Zip Code
This rare opportunity to own a ONE STORY LAKEFRONT home on A HALF ACRE lot located in the highly desirable Via’s of Winter Park. Tuscany Place is nestled on a quiet cul-de-sac and zoned for top A-rated schools. This beautifully maintained 4 bedrooms/2 full baths offers stunning views of Lake Temple from almost every room. The spacious interior provides the perfect canvas for you to create your dream home and the oversized lot provides so much space to build your dream home if you desired. Featuring a split bedroom floor plan that includes a separate living room, dining room and family room, it truly is the perfect plan for any family. The kitchen features solid wood cabinets, granite countertops and overlooks the family room that boasts beautiful bookcases and a wood burning fireplace with granite surrounding it. This open layout with hardwood floors throughout makes it easy to entertain and has tons of natural light flooding into all rooms. The master suite with lake views features a walk-in closet, dual sinks and a separate shower plus direct access to the rear porch. The 3 additional guest bedrooms on the other side of the home offer nice privacy. Spacious inside laundry room leads to the 2 car garage with side entry. Screened in rear patio provides even more space to entertain while relaxing by the pool and spa and enjoying the peaceful lake views. Close to Park Ave and the Winter Park Racquet Club, This one-of-a-kind ½ acre LAKEFRONT lot in the Winter Park Via’s is unique and rare find. Don’t miss this amazing opportunity to live and/or build in the Vias!

1049 Tuscany Place, Winter Park
$1,479,000
Tuscany Place First Add SubDv. ⋅ 32789 Zip Code
This rare opportunity to own a ONE STORY LAKEFRONT home on A HALF ACRE lot located in the highly desirable Via’s of Winter Park. Tuscany Place is nestled on a quiet cul-de-sac and zoned for top A-rated schools. Close to Park Ave and the Winter Park Racquet Club, This one-of-a-kind ½ acre LAKEFRONT lot in the Winter Park Via’s is unique and rare find. Don’t miss this amazing opportunity to live and/or build in the Vias!

1049 Tuscany Place, Winter Park
$299,250
2 Beds ⋅ 2.5 Baths ⋅ Lazy Oaks Condo SubDv. ⋅ 32792 Zip Code
Step into this beautifully renovated 2-bedroom, 2.5-bath condo, nestled in the serene and sought-after Lazy Oaks community. Blending contemporary style with everyday convenience, this home offers an attached 1-car garage for added ease. As you enter the main level, you're greeted by new designer tile flooring, freshly painted interiors, and an open layout. The updated kitchen features sleek quartz countertops, custom cabinetry, a large stainless steel sink, stainless steel appliances and closet pantry, all complemented by a chic tile backsplash. The spacious great room invites relaxation, boasting a cozy wood-burning fireplace—perfect for chilly evenings—while seamlessly flowing into the bright and airy Florida Room. This versatile space is adorned with elegant plantation shutters, making it the ideal spot for morning coffee or unwinding after a long day. Upstairs, you'll discover two generously sized en-suite bedrooms, each offering high ceilings, plush new carpeting, plantation shutters and remodeled bathrooms with modern fixtures and finishes. Conveniently located near top shopping centers, vibrant dining spots, and endless entertainment options, this condo also offers easy access to major highways, airports, UCF, Full Sail University, and downtown Orlando, making it a prime location for both work and play.

5173 Lazy Oaks Drive, Winter Park
$479,900
4 Beds ⋅ 2.5 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code
This home won't last long!!! Beautiful home in fantastic WINTER PARK location with excellent rated schools. Home was painted inside and out 2022. New Luxury waterproof vinyl plank flooring throughout the entire home, all new light fixtures added, and plantation shutter window treatments in living room all in 2022. Both full baths have been remodeled from floor to ceiling 2022. Kitchen cabinets, subway tile backsplash, and stainless steel appliances, and granite countertops all new in 2022. The landscaping was redone with new mulch. Outside features large half circle paver driveway, there is also a paved courtyard in the back for additional parking or can be used as outdoor garden, dining area. Very nice fenced in back yard with a fairly new shed. BONUS MOTHER IN LAW SUITE with separate entrance can be used to collect rental income to offset your mortgage costs. Close to legendary Park avenue and endless shopping and restaurants, schools, and downtown Orlando. Best of all NO HOA!

3458 Arbutus Lane, Winter Park
$824,999
3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge Annex SubDv. ⋅ 32789 Zip Code
This stunning property offers contemporary design and timeless charm, plus exclusive backyard access to a private ski lake - perfect for kayaking, paddle boarding or enjoying peaceful waterfront views. Electricity and water available at shore to build dock! With three bedrooms, two bathrooms, a decked-out backyard with a hard wood Gazebo sitting on 1.41 acres, this home is an entertainers dream. Located just minutes from Park Avenue is dining and shopping, top rated schools, and beautiful parks, this Winter Park gem is the ultimate blend of luxury and convenience. Don’t miss your chance to own this Lakeside retreat.

2201 Kindel Avenue, Winter Park
$575,000
Winter Park Village SubDv. ⋅ 32789 Zip Code
Vacant Land located at 2613 Lafayette Ave in the heart of Winter Park, 6 min from Park Ave. This property comes with a ready to build Modern & luxury with area efficiency and well-Being focused Design! ( or build your Owen House) 4 Bedrooms, (Master on the 1st floor, 3 on 2nd floor including mother-in-law and a loft). 4 Bathrooms (3 full + 2 halves) 2 car garage + Extended driveway can hold another 4 cars. 3 Terraces to enjoy Florida sunshine and party time

2613 Lafayette Avenue, Winter Park
$725,000
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to this spacious and charming home located in the sought-after Winter Park Pines neighborhood! As you approach the property, a covered porch invites you to relax before stepping inside. The entryway greets you with a functional hallway featuring hanging hooks, perfect for backpacks and coats. To the right, you'll find a cozy family room, complete with a wood-burning fireplace and built-in shelving. The open flow leads to the dining room, adjacent to a massive kitchen boasting granite countertops, two dishwashers, a double oven, and even a built-in office nook—perfect for today’s modern lifestyle. The split floor plan ensures privacy, with the primary retreat nestled off the family room. This retreat features a walk-in closet, and an en suite bath with a walk-in shower. On the opposite side of the house, three additional bedrooms await. Two of these bedrooms share a Jack-and-Jill bathroom, beautifully updated with quartz countertops, dual sinks, and a walk-in shower. The third bedroom is conveniently located next to a full bathroom with granite countertops and a shower-tub combo. One of the home’s highlights is the large Florida room, providing additional living space with endless possibilities. Outside, the backyard is a true oasis, featuring a large pool with a child safety fence, lush grass, and a fully fenced yard—ideal for both relaxation and play. This home is perfectly situated near Winter Park Pines Golf Course, highly rated schools, shopping, and dining options, offering the best of Winter Park living.

417 Gilbert Road, Winter Park
$1,650,000
5 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Lakefront living in Winter Park! Enjoy serene views from this single-story ranch charmer, featuring 5 beds, 4 baths and 3,446 sq ft nestled behind a front block wall on the shores of Lake Sylvan. With 150 ft of frontage on a sprawling oversize lot, this lakefront estate provides a tranquil oasis within walking distance to downtown Winter Park. Perfect for multi-generational families, with an attached spacious mother in-law suite addition done in 2016. Seamlessly blending charm and newer construction, this house is light and bright with many living and entertaining options. The original house, with wood flooring throughout, consists of a 3-bedroom split plan and 2 baths (jack n jill and en suite) with a formal living room, dining room and sunroom. The galley kitchen has granite counters and stainless appliances and plenty of storage. A 9 x 7 bonus space connects to the mother-in law wing which consists of 1,300 sq ft including a family room/kitchen combo, primary bed and bath, guest room, guest bath, office, and laundry room with a private side entrance for easy accessibility. Other improvements include roof in 2020, whole house generator and windows on the east side replaced in 2018, AC and windows on the west side in 2016. Enjoy captivating panoramic views of the grounds, lake, and saltwater lap pool from the expansive covered, and screened, back patio. Private dock facilitates canoeing, paddleboarding or fishing. Zoned for top-rated Winter Park schools. Conveniently located to shopping and restaurants of Park Ave, Winter Park Advent Health, Winter Park YMCA, and Rollins College. Welcome home!

1458 Aloma Avenue, Winter Park
$909,000
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.

1917 S Lakemont Avenue, Winter Park
$649,000
2 Beds ⋅ 2.5 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code
Welcome to your new residence in Winter Park! This home is practically perfect with its oversized owner’s suite (with walk-in closet and jetted tub), guest room (split bedroom plan), bonus room/office/den/loft and breakfast bar on the upper floor. Indulgent bathrooms, Rinnai tankless water heater, tile and wood flooring (no carpet to replace in this one) upgrades everywhere! Granite countertops, wood kitchen cabinets with stainless appliances, range hood and a gas range top the list of creature comforts in you “culinary enthusiast’s” kitchen. The openness from the 9’ 4” ceilings and 8’ door continues to the outdoor space with French doors leading out to a screened and covered patio overlooking the beautiful backyard. This concrete block home also features a single car garage, concrete tile roof, and new turf backyard. The location is conveniently close distance to grocery stores, pharmacy, banks, restaurants, churches, and couldn’t be more convenient to Rollins College, Winter Park’s world-famous Park Avenue, Winter Park Village, and downtown Orlando, as well as I-4 or 17-92 for access to just about anywhere in Central Florida. NO HOMEOWNER ASSOCIATION/DUES!!

1120 Aragon Avenue, Winter Park
$160,000
2 Beds ⋅ 1 Baths ⋅ Waterfall Cove/Winter Park SubDv. ⋅ 32789 Zip Code
Investment and Lifestyle Opportunity in Winter Park! Discover the charm of Winter Park in this cozy and well-located condo! perfect for investors and buyers looking for a relaxed, safe, and convenient lifestyle. Spacious Condo 2 bedrooms with roomy closets, 1 large bathroom with double sink, bathtub, Ceramic tile and a new a/c unit, enjoy the confortable 881 square feet of living space with new Laminated floor throughout the property. Kitchen equipped with modern appliances with a dishwasher, microwave, refrigerator, oven, a pantry for extra storage, a new stackable washer & dryer is also included for your convenience. Living room with large windows and community views, first floor unit with a conveniente fenced terrace to enjoy the beautiful Florida weather, few steps from the community pool and recreational areas. Located in the heart of Winter Park, near Full Sail University, Rollins College and Wekiwa Springs State Park, in a quiet and safe area, this condo offers easy access to parks and is just minutes from renowned shops in winter park village, restaurants, hospital, great schools and profesional offices and much more places. The community offers a range of high-end amenities, including a community pool and bbq areas , fitness center and meeting room, 24/7 security and assigned parking recreational areas, playground and hiking trails, all designed to elevate your living experience. The strategic prime location next to I4 express and main roads and quality of the property ensure excellent profitability potential, being ideal for both owners who want to establish themselves in the area and for investors looking to generate passive income. Don't miss the opportunity to acquire this gem in Winter Park. This stunning home offers an ideal combination of tranquility and functionality, making it an attractive investment for those seeking quality of life in one of the most desirable areas of Florida. Schedule a private tour today! This condo is the perfect place to call Home Sweet Home or make a smart investment in a growing market!

1695 Lee Road Unit D113, Winter Park
$465,000
3 Beds ⋅ 2 Baths ⋅ Howell Estates 1st Add SubDv. ⋅ 32792 Zip Code
Rare opportunity to own a spacious home in one of Winter Park's most sought-after areas! Located on an oversized 0.42-acre corner lot in Winter Park, this home offers modern updates and plenty of room to enjoy. The quiet, established neighborhood provides a desirable setting, and the home itself is fully updated with stainless steel appliances and a bright, open floor plan. The large, fully fenced backyard offers privacy and space and is ideal for entertaining, pets, and family gatherings. Ample storage throughout the home adds practicality to its appeal. Reach out for a showing!

1052 Manchester Circle, Winter Park
$475,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 16 SubDv. ⋅ 32792 Zip Code
Welcome to one of the larger homes in the community, where comfort and versatility meet. This spacious 4-bedroom, 2-bath residence offers multiple areas for both entertaining and relaxation. From the foyer, to your left is the formal living room, currently utilized as office space. Adjacent to it is the elegant formal dining room, perfect for hosting dinner parties. The family room, conveniently located off the kitchen, provides a cozy gathering spot for everyday moments. For those who enjoy entertaining on a grand scale, the expansive Florida room, also known as the great room, boasts a charming wood-burning fireplace and a built-in bar, making it ideal for socializing. The split bedroom plan offers privacy for everyone. The primary bedroom offers a retro en-suite bathroom with a walk-in shower that features a built-in tile bench. The other three bedrooms share a bathroom that boasts a state of the art SafeStep walk in tub and shower(Oct.2022). The special features of this upgrade are heated seat. color changing lights, jets and bluetooth for playing music. What a way to relax after a hard day. The kitchen appliances have been updated to stainless steel(2022), with the exception of the fridge. Also, the counters are granite. Outside, you’ll find an open pool surrounded by a generous deck space, offering plenty of room for lounging and enjoying the outdoors. There is a shed to house all of your pool and lawn equipment. This home also features a list of upgrades that enhance its appeal and functionality—details of which you’ll want to review to appreciate the full value of this exceptional property. Roof-2014, A/C - 2018, Whole house water softener - 2021, pump for irrigation system on well water-2022 Come see for yourself how this home can be the perfect backdrop for your lifestyle!

3455 Athena Drive, Winter Park
$6,975,000
5 Beds ⋅ 7.5 Baths ⋅ Morse & Pennsylvania Twnhms SubDv. ⋅ 32789 Zip Code
Distinctive. Inspirational. Timeless. Casa K is the ultimate in luxury and location. Designed by internationally respected architect, Kamal Rizk and constructed in 2022, it is a sanctuary in the heart of our city. The unique fusion of innovative design, superior craftsmanship & luxury finishes shaped this almost 9,000 SF, 5 bedroom, 7.5 bathroom residence w/ guest suite into the contemporary estate that it is today. Upon entry, the retreat-like elegance of the great room is remarkable. This commodious space incorporates the foyer, formal living, dining, bar & family rooms. It seamlessly opens to the outside via a Pella made “wall of sliding glass.” Italian wood flooring & elaborate millwork are appreciated features, as well as modern lighting, custom window treatments & sound operated w/ ease via Lutron. Beyond the family room is the kitchen & hidden scullery where livable luxury resides. Poliform cabinetry, Cambria countertops & top of the line appliances complete these exceptionally versatile spaces. The showcase glass enclosed floor to ceiling wine refrigeration anchors the kitchen & artfully displays up to 975 bottles. The outdoor living is a natural extension of the interior spaces & features a courtyard style pool complete w/ a hand carved, granite rear wall & 16’ linear in-pool fire feature. The kitchen terrace offers a DCS grill, motorized screens, cooling misters & more. A private office, lounge & 1.5 bathrooms complete the downstairs. Bathrooms on both levels showcase elevated selections from Boffi, Zucchetti, Poliform, Inbani, Paffoni & other iconic brands that enforce the refined, contemporary style & quality throughout. Notable lighting in the office, lounge & throughout include artistic fixtures by FLOS, Moooi, Serge Mouille & more. Access to the 2nd floor is provided via the elevator or stairwell. The upper floor is composed of the primary suite, 2 alternate bedroom suites, a 2nd office/flex room w/ en-suite bath, laundry room, gym & flex use guest apartment. The dreamy primary bedroom was designed with a soft entry, private terrace & hidden closets. The closets are part luxury boutique, part meticulously organized space w/ Poliform customization, motion activated light & windows w/ motorized shades made w/ UV protection to shield the interior spaces. The elegant approach to the primary bathroom includes floating vanities secured to stone covered walls, glass enclosed shower, standalone tub, custom-made dressing table & private water closets. Set apart from the primary, the alternate suites & living areas are finished w/ consistent quality & design. With flawless connection, the guest apartment may be used as an extension of the main home or it can be securely separated at a point just beyond the gym. The current owners use one of the bedroom suites as a craft room, which opens to the guest apartment’s main living spaces; the family room, a full kitchen w/ island seating, laundry & a final bedroom suite. Above is a magical roof top terrace with fireplace & bar. The owner’s entry is at the rear of the property, via a concealed driveway that leads to the 4-car garage, from which a hidden door opens directly into the kitchen. Guest parking is available. In this haven of opulent serenity, you may live the life you want, where you want.

654 W Morse Boulevard, Winter Park
$489,000
3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 04 SubDv. ⋅ 32792 Zip Code
Stylish fully renovated 3 bedroom 2 bath home, with an oversized lot in a cul de sac, in-ground pool, Amazing WINTER PARK SCHOOLS WITH NO HOA....what more could you ask for? Welcome to your new sanctuary in the heart of Winter Park! The extensive renovation includes new shaker kitchen cabinets with quartz countertops, luxury vinyl flooring, a contemporary master and guest bathroom, and a newer roof with SOLAR panels that have been paid off!! The AC is only 3 years old, the house has all new light fixtures, and fresh paint in and out. Don’t miss out this amazing opportunity to live in one of the most desirable neighborhoods in Winter Park, at the end of a quiet street, in a ready-to-move-in fully remodeled house with no electric bills!!!

5211 Woodcrest Court, Winter Park
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