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. 

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Newest Winter Park Homes and Condos for Sale

$293,500
2 Beds ⋅ 2 Baths ⋅ Winter Park Pines Condo SubDv. ⋅ 32792 Zip Code
Beautiful Condo in Winter Park. Cathedral ceilings, wood floors throughout with ceramic tile in wet areas, kitchen and dining room. Updated appliances, cabinets and quartz countertops in bathrooms and kitchen are a breeze to keep clean. The bamboo screened backyard welcomes you as soon as you enter the house and skylights in the living room add a tremendous amount of natural light. 2 Spacious bedrooms with bathrooms, again with each bathroom having a skylight. Easy access to washer and dryer right off the kitchen The back patio has been enclosed and added space to the living room and is currently used as studio for editing work. Full Sail University is easy to walk to as is Cady Way Park for trails, sports and community pool. The current owner has paid the full assessment for the new roof to be installed and the oversized garage is a great space for additional storage. Come by to see this beautiful space in Winter Park today. Submit offer with Proof of funds on Far Bar ASIS-6 Furniture in Living room, Kitchen and guest bedroom is negotiable. Please, only service animals at showings, owner is highly allergic.

423 Warrenton Road Unit 423, Winter Park
$449,000
3 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code
Casa Aloma community, 3 bed/2 bath ranch. Split floorplan features master suite with double closets and full bath, formal dining & living room, family room with sliding glass doors opening out to a large screened in patio, private fenced backyard. Eat in kitchen with nook area. Conveniently close to Interlachen Country Club, downtown Winter Park, Park Ave, shopping centers, restaurants, Publix, YMCA, Phelps Park, Cady Way Trail, hospitals, Rollins College, Full Sail, and more.

2615 Verde Lane, Winter Park
$299,900
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Location! Location! Location! Come check out this 3-bedroom, 2-bath pool home located in Winter Park. Property needs some TLC and updating. The seller and listing agent have little to no knowledge of the property’s history. Buyer is responsible for doing their own due diligence. ***For Sellers Convenience, they will only accept CASH or CONVENTIONAL Offers***Seller will not make any repairs***Incomplete offers and offers that do not include ALL of the attachments in the MLS will not be reviewed by the seller. ***Seller will not make any repairs*** Maximum inspection period is 7-days. Minimum EMD is $5,000. *The seller will only use their PREFERRED TITLE COMPANY (see Offer Instructions)* If it is still active in the MLS, the seller has not accepted an offer. No need to ask. Seller responds to most offers in 24 hours but please allow up to 72 hours for a response.

1408 Viburnum Lane, Winter Park
$400,000
3 Beds ⋅ 2 Baths ⋅ Willa Grove SubDv. ⋅ 32792 Zip Code
Well stablish community of single-family homes close to the heart of all, while yet you feel the peace and quiet of a small community. No! HOA fees. nice and spacious backyard with inground pool for the entertainments. This home invites you to relax, enjoy pool time or a favorite book in your own personal oasis. This is great investment opportunity for a first-time home buyer or investor to add to your portfolio. Check out the comps and submit your offer today

1771 Willa Circle, Winter Park
$199,000
2 Beds ⋅ 2 Baths ⋅ Parkview Village SubDv. ⋅ 32792 Zip Code
WHAO LOCATION! GROUND FLOOR CONDO 1018 SQUARE FEET!. Two bedrooms and two full bathrooms with an open floor plan and walk-in closet in Master bedroom! Includes Fridge, Range, Microwave, Washer & Dryer. Relax in the Resort Style Community Pool or warm up in the Hot Tub under the Gazebo, Private Screened Patio. Conveniently located across FULL SAIL School off of 436 (Semoran Blvd.) or a quick drive to Dining, Shopping, Siemens, Rollins College, UCF or Valencia Community College.

2911 Antique Oaks Circle Unit GE, Winter Park
$349,900
2 Beds ⋅ 2 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code
Welcome home to this charming 2 bedroom, 2 bathroom home in Winter Park, FL! The property features a large living room with classic Parquet flooring and neutral paint colors. The kitchen is large and open to both the living room and dining room with solid wood cabinets and granite counter tops! The dining space leads you to the outside patio that is a relaxing screened-in space with tons of privacy with your back yard view. Both bedrooms are great size, with large closet space. Put your finishing touches on this great Winter Park home! This neighborhood is lake front with community access, and has tennis courts for you to live the ideal Florida lifestyle. The location here is amazing, because you are 10 minutes to Winter Park's Park Avenue for shopping and dining, yet still in Seminole County for the low taxes and great school system. From here you are also close to 417 highway, Oviedo, Winter Springs, and Altamonte.

1664 Tremont Lane, Winter Park
$749,000
4 Beds ⋅ 2.5 Baths ⋅ Cypress Reserve SubDv. ⋅ 32792 Zip Code
Welcome to your dream home in the exclusive, gated community of Cypress Reserve in Winter Park! This stunning 4 bedroom, 2.5 bath pool home is perfectly located for your convenience, just minutes from Park Avenue in downtown Winter Park and a variety of restaurants, shops and schools such as Trinity Prep and the Master's Academy. The light and open floorplan features volume and vaulted ceilings, skylights, a ton of natural light, and luxurious tile and engineered hardwood floors that make it feel like a model home. The heart of the home is the beautiful chef's kitchen, complete with a Blanco double sink, 42" solid wood, raised and stained cabinetry, granite counters, stainless appliances, and a built-in wine cooler. It's open to the family room, which is highlighted by a fireplace with a striking antique slate mantle and a bluestone hearth - perfect for cozy gatherings. The smart split-floor plan design includes carpet in the secondary bedrooms, one of which features a coffered ceiling with hand-carved wood accents. The spacious master bedroom includes a sitting area and two organizer walk-in closets, and the remodeled master bath is like your own personal spa with a contemporary garden tub, large shower and dual sinks with Carrera marble counters. But the real showstopper is the stunning pool area, complete with stone work and a waterfall. It's perfect for entertaining or just relaxing with family and friends. And if you need some relaxation, there's a peaceful garden area in the back as well. This move-in ready home has it all, including a newer roof, resurfaced pool, double-pane windows, gutters, newer water heater, exterior paint, and interior paint. Plus, the oversized garage features a full 3rd bay that's perfect for a workshop or storage. Don't miss your chance to make this great family home your own - schedule a private tour today!

5333 Cypress Reserve Place, Winter Park
$1,575,000
4 Beds ⋅ 4.5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
Perched on a hill on a corner lot, nestled between Sylvan and Bonita along the brick streets of Winter Park, this home has so much to offer. With a privacy wall along Maiden Lane, this home truly feels like a secluded oasis. Beyond the 3-car garage, you'll be greeted by a charming gated porch that leads into a spacious living area filled with natural light, where the French doors lead to a screened patio and a resort-style pool that will take your breath away. The dining room, with tall, graceful windows on one end, leads to the kitchen, offering stone counters, a cooking island, 2nd prep sink, wine refrigerator, double built-in ovens, a water purifier, and a dinette with a large bay window. The breakfast bar offers additional seating, and overlooks the family room, with vaulted ceilings and a wood-burning fireplace, plus additional French doors to access the screened-in patio. Off the kitchen/living combo, there is a full bath that also services the pool. The spacious downstairs master suite, with plantation shutters and French doors to the screened patio, features a double-sided fireplace separating the bedroom from the master bath, with a large soaking tub, glass shower, private water closet with a bidet, and large walk-in closet. A laundry room with a utility sink and laundry chute, and a front powder bath for guests, complete the 1st floor. Upstairs includes 3 bedrooms, all with walk-in closets, 2 full bathrooms, and a balcony overlooking the sprawling backyard. Outside, you’ll enjoy lush landscaping and the soothing sound of the pool fountains! The large pool deck offers lounging, with additional seating and dining space within the screened patio. Surrounded by A-rated schools, convenient stores such as Walgreens, Publix, & Sprouts, the YMCA, the AdventHealth Hospital, Phelps Park, and around the corner from Park Avenue – this location cannot be beat!

600 Maiden Lane, Winter Park
$145,000
2 Beds ⋅ 1.5 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
INCREDIBLE OPPORTUNITY to own an updated two-story condo with lush garden views from BOTH BALCONIES! The unit underwent an enormous upgrade overhaul just a few years ago that included NEW framing, NEW stunning laminate flooring, NEW waterproof insulation and siding, NEW electrical and a NEW A/C. Currently leased for almost $2,000 per month, this could also be a great investment opportunity! Located close to some of the most impressive shops and restaurants in Central Florida, a short drive to Orlando International Airport and everything else Winter Park has to offer! Schedule your private showing today!

234 Scottsdale Square Unit 234, Winter Park
$429,000
3 Beds ⋅ 2.5 Baths ⋅ Las Casas De Indiana SubDv. ⋅ 32789 Zip Code
Mediterranean style Townhouse, granite counter tops, SS appliances, hardwood floors on first floor and carpet on second floor, private courtyard, detached one car garage plus one space right next to the garage. Great location next to Orwin Manor, minutes to the Winter Park Village and Downtown Orlando.

1769 Indiana Avenue Unit D, Winter Park
$559,000
4 Beds ⋅ 2 Baths ⋅ Lake Waunatta Woods SubDv. ⋅ 32792 Zip Code
Cozy Winter Park Pool Home in Orange County - Move-in Ready! Experience the outdoor oasis by relaxing in your screened Lanai or take a dip in the private pool. Great for hosting BBQS with family and friends. This charming home includes 4 beds and 2 baths. The kitchen features granite countertops, stainless steel appliances, tile backsplash and a modern pull-down spray kitchen faucet. For interior design lovers this home features a color palette inspired by HGTV along with newer LUXURY PLANK VINYL FLOORING. Stay cool and comfortable NEW AC unit NEW DOUBLE PANED ENERGY EFFICIENT WINDOWS THROUGHOUT and NEW ELECTRICAL PANEL all in 2022. This move-in ready home is a must-see for anyone seeking a Florida lifestyle! Great Location! Winter Park School district, near Full Sail University and only a 10 minute drive to the trendy Park Ave that has shopping, casual and fine dining, museums, galleries and great parks.

4033 Tenita Drive, Winter Park
$389,500
3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 6 SubDv. ⋅ 32792 Zip Code
Fully remodeled home in Winter Park with no association and huge backyard space. This three-bedroom, two-bath, one-car garage home has new laminate throughout the entire home and offers a living-dining area combo. Sliders off the living room lead to the screened-in patio and private, fully-fenced backyard. Updates include a brand-new kitchen with granite countertops, brand-new bathrooms, fresh interior and exterior paint, and the list goes on. A rare find at this price in Winter Park, come take residency one of Central Florida's most desirable areas and be next to the best schools, local dining, shopping, entertainment, and easy access to major roadways.

7577 Dockside Street, Winter Park
$2,950,000
4 Beds ⋅ 4.5 Baths ⋅ Alberta Place SubDv. ⋅ 32789 Zip Code
Welcome to this exquisite French Modern home that seamlessly blends classic architecture with modern amenities. With 4 bedrooms, 4.5 bathrooms, 4,055 s/f, and a detached art studio, this stunning, single story property offers the ultimate in luxury living. The open floor plan of the main living area effortlessly flows from the gathering room with a cozy fireplace to the dining and sitting room. The kitchen features Wolf, Sub-Zero appliances, custom cabinetry, and a large center island perfect for entertaining guests. Step outside into this stunning oasis, where every detail has been meticulously designed to create the ultimate in relaxation and entertainment. With a pool, Casita, fire feature, and summer kitchen, this outdoor space is the perfect retreat for enjoying the warm weather. The oversized lot extends to another highlight of this home, a separate art studio. This studio is bathed in natural light and will provide the perfect space for creative pursuits or as an office. Located in Winter Park, this stunning French Modern home offers the perfect combination of luxury and functionality. Don't miss the opportunity to make this your dream home!

1303 Alberta Drive, Winter Park
$375,000
3 Beds ⋅ 2.5 Baths ⋅ Coronado Twnhms SubDv. ⋅ 32792 Zip Code
Wanting to live in Winter Park in a newer and beautiful property? Here it is. This beautiful property is so centrally located that has it all near by within less than 10 mins away Publix, Costco, Baldwin Park, Lake Eola, Restaurants, etc. Its modern and elegant vibe makes this 3/2.5 home a cozy and comfortable living place that features a 1 car garage and green area in the back of the property. The kitchen displays beautiful cabinetry and an island that integrates with the living area. The bedrooms are all upstair allowing for more privacy and access to the laundry closet also on the second floor. The master bedroom is great size as well as its bathroom and walk in closet. Make your appointment today!

3173 Crown Jewel Court, Winter Park
$1,300,000
5 Beds ⋅ 4.5 Baths ⋅ Kenilworth Shores Section Seven SubDv. ⋅ 32792 Zip Code
BETTER THAN NEW AND READY FOR YOU! BUILT IN 2021!! Designed and built by Winter Park architect and building contractor, Stevens, Inc., this CUSTOM CRAFTSMAN style home brings so much character from the wood and tile floors to the beautiful tongue and groove clear pine ceilings. This stunning home boasts 5 bedrooms with 4 full baths and one-half bath but is designed with FLEXIBILTY to utilize them as an office and a bonus room depending on the family’s living needs. The house is bright and inviting with huge living space on the first floor with wood flooring and spacious primary suite and second bedroom/office downstairs. Gourmet kitchen offers custom cabinetry, over-sized island, tile backsplash, upgraded Monogram appliance package and an large walk-in pantry. Private primary suite boasts a large en-suite bath which includes a soaking tub, shower stall with 6 function Delta faucets, 2 WALK-IN closets, double sinks, and solid wood cabinets. The oversized laundry room includes a full-sized sink. Second floor offers flexibility with 3 bedrooms/2 baths featuring a 12x17 bedroom which could be used as a bonus room. Be sure to read the Special Features Sheet in the Attachments for more specific information. Optional HOA gives you access to Lake Berry!! Conveniently located minutes to Park Avenue, Downtown Orlando, top-rated Winter Park schools, and numerous dining options, parks, gardens, museums, golf courses, and shopping. No need to build!!! This gorgeous, immaculate, well-appointed Winter Park Home can be yours today!

1918 Summerfield Road, Winter Park