Homes For Sale in Winter Park 32792 - 175 homes

Remarks: Well-maintained 2-bedroom, 2-bath home with 1,199 sq ft in a desirable Winter Park 32792 location offering a fenced backyard, low HOA, and a flexible bonus space ideal for a home office, study, or hobby area. The functional split-bedroom layout provides privacy, while the open living and dining areas create a comfortable space for everyday living or entertaining. The kitchen offers ample cabinetry and counter space, flowing seamlessly to the main living area plus upgraded appliances. The primary suite includes a private bath and generous closet space, while the secondary bedroom and full bath provide flexibility for guests, office use, or additional living needs. Enjoy outdoor living in the fully fenced yard—ideal for relaxing, gardening, or pets. Additional highlights include driveway parking, interior laundry, and low-maintenance living. -- NEW ROOF IN PROCESS -- Prime location with convenient access to major corridors and top destinations: ˜ 3 mi to Full Sail University, ˜ 5 mi to UCF, ˜ 4 mi to AdventHealth Winter Park, and ˜ 6 mi to Park Avenue and Downtown Winter Park. Nearby shopping, dining, and grocery options are within minutes, with quick connectivity to SR-436, University Blvd, and SR-417 for commuting throughout Central Florida. An excellent opportunity to own in Winter Park with space, privacy, and strong location value.

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Winter Park “Sweet Spot”, Priced to Sell: Rare 3/2 Opportunity in Eastbrook Discover the perfect blend of value, location, and versatility in Winter Park’s highly sought-after Eastbrook neighborhood. This 3-bedroom, 2-bathroom home is ideal for homebuyers looking to make new memories or savvy investors seeking a turn-key property. Move-in Ready: From the moment you step inside this roomy, open floor plan, it’s ready to enjoy. The heart of the home—kitchen, dining and living room—is tastefully renewed and has plenty of space. The ample primary bedroom has a full ensuite bathroom and large windows. Two additional bedrooms share a full guest bathroom. Recent functional improvements provide peace of mind: new water heater, window blinds and exterior paint, and a 12-year-old insurable roof. Outdoor enthusiasts will love the massive, fully fenced backyard, including firepit for chilly (yes, chilly!) Florida nights and “grass-covered” patio. This private oasis is ready for pets, play, or future expansions. BONUS exterior features include carport and multicar driveway, large separate laundry room, lots of elevated carport storage, and an additional cross-fenced and gated side yard. Under Market Value for Quick Sale: Motivated sellers + a price well below area comparables = a win-win. Investor Advantage: This property currently serves as a high-performing, low-maintenance rental with risk-free reliable tenants. In May, renew the lease for continued cash flow or transition the home to a primary residence when the lease expires. • Location: Quiet, safe, and walkable Eastbrook, with shopping less than a mile away. • Condition: Well-maintained with modern updates. • Inclusions: Everything in the home conveys with the sale (excluding tenant furnishings). • Value: Instant ROI for investors and equity potential—priced to move fast! Don’t miss your chance to own a piece of Winter Park at an unbeatable price. Schedule your showing today!

Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)

Listing Agent: Moe Mossa (888-490-1268)

Remarks: ***PRICE REDUCTION*** **Seller offering closing credit** Nestled on a quiet cul-de-sac in desirable Winter Park, this well-maintained home offers a thoughtful layout with bright, open living spaces designed for both comfort and everyday living. The kitchen flows seamlessly into the main living and dining areas, making it ideal for gathering and entertaining. Generously sized bedrooms provide flexibility for guests, a home office, or a growing household. Enjoy a private backyard perfect for relaxing or hosting, all while being conveniently located near shopping, dining, parks, and major roadways. A wonderful opportunity to enjoy the lifestyle Winter Park is known for.

Listing is courtesy of: OAK HOLLOW PROPERTIES (407-949-8809)

Listing Agent: Jakki Kim (407-949-8809)

Remarks: This home sits at the end of a cul-de-sac with an attractive courtyard entry to the 2 car garage. The Kitchen has been updated with new cabinets and tile flooring and the baths all have been remodeled and have tile flooring. The remodeled Primary Bedroom has Luxury Vinyl Flooring. The house has had all the windows and front door replaced. The screened porch overlooks a spacious fenced backyard that includes a block building (summer cottage) with electric and plumbing that is currently being used for storage. The Roof was replaced in 2022 and the yard has a sprinkler system. Make an appointment to see today!!

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Diane Gerry Pa (407-405-5550)

Remarks: Under contract-accepting backup offers. Welcome to 2519 Windward Way, a beautifully maintained single-story townhome located in the highly sought-after Windward Square community in Winter Park. This move-in ready residence offers 2 bedrooms, 2 bathrooms, plus a versatile office. Featuring a large lot with 4 assigned parking spaces. Step inside to an open-concept floor plan designed for both everyday living and effortless entertaining. The spacious layout flows seamlessly into a well-appointed kitchen featuring gleaming stone countertops, stainless steel appliances, and ample storage space. The inviting living area opens to a covered back porch, which is ideal for relaxing, grilling, or gathering with family and friends. Beyond, you’ll find a large, private, enclosed patio that offers additional outdoor living space and privacy. The primary suite provides a peaceful retreat, complete with a walk-in closet and a private en-suite bathroom. The secondary bedroom offers flexibility for guests or family, while the dedicated office can easily serve as a workspace, playroom, or additional living area. Enjoy the convenience of tile flooring throughout the home, combining durability with easy maintenance. Windward Square residents benefit from low HOA fees and access to fantastic community amenities, including a pool, clubhouse, tennis courts, shuffleboard, and playground. Ideally located, this home is just minutes from top-rated schools, major universities, shopping, dining, and provides easy access to major highways, Downtown Orlando, and Orlando International Airport—all within a 30-minute drive.

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Itzel Sotorosa (407-435-9072)

Remarks: 3 bedroom 3 bathroom pool home. Enjoy the large backyard. Schedule your showing today!

Listing is courtesy of: ALFA REAL ESTATE LLC (407-545-9562)

Listing Agent: Thai Nguyen (407-545-9562)

Remarks: Under contract-accepting backup offers. Beautifully designed and impeccably maintained, this light-filled home offers the perfect blend of modern comfort and timeless style. Featuring an open and airy layout, the home is highlighted by abundant natural light, neutral designer finishes, and thoughtfully curated living spaces throughout. The bright and inviting living area flows seamlessly, creating the ideal space for both everyday living and effortless entertaining, while a spacious loft provides additional flexibility for a media room, lounge, or family retreat. The serene primary suite offers a true retreat-like atmosphere with soft neutral tones and abundant natural light, complemented by a well-appointed primary bath featuring dual vanities, expansive counter space, and a clean, modern design. The master bedroom is on the first floor. Additional bedrooms are upstairs, comfortable, and versatile, each filled with natural light and designed to accommodate guests, family, or personalized use. A charming flex space is also upstairs and offers endless possibilities as a playroom, creative studio, or additional living area. Secondary bathrooms are well-maintained with modern finishes and timeless appeal, enhancing both style and convenience throughout the home. Step outside to an expansive screened lanai that creates a private outdoor oasis, ideal for dining, lounging, or entertaining while enjoying tranquil views. An additional outdoor seating area further enhances the home’s indoor-outdoor lifestyle, offering the perfect setting for relaxing or gathering with guests. Move-in ready and thoughtfully styled, this home combines comfort, versatility, and elevated design in every detail, making it an exceptional opportunity for a wide range of buyers. The neighborhood also offers a plethora of amenities including a dog park, pool, clubhouse, gym, and walking trails. You are also in close proximity to dining, schools, and entertainment. Come see this home today!

Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)

Listing Agent: Liz Jones (407-619-6345)

Remarks: Under contract-accepting backup offers. Newly remodeled ranch in a prime location! Situated in a great neighborhood with easy access to everything, this move-in ready home checks all the boxes. Featuring a desirable split floor plan, this home offers both functionality and privacy. Inside, you’ll find brand new windows, beautiful new wood flooring, and new carpet in the guest bedrooms, along with fresh interior paint, new baseboards and door trim, and updated ceiling fans and light fixtures throughout. The fully renovated kitchen showcases new cabinets with soft-close features and quartz countertops, creating a clean, modern feel. Bathrooms have been refreshed with new toilets, and every detail has been thoughtfully updated. Enjoy the outdoors with a screened porch featuring new outdoor carpet and a new irrigation system to keep your yard looking its best. The home also features a newly painted exterior and a roof replaced in 2022 for added peace of mind. This is a truly turnkey home with quality upgrades throughout—ready for its next owner to move in and enjoy.

Listing is courtesy of: LISTY, LLC (561-309-9240)

Listing Agent: Nicholas Macy (561-309-9240)

Remarks: PRICED TO SELL! Charming, quaint, and character-filled 3-bedroom, 2-bath home in the heart of Winter Park. From the moment you enter, you’re welcomed by warm original cognac hardwood floors that flow throughout the main living areas, creating a timeless and inviting atmosphere. The home offers a comfortable and functional layout with open yet cozy living and dining spaces, ideal for everyday living and entertaining. The remodeled kitchen blends classic charm with modern convenience and connects seamlessly to both indoor and outdoor living. The primary bedroom and bathroom offer a cozy, intimate setting, with excellent potential for future expansion or customization to suit your needs. While there are no walk-in closets, all closets have been custom-designed by California Closets, maximizing storage and organization throughout the home. Step outside to a private backyard retreat designed for Florida living. The saltwater pool, fully equipped outdoor kitchen with built-in bar, and tranquil pond with waterfall create a serene, zen-like setting perfect for relaxing or entertaining. Additional features include a tiled 2-car garage with abundant storage space, roof (2023), AC (2023), ductwork (2022), and a hybrid energy-efficient water heater (2020). Ideally located near top-rated schools, shopping, dining, and parks, this home offers a rare blend of charm, lifestyle, and opportunity in a prime Winter Park location.

Listing is courtesy of: ZEN LIVING HOMES LLC (407-800-2717)

Listing Agent: Nydia Marrero (407-620-6221)

Remarks: One or more photo(s) has been virtually staged. Experience elevated living in this beautifully appointed 1-bedroom, 1-bath residence located on the second floor in the heart of Winter Park, Florida. The home showcases elegant wood-look tile flooring throughout, creating a seamless, upscale aesthetic with both style and durability. The primary bedroom is enhanced with classic plantation shutters, offering timeless sophistication, privacy, and beautiful natural light control. Step onto your private balcony overlooking the resort-style pool, providing a serene backdrop for morning coffee or evening relaxation. Designed for modern convenience, the residence includes a private in-unit washer and dryer, elevating everyday comfort. Perfectly positioned just minutes from Park Avenue, enjoy immediate access to Winter Park’s renowned cafés, fine dining, boutique shopping, and cultural attractions, as well as close proximity to Rollins College. This refined condo seamlessly blends luxury, lifestyle, and location, making it an exceptional opportunity in one of Central Florida’s most desirable neighborhoods.

Listing is courtesy of: RE/MAX ADVANTAGE (386-846-1515)

Listing Agent: Eric Zimmerman (386-846-1515)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully designed, move-in-ready townhome— the largest end-unit in one of Winter Park’s most sought-after gated communities! This spacious townhome is conveniently located in the gated community of Hawks Crest, offering 2,312 sq ft of low-maintenance living. With 3 bedrooms, 2.5 bathrooms, a 2-car garage, filled with natural light thanks to abundant windows and soaring ceilings. The paved driveway and lush landscaping welcome you home. Step inside to find a flex space ideal for a home office, den, or second living area. The open-concept main level boasts 9-foot ceilings and seamlessly connects the expansive living room, dining area, and chef-style kitchen complete with quartz countertops, shaker cabinetry, stainless steel appliances, and a large center island perfect for entertaining. Glass sliders lead to the covered patio perfect for your morning coffee or relaxing evenings outdoors. Upstairs, a spacious loft provides a versatile bonus area—great for a media room, playroom, or home gym. The oversized primary suite impresses with tray ceilings, a spa-like en-suite bathroom featuring dual vanities, a walk-in shower, private water closet, and a generous walk-in closet. Two additional bedrooms also offer walk-in closets and share a stylish full bathroom. A conveniently located upstairs laundry room (washer and dryer included) completes the upper level. Residents of Hawks Crest enjoy access to a suite of resort-style amenities including a community pool, playgrounds, parks, picnic areas, and more. Ideally located just steps from Park Maitland Preschool and neighborhood favorites like Foxtail Coffee, Kelly’s Homemade Ice Cream, and Donut King, with quick access to Downtown Winter Park and major highways. Don’t miss your chance to own this exceptional home in one of Winter Park’s most desirable communities!

Listing is courtesy of: ATRIUM REALTY, LLC (833-919-1190)

Listing Agent: Kristan Hayden (407-489-7411)

Remarks: Tucked behind the gates of Cypress Reserve, this stunning custom-built lakefront home sits on 110 feet of private waterfront along the serene shores of Bear Gully Lake. Inspired by a featured Southern Living plan and thoughtfully expanded, the home blends timeless architecture with generous, well-appointed living spaces — all framed by panoramic water views, rolling greens, and towering oaks and cypress trees that define the lakefront lifestyle at its finest. Inside, the main level offers a gracious and versatile floor plan with formal living and dining rooms, a family room anchored by an electric fireplace, and a dedicated office or flex space. The spacious kitchen features custom cabinetry, generous prep space, and an adjoining dinette — with plenty of room to add an island — while a large laundry room with extensive cabinetry and a utility sink, plus a half bath, ensure exceptional everyday functionality. The first-floor primary suite is a true sanctuary, offering breathtaking lake views, a spa-inspired en suite with a jetted tub, walk-in shower, a very desirable his and her split bath with abundant counter space and storage, and an oversized walk-in closet complete with built-in shelving and dresser drawers. Upstairs, two oversized bedrooms each enjoy their own private en suite with tub/shower combination, ample closet space, and comfortable proportions. The enormous bonus room above the garage fills with natural light through dormer windows and offers endless possibilities. A walk-in attic provides exceptional storage rarely found in homes of any size. Step out to the covered back porch and take in sweeping panoramic views of Bear Gully Lake — a breathtaking backdrop that shifts beautifully with the light throughout the day - this is Florida lakefront living at its absolute finest. Meander down to your private dock for a morning kayak or a sunset boat ride, then rinse off at the east-facing porch complete with a sink and outdoor shower before heading back inside. The rolling greens, ancient oaks, and towering cypress trees frame the property in natural splendor, and an additional storage room with its own entrance and hurricane shutters ensures everything you need for lake life is right at hand. Set in the gated community of Cypress Reserve with easy access to top private schools including The Geneva School and Trinity Prep, and with convenient proximity to SR-417 for effortless travel to Orlando International Airport and beyond, this is a rare opportunity to own a one-of-a-kind lakefront estate in one of Winter Park's most coveted settings.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Kelly Price (407-645-4321)

Remarks: This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were professionally serviced, including roller replacement, track repairs, and installation of new locks to ensure smooth, secure operation. Deluxe vinyl fencing was installed throughout the community by the HOA replacing the older wooden fencing. The fencing was replaced with the vinyl after the listing photos were taken, please view the video to see the replacement vinyl fencing. Enjoy convenient features including an in-unit washer and dryer combo, storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens to a large screened-in balcony. Ideally located just 15 minutes or less to UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes to Orlando International Airport. Whether you’re a first-time home buyer, student, investor, or looking to make your move into Winter Park, this home offers affordability, convenience, and plenty of potential!

Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)

Listing Agent: Karen Salter (352-227-0451)

Remarks: Welcome home! You've found it, a spacious end unit townhome style condo with private 1 car garage with extra storage space. Open floorplan first floor, when you walk in the front door you walk into a huge living room/dining room combination room with views out the back of your private screened patio overlooking a pond. The kitchen features lots of counter space, breakfast bar on the kitchen island and all appliances included! upstairs you will find a HUGE master suite with walk-in closet and ensuite bathroom with dual vanities, separate water closet and shower. Down the hall you have your indoor laundry closet, as well as two additional bedrooms with view of the pond. Easy commute to Downtown, Baldwin Park, Winter Park with quick access to the 408 and 417!

Listing is courtesy of: COMPLETE FLORIDA REALTY LLC (407-222-7281)

Listing Agent: Greg Traub (407-222-7281)

Remarks: Enjoy Winter Park lifestyle in this great, first floor, 1 bedroom 1 bath condo. Built in 1973 with a well-planned 678 sq.ft. floor plan. Featuring Laminate flooring, this condo offers a functional and inviting home. The kitchen comes equipped with a range, refrigerator, dishwasher and microwave. The oversized bedroom comes with stackable washer an dryer and two closets. New bedroom window, new sliding glass door, new bathroom vanity. Updated wiring and electrical panel. Enjoy all your community amenities including a two pools, tennis courts, clubhouse and 24/7 fitness center. The HOA covers water, trash removal, Internet, common area pest control, grounds maintenance, and exterior maintenance while the pool is maintained for your enjoyment. A convenient on-site laundry room features two washers and two dryers free of charge, and the clubhouse is available for rental for gatherings or events. Situated in a prime Winter Park location, this condo is close to grocery stores, shopping centers, and major routes like the 408, Semoran Blvd and St. Rd. 50 for quick access across the area. This condo is just 20 minutes from UCF, 10 minutes from Full Sail, Rollins College, and the vibrant Park Avenue in Winter Park. Quick access to major highways (417 and I-4), everything you need is within reach. Welcome Home!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Susan Tamlin (407-808-3104)

Remarks: Discover the opportunity to own in Winter Park at 1952 Spring Street—a well loved 3-bedroom, 2-bath townhouse offering charm, functionality, and a private yard, a rare find in this desirable area. Nestled in a well-established neighborhood, this home provides a peaceful residential feel and tranquility while remaining just minutes from everything Winter Park has in store. The interior features new appliances, making it move-in ready with modern convenience. A brand-new roof will be installed once the property is under contract, offering added value and peace of mind to the future owner. Whether you’re seeking a primary residence or an investment opportunity, this property delivers flexibility, comfort, and location. Enjoy nearby parks, shopping, dining, and easy access to major roads—convenience meets lifestyle in one of Central Florida’s most sought-after communities. Don’t miss this exceptional opportunity—schedule your private showing today.

Listing is courtesy of: BEAR TEAM REAL ESTATE (407-228-1112)

Listing Agent: Bethanne Baer (407-228-1112)

Remarks: Motivated Seller....Fantastic 3-Bedroom, 2-Bathroom Condo Located in the Highly Desirable Winter Park Area! This Home Features an Open Galley Kitchen with a High Vaulted Ceiling and a Convenient Pantry. The Spacious Living/Dining Room Combination Also Boasts Vaulted Ceilings and Fills with Natural Light Through the Sliding Glass Doors, Creating an Inviting Yet Cozy Atmosphere. Beautiful Laminate Flooring Flows Throughout, and the Split Floor Plan Offers Ideal Privacy. Down One Hallway, You Will Find Two Well-Sized Bedrooms and a Shared Full Bathroom with a Shower/Tub Combo. Off The Family Room, The Master Suite Is Generously Sized and Includes Two Separate Sinks. A Large Walk-In Closet Provides Excellent Storage, and the Sliding Glass Door Leads to Your Own Private Fenced-In Yard, Perfect for Plants, Gardening, or Extra Seating When Entertaining. Just A Short Walk from Your Reserved Parking Spaces, You'll Find the Clean and Refreshing Community Pool, Making Relaxation Effortless. Don’t Miss This Opportunity—Call Today to Schedule Your Showing! Lease Must Be Honored Until 11/30/26 with a Rental Rate of $1,850.00 Monthly

Listing is courtesy of: OUTLET REALTY (407-353-5518)

Listing Agent: Ivan Tobon (407-353-5518)

Remarks: One or more photo(s) has been virtually staged. Modern Charm in Prime Winter Park Location! Step into this beautiful 2-bedroom, 2.5-bath townhome located in the desirable Hidden Oaks community of Winter Park. Freshly painted with brand-new carpeting throughout, this stylish 1,031 sq. ft. home offers both comfort and flair. Enjoy peace of mind with a new roof installed in 2023. The exterior is thoughtfully landscaped, enhancing the home’s inviting curb appeal. Conveniently located just: 10 minutes to Downtown Orlando, 15 minutes to Orlando International Airport, 10 minutes to shopping and dining, 15 minutes to Valencia College, 25 minutes to UCF, 30 minutes to Disney World. Top schools such as Aloma Elementary, Glenridge Middle School, and Winter Park High School. Whether you're looking for a place to call home or a savvy investment, this gem combines timeless design, modern updates, and unbeatable location. Don’t miss this opportunity!

Listing is courtesy of: FLORIDA PRESTIGIOUS HOMES INC (754-246-2070)

Listing Agent: Ian Trumbach (754-246-2070)

Remarks: Rare opportunity in a quiet Winter Park neighborhood! This oasis home offers nearly 2,000 sq ft of living space PLUS a fully equipped studio apartment with private entrance, kitchenette, full bath, fireplace, separate A/C, and generous storage—ideal for guests, multi-generational living, or rental income. The main home features a freshly painted interior and exterior, new LVP flooring throughout, and a completely remodeled kitchen with new appliances. The primary suite includes an en suite bath that has been remodeled, and three additional bedrooms provide ample space for family or home office needs. Enjoy the Florida room overlooking a fenced, private backyard, perfect for entertaining. Roof replaced in 2024. A/C replaced in 2016. Zoned for top-rated Winter Park High School and conveniently located near Park Ave, shopping, dining, Costco, and major roadways. Move-in ready with room to personalize. Don't miss this versatile and rare Winter Park find!

Listing is courtesy of: HONEST REAL ESTATE COMPANY (407-417-1314)

Listing Agent: John Hwangbo (516-708-6207)

Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.

Listing is courtesy of: EQUITYPRO LLC (407-203-6860)

Listing Agent: Navid Rokh (321-900-5977)