Homes for Sale in Winter Park

Under contract-accepting backup offers. BELOW MARKET VALUE Stunning Updated Home in Howell Estates, Winter Park, FL Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Key Features: Brand New Roof (2024) Replumbed (2024) New HVAC System Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower Inviting Family Room: Spacious layout with a cozy wood-burning fireplace, leading to a screened room with an insulated roof Oversized Garage: Perfect for larger vehicles, including SUVs This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!

Introducing a charming 1 bed, 1 bath condo located on the serene shores of Lake Killarney in Winter Park Florida. Enjoy the perfect balance of lakeside tranquility, urban convenience, with a stunning sunset and being just a short walk to Trader Joe's, movie theaters, restaurants, and coffee shops. This home is ideal for someone seeking a peaceful retreat with all the benefits of a vibrant neighborhood. Don't miss your opportunity to live in this coveted Winter Park location.

Stunning, custom-built home in the Winter Park Tree Streets. This beautifully designed, Mediterranean-style home features 4 bedrooms, 3 full-baths, and an open layout complimented by engineered wood and travertine flooring, high ceilings, crown molding, and bright natural light. First floor layout includes a spacious living/dining room and open concept kitchen/family room. The kitchen offers stainless steel appliances, a built-it oven and microwave, gas range, granite counters, bar top seating, and a walk-in pantry. Off the family room are French doors that open to a screened patio which overlooks the perfectly manicured backyard. The first floor primary bedroom is very comfortably sized and has a private en suite with double vanities, a walk-in shower, and jetted tub. There’s an additional guest room with full bath on the first floor as well, ideal for visiting guests. Upstairs are two generously sized bedrooms, each with ample closet space, and a shared hall bath. Additional highlights include natural gas, a Rinnai tankless hot water heater system, paver walkways, a detached Tuff Shed, tile roof, and more. Located in Winter Park’s desirable “tree streets” neighborhood this home is zoned for the A-rated Winter Park School District and is close proximity to the Winter Park Raquet Club, Interlachen Golf & Country Club, Rollins College, Park Avenue, and all of the fantastic shops and dining the area has to offer. This charming home won't last so schedule your showing today.

Under contract-accepting backup offers. Well-Priced THREE-Bedroom, Two-Bath Half-Duplex Centrally-Located in WINTER PARK with Metal Roof, a LARGE Yard and NO HOA…all within Walking Distance to Full Sail University! HOLY COW!

Your SCREENED BACK PORCH overlooks an Expansive Yard that goes WAAYYY Back (the Largest Lot in the Community) …with TWO Storage Sheds as Well! Bonus! NO HOA and Septic System ensures Low Monthly Bills, making this an AFFORDABLE Home to Live in and an Ideal Rental Property!

Home Already has all the UPGRADES Done… like a 40-Year METAL Roof in 2011, a New Heat & AC in 2019, having been Totally Replumbed…even Brand-New Water Heater Just Installed…that together will give you YEARS or Worry-Free Low-Maintenance Living! Open Floorplan with Large Indoor Laundry Room!

Located in the Highly-Sought After, “A” Ranked WINTER PARK SCHOOL DISTRICT, including Winter Park High School which is among the Top Public High Schools in the State of Florida! Within Walking Distance to FULL SAIL UNIVERSITY …with either UCF or Rollins within a short 15-minute drive as well!

You Will Love Centrally Living in WINTER PARK with Major Shopping like Costco, Target & Publix with 5 minutes just around the corner! Enjoy the environs of Upscale Living with Baldwin Park, Winter Parks PARK AVENUE and DOWNTOWN Orlando all within 15 minutes!

Property is All on ONE Level with No Stairs. Washer-Dryer Hookup are in Large Inside Dedicated Laundry Room! REFRIGERATOR, WASHER & DRYER are Negotiable, and If Included, Are Sold in As-Is Condition. Room Sizes, Schools, HOA Info and Square Footage are Deemed Accurate, but are not Warranted. Property is Being Sold As-Is with Right to Inspect!

Highly Sought-After, A-Rated Schools: Aloma Elementary, Glenridge Middle School, Winter Park High School! Say YES!

Largest unit at Killarney Bay, set up as a town home -bedrooms upstairs town house with large screened in area back pooch, new washer and dryer - wood floors throughout, close to Winter Park Village - complex is a small great location with great access to I-4 - Killarney Bay sits on Lake Killarney with private pool overlooking. Only 5 rental units are allowed at KB at any given time. Super clean and ready for new owner. Beautiful wood ceilings in main living areas and wood floors and stairway! tastefully done. Current tenant has flexibility in moving.

Welcome to this beautifully updated 2 bedroom/ 2 bath  first floor condo.  This open floor plan has tiled flooring throughout the common areas, along with granite counter tops in the kitchen and bathrooms. The energy efficient AC is less than a year old (12/2023)!  Included appliances are: Washer, dryer, stove, microwave, dishwasher, and refrigerator are all less than 5 yrs old. The garbage disposal is also new.  The interior boasts thoughtful details like ceiling fans, window blinds and drapes. The building is newly painted 2024, with new roof 2023.  Included in HOA is  water, trash, outside maintenance and private pool.  This condo is conveniently located just minutes from top rated schools, Full Sail, UFC, great dining spots, and major highways.  Don't miss the opportunity to own this beautiful condo in a central location.

Under contract-accepting backup offers. This tucked away neighborhood has only one way in and out, preventing any cut through traffic, and making it a great place to call home! Tastefully updated with luxury vinyl flooring throughout and ceramic tile in the kitchen and baths. 3 bedroom/2 bath split floor plan has a spacious living room with wood burning fireplace, updated ceiling fans in all the rooms and updated bathroom vanities. With cooler weather now, you will be spending all your time in the large screened back patio enjoying the open space and no rear neighbors. 2 car garage with plenty of additional storage in the floored “stand-up” attic space with collapsing stairs for easy access. Your big-ticket items have been done – Roof (2022), AC (2022), Replumbed with PEX (2013), electrical panel is good, and water heater is 2009. Centrally located with easy access to the 417, minutes from UCF, Valencia and Full Sail along with many shopping and dining options. This charming home is move in ready!

Welcome to this stunning modern, custom-built home in the heart of Winter Park, FL! This beautifully remodeled 3-bedroom, 2.5-bath residence offers 1,898 sq ft of inviting living space. The home features an eat-in kitchen with custom bench seating, earthy wood-tone cabinets, a large waterfall island, and elegant countertops. Sleek black appliances perfectly complement the modern design. All bedrooms are located on the second floor, with the primary suite boasting cool contemporary lines, a walk-in shower, double sink vanity with quartz countertops, and plenty of natural light. The suite also includes a spacious walk-in closet, fully built-in for optimal organization. The home’s outdoor space is equally impressive, with gorgeous landscaping that enhances the fenced, private yard—perfect for entertaining guests or enjoying quiet moments with loved ones. The 1-car wide garage extends two cars deep, providing ample storage, while the paved driveway offers room to securely store a boat or RV behind the fence. With only two original block walls retained, the rest of the home is entirely new, including updated sewer pipes, plumbing, electrical systems, and a fully installed irrigation system. Located in an excellent A+ rated school district, this home is just minutes from Winter Park Hospital, Park Avenue, Rollins College, museums, galleries, shopping, restaurants, and major highways—everything you need is close by. Call today to schedule your private showing and make this dream home yours! Pool renderings are only showed as an illustration of what is possible and can be built for additional cost.

Welcome to 2821 Chantilly Avenue Winter Park FL 32789! A unique opportunity to own this .75 acre lot and the ONLY home on Lake Vella. Classic 3/2 bungalow with lake views zoned for Dommerich, Maitland & Winter Park High. Large back yard offers room to expand, renovate existing home or build new. Great location just minutes to Park Avenue. Extras include: updated electric panel, 2017 AC, updated plumbing & 24x12 backyard shed. WELCOME HOME!

Nestled in the heart of Winter Park, this enchanting Mediterranean-inspired condominium beckons those with a discerning eye for comfort and potential. This newly listed condo offers a unique opportunity to embrace a lifestyle of elegance while potentially reaping the rewards of rental income in a highly sought-after neighborhood. As you step into this two-story condominium, you'll be immediately captivated by the spacious open floor plan adorned with high vaulted ceilings. The kitchen boasts direct access to the dining space via a charming pass-through, perfect for those who love to entertain with flair. Off the kitchen is also a small bar/coffee station. The living area serves as the heart of this abode, featuring a corner fireplace that adds a touch of romance to chilly Florida evenings. An in-unit laundry closet, a true luxury in condominium living, is convenient for the busy homeowner. As you head upstairs, you will find the large Master bedroom with a private en-suite bathroom and a private sanctuary for rest and rejuvenation. The 2nd bedroom is located on the main floor, with a full bath adjacent to the space. For those who appreciate the great outdoors, a private patio and fenced backyard space await your personal touch. This property offers a beautiful living space and presents an attractive opportunity for those considering rental income. The desirable Winter Park location, close to UCF and Valencia College, and the condominium's charming features make it a magnet for homeowners, and potential tenants seeking a slice of Florida paradise. In this vibrant neighborhood, you'll be surrounded by an eclectic mix of culture, cuisine, and community. From quaint cafes to upscale boutiques, every amenity you could desire is just a stone's throw away. Seize this opportunity to own a piece of Mediterranean-inspired luxury in the heart of Winter Park. This won't last long! Schedule your showing today!

First time ever on the market - for sale by the original owner. Welcome to this meticulously maintained 3-bedroom, 2-bathroom home located in Casa Aloma community of Winter Park. As you arrive you are treated with warm curb appeal with landscaping and fresh exterior paint. Walking entry is brick paver lined with a wonderful front porch seating area. Upon entry the welcoming foyer leads into a spacing living room and dining room which all flows seamlessly into the kitchen and breakfast nook. The kitchen offers ample cabinetry and is open to the family room with access to the Florida sunroom. This large sunroom is a great addition which is perfect for sitting, reading and relaxing. Just outside the Florida room is access to the fenced in backyard. The layout of the home offers ideal privacy with a split floor plan. The primary bedroom is conveniently located off the foyer and features two closets and an ensuite bathroom, offering a serene retreat from the main living spaces. Two additional bedrooms are situated on the opposite side of the home, providing separation for guests or family members. The home has undergone significant improvements, including pipe relining in 2022—a $20,000 investment—ensuring long-term peace of mind, the ceiling in the garage has been replaced, and blown-in insulation has been added to the attic for energy efficiency. A new roof was installed in 2014, new flooring (2021), new front windows (2018), Leaf Filter gutters with a transferable warranty, ensuring hassle-free maintenance for years to come. Outside, the fenced-in backyard is perfect for outdoor gatherings or quiet afternoons, surrounded by shady mature trees. Located in a highly sought-after area, this home is zoned for top-rated Tuskawilla Middle School and Lake Howell High School. With easy access to Highway 436, a variety of shopping and dining options are just moments away, simplifying your daily routine. Don’t miss out on the chance to own this well maintained, move-in ready home that’s waiting for you to make it your own!

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Don't miss this immaculate and move-in ready 2-bedroom/2-bath Winter Park home, with a 1-car garage, and a NEW ROOF coming soon! Recently updated, this home features fresh paint inside and out, improved landscaping, new lighting, a new dishwasher, and a new microwave. The desirable, open floorplan features a spacious family room/kitchen combo, separated by an island that offers extra storage and seating. Stainless steel appliances and a window overlooking the backyard enhance the kitchen, while an adjacent dining area flows into a bright Florida room, making this home ideal for entertaining. Both bedrooms have walk-in closets, and there’s plenty of extra storage with 2 hall closets. The backyard steals the show, featuring a large (22’x15’) covered porch with ceiling fans, two storage sheds, and raised garden boxes—perfect for your gardening projects! The freshly painted, attached 1-car garage offers washer & dryer hookups and shelving for more storage. Tucked away on a quiet street, yet minutes from downtown Winter Park, College Park, and downtown Orlando, this home is close to Trader Joe’s, Whole Foods, Publix, Home Depot, and more...and offers easy access to I-4 for commuting. Request a floorplan and list of recent updates!