Homes for Sale in Winter Park

Experience unparalleled sophistication and tranquility with this extraordinary two-bedroom, two-bath condominium, boasting one of the rare and coveted water views in The Cloisters. Nestled on the serene shores of Lake Osceola, this residence offers a unique opportunity to enjoy stunning lake vistas that are available in only a small number of units within the complex. Spanning 1,351 square feet, this haven of light and serenity is designed to accentuate its breathtaking views. The primary suite is a harmonious retreat featuring an en-suite bath, a spacious dressing area with ample closet space, and potential for an added washer and dryer, ensuring both comfort and convenience. The separate kitchen opens to a generous living and dining area, offering picturesque views of glistening Lake Osceola – perfect for intimate gatherings or quiet evenings at home. More than just a place to call home, this condominium is a gateway to a lifestyle of elegance and ease. Exclusive amenities such as covered parking with a dedicated space conveniently close to the elevator, enhance the living experience. Additionally, boat docks, a gym, and an elegant community room within the complex provide leisure options. Managed expertly by FirstService Residential, this property promises a seamless and harmonious living experience. Located just steps from the vibrant shopping and dining of Park Avenue, the charm of Winter Park Village, nearby fitness centers, and the intellectual allure of Rollins College, this home places you at the center of Winter Park's most coveted attractions. Embrace the rare opportunity to own a unit with one of the most desirable water views in The Cloisters. Schedule your private viewing today and discover how this exceptional residence can become your canvas for an extraordinary life.

Introducing an exceptional opportunity at The Mondrian Winter Park, a stunning waterfront community featuring 30 contemporary townhomes elegantly situated along the serene shores of Lake Killarney. This remarkable residence is truly a standout, showcasing top-tier finishes that exemplify both quality and value. As you enter, you'll be greeted by fresh interior paint and updated flooring that enhance the home's modern appeal. Enjoy the added comfort of privacy shades, stylish light fixtures, and ceiling fans that enhance the overall ambiance. The chef-inspired kitchen is a culinary dream, equipped with a natural gas cooktop and a wine refrigerator, perfect for entertaining. Retreat to the luxurious master suite, which offers a walk-in glass shower, a separate water closet, and ample closet space for all your storage needs. Your own personal oasis awaits on the expansive rooftop terrace, complete with a hot tub spa, grilling station, and generous lounge area, ideal for hosting gatherings or relaxing under the stars. With soaring 10'6 ceilings on the second level and expansive storefront-style windows, natural light floods the living space, creating a bright and inviting atmosphere. Each of the three spacious bedrooms comes with its own bath, ensuring privacy and comfort for family members or guests. Nestled in the heart of beautiful Winter Park, just north of downtown Orlando, this luxury enclave offers an unparalleled lifestyle. Experience breathtaking views of Lake Killarney from the newly constructed dock or unwind in the lakeside Pavilion as you watch the sunset. For those who enjoy water activities, a private boat slip is available for purchase, allowing you to cruise across the lake to visit Trader Joe’s or enjoy a meal at Shake Shack. Outdoor enthusiasts will appreciate the community’s kayak and paddleboard racks, providing easy access for fishing, exercising, or simply soaking in the tranquil waters. Nearby, Winter Park Village boasts a variety of shopping and fine dining options, while the vibrant Farmer’s Market and renowned Enzian Theater offer an array of local culture and entertainment. Discover the ultimate blend of luxury, comfort, and convenience at The Mondrian Winter Park—where every detail is meticulously crafted for your enjoyment and every moment holds the potential for adventure. Welcome to your new home.

Under contract-accepting backup offers. Experience the pinnacle of waterfront luxury at Lake Killarney Townhomes. Welcome to Lake Killarney Townhomes, an exclusive enclave of luxury living nestled in the heart of Winter Park, just north of downtown Orlando. Immerse yourself in the beauty of urban contemporary design, where each spacious townhome features private terraces that invite you to unwind in style. These brand-new residences are a testament to sophistication, meticulously crafted with exquisite designer finishes and thoughtful upgrades. Step inside to discover bright, open interiors illuminated by expansive storefront-style windows and soaring 10'6 ceilings, creating an atmosphere of elegance and comfort. The exterior sets a stunning precedent with two-story concrete block construction, complemented by woodgrain composite siding and striking balconies adorned with distinctive glass railings. Each home is equipped with steel insulated flush garage doors and comes with a 10-year structural warranty for peace of mind. Designed with family living in mind, this remarkable layout offers three spacious bedrooms and three-and-a-half luxurious baths. The heart of the home—the kitchen—exudes modern culinary luxury, featuring sleek white cabinetry paired with a bold black-and-white center island. A premium Samsung appliance package, including a natural gas cooktop and built-in wall oven, elevates your cooking experience, while expansive quartz countertops and a solid backsplash create a seamless and sophisticated aesthetic. A generous walk-in pantry adds a touch of convenience for all your culinary endeavors. Ascend to the second level, where a tranquil haven awaits with three well-appointed bedrooms and three full bathrooms, each showcasing unique porcelain tile, modern backlit mirrors, frameless glass shower enclosures, undermount sinks, and custom-built closet systems. Step outside to your expansive outdoor patio, designed with glass railings and pre-plumbed for a future summer or cocktail kitchen, perfect for hosting gatherings or simply enjoying the outdoors. Every detail has been thoughtfully curated to ensure ultimate comfort and style. Embrace the rich history and cultural charm of Winter Park, where boutique shopping, sidewalk cafés, museums, and dog-friendly destinations are just a stone's throw away. Delight in the serene beauty of Lake Killarney right from your side patio or relax at the inviting lakefront pavilion. With your private boat slip, accessing nearby amenities like Trader Joe’s and Shake Shack is effortless. Plus, enjoy community kayak, canoe, and paddleboard racks for a leisurely day on the water. Live the lakefront lifestyle you’ve always dreamed of, where Winter Park's vibrant shopping, dining, and entertainment options are merely moments away. Discover the perfect blend of luxury and convenience at Lake Killarney Townhomes—your new home awaits.

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.

Under contract-accepting backup offers. Welcome to this stunning Mid-century style 3 bedroom, 2 bath, 1930 sq ft home with a 2 car garage, where sleek modern design meets functionality. Step into the open-concept living space and be captivated by the abundance of natural light streaming through the large windows, creating a warm and inviting atmosphere. The centerpiece of this home is the gourmet kitchen, featuring top-of-the-line appliances that are sure to impress any culinary enthusiast. The Samsung Fridge and new natural gas range are equipped with cutting-edge technology, including the ability to air fry, dehydrate, and even bread proof. The kitchen also boasts stylish two-tone cabinets with a 42 upper configuration. Prepare meals with ease using the convenient split oven, perfect for hosting and baking multiple dishes simultaneously. The oversized island, measuring an impressive 8'x4', offers a spacious area for meal preparation, dining, or casual gatherings. Wood beams on the ceiling in the open area add a touch of rustic charm to the modern aesthetic. The mature landscaping surrounding the property provides a serene and private outdoor oasis, perfect for relaxing. Enjoy the convenience of having the laundry facilities conveniently located inside the home. Additionally, the remote blinds in the public areas allow for easy light control and privacy adjustments at the touch of a button. Arlo security system included. This home is located in beautiful Winter Park, near Park Ave, with restaurants, shopping, Rollins College, and events close by. Also enjoy Winter Park's convenient transportation via the Sunrail to downtown or Amtrack throughout FL. Call today for a private tour! Room Feature: Linen Closet In Bath (Primary Bedroom).

NEW PRICE! Come discover this stunning Winter Park home! Beautifully updated with a brand-new kitchen featuring new, LG STUDIO Series appliances in modern white, a convenient breakfast bar, sleek quartz countertops with matching slab backsplashes. This home boasts 4 bedrooms, 2.5 baths, and 2046 sq ft of refined living spaces. A large, sunken family room flows into an open, centrally located, Living/ Dining areas featuring a bright Garden Window, a Slider and easy access to the Kitchen and Back Yard. The all-new bathrooms showcase all new porcelain/ ceramic tiles and high-end finishes while the rest of the home has all new, light oak finish, LPV flooring and large windows throughout for an abundance of natural light. Additional highlights include a new AC system, an oversized 2-car garage with storage cabinets, a breezeway, fresh sod, and a convenient in-house laundry area. Don’t miss your chance to own this beautiful home located in a quiet neighborhood of Winter Park surrounded by well-maintained homes and is only minutes to Downtown Orlando, Shopping, Dining and Entertainment!

Quiet Virginia Heights Neighborhood with Stunning: private lake access park, walk to town around lake Virginia, directly across street from Mead Gardens, 2 short blocks to WP Tennis Center, Azalea Playground Park, New 7 Oaks Park, And less than a 1/2 mile stroll to New Orange Avenue Shops & Dinning. Easy in / out access via private drive; QUIET side with private drive, easy entry exit. Distinctive and dramatic 3 bedroom, 2.5 bath unit boasts custom wood cabinets, granite counter tops, walk-in butler's pantry, kitchen island, Front load washer and dryer, designer lighting fixtures, hard wood floors and spiral staircase with decorative wrought iron, travertine stone bathrooms, zoned air conditioning, and much more. You'll love relaxing or entertaining in the private South screened atrium or on the spacious rooftop terrace with bonus storage room or conversion! This unit is in the Charming Virginia Heights Neighborhood and a beautiful walk to Park Ave. It also has access to a private lakefront neighborhood park with direct access to Lake Virgina (chain of lakes) for easy paddle boarding and kayaking (with new storage racks). Zoned for the highly sought after Audobon K-8 school district. -Building, newly repainted and has brand new roof. specific unit is on the non-street side for your own very private oasis.. Building pre-built for Elevator option to Rooftop! (Currently extra storage all three levels)

Under contract-accepting backup offers. ***VERY RARE CORNER DOUBLE CONDO WITH 2 COVERED PARKING SPACES*** Stunning is the first word that comes to mind when describing this casual but elegant 2 bedroom, 3 bath condominium in the highly sought after Winterset building. Designer touches and quality finishes are evident the minute you walk through the front door. The gracious owner's retreat is large with a spa-like bath and 2 walk-in closets with built-ins. The secondary bedroom offers a private bath and walk-in closet. The gourmet kitchen and breakfast area offers custom wood cabinetry, granite counter tops, tile backsplash, under cabinet lighting and high end appliances. Other features include beautiful hardwood flooring, built-in bar and cabinetry. The secured building requires a code to access the lobby, along with a call box for your guests to be buzzed into the building. This condo boasts wonderful closet spaces throughout along with a separate storage closet and 2 convenient covered carport spaces. Just steps away from the stylish shops and restaurants on Park Avenue and other popular Winter Park amenities this unique and spectacular condo will not disappoint! Call today for your private viewing! NOTE: NO RENTALS OR PETS.

Welcome to your very own private personal retreat! This truly one of a kind oasis of a property features 1.9 acres of lushly landscaped garden in Winter Park. A four-bedroom, three-bathroom main house with a two-car attached garage and a luxurious pool. With paid-for solar panels and a 37 seer Geo-Thermal HVAC means you will enjoy significant savings on your power bills. The additional detached garage (24x36) includes a roughed-in 20x22 space, perfect for an in-law suite, workshop, more garage space (the possibilities are endless) and an additional one car garage. This property boasts a picturesque pond and a private creek with a charming dock and seating areas for serene relaxation. As you approach the home the circular driveway leads to a large tranquil fountain welcoming you, setting the tone for the beautifully landscaped property. Step inside to find a spacious living room with a wood-burning fireplace, seamlessly flowing into the dining room and a dream kitchen. The kitchen is a chef's paradise, featuring a gas range, built-in oven, large island with seating, granite counters, a stylish tile backsplash and so much more. A bonus room off the kitchen and living room leads to the screened-in pool deck, perfect for entertaining. The saltwater pool with a spa and gas heater offers year-round enjoyment. Back inside, the split bedroom plan ensures privacy for all. The large primary suite includes an ensuite bathroom with a soaking tub, separate walk-in shower, and ample closet space with both a walk-in closet and an additional closet. The second bedroom is adjacent to a full bathroom, while the two additional bedrooms at the rear of the home share the third full bathroom. The outdoor space is equally enchanting, with your own pond and creek. Zoned agricultural, the property also includes a chicken coop, making it ideal for those looking to embrace a more self-sufficient lifestyle. This property is very unique in that the part to the west of the pond is not in the HOA, while the part East of the pond is. The wall along Dike Rd in front of this parcel is owned by the parcel The great location has you able to enjoy the best of Winter Park! Great shopping and dining awaits you! Don't miss the opportunity to see this beautiful property in person. Schedule your showing today and experience the tranquility and luxury of this unique home!

Discover the charm and convenience of this beautiful one-story home in the desirable Winter Park Hills. It offers four bedrooms with 2.5 baths, and the fifth room can be used as an office or an additional bedroom, and 2,441 square feet. This residence offers a spacious and comfortable living environment for families and guests. The heart of the home is the inviting family room, featuring a cozy wood burning fireplace with built-in shelving that adds warmth and character. The open floor plan ensures easy flow between the living areas, making it ideal for everyday living and entertaining. The kitchen offers wood cabinets and stainless appliances. The living room area is wonderfully renovated with built-in cabinetry, wood floors and French doors out to the pool area. The beautiful renovated primary suite has travertine floors, French doors, an en-suite bath with dual sinks, oversized double shower head shower, Jacuzzi tub and custom walk-in closet with custom shelving, along with a separate makeup area. Step outside to your private haven on a generous .28-acre lot. The covered lanai provides a spot for alfresco dining or relaxing, while the paver pool area is ideal for enjoying sunny Florida days and hosting gatherings. The home boasts several recent updates for added peace of mind including a new roof in 2022, air conditioner compressor replaced in 2018, re-plumbed, tankless water heater, propane tank and more. These modern upgrades complement the home’s classic appeal. In a neighborhood known for its top-rated schools such as Dommerich, Maitland Middle and Winter Park High School! Don’t miss your chance to own this exceptional Winter Park Hills home where comfort, style and practicality come together in harmony.

Discover your dream oasis in this exquisite 3-bedroom, 2-bathroom POOL home nestled on a coveted street in Winter Park on the 3rd hole on the GOLF COURSE. With designer-inspired upgrades and custom features throughout, this home offers a truly unique and luxurious living experience. As you approach the home, you'll be immediately impressed by the charming tile work adorning the walkway and accentuating the home's exterior. Step inside to be greeted by charming features such as crown moldings, gorgeous wood-look porcelain flooring, energy efficient LED lights and designer style lighting features throughout. Immediately to the right is a nice sized office/flex space with the potential for a 4th bedroom, featuring gorgeous built ins and natural light! The heart of the home is the oversized kitchen, a chef's masterpiece featuring custom soft-close cabinets with pull-out shelves, stainless steel appliances, and an ENORMOUS ACCENTED ISLAND with storage, perfect for entertaining. The adjacent family room is equally impressive, boasting custom built-ins, a wood-burning FIREPLACE, and surround sound. Both areas flow into an oversized canyon-like patio and sparkling pool with waterfall, protected by golf ball resistant screens and windows! French doors create a seamless indoor -outdoor flow perfect for gatherings with family and friends! The primary bedroom is a spacious haven with extra seating area and a large WALK IN CLOSET (the original 4th bedroom-converted). Bathroom with gorgeous warm tone tile work and cabinetry with a large walk-in shower and designer fixtures. Second and third bedrooms provide ample space with closets and new carpeting with a 25 year warranty! For added security, cameras are installed around the exterior of the property, and the home has been freshly painted with an EXPANDED concrete driveway. Roof replaced in 2013, and the AC system was updated in 2017. Partial repipe was done in 2017 during renovation in kitchen and the rest is brand new! The home also boasts a new STATE OF THE ART water heater. Conveniently located across the road from Cady Way Trail and near the GOLF COUNTRY CLUB, this home offers easy access to downtown Winter Park and Baldwin Park, where you'll find a vibrant array of restaurants, entertainment, and attractions. Don't miss this opportunity to own a truly exceptional property. Schedule your private tour today!

Welcome to this newly renovated gem nestled along the ninth hole of the WP18 golf course. This stunning property features 2584 square feet of living space, ideal for both relaxation and entertaining. Upon entry, you'll find an inviting open concept living area and kitchen, perfect for hosting guests or unwinding after a long day. With 4 bedrooms, this home offers flexibility for a home office or additional bed rooms. The split floor plan provides a primary bedroom that is a serene escape, complete with an en-suite spa bathroom. This sought after location in Winter Park has dining, shopping, entertainment, and the highly desired Brookshire Elementary just minutes away. Don't miss out on the opportunity to make this remarkable property your new home. Schedule a showing today!