Winter Park FL Real Estate & Homes for Rent

LOCATION, LOCATION, LOCATION! Well maintained home with a beautiful garden backyard. Close to Windsong and Baldwin Park. Bike or walk around Lake Baldwin and Cady Way Trail.

Private deeded lake access (see pics) to Lake Virginia on the Winter Park chain of lakes overlooking gorgeous Rollin College. Also includes access to huge private park on lake and deeded boat slip.This home is located on one of the most sought after tree-lined brick streets in Winter Park. This newly renovated 5/4 pool home is within a short walk to Park Avenue.New tile roof 2019. Kitchen remodeled/new appliances 2024. Whole home water filtration/softener system, Paver driveway, travertine tile front and back, and fully automated outdoor LED lighting front and back.Interior renovations include new plumbing, tankless instant hot water heater, light fixtures w/LED lighting, modern classic mixture of Spanish tile and wood flooring, quartz countertops, bathrooms completely remodeled in 2023. Gas connection for stove, dryer, and outdoor grill.Feel like you're on permanent vacation out back w/ luxurious tropical paradise, covered summer kitchen, heated salt water LED remote controlled pool w/ built in hot tub (gas for utility savings) and two soothing waterfalls. Grass for the young ones to play, or work on your golf game, and 8 ft permitted fence for 100% privacy.Master bedroom 1st floor w/master bath featuring jacuzzi tub, skylight, and 3 walk in closets.*NOTE: some kitchen pics contain photos before granite was replaced w/ white. Quartz in 2022. *Walk-through video filmed before kitchen, bathrooms, and whole house repainted in 2022.

Discover a beautiful Winter Park Condo overlooking the picturesque Lake Killarney. Experience the magic of Orlando's most captivating sunsets from the comfort of your own home. This 2/1 is Midcentury modern with a twist. Convenience is within reach with nearby Publix, Trader Joe's, a movie theater, and an assortment of eateries and boutiques all walking distance. Just under a one-mile stroll to Park Avenue to immerse yourself in everything Winter Park has to offer. Enjoy the pool overlooking the lake, a fitness room, private boat ramp and community dock providing simple pleasures amidst the tranquil setting. Come live the laidback lakeside lifestyle!

Just Listed. Studio Apartment with utilities included, excellent location..in Winter Park, close to I-4.

Luxurious Winter Park Retreat with Stunning Features! Welcome to 1661 Hillcrest Avenue, a masterpiece of coastal design nestled in the heart of the highly sought after Winter Park. This exceptional property presents an exclusive opportunity to own a home crafted by the Parade of Home Winner, Lazarus Development Group. This elegant home boasts 4 bedrooms, 3.5 baths, and a 2 car garage. As you step inside, you are greeted by a bright open, airy ambiance that invites you to effortlessly call it your home. The first floor boasts a seamless open floor plan concept with Great American wire brushed oak throughout, featuring a sprawling great room with decorative Faux and woods beams, a soaring foyer that leads to a private home office space and, a classy dining area. A meticulously designed kitchen equipped with Viking appliances, including a refrigerator and stove, along with a KitchenAid dishwasher make this kitchen a culinary enthusiast's dream. The home features an electric blind on kitchen window and shutters throughout. A large walk-in pantry ensures ample storage space, while an indoor gas fireplace adds a touch of elegance and warmth. Escape to your own private paradise with the impressive outdoor amenities. Host unforgettable gatherings in the outside summer kitchen, where al fresco dining becomes a daily delight with a fireplace and pool footsteps away. Backyard has K9 turf for dogs from Forever Lawn. The rent price includes the maintenance of the lawn and pool! The second floor is dedicated to the luxurious master suite that will be your own private sanctuary at the end of the day. Need more space? This home includes an upstairs versatile flex space that can be tailored to your needs that'd be perfect for movie nights, a home theater, a game room or play area. For added convenience, the upstairs offers a laundry room. Presented in immaculate condition with custom shutters, a third floor balcony that has expansive views offering additional outdoor living. This home is ready for you to move right in and start living the life of luxury. Every detail has been carefully considered, from the sleek finishes to the abundance of natural light that fills each room. Located in one of Winter Park's most coveted neighborhoods, this property offers not just a home, but a lifestyle. Excellent schools, fine dining and boutique shopping options on Park Avenue and Baldwin Park, very close proximity to Park Ave, Art shows or Rollins College and, easy access to downtown Orlando make this the perfect place to call home. This is more than a home"it's an unparalleled opportunity to own the lifestyle you deserve and a piece of Winter Park's finest living.

Welcome to 120 Spring Lane. This modern, 1-story home is located in gorgeous Winter Park. From the moment you enter through the custom gate into the courtyard with reflecting pools and fountain - you will be impressed. This incredible Smart home has a spectacular, open floor plan with exquisite finishes though out. The home boasts 5 bedrooms, 5 full bathrooms & 3 half baths. Each bedroom has a walk-in closet. There is also a "hotel like' guest/mother-in-law suite with private entrance off the courtyard. The home is situated on huge, private lot and the outdoor space is just as impressive as the interior. It has massive sliding doors that pocket within walls to achieve a fully integrated indoor/outdoor space. Artificial turf terrace by the pool. Heated pool & spa (natural gas), Outdoor ice maker, Outdoor refrigerators x2, Natural gas grill, Sunken, Natural gas fire pit (outdoor) and Centralized outdoor Mosquito repellent system. The kitchen features an induction cooktop, Heating drawer, Convection oven, Large pantry, a Wine cellar with separate temperatures for white and red wines, Large outdoor lanai with electric sunshade Heated infinity pool and spa (natural gas), custom cabinetry, Butler's second kitchen in pantry and much more. Additional features include: Imported custom made 10' wooden doors throughout, Imported wood for all baseboards, Hurricane proof windows, Natural gas power generator, Automated electric shades in social areas, with a Surround sound system outside/master bedroom/living room/den and study room. Natural gas water heaters, Natural gas fireplace, Alarm system with security cameras, 2 Large A/C energy efficient units controlled with NEST system. This home can be be rented un-furnished or furnished. To rent furnished, the rent is $20,000/month and there will be an additional furniture deposit required.

Cozy remodeled 2 bed 2bath in Winter ParkBeautiful home located on a quaint, tree lined, brick street in desirable Winter Park. You will walk in a large family room with a wood burning fireplace and an open kitchen with beautiful new granite countertops and backsplach. Two bedrooms with walk in closets and a split bathroom with 2 vanities and 2 toilets. All new interior paint throughout. Kitchen was updated with custom backsplash and drop down soffits. The kitchen cabinets were also refreshed with paint and new hardware. Nice size Garage. This home is in close proximity to Park Avenue, Winter Park Village, Rollins College, the new Trader Joe's, WP Farmer's Market, Winter Park Community Center, the Central Park Sun Rail Train Station and zoned for Winter Park's outstanding schools. Grounds care included in rent. Pets accepted - pet feeIncome 3x the rentNo prior evictionsMust enroll in Resident Benefits package - more details upon request

Elegant Spanish 4 bedroom, 2.5 bathroom home. Beautifully updated Winter Park home. Enjoy all the luxuries and upgrades this home has to offer including triple crown molding, tall baseboards, refinished original hard wood floors, recessed lighting, French doors, paver driveway and newer windows though out with new plantation shutters. Large living room has a fabulous brick wood burning fireplace. There is extra living space in the front family room which has three huge beautiful windows that let in tons of natural light with new wood floors. The kitchen is updated with stainless steel appliances, solid wood cabinets, solid counter tops, marble backsplash, under cabinet lighting, wainscoting and gourmet 4-chair island kitchen features a stainless steel induction/convection stove, solid wood cabinets with solid stone countertops and Carrera marble backsplash. There is also a lovely eat-in area off the kitchen that is perfect for a kitchen table. There is a large dry bar complete with solid wood cabinets, stone counter tops and backsplash and wine fridge. The first floor master bedroom has a large walk in closet and plenty of space and natural light. The master bathroom has a built in jacuzzi tub, separate shower with multiple sprayers, pedestal sink and marble top vanity and separate commode. There is a door that leads to the back yard that has plenty of room for a pool. The wood staircase leads you to the other three bedrooms and second full bathroom. Each bedroom has a large walk in closets. The upstairs bathroom has been recently renovated with a large walk in shower, tile floors. There is also a linen closet for additional storage in the hall. The very large back yard can be accessed through the kitchen through a beautiful pair of French doors. There is also a storage shed, patio area off of the kitchen and patio off of the master bedroom. Newer triple pane low E-windows, roof: 2011 tile. ac: 2008, 16 seer, electrical: 2009, plumbing: pex. Centrally located to Rollins College and Park Avenue.

Tucked into a prime Winter Park location, on a brick-paved street, find your slice of retreat on Magnolia Ave. This well-appointed 4 bed, 3.5 bath pool home is being offered for mid-term rental through the end of the year (Min one month rental). Plenty of living nooks to spread out amongst the 4400 total sq feet; a beautiful scape outside including a secluded front lawn, a covered back patio with auto-screens, and multiple lounge spots by the well-designed modern pool area. The 3-level home is set up well for private and relaxed living. 2nd floor hallway Laundry room makes things easy. This coastal-chic abode includes a wine fridge, outdoor alfresco dining table, coffee bar, Viking appliances, pool floats, board games, 3 flat screen T.V.s, and outside sports games. Accessibility is key; minutes from downtown Winter Park and all of the first-class shops and restaurants one can fathom. You'll easily access Disney, Universal (31 min), and Florida beaches for quick day trips or weekend getaways. Utilities, weekly pool and lawn maintenance are included. Select Magnolia Ave as your home base for this summer! (Owner may consider longer tenancy.)

Move in Ready Spotless Rental with New Carpet! Located in beautiful neighborhood of million-dollar homes in Winter Park. One of a Kind! Lots of natural light inside the home. This single-family home has three carpeted bedrooms, and tile throughout rest of the home. It also has bonus room off the kitchen and could be used as an office. Enjoy leisurely break in the screened lanai overlooking a large paver patio and fenced yard. This home has all the appliances, ceiling fans, and LAWN SERVICE included in the rent. This home is ideally situated in quiet area of Winter Park with mature landscaping throughout the neighborhood which make walking or jogging a pleasant experience. The location has excellent access to main roads of Howell Branch and State Road 436. Take a 10 minute drive to famous Park Avenue enjoy the Restaurants, Museums, Post Office, Amtrak Stations, and Farmers Market every Saturday. Winter Park Village Movies, Restaurants, Home Goods, Ross, Marshalls, TJ Maxx, Walmart and YMCA are within 5-10 minute drive. There are so many grocery stores to choose from within a 5 to 10-minute drive, Publix, Sprouts, Trader Joes, and Whole Foods. Winter Park has its own library, and Winter Parks Advent Health Hospital is nearby. When traveling, Orlando International Airport is a 35-minute drive. What a great opportunity to live in an area with so much to offer.

Rare 1/1 Garage Apartment in Winter Park's College Quarter. Apartment includes a private 1-car garage, washer/dryer, landscaping and pest control. Offered at $1,800/mo this 2nd floor apartment has a large living space, full kitchen, oversized bedroom with full bath, and a walk out balcony. Unit comes furnished. No smoking. Pets will be considered and are subject to owner approval. Fantastic opportunity to live in the downtown Winter Park area, walking distance to Park Avenue, Rollins College and more.

RARE FIND - Walking Distance to Park Avenue - Charming 2/2 with 2-car garage near Rollins College! This beautiful 1940's bungalow has been updated and offers an open floorplan with 2 bedrooms and 2 full baths, complemented throughout by hardwood floors, a wood burning fireplace, arched entries, crown molding, corner built-ins, and more. The kitchen features newer cabinetry with granite countertops, stainless steel appliances, and a large pass thru window to the dining room. A detached garage provides a separate 2-car garage for secured parking and/or storage. Washer & dryer are included. Property also has a 1/1 garage apartment above the 1-car garage being offered at $1,800/mo. Both units can be rented together. Lawncare and pest control are included in the rent. No smoking allowed. Pets will be considered and are subject to owner approval. Tenants must carry renter's insurance and are responsible for all utilities. Home available 04/15/2024.

FURNISHED 6-9 month executive rental available immediately in Lake Killarney Condominiums. Perfect for one or two residents, this condo offers a bedroom with King size bed and walk in closet, a separate Office, and Sunroom with floor to ceiling windows. Brand new bathroom and central air. One dedicated parking space plus one open resident space. Residents will enjoy the private lakefront park, waterfront swimming pool and kayak. Located adjacent to the Trader Joe's plaza and only one mile to Park Avenue.

Discover Luxury Living in the Heart of Winter Park - Stunning 3 Bedroom, 2.5 Bathroom Townhome at 1761 Indiana Avenue!Welcome to your dream home nestled in the prestigious Winter Park community! Step into elegance and comfort with this magnificent 3-bedroom, 2.5-bathroom townhome. Offering a perfect blend of sophistication, convenience, and modern amenities, this residence is sure to exceed your expectations.Key Features:Elegant Interior Design:Experience luxury living at its finest with meticulously crafted interiors boasting high-end finishes, premium fixtures, brand new flooring throughout, brand new paint throughout, and exquisite attention to detail.Spacious Living Areas:Entertain in style with generously sized living areas that seamlessly flow from room to room, providing ample space for relaxation, gatherings, and everyday living.Gourmet Kitchen:Channel your inner chef in the gourmet kitchen featuring top-of-the-line appliances, sleek granite countertops, and custom cabinetry. Prepare culinary masterpieces with ease in this chef's paradise.Tranquil Bedrooms:Retreat to the serenity of the spacious bedrooms, each offering new plush carpeting, ample closet space, and large windows that fill the rooms with natural light. Unwind and rejuvenate in your own private sanctuary. Each guest bedroom has access to the 2nd story balcony as well!Luxurious Master Bathroom:Indulge in the spa-like ambiance of the meticulously designed bathroom, featuring modern fixtures, elegant tilework, oversized jet tub, and luxurious amenities that elevate your daily routine to a new level of comfort.Convenient Parking:Benefit from convenient parking options including a private 1 car garage with bonus spot out back and convenient street parking at the front ensuring hassle-free access to your residence at all times.Prime Winter Park Location:Ideally situated in the heart of Winter Park, this townhome offers easy access to a wealth of shopping, dining, entertainment, and recreational opportunities, allowing you to experience the best of the vibrant community. Located just 1-2 miles from the Fairbanks I-4 exit/on ramp!

Welcome to an unparalleled rental opportunity in Winter Park's prestigious Via Tuscany. Situated minutes away from the charming boutiques and eateries of downtown Park Avenue, this lakefront estate stands as a beacon of timeless elegance and historic significance. This distinguished property, dating back to 1919 and embodying the classic Georgian Revival style, occupies an impressive 1.57-plus acres gracefully perched above the tranquil waters of Lake Maitland. With 138 feet of coveted water-frontage, every moment here is adorned with breathtaking vistas from dawn to dusk. Immerse yourself in the grandeur of yesteryears seamlessly blended with modern comforts. Adorned with mature landscaping and a park-like backyard, this estate offers an enchanting ambiance for leisure and entertainment. Discover the allure of a gazebo, a sprawling lawn leading to the lake, a boat dock, an outdoor fireplace, and a captivating screened indoor pool. Step through the grand entry foyer into a world of refined living spaces, perfect for both intimate gatherings and lavish events. The first floor boasts an oversized living room, a formal dining room, a den, a study, a fully equipped kitchen, a breakfast room, a butler's pantry, and two sun porches. Ascend the dual staircases to find five bedrooms, four full baths, and numerous flex spaces, all adorned with timeless finishes and thoughtful details. The luxurious owner's suite exudes opulence, featuring a fireplace, a sitting area, oversized walk-in closets, a small bar area, elevator access, a private porch, and a rooftop terrace. Additionally, a charming guest cottage awaits, complete with a bedroom, a bath, a living room, and a kitchen, offering privacy and comfort to visitors. Ample storage is provided by the expansive attic and basement, complementing the four-car garage. With soaring ceilings, heart pine floors, plantation shutters, intricate millwork, and crown molding, every corner of this estate exudes sophistication and craftsmanship. Meticulously maintained and cherished, this property stands as a testament to quality and pride of ownership. With a total of 8,353 heated square feet, including 7,367 square feet in the main house and 986 square feet in the guest cottage, this residence offers unmatched living space in an unrivaled location. Seize the opportunity to experience the epitome of luxury living in Winter Park's most esteemed enclave.

Discover the allure of this Winter Park retreat! Nestled in a prime location, this delightful 3 bedroom, 2 bathroom abode boasts a sunlit open floor plan that invites comfort and relaxation. Adorned with warm wood flooring and custom millwork, the home exudes charm at every turn. The heart of this residence is its inviting kitchen, complete with ample counter space, abundant storage, and a cheerful window overlooking the lush surroundings. The expansive breakfast bar seamlessly connects the kitchen to the living spaces, making it an ideal spot for entertaining guests. Retreat to the owner's suite, where tranquility awaits with a beautifully tiled shower, dual sinks, and French doors leading to a serene backyard oasis enveloped by privacy hedging. Modern accents such as plantation shutters and sleek light fixtures complement the soothing paint palette throughout. Outside, a meticulously designed brick paver patio beckons gatherings with loved ones, while the fully fenced corner lot offers both privacy and tranquility. Nestled within a sought-after neighborhood, this gem resides in top-rated school zones and offers easy access to local amenities including AdventHealth Winter Park, Sprouts, and Publix shopping center. Explore the vibrant culinary and retail scene of Park Ave, or venture downtown Orlando just 20 minutes away. Embrace the quintessential Winter Park lifestyle in this captivating retreat! As part of Keller Williams' dedication to resident satisfaction, you'll have access to our exclusive Resident Benefits Package (RBP). This includes perks such as HVAC air filter delivery, renters insurance, credit-building opportunities, $1M Identity Protection, and utility concierge service, ensuring a stress-free move-in experience. Don't miss out on this exceptional opportunity!

Discover the epitome of convenience and comfort in this fully furnished 2-bedroom, 1-bathroom (1 extrabedroom) apartment located in the heart of Winter Park. With its prime location and array of amenities, this apartment offers a delightful living experience. Nestled at 151 N Orlando Ave APT 118, this apartment boasts a coveted location in Winter Park, offering easy access to a plethora of dining, shopping, and entertainment options. With parks, cultural venues, and transportation hubs nearby, everything you need is within reach.Don't miss out on this opportunity to live the Winter Park lifestyle to the fullest. Contact us today to secure your new home!

FURNISHED 6 to 12 month executive rental, available immediately in Lake Killarney Condominiums. Perfect for one or two residents, this second floor condo offers a bedroom with king size bed and walk-in closet, plus a sunroom with floor to ceiling windows and a large work desk. Open concept newer kitchen plus two 55" streaming Roku SmartTVs. European-style combination washer/dryer unit for small loads in unit, plus additional large capacity card-operated laundry room within building. One dedicated reserved parking space plus one open resident space per unit. Residents will enjoy the private lakefront park, waterfront swimming pool and access to a kayak for paddling on Lake Killarney. Located adjacent to the Trader Joe's plaza and only one mile to trendy Park Avenue. Sorry, no pets allowed.

This charming property, nestled in the heart of Winter Park, offers a prime location with easy access to all that Winter Park/Central Florida has to offer! This completely renovated 3 bed & 2 bath home is just a short distance from Winter Park Village, Park Avenue, public transit, the Sunrail, the Winter Park golf course, Whole Foods Market, Hannibal Square and so much more. The kitchen features . The bathrooms . Gorgeous porcelain tile throughout this light filled home. The large backyard is fenced, has a patio ready for your grill! The washer & dryer are inside, in a convenient utility closet right next to the kitchen. This home has newer AC to keep you cool in the hot, summer months.Winter Park is a fantastic place to call home, with so much to see and do! Call for your showing today!

Available now!!! Amazing 3 bedroom, 2.5 bath townhouse with quaint outside courtyard and all the charm! As soon as you step through the front door you will feel relaxed and excited to be home. Featuring an oversized kitchen, separate laundry room, attached garage, and lawn care included. All 3 bedrooms upstairs, walk in closet in primary bedroom, guest bath downstairs. Desirable locations close to restaurants, Park Avenue or Rollins campus. Convenient to Interstate 4 to make commuting through central Florida a breeze. Won't last long schedule a showing today! We offer Obligo for a no deposit option.

CURRENT PROMOTIONAL SPECIAL OFFER $1,000 off the first month's rent, along with waived application and administrative fees. Welcome to resort-inspired living at its best! Westmount at Winter Park presents a stunning opportunity to reside in the heart of vibrant Winter Park. Currently offering luxurious Three Bedroom Apartment Homes for immediate and future move-in dates, indulge in the epitome of upscale living. Introducing "The Park," our expansive Three Bedroom Floor Plan spanning 1,218 square feet of refined elegance. These newly renovated homes boast upgraded features such as granite countertops, stainless steel appliances, and hardwood-style flooring throughout. Stay organized effortlessly with spacious walk-in closets featuring built-in shelving. Step outside onto your screened-in patio or balcony and bask in the Florida sunshine. Nestled alongside a serene lake, Westmount at Winter Park harmonizes the tranquility of nature with modern conveniences. Discover a plethora of amenities designed for your enjoyment. Lounge by the resort-style pool, meander along lakeside trails, sway in hammocks, or cozy up next to fire pits. Your furry companions will relish the off-leash dog park, ensuring their happiness and vitality. Ideally positioned near I-4, Westmount at Winter Park provides a tranquil oasis amidst the vibrant Orlando area. Explore world-renowned attractions including Disney World, Universal Studios, Park Avenue, and Harry P. Leu Gardens, all just a stone's throw away. Closer to home, indulge in shopping sprees at Winter Park Village or evenings at the Enzian Theater. With esteemed institutions like Rollins College and Full Sail University nearby, experience the perfect blend of luxury and convenience at Westmount at Winter Park. Schedule your tour today and embrace a lifestyle of unparalleled sophistication and serenity. *** Rent price, promotions and availability are subject to change.

Embrace luxury living in Winter Park, Florida, with this stunning five-bedroom, five-bathroom rental home spanning over 4,200 square feet. Featuring a beautiful pool in the backyard, a stunning chef's kitchen, a bonus room upstairs, and spacious living areas, this two-story residence offers elegance and comfort. Located in the heart of Winter Park, you'll enjoy easy access to popular Park Avenue and a variety of great restaurants, bars, shopping centers, and grocery stores. Experience the best of Florida living"schedule a showing today!

Great location in Winter Park 32789 on an oversized 0.27 lot steps away from beautiful Lake Killarney. Charm radiates throughout this inviting 3 Bedroom, two & a half bath home. Open, bright, and spacious living and entertaining. The kitchen opens up to the breakfast area with views of the large fenced in backyard. The second story has three spacious bedrooms, two baths and a separate area that would be great for nursery or as an office, playroom or flex space. All wood flooring on the second floor including the stairway. Enjoy the lake breeze on your front porch swing with a cup of coffee or glass of wine at the end of the day. Close to Park Avenue, Winter Park Village, dining, entertainment and major highways to downtown Winter Park and Orlando. Call today to make your appointment.

MOVE-IN READY! WINTER PARK HOME! Experience the charm of this 1948 Winter Park gem located in Orwin Manor, a highly-desired neighborhood. This renovated 3 bedroom 2 bathroom home is the perfect place for anyone looking to live in easy commute to Downtown Orlando, Winter Park, and College Park. With great space, you'll have the perfect set up for a living room and dining room area. The kitchen has been remodeled with new appliances, bathrooms have been revamped, and the home has a new water heater & HVAC! Interior laundry room with a washer and dryer included!! Beautiful vinyl flooring throughout the house and great natural lighting! In addition to the home, take advantage of one of the biggest fenced-in backyard!! Those who live on Clay St. will appreciate the convenience of access to I-4. Find some of the best shopping, upscale restaurants, and cultural entertainment in the area. Enjoy being near Publix, Trader Joe's, and Whole Foods! Right down the road from Advent Health and a short drive to Park Ave, this truly is an ideal location. Don't miss out on this rental opportunity! Call to schedule an appointment today! Note: Two structures on property. Mother In law suite - tenant occupied.

Recently Remodeled Bottom Floor 2 Bedroom, 2 Bath Condo with Covered Patio, Community Pool, and Lakefront on Lake Killarney in a Park Like Setting. All Ceramic Tile Wood Look Floors throughout. All Kitchen Appliances, Community Laundry Room, and Reserved Parking. Rent includes Water, Sewer, Garbage, & Exterior Maintenance. Located off 17-92 across from Winter Park Village with Grocery Store, Upscale Restaurants, Movie Theater & More! Minutes to Advent Health & Downtown Orlando.