Apartments for Rent in Winter Park, FL

Property Status: Active Live in the heart of Winter Park, just steps from the city's most loved restaurants, cafes, yoga studios, and boutique shops. This beautifully renovated unit offers the perfect blend of walkability, comfort, and style. Zoned for top-rated Winter Park schools and within walking distance to a renowned private school, the location alone makes this an exceptional find. Inside, the home features a double-master layout, ideal for roommates, families, or anyone wanting extra space and privacy. Enjoy the convenience of in-unit laundry and the peace of mind

Property Status: Active BEAUTIFUL 3-BEDROOM, 2.5-BATH TOWNHOME WITH POND VIEWS AND A 2-CAR GARAGE IN THE GATED COMMUNITY OF GRAYSON SQUARE! This spacious CORNER-UNIT TOWNHOME offers additional privacy, generous outdoor space, and a thoughtfully designed floor plan, combining modern finishes with comfortable everyday living in a desirable Winter Park location. The bright and inviting OPEN-CONCEPT FIRST FLOOR features a spacious living and dining area, perfect for relaxing or entertaining. The BEAUTIFULLY APPOINTED KITCHEN showcases QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIA

Property Status: Active Charming 3-bedroom, 2-bath home situated on a corner lot in Winter Park. Features include a screened porch, spacious yard with lawn care included, and a 1-car garage. Conveniently located within walking distance to the Cady Way Trail and zoned for Winter Park High School. Pets are welcome with a pet fee and monthly pet rent. All Team Drawdy residents are enrolled in the Resident Benefits Package (RBP) which includes HVAC air filter delivery (for applicable properties), renters insurance, credit building to help boost your credit score with timely re

Move-in ready Townhouse For rent 3 bed - 2.5 bath ~ Excellent Winter Park Location! Prime townhome in Winter Park offers tranquil setting in a great location. This easy to maintain home has beautiful hardwood floors in the main living area, vaulted ceilings, breakfast bar and dining area. Home is very open and spacious. This three bedroom 3 and 2.5 half bathroom home. Spacious Master bedroom has designer featured tray ceiling and large walk-in closet. Master bath offers dual sinks, tub and separate walk-in shower. Enjoy your cup of coffee on the Open Patio overlooking gr

Property Status: Active This luxury rental offers something hard to find in Winter Park: single-story living in a 2024 custom build by Main Street Builders, with high-end finishes throughout. Adjacent to the Vias, this 4-bedroom, 3-bath pool home has an open layout with 10-ft ceilings, 8-ft doors, oversized baseboards and wood-look tile floors throughout. The kitchen is the centerpiece. It has a large quartz island, white shaker cabinets stacked to the ceiling with soft-close doors, a gas range with hood, a built-in microwave, a dishwasher and a walk-in pantry. It opens to

Property Status: Active Welcome to The Douglas Grand, just steps from Park Avenue in Downtown Winter Park. This 2-story, 2,900 sq ft condo features fine craftsmanship and modern comforts throughout. It features three spacious ensuite bedrooms with custom closets and ample storage. The gourmet kitchen has top-of-the-line appliances, including a wall-mounted convection and microwave ovens, a Wolf induction cooktop, and a breakfast bar. This is the only unit that has an air-conditioned storage room. The primary suite has a spa-like bath with a soaking tub, large walk-in showe

Discover your ideal living space in charming Winter Park, FL. This inviting property boasts a spacious layout designed for comfortable living. With well-appointed bedrooms and an expansive floor area, you’ll have plenty of room to relax and unwind after a long day. The home's proximity to a variety of excellent restaurants and department stores makes it a convenient choice for your everyday needs. Enjoy year-round comfort with central heating and air conditioning, complemented by ceiling fans throughout the property. This feature ensures that you stay cozy in the winter a

Property Status: Active Welcome to 2181 Linden Road, where modern updates meet the everyday convenience of Winter Park living. Thoughtfully renovated and designed with flexibility in mind, this home offers a versatile layout, contemporary finishes, and a private separate-entry suite that adds valuable space for guests, a home office, or additional living arrangements. With no HOA, the property offers added flexibility rarely found in this sought-after area. This lovely home is for rent and for sale. The location is a standout. Enjoy easy access to Winter Park's renowned Pa

Property Id: ACC3Z53V Welcome home to 2708 Lion Heart Road, a completely remodeled 3-bedroom, 2-bath pool home in Winter Park Pines, one of Winter Park’s most established neighborhoods. Mature oaks and a lamp-lit walkway lead to a classic single-story ranch home that has been updated from top to bottom. Inside, new light-oak wood-look flooring runs through bright, open living spaces with oversized windows that bring the outdoors in. The kitchen is the heart of the home. It has white upper cabinets, deep blue lower cabinets with brushed-bronze hardware, quartz countertops

Property Id: NZU8TBPJ Beautiful 1-Bedroom Condo for Rent in Winter Park Available Now! Enjoy comfortable living in this beautiful 1-bedroom, 1-bathroom condo located in the highly desirable Four Seasons Condominium Community in Winter Park. Conveniently situated at 200 St. Andrews Blvd, Winter Park, FL 32792, this condo offers an unbeatable location just minutes from AdventHealth Winter Park, Crosby Wellness Center, Rollins College, Full Sail University, Downtown Winter Park, grocery stores, restaurants, shopping, and major employers. Easy access to SR-436, Aloma Avenu

Property Status: Active MID-CENTURY CHARM MEETS MODERN LUXURY! Experience elevated Winter Park living in this beautifully remodeled 5 bedroom, 2 bath residence, offering approximately 2,750 square feet of thoughtfully updated living space on an oversized corner lot, where modern design, generous indoor and outdoor space and an ideal location come together to offer the best of the Winter Park - Baldwin Park lifestyle. Recently renovated with designer finishes throughout, this home offers a fresh, sophisticated interior with an open and inviting floor plan designed for both

Property Status: Active Back in the market. A rare find at an unbeatable price, this beautifully updated 4-bedroom, 3-full-bath townhome features brand-new laminate flooring throughout, fresh interior paint, a stylish kitchen with abundant cabinets, granite countertops and stainless-steel appliances, plus a new laundry room and tons of storage. The primary suite offers a private balcony, while the living room opens to a screened and covered lanai perfect for relaxing or entertaining. Updated bathrooms, generous living spaces, and convenient parking with a carport and space

LIMITED SPECIAL: Lease by 11/30/2026 and get your second months RENT FREE! Limited time ONLY Move right into this beautifully updated 1-bedroom, 1-bathroom home in the quiet, tree-lined Parkview Village community — 750 sq. ft. at an unbeatable Winter Park address. Wood-look plank flooring flows through the open living and dining area, leading to a private screened-in patio. The updated kitchen features white cabinetry, stainless steel appliances, and a breakfast bar, while the spacious bedroom offers a large walk-in closet. Enjoy mature landscaping, brick-paved streets,

Characterized by its blend of modern elegance and timeless charm, 1415 Harmon Avenue in Winter Park, FL, is the townhouse you've been dreaming of. With three spacious bedrooms, two full baths, and an additional half bath, this 1,753 sq ft home offers both comfort and convenience for any lifestyle. As you step inside, you'll be captivated by the spacious, open-concept design that allows natural light to flood the living spaces, creating a warm and inviting atmosphere. The thoughtfully designed layout ensures that every square foot is functional, making it ideal for both rel

Beautiful Vintage Condo Home For Rent! 2 Bed 2 Bath ( AVAILABLE MOVE IN NOW! ) Come View This Amazing 2 Bed 2 Full Bath Condo home for Rent in Orlando, FL! - HOME SWEET HOME! Welcome home to this spacious 2 bed 2 Full bath home! Wood Flooring all through out the home great for entertaining family and friends. The Open kitchen highlights a beautiful open concept. There is also 2 Full Bathrooms located in the home, makes it wonderful for a guest to come over and have access to their own private bathroom. As you make your way around the house you will find a spacious master s

*** Move-in Special - 50% Off 1st Month's Rent! ($725 Value) *** a Virtual Tour Video Is Available On Our WEBSITE! This property is managed by Amy Spano at ext. 224. 2-bedroom, 2-bathroom, 1st floor Winter Park Apartment. Conveniently located near Minnesota Avenue and Fairbanks Avenue, just minutes from Park Avenue, dining, shopping, and entertainment. This spacious apartment features a unique layout with a private bathroom connected to each bedroom. The front of the unit offers a comfortable living room, while the dining area is located just off the kitchen toward the re

Welcome to your dream rental home! Two separate master suites Electric car charger hook up Expansive open-concept floor plan Gorgeous quiet conservation area Located in a highly desirable, premier gated community, this spectacular 5-bedroom property offers luxury living with ultimate privacy. The backyard backs up directly to a protected conservation area, meaning you will enjoy serene, natural views with absolutely no rear neighbors. Inside, you will find an expansive, open-concept floor plan designed for modern living and effortless entertaining. Every single bedroom in

Beautifully upgraded 2-bedroom, 2-bath condo in the heart of Winter Park! Located in a sought-after 55+ community surrounded by mature, lush landscaping, this charming condo offers the perfect blend of comfort and convenience. Enjoy a short walk to Mead Botanical Garden or the shops, dining, and entertainment along Park Avenue. With easy access to I-4, downtown Orlando, hospitals, shopping, and everything Central Florida has to offer, this is Winter Park living at its finest!

Property Id: H9C2Y8YT Fully furnished private bedroom offers the ideal blend of comfort and convenience in a beautifully designed 3-bedroom, 2.5-bathroom two-story townhouse. Located in a gated community in the heart of Winter Park, FL, this home puts you minutes away from top local universities, vibrant downtown dining, and outdoor recreation. Enjoy a fully furnished private bedroom equipped with a Smart TV and access to shared streaming services. Gated community with keyless entry to the main living space and biometric fingerprint access to your private bedroom. Share

Welcome home to Parkview Village, a quiet 21-unit community in Winter Park just minutes from Orlando. This spacious 2-bedroom, 2-bathroom unit offers 1,022 square feet of comfortable living space — plenty of room to spread out. Enjoy the ease of a well-maintained community with responsive on-site management, and rest easy knowing this home is enrolled in our filter replacement program, so a fresh air filter is delivered right to your door. Conveniently located in Orange County, Parkview Village puts you close to Winter Park's shops and dining, with easy access into Orlan

Property Id: REDT55J4 Welcome to your dream home at 258 Balfour Street! This stunning 3 bed, 2.5 bath single-family property in Winter Park features modern amenities including dishwasher, washer, dryer, and more. With a spacious garage and central heatpump, this home is perfect for you. Don't miss out on this opportunity - schedule a viewing today! Call Ben 407-474-3485

Townhouse in Winter Park! Totally Renovated 3 bed 2 bath townhouse. Large Living room. Dinette off of kitchen. Updated kitchen with stainless steel appliances. Wash and dryer hook ups inside closet. Big master suite. Good size covered porch in back. Enjoy the 2 community pools, playground, tennis and shuffleboard courts! Good schools. Zoned for Lake Howell High School. Must see! This property offers an option of a security deposit-free lease using Obligo’s billing authorization technology for qualified tenants and well as a mandatory Tenant Benefit Package. *** Hoa requi

Property Status: Active Virtually Staged. STUNNING FULLY REMODELED CORNER-UNIT TOWNHOME IN THE HEART OF WINTER PARK! AVAILABLE FOR IMMEDIATE MOVE-IN - WATER INCLUDED IN THE RENT! Welcome to this beautifully renovated 2-bedroom, 2.5-bathroom, two-story Townhome featuring high-end finishes, gorgeous flooring, a modern kitchen with stainless steel appliances, and stylish upgrades throughout! The first floor offers a spacious living area, convenient half bathroom, and indoor laundry closet, while upstairs you'll find two comfortable bedrooms with full bathrooms. Enjoy the comm

Welcome home to this beautiful 2-bedroom, 2-bath, 2nd-floor condo in the desirable Parkview Village community near Semoran and Aloma! Offering an expansive and inviting layout, the kitchen opens seamlessly to the spacious living and dining areas, creating a comfortable space for both everyday living and entertaining. Off the living area, a sliding glass door leads to your private patio—the perfect spot to enjoy your morning coffee or unwind at the end of the day. The kitchen overlooks the living and dining rooms and features a full suite of upgraded appliances, including a

Property Status: Active Virtually Staged. Looking for a 3-bedroom rental in the Winter Park/Casselberry area? This home in Villas of Casselberry offers 2.5 bathrooms, a downstairs primary suite, and a fenced backyard with a screened patio. At approximately 1,397 square feet, the home features vaulted ceilings and large windows that bring natural light into the living and dining areas. The downstairs primary bedroom includes a private bathroom and walk-in closet. Upstairs, two additional bedrooms share a full bathroom, while a half bath downstairs serves guests. The kitchen

Property Status: Active PRICE ADJUSTMENT. Cozy two badroom two bathroom condo for rent with Specious living room and Updated kitchen. This Unit futures a huge balcony that runs the length of the condo. The master bedroom has balcony access, walk in closet and ensuite bathroom. The second bedroom has access to the other full bathroom. conveniently located close to Shopping center, airport, UCF, Valencia College, Full Sail University and more! Office Phone: (407) 621-1253 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker

1381 Orchid Ave is a beautiful 3-bedroom, 2.5 bath townhome in Winter Park! This home welcomes you into the main living area which features an open floor plan feel with the kitchen overlooking the spacious living area. The kitchen has an entire suite of stainless-steel appliances including the refrigerator, range, microwave and dishwasher. Continuing upstairs, all bedrooms and both full baths are located on the second floor. The master suite features a walk in closet and en-suite bathroom, with dual vanities and glass enclosed shower. Additional bedrooms feature spacious c

Property Status: Active Enjoy the best of Winter Park living at 1751 Westchester Avenue! Ideally situated in the charming Orwin Manor neighborhood, just minutes from Park Avenue, this move-in-ready 3-bedroom, 2-bath residence offers the perfect blend of comfort, privacy, and convenience. Inside, an inviting single-story layout features updated vinyl flooring, fresh interior paint, updated fixtures, and a refreshed kitchen complete with new appliances. Step outside to a screened lanai overlooking a private, fenced backyard, offering an inviting space to relax and unwind. Ad

Property Status: Active Prime Winter Park rental opportunity! Conveniently located near top universities, shopping centers, restaurants, and major highways, this well-kept apartment delivers exceptional comfort and accessibility. Community amenities include a swimming pool and landscaped common areas. Pets considered on a case-by-case basis with size approval. Prompt scheduling is recommended, reach out today to set up your private walkthrough! Office Phone: (407) 587-9241 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/brok

Charming 2 Bed / 2 Bath Condo in Winter Park Villas – Water Included in rent! Welcome home to this charming 2-bedroom, 2-full-bathroom condo located in the desirable Winter Park Villas community. Designed for comfortable and convenient living, this bright and inviting home features durable tile flooring throughout, ceiling fans, and large windows that fill the space with abundant natural light. The fully equipped kitchen comes complete with an electric range, refrigerator, dishwasher, microwave, garbage disposal, and plenty of cabinet storage. Enjoy the ultimate convenie

Property Status: Active Lakefront 3 Bed/2 Bath Home on pristine 137-acre private ski and fishing lake in sought-after Winter Park (Seminole County) with a newly renovated dock. Located on a quiet, dead-end road, adjacent to Bear Gully Point with a private boat ramp, renovated dock, and huge, open backyard. Faces east for amazing sunrises and perfect views of Cape Canaveral launches and is 5 min walk to access Seminole County Bike and Running Trails. Located conveniently to the most exclusive private schools, Trinity Prep, Master's Academy,and Seminole County's best public

Property Status: Active Welcome to your Florida retreat! This beautifully maintained 3-bedroom, 2-bath home offers a bright, open floor plan perfect for both relaxing and entertaining. Enjoy a spacious living area filled with natural light, a modern kitchen with sleek finishes, and a serene primary suite with a private bath. Step outside to your fenced backyard-ideal for weekend BBQs or simply soaking up the Florida sunshine. Conveniently located near top-rated schools, shopping, dining, and Orlando's world-famous attractions, this home offers the perfect balance of comfor

SPECIAL!1 $300 OFF THE 1ST MO RENT IF YOU SIGN A LEASE BEFORE 11/30! This Spacious 3bd/2ba home with a fenced yard is located in the community of Winter Green in Winter Park. The Home has a Livingroom/dining room combo with tile and carpet flooring throughout. Kitchen appliances include: Refrigerator, range and dishwasher. Large master bedroom that has a walk-in closet and spacious master bath. Community amenities include: Community pool and tennis courts. VIRTUAL TOUR:https www insidemaps com app walkthrough-v2 ?projectId=twiThpsWDc&env=production To apply for this

Property Status: Active 450 Canton Avenue - Winter Park, FL | $3,000/mo Charming and spacious, this beautifully located rental sits just 2 blocks from Park Avenue, offering walking-distance access to Winter Park's best restaurants, boutique shopping, and Winter Park Village - plus easy access to the Winter Park Train Station for effortless commuting. Step inside to find a thoughtfully laid-out floor plan featuring a front living room with a cozy wood-burning fireplace, a separate family room, formal dining room, and a versatile den just off the dining area - perfect for a

Property Status: Active A charming community in the heart of Winter Park. Spacious, modern interiors welcome you inside, as a collection of convenient resident amenities allows you to relax and enjoy residential life in style. Fully equipped kitchen opens into a spacious living room. Throughout your community, you'll find elevated amenities designed to complement your day-to-day. Enjoy a relaxing happy hour in the central Zen Garden, or a lively afternoon barbecue with neighbors at the outdoor grills. You'll also have access to on-site washer and dryer facilities for seaml

Experience the best of Winter Park waterfront living in this beautifully updated ground-floor residence at Perle du Lac, ideally located just a short stroll from the boutiques, restaurants, and cafés of Park Avenue. Even more rare, this exceptional residence includes a private covered boat slip on the pristine waters of Lake Virginia, offering direct access to the renowned Winter Park Chain of Lakes. Offering just over 2,700 square feet of thoughtfully designed living space, the home features freshly painted interiors, hardwood and travertine flooring, and elegant custom m

Property Status: Active PERFECT FOR ROOMMATES AND SMALL FAMILIES! Spacious 2-bedroom townhome-style condo in desirable Winter Park; each bedroom has its own bathroom for added privacy and convenience. Enjoy NEW APPLIANCES, in-unit washer & dryer, central A/C, designated parking, community pool, playground, and a PRIVATE FULLY FENCED PATIO perfect for relaxing or entertaining. Excellent location, approximately 5 minutes to Full Sail University and convenient to Barry University Dwayne O. Andreas School of Law, UCF, Valencia College, and Rollins College. Close to shopping, r

Property Status: Active Welcome to breathtaking waterfront living at Lake Virginia Condo community in Winter Park. Gorgeous water views from every room in this fourth floor, 915 sqft, 1-bedroom, 1.5-bathroom end unit overlooking Lake Virginia and the Lake Virginia-Osceola Canal. Step inside and immediately you're greeted by Lake Virginia through the large floor to ceiling sliders. The roomy bedroom and bathroom provide comfort and convenience, while a private balcony off the master bedroom invites you to unwind by the water. The L-shaped kitchen is large enough to cook and

Property Status: Active A charming community in the heart of Winter Park. Spacious, modern interiors welcome you inside, as a collection of convenient resident amenities allows you to relax and enjoy residential life in style. Fully equipped kitchen opens into a spacious living room. Throughout your community, you'll find elevated amenities designed to complement your day-to-day. Enjoy a relaxing happy hour in the central Zen Garden, or a lively afternoon barbecue with neighbors at the outdoor grills. You'll also have access to on-site washer and dryer facilities for seaml

You will receive an Email Response within 24 Hours of your Online Inquiry Please Check your Email! Great End Unit 3/2 Townhome, Open Floor Plan on First Floor, One car garage, View of Pond and Conservation area in back. Close to Shopping, Restaurants. Sorry- no smokers, no pets, no college students. Available to See Soon.

Property Status: Active This active, single-family rental listing at 7033 Easter St, Winter Park, FL 32792. This spacious residence features a 4-bedroom, 3-bathroom split floor plan spanning 2,151 heated square feet, situated on an expansive, fenced 0.76-acre lot down a quiet, unpaved lane. The exterior highlights include a private, screen-enclosed swimming pool (with chemical and pool maintenance fully covered by the landlord), a massive backyard, and three dedicated storage sheds perfect for equipment or hobbies. Inside, the home offers open-concept living spaces, dual m

This updated Winter Park gem offers a bright, inviting layout in a highly sought-after location just minutes from Park Avenue. Unit G features a comfortable living area with plenty of natural light, a well-appointed kitchen, and a spacious bedroom designed for easy everyday living. The community has a clean, well-kept feel, with convenient access to shopping, dining, Rollins College, and major roadways. If you’re looking for a charming, move-in-ready space in one of Central Florida’s most desirable neighborhoods, this unit delivers a great blend of comfort and convenience.

Property Id: FYSP5VU5 QUIET. CLEAN. CLOSE. Welcome to 741 Minnesota Ave at The Crossing at Winter Park, a spacious 3-bedroom, 4-bathroom, two-story single-family home in a quiet, well-maintained Winter Park community. With a modern open-concept floor plan, private bedroom suites, excellent storage, and a convenient location near Park Ave, UCF, Full Sail University, Rollins College, AdventHealth, Orlando Health, parks, shopping, dining, and recreation, this home offers space, privacy, and convenience in one great location. The first floor features a bright open-concept liv

Property Status: Active Welcome to 800 W. Canton Avenue, a very cute and very clean 2 bedroom, 1 bath home in the heart of downtown Winter Park! This charming rental offers a comfortable living room plus a separate den that works beautifully as a home office, family room, or flex space. Fresh paint, tile flooring throughout, and updated appliances give the home a bright, move-in ready feel. The full bath features a tub/shower combo, and a dedicated indoor laundry room adds everyday convenience. Step outside to a little back patio overlooking a nice, big backyard with plent

Welcome to this beautifully updated 3-bedroom, 2-bathroom home, thoughtfully designed with modern finishes, abundant natural light, and comfortable spaces for everyday living and entertaining. The entire home features luxury vinyl flooring, creating a stylish and cohesive look throughout. The recently updated kitchen is truly the heart of the home, showcasing crisp white cabinetry, elegant white quartz countertops, and stainless-steel appliances, a perfect setting for anyone who enjoys cooking and entertaining. The living room provides plenty of room to welcome family an

Move in ready condo for rent at Parkview Village Condominiums in Winter Park This unit boasts: -Carpet Throughout -Stainless steel appliances -Granite Counter tops in the Kitchen -Washer and dryer -Second floor unit -Community is conveniently located across the street from Full Sail University, and just minutes from Downtown Winter Park 12 - Month Minimum Lease $85 Non-refundable Application Fee (18+) Please note, we require all applicants to have - a combined monthly, net household income of 3x the monthly rent, - good standing credit - minimum score of 600, - and no p

Property Status: Pending Nestled within the gated community of Hawks Crest, this meticulously maintained 4 bedroom 3 bath ONE story home offers a timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan creating a seamless flow throughout the home. Luxurious white ceramic tile spans the home, enhancing th

55+ Senior Living in Winter Park 100% off rent for 2 month(s) on a 12 mo lease Other Concessions: Up to 2 Months base rent free on select units, Enjoy comfort, style, and an active lifestyle in a beautiful 55+ community in Winter Park! ✨ Explore modern one- and two-bedroom apartment homes featuring stylish finishes, contemporary appliances, and thoughtfully designed living spaces. Residents can enjoy a welcoming clubhouse, fitness center, engaging activities, and a vibrant social calendar—all supported by a dedicated onsite management team. 📍 Winter Park, Florida 🏡