Apartments for Rent in Winter Park, FL

Fantastic condo! Ready move-in Aug 1st!! Super Location: 2nd floor 2/2 condo in sought-after Winter Park, walking distance from restaurants, grocery stores, etc... Convenient to Rollins College. You will love living in this small luxury complex that has been kept in superb condition. The condo is in a quiet setting with wood floors, vaulted ceilings, wood blinds, and a split floor plan. Enjoy the great Screened patio. Community features include a community pool and tennis. This complex is steps to shopping, The Mayflower, Wp Hospital, and Crealde with a short drive to down

ESTIMATED TOTAL MONTHLY LEASING PRICE: $1,099.95 Base Rent: $995.00 Filter Delivery: $5.00 Renters Insurance: $10.95 $1M Identity Protection, Credit Building, Resident Rewards, Move-In Concierge: $34.00 High Speed Internet $55 PROPERTY DESCRIPTION: Pool Access | Den/Flex Space | Clubhouse | Playground High Speed Internet $55 Discover the perfect blend of comfort and convenience at 7453 Daniel Webster Dr Apt D in Winter Park, FL. This charming apartment community offers a variety of floor plans, from studios to three-bedroom units, designed to accommodate diverse lifestyle

Property Status: Active LAKE KILLARNEY CONDO IN WINTER PARK! Enjoy the best of Winter Park living in this beautiful 2-bedroom, 2-bath corner condo in the private lakefront community of Killarney Bay. Featuring an open floor plan, stone and wood flooring, high ceilings, quartz kitchen countertops, stainless-steel appliances, generous storage, and a stunning stone-accented fireplace. Plus a utility room with a full size washer and dryer. The spacious primary suite offers an oversized walk-in closet and private bath, while the second bedroom features its own en-suite bath and

Property Status: Active Virtually Staged. Move right into this beautifully updated pool home in the highly desirable Winter Park Estates community, offering an exceptional combination of storage space, flexibility, and location. New A/C (2026), Freshly painted throughout (2026), New Kitchen Countertops coming soon (2026) this move-in-ready home features an open-concept layout filled with natural light, seamlessly connecting the living, dining, flex room and kitchen areas for effortless everyday living and entertaining. The spacious kitchen offers ample cabinetry, generous

Property Id: 2751801 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 Avenue

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

Let me present this Like new townhome in a gated new community in Winter Park. This immaculate 3 bed 2.5 bath townhome is ready to move-in. Massive 23x14 Master bedroom. Open concept family room opens to the kitchen / nook area. The downstairs dining area could be used as an office / den or add a closet for a 4th bedroom. A large loft is great for a computer area / play area. The Master bedroom has an oversized walk-in closet... ALL bedrooms have walk-in closets! Extra storage closets on both floors. One minute walk to the pool and community facility. A few minutes to Cost

Wonderful 1 bedroom, 1 bathroom half of a duplex for rent in the College Quarter neighborhood of Winter Park. The location is walking distance to Park Ave and Rollins College. Inside the property there is a spacious living and bedroom, kitchen with a stackable washer/ dryer and a bathroom. There are charming wood floors and a spacious closet. Outside there is a detached shed, perfect for storing bikes ect. Parking is behind the property or on the street.

Property Status: Active Luxury Living in Historic Winter Park. Amazing location in the heart of Winter Park and nestled within the historic Barbour House-a symbol of timeless elegance. This chic apartment offers a luxurious retreat just one block from the famed Park Avenue, where Winter Park's finest dining, shopping, and cultural experiences await. Step inside this meticulously designed space to discover a blend of modern luxury and historical charm. The apartment boasts exquisite decor and thoughtful touches, creating an inviting ambiance. Beautiful wood flooring flows t

Property Id: 439431 Property is right off of Aloma, fairly close to Park Avenue area. It is a 3 Bedroom, 2.5 Bath house, with newly installed wood floors and neutral paint throughout. It has a 2 car garage and a sun room as well as a small privacy fenced in yard. All three bedrooms are upstairs with the living and dining area being downstairs. Call Ben for showing 407-474-3485

Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue. Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage. Down the hall, you'll find three bedrooms and easy access to the spacious backyard, offering plenty of room to relax or entertain outdoors. Recent upgrades include, new carpet in all three bedrooms, a tub reglaze in the second ba

Discover your new home in this cozy 2-bedroom, 2.5-bathroom townhome! No one above or below you! Featuring an open-concept living area, updated kitchen, and private outdoor space, this inviting retreat is perfect for relaxation and entertaining. Conveniently located near shopping, dining, and parks, it offers the ideal blend of comfort and convenience. Don't miss out on this gem! Each bedroom has its own FULL bathroom!

Property Status: Active This two story 2/2.5 townhouse is in a securely located, private, gated Winter Park community and includes a private attached 1 car garage. This home features wood floors, carpet, and tile. All appliances are also included, including washer and dryer. For convenience, the laundry room is upstairs with the bedrooms. Strategically located in Winter Park, just minutes from 436, I-4, and the posh shops and fine restaurants of Park Avenue. *Bonus Amenity Included* - All residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which

Enjoy refreshed living in Winter Park! This updated duplex residence features all-new flooring, fresh paint, and a newly landscaped yard, creating an inviting place to call home. Conveniently located near Winter Park’s shopping, dining, parks, and entertainment, with access to top-rated schools, 401 Balfour Drive puts you close to everything the area has to offer. Available for lease—schedule your private showing today!

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

Winter Park 2 bedroom, 2 bathroom spacious, quiet condo with direct pool view in and 18 unit community. Amenities included: central air, central heat, dishwasher, pool, stainless steel appliance, updated kitchen, updated bathroom, storage, and laundry in building. Utilities included: water, sewer, and trash pickup. No pets, no smoking, no vaping. Currently Available. $2,000 security deposit required. Contact Rena Williams at 407-712-3874 to learn more. This property is managed by a responsible Owner/landlord.

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

COMPLETE UPGRADE - Winter Park condo, corner unit - available now! Beautiful and spacious condo with 2 bedrooms and 1 and 1/2 baths at the highly desirable Four Seasons Condominium. Tasteful upgrades throughout the entire unit, lots of light and spacious rooms. Beautiful kitchen with pantry and lots of extra storage space. Brand new stainless steel appliances and quartz countertops and backsplash. New flooring throughout the unit with tile on the first floor and laminate on the second- NO carpet. Both bathrooms were fully upgraded with a modern touch. Every detail was desi

Property Status: Active Welcome to this updated first-floor condo in the Waterfall Cove community of Winter Park. This 2-bedroom, 1-bath residence features new luxury vinyl plank flooring throughout, a bright and open living area, and a well-maintained air-conditioning system. The unit also offers an inside laundry area with washer and dryer. Community amenities include a swimming pool and playground. Conveniently located near shopping, dining, entertainment, major roadways, and Downtown Winter Park, with easy access to Downtown Orlando. Available for lease. Copyright © 20

Property Id: 502903 Amazing 3 bedroom, 2.5 bathroom house in Winter Park. Freshly painted home with vaulted ceiling throughout! Tile floor on 1st floor and carpet on 2nd floor. Spacious living room area. Great neighborhood with A+ Seminole County schools. Great location and close to schools, shopping and restaurants. Easy access to 436 and major highways. Amenities included: central air, central heat, dishwasher, hardwood floors, pool, washer dryer, yard, and washer and dryer, fenced in. Is not pet friendly. $2,550/month rent. $2,550 security deposit required. Looking f

Property Status: Active 2-bedroom, 2-bathroom first-floor unit with an open floor plan to the kitchen, living /dining area and breakfast bar. This lovely home includes newer Whirlpool stainless appliances, including Refrigerator, Microwave, cook top Range/oven, and Dishwasher. A washer and Dryer in the unit is included also. Steps from the community pool/clubhouse. Excellent school zone which includes desirable Winter Park High, and Glenridge Middle Schools. Shopping is close, Target and Publix are one block away, Costco (High quality and less expensive gas). Mere blocks f

Property Status: Active Available for move-in on 10/01. Welcome to this beautifully renovated 3-bedroom, 2-bathroom single-family home, perfectly positioned just minutes away from shopping, dining, and all the charm of Winter Park. This home combines modern luxury with everyday convenience. As you step inside, you're greeted by the elegance of Calacatta Quartz countertops, sleek waterproof flooring, and top-of-the-line appliances that set the tone for the entire space. The open layout flows seamlessly, making it perfect for both daily living and entertaining. With the late

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

Property Status: Active Welcome to this beautifully renovated 2-bedroom, 1-bathroom second-floor condo on picturesque Lake Killarney. This move-in-ready gem offers the perfect blend of modern conveniences and serene lakefront living. The stylish kitchen features granite countertops, a contemporary backsplash, and new stainless-steel appliances, including a dishwasher and a convenient combination washer/dryer. The bathroom is tastefully designed with a walk-in shower, while new luxury vinyl flooring flows seamlessly throughout the condo. A screened-in patio provides lake vi

This beautiful 2-bedroom, 2.5-bathroom, 2-Story condo located in the highly desirable Colonies community of Winter Park, Florida, offers 1,079 square feet of thoughtfully designed living space while featuring modern updates throughout, including durable tile flooring in the main living areas, crisp white cabinetry, and sleek stainless-steel appliances. The layout transitions seamlessly into a bright dining area equipped with a modern ceiling fan, and a convenient half-bath with a dedicated laundry area featuring a stacked washer and dryer. The spacious living room boasts l

Welcome to this 4-bedroom, 3-bathroom home nestled in the desirable Winter Park Pines area of Winter Park. This spacious residence features a well-equipped kitchen complete with all major appliances and an abundance of cabinet space, making it perfect for any home chef. The inviting den and family room serve as the heart of the home, featuring a cozy fireplace ideal for relaxing evenings. The common areas are finished with durable, stylish vinyl wood flooring, while the bedrooms offer the comfort of plush carpeting. There's also a washer and dryer for your convenience. Ste

Property Status: Active Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your back door for morning runs, bike rides, and everything in between. One of the standout features is having the Cady Way pool, pickleball courts, and beach volleyball courts all just a short walk away. The home is zoned for Brookshire Elementary School, Glenridge Mi

Adorable 3 bedroom, 2 bathroom one story home in Winter Park. Minutes from Baldwin Park and downtown Park Ave. The home has been beautifully renovated. There is a large backyard with paver patio area. Inside utility room with access to kitchen and carport area. Kitchen and family room are open to each other and boast plenty of built in storage. Designer light fixtures throughout the home.

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

Property Status: Active This charming 2-bedroom, 2-bathroom condo offers 1,018 sq. ft. of comfortable living space on the first floor in the desirable Parkview Village community in Winter Park. The unit features an open-concept living and dining area, a screened-in rare porch perfect for relaxation, and an inside utility closet with washer/dryer. Located just steps from the community pool, this condo is also ideally situated near shopping, dining, and top-rated schools. Enjoy easy access to Full Sail University, Rollins College, Baldwin Park, and major roadways like SR 436

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

Property Status: Active Exceptional luxury rental opportunity in the heart of Winter Park! Located along a beautiful tree lined brick street, this custom built residence offers an impressive combination of sophisticated finishes, generous living spaces and resort style outdoor living. Featuring 6 bedrooms, 4.5 baths and a 3-car garage, the thoughtfully designed two-story floor plan provides exceptional flexibility for everyday living, entertaining, working from home and hosting guests. Step inside to an open, light filled interior highlighted by beautiful wood flooring, cu

Property Status: Active EVERYTHING IS NEW! Available 9/1! Come see this beautifully renovated 3-bedroom, 2-bathroom townhome in highly sought-after Winter Park for yourself! With 1,332 sq. ft. of living space, this spacious two-story home is completely move-in ready and packed with updates including new flooring and updated fixtures, renovated kitchen with tons of storage, brand-new stainless steel GE appliances, renovated bathrooms, new roof, and a fenced backyard! Note washer and dryer and lawn service are included! Enjoy your morning coffee or unwind with a cold drink o

!PRICE DROP! Graceful, distinctive, and effortlessly inviting, 1403 Michigan Avenue captures the essence of modern Winter Park elegance. A distinctive Winter Park residence offering 4 bedrooms and 3.5 bathrooms, where timeless charm meets a fully elevated modern lifestyle. Beyond its inviting design and prime location, this home has been thoughtfully enhanced with features that bring comfort, convenience, and peace of mind to a new level. A newly added private swimming pool transforms the outdoor space into your own personal retreat; perfect for relaxed afternoons, eleg

Property Status: Active Whole apartment to your self. 2BR/2BA - This apartment has Good vibes - Cozy - Minutes away from everything !!! Really!!! Fully renovated Winter Park condo. What truly sets it apart, however, is the time you'll save. Centrally located, minutes from shopping, groceries, restaurants, universities, hospitals, entertainment, and everyday essentials. Believe-me you'll spend less time driving and more time on what's important to you. Used to live here and that's what I miss the most. Less than 9 min away: Target Publix Ross Dress for Less Full Sail Univer

Property Status: Active Discover refined living in the heart of Winter Park in this beautifully appointed 4-bedroom, 2.5-bathroom single-family pool home. Immediately to the right of the entryway, a beautiful private office provides a convenient and quiet space for working from home or studying. Filled with natural light, the home features an inviting open layout, and a spacious living area centered around a cozy fireplace. The stylish kitchen showcases light gray cabinetry, sophisticated gold-tone accents, a center island, and generous space for cooking and entertaining.

Property Id: 346094 First floor, spacious living area, quiet neighborhood, shaded and screened patio faces a courtyard/garden w/ seating. Incredible location short distance to Park Avenue, Rollins College, Trader Joes/Whole Foods/Publix, I4 exit, & shopping plazas. Ten minute drive to Downtown. -One reserved parking spot in front of unit door. Several visitor parking spots along side unit -Ramp or stair access -Community pool -On-site laundry facility with several machines -Zoned for Killarney Elementary School, Glenridge Middle School and Winter Park High School. FEES

Property Status: Active In the heart of Winter Park on a quiet cobbled street, this Mediterranean style 3-bedroom, 3-bathroom house is available to rent today. With beautiful Travertine floors throughout the downstairs of the home, granite countertop kitchen, marble countertop bathrooms, and limestone ornate pillars throughout the home, this home boasts character. Upstairs the home enjoys three bedrooms, two bathrooms, two balconies, and an upstairs utility room. The powder room is downstairs, and patio and a nice size back garden that the tenant can tend to as their own.

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 or to schedule your showing today, please visit www Specializ

Property Status: Active A Townhome for our times. Renovated and Made Ready; this luxurious 2 bedroom/2.5 bath residence includes a private attached garage and has been redesigned for today's needs. Securely located in a private gated Winter Park Community. "Eating In" takes on a Whole Foods new meaning with a gourmet modern kitchen. Upstairs, the Master Suite includes ample storage and a luxurious, light-filled bath. A large bonus area and a well-sized guest suite are perfect for a Home Office or guests and have vaulted ceilings, extra-large ceiling fans, and a renovated f

Property Status: Active 450 Canton Avenue - Winter Park, FL | $3,200/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

ONE MONTH FREE! Beautiful home located on a quaint, tree-lined brick street in desirable Winter Park. Step inside to a large family room featuring a wood-burning fireplace and an open kitchen with beautiful new granite countertops and backsplash. The home features two bedrooms with walk-in closets and a split bathroom with two vanities and two toilets. Fresh interior paint throughout gives the home a clean and refreshed feel. The kitchen has been updated with a custom backsplash and drop-down soffits, while the cabinets have been refreshed with new paint and hardware. T

A beautiful tile roof single-family house is available in Hawks Crest, the only gated community in Winter Park! UV sanitizing lights are installed in all bathrooms. A water filter system is installed in the kitchen sink. This 4-bed 3.5-bathroom plus an office and second-floor loft is ready to move in. When you enter the home, an open-concept floor plan leads you to the family room and the kitchen/nook area combined. 20-foot high ceiling family room with wide sliding doors to the back patio and high windows gives you plenty of natural sunlight. The large covered lanai woul