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Homes & Apartments for Rent in Winter Park, FL 32789

1-20 of 30 rentals

Townhouse for rent at 1381 Orchid Ave, Winter Park, FL 32789

1/20

Featured

Managed by Innovative Realty

$2,995

$3,045/mo with required fees

Townhouse3 Beds2.5 Baths1,744 ft²

1381 Orchid Ave

Winter Park, FL 32789

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 closets and have easy access to the second full bath.

1/20

Featured

Managed by Wilson Management Group

$1,495

$1,545/mo with required fees

Apartment2 Beds2 Baths953 ft²

1111 Washington Ave #3

Winter Park, FL 32789

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 rear of the apartment. The unit includes two assigned parking spaces.

1/15

Featured

Managed by TrustHome Properties

$1,350

$1,409/mo with required fees

Apartment2 Beds1 Bath881 ft²

1695 Lee Rd #A103

Winter Park, FL 32789

2 Bedrooms, 1 Bathroom located on the first floor. IGalley kitchen (with a dishwasher, microwave, range, refrigerator, and a washer/dryer combo), walk-in closet in the primary bedroom, and an open living/dining room combo filled with natural light. A private patio, playground, and park. It includes 1 assigned parking space. We're offering a refund on Application Fees (2 Max) for approved applicants after move-in and Move and receive Half Off your 3rd month's rent. 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 Resident Benefit Package.

1/10

Managed by Cameron Stevens

$1,750

House3 Beds1.5 Baths1,024 ft²

731 W Comstock Ave

Winter Park, FL 32789

Charming Winter Park Home - Fenced Backyard & New Bedroom Carpet. Available For Immediate MOVE-IN. Enjoy the convenience of living close to Downtown Winter Park, Winter Park Village, and Park Avenue, with shopping, dining, entertainment, and everyday conveniences just minutes away. This charming 3-bedroom, 1.5-bath home offers comfortable living with a practical floor plan and great features throughout. The main living areas feature easy-care tile flooring, while the bedrooms have NEW carpet for added comfort. Additional features include: 3 bedrooms and 1.5 bathrooms. Single-car carport. Fenced backyard - great for enjoying your outdoor space. Ceiling fans and blinds throughout.

1/10

Managed by Florida Dreams Realty Group

$1,900

House3 Beds2 Baths1,500 ft²

151 N Orlando Ave #118

Winter Park, FL 32789

Discover this affordable and well-located 3-bedroom, 2-bathroom home in the desirable Winter Park area, perfect for those seeking comfort, convenience, and long-term stability. Amenities: Pet Fee.

1/10

Managed by Fannie Hillman + Associates

$1,995

Condo2 Beds2 Baths1,074 ft²

700 Melrose Ave #A-5

Winter Park, FL 32789

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.

1/10

Managed by Homevest Management

$1,800

Townhouse2 Beds1 Bath805 ft²

1618 Indiana Ave

Winter Park, FL 32789

Minimum Deposit $1800. Rent $1800. Water and Lawncare Included in rent price. Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been established Freshly reimagined and ready for its next resident, this newly remodeled duplex in the heart of Winter Park pairs modern updates with an unbeatable central location. Offering two bedrooms, one bathroom, and 805 square feet of thoughtfully arranged living space, this half of a charming duplex feels both smart and welcoming from the moment you step inside.

1/8

Listed by Alicia Alvarado

$1,900

Condo2 Beds2 Baths1,000 ft²

1250 S Denning Dr

Winter Park, FL 32789

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. $50 Condominium Application fee p/person. $800 Refundable Security Deposit. $100 Cleaning Move Out Fee, deducted from security deposit at end of lease.

1/10

Managed by Citron Property Management

$2,100

House3 Beds2 Baths1,158 ft²

301 S Capen Ave

Winter Park, FL 32789

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 bathroom, and a regrouted/stained primary shower.

1/10

Managed by PMI Property Alliance

$2,995

$3,007.95/mo with required fees

House3 Beds2 Baths

2545 Madeline Ave

Winter Park, FL 32789

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 and friends, while a custom-built bar with a wine cooler adds a unique touch and creates the perfect spot for entertaining.

1/10

Featured

Managed by C F R P Realty

$1,800

Townhouse3 Beds3.5 Baths1,413 ft²

235 Sandlewood Trail

Winter Park, FL 32789

Welcome home to this great 3 bedroom, 3.5 bath, 3 story townhome in Winter Park. The kitchen is open, light and bright with all appliances, a breakfast bar and is open to the living room/dining area. The living room features a fireplace and sliding glass doors that open out onto the screened porch. Downstairs you will also find the half bath for guests. The primary bedroom is located on the third floor and features a private balcony with wooded view and walk-in shower stall. The other 2 bedrooms and bathrooms are upstairs on the second floor.

1/5

Managed by Real Property Management & Realty

$1,195

House1 Bed1 Bath620 ft²

1600 Indiana Ave

Winter Park, FL 32789

Available Now. This 1 bedroom, 1 bathroom home is located in the heart of Winter Park. Enjoy all Downtown Winter Park has to offer, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include tile throughout the main living area, dining room, utility room with washer/dryer hookups, and a carport. Water is included. At RPM Realty, we're here to make your time in the home as enjoyable and convenient as possible.

1/10

Listed by a leasing agent

$4,950

House4 Beds3 Baths2,406 ft²

1580 Oakhurst Ave

Winter Park, FL 32789

Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park. This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are welcomed by an abundance of natural light filling the entryway, dining room and formal living room. The inviting family room includes a stylish wood burning fireplace and French doors that lead out to the backyard.

1/10

Listed by a leasing agent

$2,880

House3 Beds2 Baths1,496 ft²

2992 Chantilly Ave

Winter Park, FL 32789

Welcome to this inviting 3-bedroom, 2-bath single-family pool home. In addition to the main living areas, the home features a large bonus room that can easily be used as an extra bedroom, game room, home office, or entertainment space to fit your lifestyle. Enjoy year-round relaxation in the bright sunroom, which opens directly to the private pool, creating the perfect indoor-outdoor living experience. The spacious backyard provides plenty of room for entertaining, play, or simply unwinding. Lawn and pool maintenance are included in the rent, allowing you to enjoy the home without the hassle of upkeep.

1/10

Managed by Atrium Management Company

$4,195 - $4,995

Townhouse3 Beds3.5 Baths1,846-1,965 ft²

Oxford at Winter Park

700 Annesley Place, Winter Park, FL 32789

Limited Special: Lease by 12/31/2026 and get your second months Rent Free. Limited time ONLY. The Phelps is a three-bedroom, two-and-a-half-bath townhome designed for the way people actually live - with room to spread out across two floors without sacrificing that connected, neighborhood feel. An open main level keeps entertaining easy, while the upper level gives each bedroom its own space. It's the right size for families, roommates, or anyone who just wants a little extra breathing room. Rental Requirements: Combined gross household income of at least 3 times the monthly rent. Minimum 600 credit score.

Townhouse for rent at 307 Sandlewood Trail, Winter Park, FL 32789

1/10

Price cut $45

Managed by Real Property Management & Realty

$1,850

Townhouse2 Beds2.5 Baths960 ft²

307 Sandlewood Trail

Winter Park, FL 32789

Available Now. This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy all Winter Park has to offer, Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a gorgeous kitchen with quartz countertops and breakfast bar, a lovely primary suite with custom bathroom finishes, laundry closet, and a rear patio. Community amenities include a pool.

1/10

Managed by Susan Lattimore

$2,500

House5 Beds3 Baths2,472 ft²

2612 Roxbury Rd

Winter Park, FL 32789

Beautifully updated 5-bedroom, 3-bath home featuring a private 2-bedroom, 1-bath in-law suite with its own entrance-ideal for extended family, guests, or a home office. The main home offers an open-concept layout with luxury plank flooring, fresh neutral paint, abundant natural light, and a designer kitchen featuring shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances. Enjoy the spacious Florida room, perfect for relaxing or entertaining. Conveniently located just a 3-minute walk to Killarney Elementary, a 10-minute walk to Lake Killarney, only 2 minutes from I-4, and 10 minutes from Park Avenue in Winter Park.

1/10

Managed by Citron Property Management

$8,500

Apartment3 Beds3.5 Baths2,714 ft²

660 Osceola Ave #101

Winter Park, FL 32789

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 cafes 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 millwork throughout.

1/20

Featured

Managed by Lukasz Sokolowski

$3,400

Townhouse3 Beds2.5 Baths1,753 ft²

1415 Harmon Ave

Winter Park, FL 32789

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 relaxation and entertaining.

1/10

Featured

Listed by Nicole Smith

$3,995

House3 Beds3.5 Baths1,810 ft²

741 Minnesota Ave

Winter Park, FL 32789

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 living and dining area connected to a spacious modern kitchen with stainless steel appliances, abundant cabinetry, generous counter space, and a breakfast bar.

Viewing 1-20 of 30 rentals in 32789

What to Know About

Life in Winter Park & Beyond

Winter Park shares many of the great qualities that make Florida a desirable place to live.

Florida is a sunshine-filled state known for its beautiful beaches, warm weather, and world-famous theme parks like Walt Disney World, Universal Studios, and Sea World. From its iconic beaches to vibrant cities, you have a unique blend of outdoor adventure and urban excitement. Explore the state's past by visiting attractions like the Kennedy Space Center, the Museum of Florida History, or the Perez Art Museum Miami. In addition, Florida is home to renowned universities such as the University of Florida and Florida State University, University of Miami.

With hundreds of miles of sandy beaches, crystal-clear springs, and lush everglades, Florida is a paradise for visitors and residents alike. The state is also home to several professional sports teams, including the Miami Dolphins (NFL), Tampa Bay Buccaneers (NFL), Florida Panthers (NHL), Tampa Lighting (NHL), Miami Marlins (MLB), Orlando Magic (NBA), and Miami Heat (NBA). Experience all that Florida has to offer, from its stunning beaches and vibrant atmosphere to its rich traditions and thriving economy.

Discover the magic of living in Florida, where the sun shines bright, the economy thrives, and the quality of life is unparalleled, making it the perfect place to call home.

Rental Market Trends

Winter Park, FL

View full report

As of November 2026, Winter Park's rental market is balanced, with rentals spending about 36 days on the market, slower than in Florida (30), and rents down 1.7% over the past year. Winter Park's average rent is 11.7% ($303) lower than the Florida average of $2,584 and 12.0% ($245) higher than the U.S. average of $2,036.

Average Rent

$2,281

Monthly ChangeMonth Over Month Change

0.34% ($8)

Yearly ChangeYear Over Year Change

1.7% ($40)

Days on Market

Unit Type	Average Rent	Monthly ChangeMonth Over Month Change	Yearly ChangeYear Over Year Change
1 Bed	$1,364	0.56% ($8)	3.5% ($49)
2 Beds	$1,742	0.01%	1.1% ($19)
3 Beds	$3,009	0.79% ($24)	0.2% ($5)

Nearby Cities	Average Rent	Avg. Rent vs. Winter ParkAverage Rent vs. Winter Park	Days on Market
Maitland	$1,931	15.3% ($350)	34 days
Fern Park	$2,428	6.4% ($147)	33 days
Casselberry	$1,692	25.8% ($589)	35 days
Altamonte Springs	$1,546	32.2% ($735)	36 days
Winter Springs	$1,919	15.9% ($362)	34 days

Based on rentals advertised on RentalSource in and around Winter Park.

Frequently Asked Questions

Winter Park Rental Market FAQs

Explore rental prices, market conditions, and affordability in Winter Park, FL.

What is the average rent in Winter Park, FL?

The average rent in Winter Park, FL is $2,281 per month.

What is the average rent for different bedroom sizes in Winter Park, FL?

In Winter Park, the average rent is $1,364 per month for a 1-bedroom home, $1,742 for a 2-bedroom home and $3,009 for a 3-bedroom home.

How do rent prices in Winter Park, FL compare with the national average?

The average rent in Winter Park is 12% ($245) higher than the national average of $2,036 per month.

How competitive is the rental market in Winter Park, FL?

The rental market in Winter Park, FL is currently balanced, with rentals spending about 36 days on the market, slower than in Florida (30), and rents down 1.7% over the past year.

Can I afford to rent a home in Winter Park, FL?

Based on the current averages, a household would need an annual income of $69,700 to comfortably afford a 2-bedroom home in Winter Park.

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