$1,890 Per Month
2510 Roxbury Rd, Winter Park, FL 32789
This beautifully renovated half-duplex is just blocks from Lake Killarney, ideally situated between College Park and the Winter Park shopping district. Enjoy quick access to local favorites like the Orlando Science Center, Winter Park Village, and Mead Gardens—all just minutes away.The home features 2 bedrooms, 1 bathroom, and a dedicated carport for convenient parking. Inside, you'll
$9,900 Per Month
1442 Palm Ave, Winter Park, FL 32789
Gorgeous 5-bedroom /6-bathroom Luxury Estate with Guest House & Pool in Winter ParkThis stunning two-story home offers the perfect blend of luxury and comfort right in the heart of Winter Park. At the center of the home is a beautiful open kitchen outfitted with high-end appliances, solid wood cabinets, and granite countertops . A true chef’s layout that flows into the living spaces. You'll
Magdalena Cuprys KELLER WILLIAMS REALTY AT THE PARKS
$3,150 Per Month
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
$2,095 Per Month
2028 Albert Lee Pkwy, Winter Park, FL 32789
This charming 3 bedroom, 2 bathroom home is located in the heart of Winter Park. Enjoy the best of Downtown Winter Park, 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 a spacious main living area, a lovely kitchen, dining room, large bedrooms, a cozy
Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
$1,895 Per Month
1100 Aragon Ave, Winter Park, FL 32789
1/1 Winter park cottage home with 1 car garage and private fenced in yard. This large renovated home has beautiful tile flooring throughout, a sunroom in the front of the home under air, a fully equipped kitchen including dishwasher, plenty of storage space, an included washer/dryer in the 1 car garage, central air-conditioning and a private fenced in yard. Enjoy walking to the many local
$4,677 Per Month
350 N Phelps Ave, Winter Park, FL 32789
Beautifully updated home in the heart of Winter Park - available November 1! Welcome to 350 North Phelps Avenue. This move-in-ready home offers four bedrooms, three full bathrooms, an open split floor plan, a bonus room with French doors, and a large fenced backyard, blending modern elegance with timeless charm. The house has a Tesla Level 2 fast charger and a state-of-the-art reverse osmosis
AJ Lash GOYAL & DECOSTER REALTY
$2,200 Per Month
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
$7,250 Per Month
1368 Hibiscus Ave, Winter Park, FL 32789
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
Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO
$1,800 Per Month
759 Antonette Ave, Winter Park, FL 32789
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
$2,500 Per Month
Unlisted Address
Rare Winter Park Lakefront Boathouse - $2,500/Month Experience the quintessential Central Florida lifestyle in this exceptional boathouse rental on the renowned Winter Park Chain of Lakes. This direct lakefront property offers unparalleled access to year-round water activities, from kayaking and paddleboarding to boating and fishing right from your doorstep. Positioned just off the scenic
Kelly Price KELLY PRICE & COMPANY LLC
$2,495 Per Month
720 Killarney Bay Ct, Winter Park, FL 32789
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
$1,800 Per Month
1107 S Pennsylvania Ave, Winter Park, FL 32789
Charming and well-maintained duplex for rent in Winter Park’s highly sought-after “College Quarter.” This 2-bedroom, 1-bath home features a spacious laundry room with washer and dryer included, and is filled with natural light thanks to energy-efficient double-pane windows. Located on a beautiful tree-lined brick street surrounded by luxury townhomes and lakefront estates, the property is just a
Simone Pinto de Almeida Santos NOVA REAL ESTATE SERVICES INC
$1,795 Per Month
731 W Comstock Ave, Winter Park, FL 32789
Close to downtown Winter Park, Winter Park Village, and Park Avenue - Charming 3 bedroom 1.5 bath home, with single carport, fenced backyard, ceiling fans and blinds. Tile floors in main living areas and NEW carpet in bedrooms. Additional sun room located off the kitchen with entry to/from carport. This home is available for immediate move in. PETS NEGOTIABLE. Please call to schedule an
$3,500 Per Month
1667 Mizell Ave, Winter Park, FL 32789
Welcome to your dream Winter Park home! This charming 3-bedroom, 3 full bathroom gem is the epitome of comfort and style. As you step inside, you'll immediately be captivated by the character and warmth this home exudes. The spacious living areas boast detailed archways, adding a touch of elegance and sophistication to the ambiance. Natural light floods the rooms, creating an inviting atmosphere
Justin V LaManna HOMEVEST REALTY
$8,900 Per Month
660 Osceola Ave, 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 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
$4,200 Per Month
1741 Mizell Ave, Winter Park, FL 32789
Discover refined living in the heart of Winter Park, where timeless luxury meets an unmatched lifestyle. This beautifully designed single-story residence offers three spacious bedrooms, a private office, two elegantly appointed baths and over 2,000 square feet of living space complete with a two-car garage. Thoughtfully curated with sleek tile flooring throughout and no carpeting, the home exudes
Farah Novin PREMIER SOTHEBY'S INTL. REALTY
$3,600 Per Month
2252 Howard Dr, Winter Park, FL 32789
SOLAR POWERED ... RENOVATED...WINTER PARK GEM! This lovely home features 3 bedrooms, 2 baths, stylish upgraded open concept kitchen, stainless steel appliance package, luxury vinyl plank floors and OH SO MUCH MORE! Private fenced back yard with deck, paver stone patios and entrance, 2 gated carports which can be used however you choose. And best of all Flat Fee Power $150 per month. Lawncare
$1,495 Per Month
1434 Minnesota Ave, Winter Park, FL 32789
Renovated two bedroom and one bath Midcentury Modern unit with a garage and laundry room located in the heart of Winter Park's industrial district.
Ruth Harris COLDWELL BANKER REALTY
$2,750 Per Month
2401 Albert Lee Pkwy, Winter Park, FL 32789
Gorgeous DIRECT LAKEFRONT 3/2 Mid-century Modern Style Home with a Covered Patio and a Large Backyard in the Desirable Albert Lee Ridge Community - Winter Park! Available Now!Nestled in Lake Wilderness is a hidden gem, with homes only lining one side of the lake offering picturesque sunsets and views. This gorgeous home welcomes you into a bright and airy living space with a floor plan
$4,579 Per Month
2341 Devon Ct, Winter Park, FL 32789
OWNER OFFERING A 10% DISCOUNT PER MONTH IF RENTED BY OCTOBER 1ST!!Welcome to your private Winter Park retreat! This beautifully updated home offers comfort, charm, and plenty of space to settle in and enjoy. Inside, you’ll find a bright and inviting layout with stylish finishes, cozy living spaces, a well-equipped kitchen, comfortable bedrooms, and thoughtful touches
Gabriel Cancel Rivera EXIT REALTY PREMIER LEGACY
$2,995 Per Month
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
$2,000 Per Month
1695 Lee Rd Unit E115, Winter Park, FL 32789
Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the
Yigit Orer EMPIRE NETWORK REALTY
$1,900 Per Month
151 N Orlando Ave, 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.This property offers a functional layout with comfortable living spaces, ideal for families or individuals looking for a practical and welcoming place to call home.
$1,900 Per Month
151 N Orlando Ave Unit 118, Winter Park, FL 32789
Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,
Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC
$2,899 Per Month
101 S Lakemont Ave, Winter Park, FL 32792
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
Robert Isaac Rodriguez RE/MAX DOWNTOWN
$8,500 Per Month
440 Clarendon Ave, Winter Park, FL 32789
Just a short stroll to Winter Park’s charming shops and restaurants, this beautifully updated home offers spacious living, high ceilings, plantation shutters throughout, white oak hardwood floors, and elegant crown molding. The home features updated primary suites on both the first and second floors, providing flexible living arrangements. The modernized gourmet kitchen includes a dine-in area
Meg Dolan FANNIE HILLMAN & ASSOCIATES
$2,295 Per Month
700 Melrose Ave Unit A5, 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
Nicole Howell FANNIE HILLMAN & ASSOCIATES
$2,400 Per Month
2809 W Fairbanks Ave, Winter Park, FL 32789
Updated and move-in ready 3-bedroom, 2-bathroom home conveniently located near the I-4/Fairbanks corridor in Winter Park. The spacious living and dining area features large sliding glass doors that open to a private patio and fully fenced backyard, creating a great space for relaxing or entertaining. The lovely, spacious kitchen has been thoughtfully updated with new appliances, new countertops,
Anne Coburn H. & H. REALTY, INC.
$7,500 Per Month
1750 Carollee Ln, Winter Park, FL 32789
Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the
Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY
$4,250 Per Month
544 N Knowles Ave Unit 540, Winter Park, FL 32789
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
Richard Traynor FLORIDA ONE REAL ESTATE LLC
$2,500 Per Month
800 W Canton Ave, Winter Park, FL 32789
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
Kelly Price KELLY PRICE & COMPANY LLC
$10,000 Per Month
1620 Palm Ave, Winter Park, FL 32789
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
Rob Gaudreau MAINFRAME REAL ESTATE
$1,450 Per Month
Unlisted Address
2 Bedrooms, 1 Bathroom located on the first floor. Galley 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.
Kirsten Cantello TRUSTHOME PROPERTIES INC
$5,600 Per Month
1136 S Pennsylvania Ave, Winter Park, FL 32789
Welcome home to this beautifully appointed end-unit Georgetown townhome in the highly desirable Virginia Heights community. Ideally located just minutes from Rollins College, Park Avenue, and the best shopping, dining, and entertainment that Winter Park has to offer, this exceptional residence offers the perfect blend of elegance, comfort, and convenience. Step inside to discover a bright, open
Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC
$1,600 Per Month
1695 Lee Rd Unit C103, Winter Park, FL 32789
Charming condo for Lease! location , Location , location ! This 2-bedroom, 1-bathroom apartment offers an open layout with plenty of natural light, a spacious living area, and a well-equipped kitchen with brand new interior paint job.Enjoy the convenience of in-unit laundry and modern amenities throughout. The apartment is situated in a serene community, offering easy access to shopping, dining,
Yigit Orer EMPIRE NETWORK REALTY
$1,600 Per Month
1695 Lee Rd Unit A113, Winter Park, FL 32789
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
Yigit Orer EMPIRE NETWORK REALTY
$3,995 Per Month
737 Minnesota Ave, Winter Park, FL 32789
Elegant Single Family Home Located in Winter ParkExquisite two-story home located in one of Winter Park's most desirable neighborhoods. This spacious residence boasts 3 bedrooms and 3.5 bathrooms, with each bedroom having its own private en-suite bathroom, as well as a convenient half bath on the main floor for guests.The primary suite is conveniently situated on the first floor, offering
Marilyn Kuczynski FLORIDA HOMES SALES & MANAGEMENT LLC
$8,900 Per Month
660 Osceola Ave Unit 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 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
Jennifer King CORCORAN PREMIER REALTY
$3,150 Per Month
1409 Michigan Ave, Winter Park, FL 32789
Move-in ready and freshly painted inside and out, this spacious 3-bedroom, 2.5-bathroom Winter Park townhome features a private 2-car garage and a prime location.The bright, open-concept floor plan features a generous main living area alongside a versatile front flex room - ideal for a formal dining room or a dedicated home office. At the heart of the home is a well-appointed kitchen boasting
Kyle Li UNIONE REALTY INC
$2,200 Per Month
1751 Westchester Ave, Winter Park, FL 32789
Move-in ready 3-bedroom, 2-bath home in a convenient Winter Park location just off Orange Avenue and minutes from Park Avenue. The home features updated vinyl flooring, fresh interior paint and fixtures, a kitchen with new appliances included, comfortable single-story layout, screened lanai, covered carport, and private backyard. Enjoy quick access to Downtown Winter Park, Park Avenue’s shops,
Ahmad Hassan COMPASS FLORIDA LLC
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