$2,975 per month
- 3 Beds
- 2 Baths
- 1,195 Sq Ft
- House for Rent
1891 Oglesby Ave, Winter Park, FL 32789
1891 Oglesby Ave, Winter Park, FL 32789$2,975 per month
1891 Oglesby Ave, Winter Park, FL 32789
1891 Oglesby Ave, Winter Park, FL 32789$1,799 per month
151 N Orlando Ave Unit 101, Winter Park, FL 32789
151 N Orlando Ave Unit 101, Winter Park, FL 32789$1,775 per month
2420 Euston Rd, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Beautifully mainted and move-in ready home available for rent in a convenient location. This property features a bright and inviting interior with functional layout, spacious living areas, and well-sized bed rooms. The home offers a clean feel with plenty of natural light throughout, creating a comfortable and welcoming environment. Enjoy a private
Paula Wells PRIMAC GROUP, INC
$1,450 per month
1555 Michigan Ave, Winter Park, FL 32789
Are you looking for a spacious 1 bedroom 1 bathroom unit to call home? This home features its own washer and dryer, a large bedroom and living room, a spacious kitchen with ample countertop space, plenty of cabinets. The back sunroom would make a great office or a bright sitting area. The home is located 1 mile from Park Avenue. In addition, the home is located within walking distance of
Troy Hensley BHHS FLORIDA REALTY
$5,250 per month
1640 Palm Ave, Winter Park, FL 32789
Fully renovated with stylish charm, this four-bedroom, three-bath home is in one of the most desired neighborhoods in Winter Park, the Tree Streets. A brick drive and path welcome you into this open living plan on a large 75-foot by 150-foot lot with tons of room to grow. Warm wood floors throughout and this home enjoys an open kitchen family plan with spaces that are flexible for your needs. The
Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
$2,825 per month
2356 Coldstream Dr, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Lovely home in Winter Park school district. Closet to downtown Winter Park. Updated kitchen and baths on a Quiet street. Lawncare included.
Donna Peebles VIA PROPERTIES LLC
$1,350 per month
2929 Antique Oaks Cir Unit 53, Winter Park, FL 32792
Welcome to this fully renovated residence in the heart of Winter Park, where modern upgrades meet timeless charm in one of Central Florida’s most desirable communities. Thoughtfully updated throughout, this home offers a fresh, move-in-ready living experience with stylish finishes and enhanced comfort. Ideally situated near Full Sail University and Rollins College, this property is well-suited
Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK
$3,895 per month
1430 Lone Feather Trail, Winter Park, FL 32792
Welcome to this newly built and well-maintained home in the fabulous Winter Park gated community of Hawk's Crest. A gorgeous open floor plan single-family home with 4 bedrooms, 3.5 bathrooms and office / den room on the first floor. Be amazed by the spacious bright entrance and soaring ceilings in the family room and loft open to below. Tile throughout living areas, carpet in all four bedrooms.
Mo Jabr RE/MAX 200 REALTY
$2,890 per month
524 Byron Rd, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home located in the heart of highly desirable Winter Park area. Offering a rare combination of space, comfort and prime location. This home offers a spacious and functional layout with multiple living areas, abundant natural light, and well-sized bedrooms. The flexible floor plan provides
Razan Mohamed SOUTHERN PRESTIGE REALTY INC
$2,550 per month
110 Killarney Bay Ct Unit 1, Winter Park, FL 32789
Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer generous space, with a private primary suite
David Drawdy KELLER WILLIAMS REALTY AT THE PARKS
$2,500 per month
2846 Euston Rd, Winter Park, FL 32789
Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes form I4, close to Park Avenue District, College Park, major shopping centers and many more. Big backyard with a nice sized paved courtyard and
Vanessa Laboy 365 REALTY, INC.
$3,600 per month
1461 Lone Feather Trail, Winter Park, FL 32792
Beautiful newer two-story home in Winter Park’s exclusive Gated community of Hawk’s Crest. Community has lake access with canon launch. The home has a great floor plan that features open dining and living rooms. Mastered room is conveniently located on the first floor. also Study room. This gated community features a resort style swimming pool, fitness center, splash pad, clubhouse, playgrounds,
Steve Kim MARVIEW INTERNATIONAL REALTY LLC
$1,350 per month
4818 Tangerine Ave Unit 4818, Winter Park, FL 32792
One or more photo(s) has been virtually staged. The 1 bed, 1 bath unit is ideally located in Winter Park, close to Full Sail and UCF. Rent includes water, and all appliances including washer & dryer. A spacious Living/Dining space and a Huge bedroom make this the best one bed/one bath you'll find. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet
Torey Eisenman BENCHMARK REAL ESTATE GRP INC
$2,167 per month
717 Denton Rd, Winter Park, FL 32792
Winter Park 4 Bedrm Home for Rent!Priced Low, Call Now!, 2 Car Carport, Bonus Room Too!, Eat In Kitchen, JUST 20 MINUTES To: Downtown Orlando, JUST 30 MINUTES To: The Orlando Airport, CONVENIENT To: 436, CONVENIENT To: Major Roads, Shopping & Schools, CONVENIENT To: Full Sail University, Stainless Steel Appliances INCLUDED, Blinds INCLUDED. The deposit amount is based upon the application
Jay Myers ORLANDO REALTY & PROPERTY MGNT
$4,000 per month
1091 Wildmeadow Run, Winter Park, FL 32792
1
Maggie Walas FORTUNE INTERNATIONAL REALTY
$1,650 per month
2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792
Call to schedule your private showing of this well-maintained 2 bedroom, 2 bathroom condo located on the second floor in the desirable Parkview Village Subdivision.This bright and open floor plan features a spacious living room with vaulted ceilings, perfectly positioned at the front of the home and open to the kitchen. The kitchen has all new appliances with a corner window that is perfect for
Jacqueline Ramos JML REALTY INVESTMENTS LLC
$4,500 per month
1802 Arbor Park Dr, Winter Park, FL 32789
Welcome home to this beautifully maintained 4-bedroom, 3-bath pool home located in Winter Park’s highly desirable Tree Streets neighborhood—an area known for its charming, tree-lined roads and peaceful atmosphere. Situated on an oversized .27-acre lot, one of the largest in the community, this property offers rare space and privacy while still being close to everything Winter Park has to offer.
Jorge Perez Gonzalez TBRO REALTY LLC
$5,900 per month
220 W Reading Way, Winter Park, FL 32789
Welcome to your dream home! This recently renovated gem in the highly coveted Forrest Hills area of Winter Park is now available for rent. Surrounded by enchanting brick streets and majestic trees, this charming residence has been thoughtfully upgraded by the new owner, offering a perfect blend of modern amenities and classic charm. As you step onto the inviting front covered porch, you'll be
Thomas Hewitt HEWITT RESIDENTIAL, LLC
$13,500 per month
1860 Via Contessa, Winter Park, FL 32789
Exceptional Lease Opportunity | The Vias, Winter Park$13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available NowRarely does a home of this caliber come to market for lease. Set on a quiet cul-de-sac in one of Winter Park's most prestigious enclaves — the coveted Vias neighborhood — this magnificent 7,000 SF residence delivers an unmatched
Kelly Price KELLY PRICE & COMPANY LLC
$1,500 per month
7326 Swallow Run Unit 7326, Winter Park, FL 32792
Bright and freshly updated ground-floor 2-suite condo in a peaceful, well-kept community. This move-in-ready home features new interior paint, new water heater, granite countertops, and durable vinyl plank flooring throughout. The split-suite layout offers privacy and flexibility for roommates or professionals. Zoned for Cheney Elementary, with convenient access to A-rated middle and high
Jiny Lee NOBSKA REAL ESTATE LLC
$5,895 per month
1235 Via Estrella, Winter Park, FL 32789
Rare opportunity to lease a spacious 4-bedroom, 3-bath home in one of Winter Park's most coveted enclaves — The Vias. Spanning 2,207 SF, this sun-drenched residence sits just a short stroll from the prestigious Winter Park Racquet Club. Flooded with natural light, the open-concept living spaces feature beautiful bamboo wood floors, a well-appointed kitchen with white cabinetry and a large island,
Kelly Price KELLY PRICE & COMPANY LLC
$1,750 per month
200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
Cozy and well-maintained 2-bedroom, 2-bath condo, washer and dryer inside, located in the desirable Winter Park area. This spacious unit features an open and comfortable layout with abundant natural light, a functional kitchen, and a small patio perfect for relaxing. The community offers great amenities including a pool, tennis courts, shuffleboard, clubhouse and beautifully maintained grounds.
Nohora Gomez COLDWELL BANKER REALTY
$1,850 per month
609 Montego Bay Ct Unit 609, Winter Park, FL 32792
2-bedroom, 2-bathroom townhome. Near to shopping malls and Sail University
Jose Rodriguez JOSE ORLANDO RODRIGUEZ
$6,750 per month
527 Langholm Dr, Winter Park, FL 32789
Beautiful custom home with an open floor plan featuring 4 bedrooms, 3.5 baths, downstairs office, 2 car garage, huge loft for gaming and an additional private Bonus Room that can be utilized as a gym or flex room. Master Bedroom and office are conveniently located on the first floor. Additional features of this home include a gourmet kitchen with island, stainless steel appliances, granite
Nancy Woodruff WOODRUFF REALTY, INC.
$1,875 per month
307 Sandlewood Trail, Winter Park, FL 32789
This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy 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
Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
$2,200 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
$4,000 per month
1815 Barker Dr, Winter Park, FL 32789
Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. Pricing includes utilities/wifi. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals,
Benjamin Cole, IV SOTERA LIVING
$2,695 per month
1611 Little Wren Ln, Winter Park, FL 32792
This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Hawks Crest along the southern shores of beautiful Lake Howell, this ideal location provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Avenue and Winter Park Village. The home has an open floor plan with tile flooring throughout the downstairs living
Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
$3,750 per month
421 W Fairbanks Ave, Winter Park, FL 32789
Occupying the entire second floor of a landmark 1925 brick building in the heart of Winter Park, this fully reimagined residence offers a rare opportunity to lease a true designer 3 bedroom, 3 bathroom loft just two blocks from Park Avenue. The open concept interior features high ceilings, abundant natural light from skylights and brand new windows, and a refined industrial aesthetic anchored by
Nicholas Cadwallader REALTY ONE GROUP MVP
$2,195 per month
1724 Peruvian Ln, Winter Park, FL 32792
Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *Bonus Amenity Included* - All residents are enrolled
Mo Jabr RE/MAX 200 REALTY
$1,850 per month
612 Trinidad Ct Unit 612, Winter Park, FL 32792
Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area
Carolina Barriento JEXOR LLC
$1,400 per month
1695 Lee Rd Unit C110, Winter Park, FL 32789
Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.
Yigit Orer EMPIRE NETWORK REALTY
$1,450 per month
3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
Beautiful 2-bedroom, 2-bath condo available for rent in the highly desirable Winter Park area. This inviting home is thoughtfully designed for comfortable family living and features no carpet, with durable laminate flooring throughout perfect for easy cleaning and everyday use. The condo offers a spacious and functional layout, including a bright living area ideal for family time and
Praveen Setty RIGHTHOUSE REALTY LLC
$8,950 per month
311 E Morse Blvd Unit 1-5, Winter Park, FL 32789
Enjoy elevated lakeside living in this top-floor residence overlooking tranquil Lake Osceola in downtown Winter Park. Located on the top level of the Whispering Waters condominium community, this fully remodeled home features three spacious bedrooms (one currently used as a den), three full baths and an open layout designed to showcase expansive water views. The primary suite features an
Drew Henner PREMIER SOTHEBY'S INTL. REALTY
$1,800 per month
205 Lewfield Cir Unit 205, Winter Park, FL 32792
Wonderful! Owners pays Water & Internet. Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a barbeque with family and friends at the community
Eimi Moreno Carrera LPT REALTY, LLC
$3,150 per month
1835 Edwin Blvd, Winter Park, FL 32789
Charming bungalow on a brick street in beautiful Winter Park, available March 1, 2026. This 3-bedroom, 2-bathhome offers a great split floorplan and newer finishes. The kitchen and both primary en-suite and secondary bathroomshave been completely remodeled with premium finishes. The home boasts a newer roof, hardwood and stone floorsthroughout, with granite counters, white cabinetry,
Vincent Scarlatos CORCORAN PREMIER REALTY
$3,995 per month
438 W Swoope Ave, Winter Park, FL 32789
SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 3/31!! PRIME LOCATION! JUST STEPS FROM PARK AVENUE, WALKING DISTANCE TO EVERYTHING! This beautiful TOWNHOME is located in the exclusive 400 West community, just moments from Park Avenue. It offers a PERFECT COMBINATION OF SUPERIOR CRAFTSMANSHIP, ELEGANT INTERIORS, and GREAT WALKABILITY. You can enter via the PRIVATE GARAGE or the charming
Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT
$1,499 per month
200 Saint Andrews Blvd Unit 1803, Winter Park, FL 32792
2-bedroom, 1.5-bathroom, two-story condo in Four Seasons Condos of Winter Park. This well maintained condo includes a French country kitchen, which has been renovated with a faux tiled backsplash, custom maple cabinets, and complimentary appliances. This unit includes a half bath downstairs and full bathroom upstairs. Windows are double-pane, double-hung with a Pella sliding glass door with
Amy Spano WILSON MANAGEMENT GROUP
$3,850 per month
1302 Michigan Ave, Winter Park, FL 32789
This is a unique opportunity to live in this glamorous, impeccably maintained 3 bedrooms, 2.5 baths in the heart of Winter Park (Unfurnished). This beautiful home features formal living and dining rooms that open to the impressive gourmet kitchen fitted with wood cabinetry, stainless steel appliances, granite countertops, a breakfast bar, there is also room for a breakfast nook. Through the
Mo Jabr RE/MAX 200 REALTY
$1,600 per month
2523 Alexa Ct, Winter Park, FL 32792
Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard
Joseph LaRosa LA ROSA REALTY LLC
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