$1,350 Per Month
- 1 Bed
- 1 Bath
- 645 Sq Ft
- Condo for Rent
2500 Lee Rd Unit 244, Winter Park, FL 32789
2500 Lee Rd Unit 244, Winter Park, FL 32789
44
Winter Park, FL Condos for Rent under $2,000
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$1,675 Per Month
- 1 Bed
- 1 Bath
- 835 Sq Ft
- Condo for Rent
200 St Andrews Blvd Unit 316, Winter Park, FL 32792
200 St Andrews Blvd Unit 316, Winter Park, FL 32792Property 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
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$2,000 Per Month
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- Condo for Rent
1250 S Denning Dr, Winter Park, FL 32789
1250 S Denning Dr, Winter Park, FL 32789Property Id: 346094 Spacious living area, large master bedroom w/ private bathroom & linen closet. Wide Closets in each bedroom. Quiet neighborhood. Lots of sunlight enters the apartment. Shaded and screened patio faces a courtyard/garden w/ seating. Brand new sliding glass patio door. Incredible location short distance to Park Avenue, Trader Joes/Whole Foods/Publix, I4 exit, & shopping
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$1,730 Per Month
- 2 Beds
- 2 Baths
- 1,037 Sq Ft
- Condo for Rent
659 Montego Bay Ct, Winter Park, FL 32792
659 Montego Bay Ct, Winter Park, FL 32792Welcome to your dream condo in Winter Park! This charming **2-bedroom, 2-full bathrooms** home offers the perfect blend of comfort, convenience, and an unbeatable location, making it an ideal place to call home. With 1,037 square feet of well-designed living space, you'll enjoy modern conveniences, desirable community amenities, and easy access to everything you need for everyday
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$2,000
Total Monthly Price
- 2 Beds
- 2 Baths
- 911 Sq Ft
- Condo for Rent
1250 S Denning Dr Unit 127, Winter Park, FL 32789
1250 S Denning Dr Unit 127, Winter Park, FL 32789Updated 2BR/2BA First-Floor Condo in Winter Park – Pool View, Water Included!1250 S. Denning Drive – Winter Park, FLEnjoy comfortable, low-maintenance living in this beautifully updated 2-bedroom, 2-bathroom condo located in one of Winter Park's most convenient neighborhoods.This 910-square-foot, first-floor unit features luxury vinyl plank flooring throughout, a modern
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$1,245
Total Monthly Price
- Studio - 1 Bed
- 1 Bath
- 615 Sq Ft
- Condo for Rent
2037 Linden Rd, Winter Park, FL 32792
2037 Linden Rd, Winter Park, FL 32792Mother in law suite 1 bd /1 bath 613 Sqf Nice neighborhood, washer and dryer. Parking Garage Cable, internet, Electricity. Include in the rent Not Smoking. Small pet. Cat. Independent Entrance Door
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$1,950
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,236 Sq Ft
- Condo for Rent
1920 Woodcrest Dr Unit 13, Winter Park, FL 32792
1920 Woodcrest Dr Unit 13, Winter Park, FL 32792Unit 13 is a direct pool front unit. Large (1,236 sq. ft.), quiet first floor 2 bedroom 2 bathroom condo in smaller community with only 18 units in the City of Winter Park, Florida. The Floor plan has a double primary bedroom layout. Ceramic tile flooring in the foyer, living/dining area, kitchen, and both bathrooms. Both bedrooms have new easy-care luxury vinyl wood-look flooring. Primary bath
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$1,245
Total Monthly Price
- Studio - 1 Bed
- 1 Bath
- 615 Sq Ft
- Condo for Rent
2037 Linden Rd, Winter Park, FL 32792
2037 Linden Rd, Winter Park, FL 32792Mother in law suite 1 bd /1 bath 613 Sqf Nice neighborhood, washer and dryer. Parking Garage Cable, internet, Electricity. Include in the rent Not Smoking. Small pet. Cat. Independent Entrance Door
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$1,100
Total Monthly Price
- 1 Bed
- 1 Bath
- 305 Sq Ft
- Condo for Rent
2333 E Winter Park Rd Unit Guest House, Winter Park, FL 32789
2333 E Winter Park Rd Unit Guest House, Winter Park, FL 32789Charming one-bedroom guest house located in a beautiful Winter Park neighborhood. Enjoy a peaceful setting just steps away from local shops, dining, and everyday conveniences. This inviting space offers both comfort and walkability in one of the area’s most desirable locations, along with the convenience of private parking.
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$1,650 Per Month
- 3 Beds
- 2 Baths
- 1,149 Sq Ft
- Condo for Rent
1695 Lee Rd Unit A101, Winter Park, FL 32789
1695 Lee Rd Unit A101, Winter Park, FL 32789Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center, Basic tenant requirements: 650+ credit score, no BAD history, no BAD rental history, income 3 times monthly rent as a household. FIRST, LAST and SECURITY DEPOSIT MAY required.
Daniel Zheng CINO INTERNATIONAL INC
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$1,600 Per Month
- 2 Beds
- 2 Baths
- 964 Sq Ft
- Condo for Rent
3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792
3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792 -
$1,500 Per Month
- 2 Beds
- 1 Bath
- 881 Sq Ft
- Condo for Rent
1695 Lee Rd Unit B204, Winter Park, FL 32789
1695 Lee Rd Unit B204, Winter Park, FL 327892 bedroom, 1 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. New tile floor was installed and freshly painted. Washer & Dryer in the unit. No min credit score is required. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village, shopping, dining, and more. Community amenities include a pool, dog park, and mature
Mauricio Toro MTRE GROUPE LLC
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$1,450 Per Month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Condo for Rent
151 N Orlando Ave, Winter Park, FL 32789
151 N Orlando Ave, Winter Park, FL 32789Discover comfortable living in this charming 1-bedroom, 1-bathroom residential condo at 151 N Orlando Ave, Winter Park, FL. Spanning 600 sq ft, this unit features modern hardwood flooring, large closets, and a private patio perfect for relaxing or entertaining. The kitchen is equipped with a range and refrigerator, complemented by air conditioning for year-round comfort. Water and trash services
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$1,650 Per Month
- 2 Beds
- 2 Baths
- 1,062 Sq Ft
- Condo for Rent
3045 Aaron Burr Ave Unit 12, Winter Park, FL 32792
3045 Aaron Burr Ave Unit 12, Winter Park, FL 32792Condominium located in The Colonies in Winter Park. Conveniently situated near UCF (University of Central Florida) and Full Sail University, with easy access to shopping centers, major highways, restaurants, and Orlando's world-famous theme parks. Just 11 minutes from Orlando International Airport (Orlando International Airport).This cozy 2-bedroom apartment is perfectly located for quick access
Angel Ramirez LPT REALTY, LLC
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$1,799 Per Month
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
- Fabulous 2/2 Condo @ Winter Park x Rent Next to Full Sail.
610 Saint Johns Ct Unit 610, Winter Park, FL 32792
610 Saint Johns Ct Unit 610, Winter Park, FL 32792Amazing Winter Park Condo for Rent – Prime Location!Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo in the heart of Winter Park, conveniently located just minutes from Park Avenue, Full Sail University, shopping, restaurants, and entertainment.This spacious home features a modern kitchen with granite countertops and stainless steel appliances, beautifully
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$1,445 Per Month
- 2 Beds
- 2 Baths
- 756 Sq Ft
- Condo for Rent
7302 Swallow Run, Winter Park, FL 32792
7302 Swallow Run, Winter Park, FL 32792This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35 lbs. Schedule a showing or submit an application online. All Real
Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
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$1,850 Per Month
- 2 Beds
- 2 Baths
- 1,043 Sq Ft
- Condo for Rent
419 Warrenton Rd Unit 419, Winter Park, FL 32792
419 Warrenton Rd Unit 419, Winter Park, FL 32792AVAILABLE NOW! Please call or text to schedule a showing. This 2 bedroom, 2 bathroom townhome is located in Winter Park's desirable Winter Park Pines 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.
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$2,000 Per Month
- 3 Beds
- 2 Baths
- 1,149 Sq Ft
- Condo for Rent
1695 Lee Rd Unit E115, Winter Park, FL 32789
1695 Lee Rd Unit E115, Winter Park, FL 32789Spacious 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
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$2,000 Per Month
- 2 Beds
- 2 Baths
- 902 Sq Ft
- Condo for Rent
2404 Gallery View Dr, Winter Park, FL 32792
2404 Gallery View Dr, Winter Park, FL 32792Fantastic 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
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$1,150 Per Month
- 1 Bed
- 1 Bath
- 735 Sq Ft
- Condo for Rent
1000 S Semoran Blvd Unit 715, Winter Park, FL 32792
1000 S Semoran Blvd Unit 715, Winter Park, FL 32792Enjoy comfortable living in the highly sought-after Winter Park area! Close to shopping, dining, and major roadways, this well-located rental provides exceptional value in one of Central Florida's most desirable communities. This first-floor condo is ideally located just steps from the community pool and on-site laundry facilities, offering convenience and easy access to everyday amenities. Don't
Lety Morales LPT REALTY, LLC
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$1,645 Per Month
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
- Condo for Rent
7526 University Garden Dr, Winter Park, FL 32792
7526 University Garden Dr, Winter Park, FL 32792Fantastic 3 Bedrooms & 2 Bathrooms Home in Orlando ***Available 08/15/26***Located at 7526 University Garden Dr Winter Park, FL 32792Limited-time offer! Enjoy $150 off the base rent of $1,795 during months 2, 3, and 4 — advertised rent reflects this temporary discount.Tile Throughout Main Parts of Property and Master Bedroom.Carpet in Bedrooms.Private Covered Patio and One Car
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$2,000 Per Month
- 2 Beds
- 1 Bath
- 1,500 Sq Ft
- Condo for Rent
151 N Orlando Ave Unit 118, Winter Park, FL 32789
151 N Orlando Ave Unit 118, Winter Park, FL 32789Investment 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
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$1,175 Per Month
- 1 Bed
- 1 Bath
- 656 Sq Ft
- Condo for Rent
3035 George Mason Ave Unit C, Winter Park, FL 32792
3035 George Mason Ave Unit C, Winter Park, FL 32792Water/Sewer INCLUDED! Second floor perch where price and location put you right where you want to be, with no noisy neighbors above you! Walking distance to grocery and commerce. Washer & Dryer included! Cool, easy-to-clean laminate flooring, and ceiling fans. Community pool, playground. Perfect for first time renter! Plan to see this condo and get your application in today!For A 3D Tour
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$1,450 Per Month
- 2 Beds
- 2 Baths
- 840 Sq Ft
- Condo for Rent
3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792Beautiful 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
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$1,745 Per Month
- 3 Beds
- 2 Baths
- 1,149 Sq Ft
- Condo for Rent
1695 Lee Rd Unit Apartment D215, Winter Park, FL 32789
1695 Lee Rd Unit Apartment D215, Winter Park, FL 32789*** TENANT OCCUPIED UNTIL 7/31/26 - Showings by appointment ONLY! MOVE-IN SPECIAL! 50% off one month's rent for approved and signed leases by 7/31/2026!! ***This fabulous 3BD/2BTH second-floor condominium end unit. The kitchen features stainless steel appliances, oak cabinets and stunning wood floors greeting you as you enter the unit. Flowing from the living room to the dining room
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$1,250 Per Month
- 1 Bed
- 1 Bath
- 549 Sq Ft
- Condo for Rent
3035 George Mason Ave Unit 20, Winter Park, FL 32792
3035 George Mason Ave Unit 20, Winter Park, FL 32792Welcome to 3035 George Mason Avenue, Unit #20B—a cozy and inviting 1-bedroom, 1-bathroom retreat in the heart of beautiful Winter Park, Florida! This charming home offers a bright and comfortable living space, perfect for anyone looking for convenience and tranquility. Nestled within a friendly community, you'll enjoy access to a sparkling community pool, nearby shopping centers, supermarkets,
Myland Roo De Vargas EXP REALTY LLC
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$1,595 Per Month
- 2 Beds
- 1 Bath
- 881 Sq Ft
- SPACIOUS 2BR CONDO | MOVE-IN READY | LIMITED AVAILABILITY
1695 Lee Rd, Winter Park, FL 32789
1695 Lee Rd, Winter Park, FL 32789MOVE-IN SPECIAL – $1,000 RENT CREDIT*Beautiful and move-in ready 2 Bedroom / 1 Bathroom condo located on the second floor in a quiet, well-maintained community.Take advantage of a limited-time move-in special and receive a $1,000 rent credit applied toward your first month's rent. Certain terms and conditions apply.This unit offers the perfect combination of comfort,
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$1,500 Per Month
- 2 Beds
- 1 Bath
- 881 Sq Ft
- Condo for Rent
Unlisted Address
Unlisted Address2 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.
Kirsten Cantello TRUSTHOME PROPERTIES INC
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$1,400 Per Month
- 2 Beds
- 2 Baths
- 840 Sq Ft
- Spacious 2/2 Condo In Lancelot at Winter Park
3651 N Goldenrod Rd Unit B203, Winter Park, FL 32792
3651 N Goldenrod Rd Unit B203, Winter Park, FL 32792AVAILABLE NOW!!! This beautiful 2 bedroom, 2 bathroom condo in the Lancelot at Winter Park community near local shops, restaurants, and schools. Features include tile throughout, vaulted ceilings, a fully equipped and remodeled kitchen with granite counters and a breakfast bar, updated bathrooms, and spacious bedrooms. Community amenities include a pool and clubhouse. MUST SEE! Won't last long!
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$1,600 Per Month
- 2 Beds
- 1 Bath
- 881 Sq Ft
- Condo for Rent
1695 Lee Rd Unit C103, Winter Park, FL 32789
1695 Lee Rd Unit C103, Winter Park, FL 32789Charming 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
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$1,375 Per Month
- 2 Beds
- 2 Baths
- 1,045 Sq Ft
- Condo for Rent
1000 S Semoran Blvd Unit 806, Winter Park, FL 32792
1000 S Semoran Blvd Unit 806, Winter Park, FL 32792LB/O - Nice 2 bedroom 2 bathrooms, 2nd Floor Unit, Open Floor Concept, Living Area, Breakfast Area, Community Pool, Water Included! Apply Today!TO SCHEDULE A SHOWING YOU MUST EMAIL US WITH YOUR CONTACT INFORMATION AND THE PROPERTY YOU WISH TO SEE AT AND AN AGENT WILL RESPOND BACK WITH THE AVAILABLE SHOW TIMES.HOW TO APPLY/ABOUT OUR APPLICATION PROCESS: Our application process
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$1,700 Per Month
- 2 Beds
- 2 Baths
- 927 Sq Ft
- Condo for Rent
205 Lewfield Cir Unit 205, Winter Park, FL 32792
205 Lewfield Cir Unit 205, Winter Park, FL 32792Wonderful! 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
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$1,400 Per Month
- 1 Bed
- 1 Bath
- 678 Sq Ft
- Condo for Rent
302 Lewfield Cir, Winter Park, FL 32792
302 Lewfield Cir, Winter Park, FL 32792Welcome home to this charming and light-filled 1-bedroom, 1-bathroom condominium, offering the perfect blend of comfort and convenience. Featuring beautiful wood flooring throughout, this cozy residence boasts an open-concept living and dining area that creates a warm and inviting atmosphere. The kitchen is equipped with modern appliances, while ceiling fans throughout the home enhance year-round
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$1,500 Per Month
- 2 Beds
- 2 Baths
- 802 Sq Ft
- Condo for Rent
7340 Swallow Run Unit 7340, Winter Park, FL 32792
7340 Swallow Run Unit 7340, Winter Park, FL 32792Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.
Jennifer Linton METRO CITY REALTY
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$1,595 Per Month
- 2 Beds
- 2.5 Baths
- 1,079 Sq Ft
- Condo for Rent
3004 George Mason Ave Unit K5d, Winter Park, FL 32792
3004 George Mason Ave Unit K5d, Winter Park, FL 32792This 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
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$1,600 Per Month
- 2 Beds
- 2 Baths
- 840 Sq Ft
- 2 Bedroom/2 Bathroom at Lancelot AVAILABLE AUGUST 10th!
3651 N Goldenrod Rd Unit A103, Winter Park, FL 32792
3651 N Goldenrod Rd Unit A103, Winter Park, FL 32792Super nice, 2 bed/2 bath, ground floor unit. Wonderful open floor plan, laminate and tile flooring, updated bathrooms, all kitchen appliances, washer and dryer, and ceiling fans. Water is included. No Pets Allowed. Conveniently located. Call today for an appointment!EQUAL HOUSING OPPORTUNITYFEATURES:Ground Floor UnitAll AppliancesBreakfast BarLiving Room/Dining
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$1,445 Per Month
- 2 Beds
- 2 Baths
- 756 Sq Ft
- Condo for Rent
7302 Swallow Run Unit 7302, Winter Park, FL 32792
7302 Swallow Run Unit 7302, Winter Park, FL 32792AVAILABLE NOW! Please call or text to schedule a showing. This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35
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$1,250 Per Month
- 2 Beds
- 2 Baths
- 840 Sq Ft
- Spacious and Affordable 2/2 Condo In Lancelot at Winter Park
3651 N Goldenrod Rd Unit B202, Winter Park, FL 32792
3651 N Goldenrod Rd Unit B202, Winter Park, FL 32792AVAILABLE NOW!!! This beautiful 2 bedroom, 2 bathroom condo in the Lancelot at Winter Park community near local shops, restaurants, and schools. Features include tile throughout, vaulted ceilings, kitchen with stainless appliances and breakfast bar, two full bathrooms, and spacious bedrooms. Community amenities include a pool and clubhouse. MUST SEE! Won't last long! Schedule your showing
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$1,500 Per Month
- 2 Beds
- 2 Baths
- 840 Sq Ft
- 2 Bedroom 2 Bath in Winter Park AVAILABLE AUGUST 17th!
3651 N Goldenrod Rd Unit E107, Winter Park, FL 32792
3651 N Goldenrod Rd Unit E107, Winter Park, FL 32792Ground Floor condo in Winter Park, convenient to UCF, Fullsail, shopping, dining and so much more! Water and Ground Maintenance Included. This condo features all tile flooring, ceiling fans, breakfast bar, open patio and an inside utility w/Washer and Dryer. The kitchen is open to the dining area/living room with 840 sqft of living space! The community features a swimming pool.EQUAL
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$1,800 Per Month
- 2 Beds
- 1 Bath
- 750 Sq Ft
- Condo for Rent
2510 Boyd Ave, Orlando, FL 32803
2510 Boyd Ave, Orlando, FL 32803Step into the allure of this meticulously renovated one-bedroom and bathroom apartment unit. The open-concept space boasts a granite countertop and stainless steel appliances, creating a modern and inviting ambiance. The unit also features an extra room, perfect for an office, with direct access to the private backyard. Conveniently situated near Baldwin Park, downtown Orlando, and a plethora of
Showing Results 1 - 40, Page 1 of 2
Condo Rental Trends in Winter Park, FL
There are currently 42 condos available for rent in Winter Park, FL. The median rent is $1,650 per month, with 1-bedroom condos renting at $1,350, 2-bedroom condos at $1,680 and 3-bedroom condos at $1,950.
Rental Home Trends
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Number of Condos for Rent
42
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Median Condo Rent
$1,650
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Median 1 Bedroom Condo Rent
$1,350
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Median 2 Bedroom Condo Rent
$1,680
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Median 3 Bedroom Condo Rent
$1,950
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