Listed by Nydia Maldonado

Days on market: 3474

Four Seasons Condominium. Fully remodeled 1st floor One bedroom, One bathroom. Great location in the heart of Winter Park, in a very popular area. Bamboo wood flooring throughout home and tile in kitchen and bathroom. Brand new appliances in kitchen. Big bedroom with a great sized walk in closet. Large living room leads to the new and beautifully enclosed screened porch. Community offers 3 pools, 3 laundry facilities, a tennis court, and shuffle board. WATER INCLUDED! HOA approval required. Pets are allowed with approval and non-refundable pet fee. Call Nydia today at 407-571-3618 to get more details on this rental.

Listed by ATEF BAKHSH

Days on market: 2708

Great location, in Four Season Winter Park. Community includes 3 pools, tennis courts and clubhouse. walk to many banks, grocery stores, hospital, pharmacies, restaurants in the area. First floor unit. Very spacious with walk in closet tile floor and more. Please email **** or text Atef at (407) 437 5273

Listed by Michael A. Agranoff

Days on market: 392

Available May 24, this updated 1 bedroom, 1 bathroom ground-floor condo is located in the Four Seasons community in Winter Park. The unit features a screened patio, central air, stainless steel appliances, a dishwasher, and a renovated bathroom. Community amenities include multiple pools, a clubhouse, laundry facilities, and an on-site management office—all conveniently located across the street. Rent includes water, sewer, and pest control. Price reflects discounts for single occupancy, ACH auto-pay, and a 12-month lease. A minimum lease of 7 months is required. Furnished option is available for a small monthly fee. One small pet may be considered on a case-by-case basis with pet fee and pet rent. UPDATED A/C. No HIDDEN monthly trash valet, parking, pest control, water, cable, or amenity fees. HUGE walk-in closet!

Listed by Four Seasons Condo in Winter Park

Days on market: 365

Live in this 1 bedroom, 1 bath, 2nd floor condo at Four Seasons in Winter Park. This condo includes 1 covered parking, living room, dining area, ceramic tile & carpet, community pool, clubhouse, tennis court, shuffleboard. *Bonus Amenity Included* -All RE/MAX 200 Realty Property Management Division residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which includes liability insurance, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery (for applicable properties), move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, on-demand pest control, and much more! More details upon application. Pet Friendly Property! Small pets are ok (with approval and non-refundable pet). Contact Mo at 407-571-1441 for more information.

Listed by Patty Farless

Days on market: 101

** Move-in Special* $300 off first month's rent if approved and lease signed for move-in date to begin Feb15th!! Charming Winter Park Condo for Rent. Where vintage meets modern in fantastic Winter Park. Amazing 1 bedroom, 1 bathroom condo in Winter Park. Amenities included: central air, dishwasher, pool, stainless steel appliance, updated kitchen, updated bathroom, storage, washer dryer, and beautiful screened patio. . No Utilities included. Is pet friendly. Date Available: Feb 2nd 2026. $1,350/month rent. $1,000 security deposit required. Please submit the form on this page or contact Patty Farless at 407-924-7024 to learn more. This property is managed by a responsible landlord using Avail landlord software. Landlord is licensed broker. First and last month as well as deposit due to secure property. Full background check (credit, employment and criminal) required. Must be approved by HOA which requires $100 non-refundable application fee.

Listed by Emmanuel

Days on market: 338

Fantastic location with Winter Park address. This condo is one bedroom and one bathroom. Having a separate dining room in a one bedroom condo is unique. The living room leads out to a balcony through a sliding glass door with a storage closet and a view of the courtyard. The Four Seasons Community has it all! Pools, Jacuzzi, tennis court, playground, shuffleboard, a clubhouse and many courtyards and walking paths in a beautifully maintained landscaped surrounding. Centrally located to everything, restaurants, hospital, and much more.

Listed by 1671 Dale Ave. - 1

Days on market: 289

BEST UNIT LOCATION IN THE FOUR SEASON COMPLEX! This large one bedroom condo is available for lease immediately. The freshly-painted second floor home features a huge bedroom and a spacious walk-in closet. Since it's an end-unit, there are no neighbors on one side. It's located above the laundry room so you're close by and don't have to deal with neighbors below you. You're also right next to the dumpster so you don't have to drive with your trash! Tons of parking, multiple swimming pools, and tennis courts make the Four Seasons one of the best gems in Winter Park. Text today to make your viewing appointment!

Listed by Lukasz Sokolowski

Days on market: 142

WELCOME HOME to this beautifully renovated, move-in ready condo in the centrally located Four Seasons Condominium community in Winter Park, FL! Step inside to a bright, spacious living and dining room combo featuring new flooring throughout, fresh paint, totally re-done bathroom with new fixtures in both the bathroom and kitchen. The home includes blinds and ceiling fans, plus a generous walk-in closet. You’ll love having a washer and dryer provided for tenant convenience, along with well-maintained space. Enjoy Florida living from your screened-in lanai which is perfect for fresh air and relaxing evenings, with the added perk of extra storage in the lanai area. The sliding glass door brings in plenty of natural light, making the whole unit feel open and airy. As a bonus, you’re just minutes from shopping, dining, and entertainment. You’ll be relieved to drive home and park in your covered, designated parking spot located just steps away. The Four Seasons Condo community offers resident amenities that include 3 pools, tennis court, shuffleboard and a clubhouse! Contact us today to schedule a showing! There is flexibility to rent this home with a seven to twelve month period. Prospects must view property prior to applying. After viewing, listing agent will provide application link, upon request. Tenant requirements include: Tenants must apply and be approved by HOA. The HOA application process can take up to 30 days (usually less) and HOA application fee is $100/adult or per married couple. Minimum gross household income of 3x the monthly rent amount, a favorable background and credit screening, favorable rental history and references, proof of income/employment. A security deposit (same as rent) is due upon applicant approval (within 24 hours) to mark listing as Pending. First month rent and last month's rent are due 7 business days prior to lease start date. The owner does not allow smoking in or around the home. Tenants are required to provide proof of renter's insurance and a $1/month convenience fee applies for use of management platform and tenant portal. Tenants are responsible to pay all utilities and put in their name. Lease agreements are drafted by an attorney after the deposit is received and are non-negotiable. Deposits are fully refundable until lease signing. Please review these requirements BEFORE requesting a showing. After viewing, listing agent will provide application link, upon request. If a tenant-prospect chooses to apply for one of our rental properties, that DOES NOT guarantee that the prospect's application will be approved. The application fee is NON-REFUNDABLE. Tenant approval is contingent on a lease start date within 30 days of application.

Listed by Amy Spano

Days on market: 1044

A VIRTUAL VIDEO TOUR IS AVAILABLE ON OUR WEBSITE! ! 1-bedroom, 1-bath, first-floor condo in Four Seasons Condos of Winter Park. This well-maintained condo has a back porch that is located with a view of the pool. It features new vinyl plank flooring and has been freshly painted. It provides washer/dryer unit (no warranty) in the walk-in closet. Sewer and landscaping included. The Four Seasons Condos are located within the city limits of Winter Park. There are three community pools and laundry facilities, which are gated and keyed. Close to shopping, restaurants, the Winter Park Medical Center, Cady Way Recreational Trail, and more. Living and total sq. ft is approximately 727. Additional HOA application and approval is required. DIRECTIONS: FROM THE INTERSECTION OF LAKEMONT & ALOMA IN WINTER PARK, GO EAST ON ALOMA TO THE TRAFFIC LIGHT, TURN RIGHT ONTO ST. ANDREWS BLVD. & GO TO THE END, TURN LEFT INTO FOUR SEASONS, TAKE A LEFT AT THE STOP SIGH, BUILDING 300 IS ON THE LEFT, ACROSS FROM THE CLUBHOUSEAll information deemed reliable, but not guaranteed. Wilson Management Group does not discriminate on the basis of race, color, religion, national origin, sex, disability or familial status. Animals By Owner Approval. Additional Security Deposit: $300 per approved animal Nonrefundable Animal Fee: $200 per approved animal Property Manager: Amy Spano 407-896-1200 ext 224 **** TO APPLY ONLINE, please go to our Home page and click the Apply Online link at the top left corner of the page. APPLY NOW: https wmgi quickleasepro com d apply 103802View All Listings: www wilsonmanagementgroup com

Listed by Locayt

Days on market: 152

WELCOME HOME to this beautifully renovated, move-in ready condo in the centrally located Four Seasons Condominium community in Winter Park, FL! Step inside to a bright, spacious living and dining room combo featuring new flooring throughout, fresh paint, totally re-done bathroom with new fixtures in both the bathroom and kitchen. The home includes blinds and ceiling fans, plus a generous walk-in closet. You’ll love having a washer and dryer provided for tenant convenience, along with well-maintained space. Enjoy Florida living from your screened-in lanai which is perfect for fresh air and relaxing evenings, with the added perk of extra storage in the lanai area. The sliding glass door brings in plenty of natural light, making the whole unit feel open and airy. As a bonus, you’re just minutes from shopping, dining, and entertainment. You’ll be relieved to drive home and park in your covered, designated parking spot located just steps away. The Four Seasons Condo community offers resident amenities that include 3 pools, tennis court, shuffleboard and a clubhouse! Prospects must view property prior to applying. After viewing, listing agent will provide application link, upon request. Tenant requirements include: minimum gross household income of 3x the monthly rent amount, a favorable background and credit screening, favorable rental history and references, proof of income/employment. A security deposit (same as rent) is due upon applicant approval (within 24 hours) to mark listing as Pending. First month rent and last month's rent are due 7 business days prior to lease start date. The owner does not allow smoking in or around the home. Tenants are responsible to pay all utilities and put in their name. Lease agreements are drafted by an attorney after the deposit is received and are non-negotiable. Deposits are fully refundable until lease signing. After viewing, listing agent will provide application link, upon request. If a tenant-prospect chooses to apply for one of our rental properties, that DOES NOT guarantee that the prospect's application will be approved. Tenant approval is contingent on a lease start date within 30 days of application.

Listed by Leasing Office

Days on market: 3811

(RLNE1955921) 2/2 Condo near Rollins College This is a 2 bedroom, 2 bathroom upstairs unit in the Four Seasons condo community, located off Fairbanks Road and convenient to shopping, Rollins College, Park Avenue and 436. The property features slate floors throughout, travertine tile in the kitchen, spacious bedrooms, stack-able washer/dryer available. Also included is one covered parking space. The Four Seasons community features a tennis court, 3 sparkling pools, spa, on-site laundry, mature landscaping throughout the community.Call today for an appointment to view! 407-897-3366

Listed by Deborah Alder

Days on market: 3487

Deposit is $995.00 with a good application. Community Pool, Tennis Court, stackable w/d. 2/1, covered parking, close to Rollins College, minutes from Winter Park Hospital, Full Sail College nearby. Must pass HOA background check,

Listed by Terri Selsor

Days on market: 3486

Deposit is $995.00 with a good application. Community Pool, Tennis Court, stackable w/d. 2/1, covered parking, close to Rollins College, minutes from Winter Park Hospital, Full Sail College nearby. Must pass HOA background check,

Listed by Leasing Office

Days on market: 2660

2 Bedroom Upstairs Condo in Winter Park - Great Winter Park Condominium Complex-Monthly Pest Control,Water and Garbage Collection Included- Near Shopping, Restaurants, Park Ave. Community Tennis Courts, and Pools. Private Exterior Storage with this unit. No Dogs Allowed

Listed by Leasing Office

Days on market: 3194

2 bd / 2 ba - Beautiful Winter Park Condo - This 2/2 983 square foot Condo in Winter Park located in the beautiful Four Season Condominium! Bike to Park Avenue and Rollins college, walk to Publix, Whole Foods, Starbucks...everything is close by!! This is in a prime location in Winter Park. West of 436 near Lakemont avenue. Condo features wood flooring through out, w/d in unit, eat-in kitchen, patio and so much more! Complex features 4 pools, tennis courts, clubhouse and is adjacent to large parks. Small Pet (under 15lb) Negotiable: $250 fee + $250 deposit Application Fee: $50 / adult Condo App Fee: $100 / adult or married couple

Listed by Leasing Office

Days on market: 2920

- No Pets Allowed

Listed by Rental Home Management Services, Inc.

Days on market: 2809

---- SCHEDULE A SHOWING ONLINE AT: http showmojo com lz 013b5fa089 ---- Fabulous Winter Park location! Four Seasons Condominium 2 bed 2 bath upstairs unit. Living, dining and kitchen. Nicely renovated kitchen, floors, masterbath & more! Large master suite with walk-in closet. Master bath completely updated with walk-in shower. Community pool with kiddie pool! Also has a clubhouse for residents use (additional charge). Close to shopping, restaurants & WP Hospital! Winter Park School District. Also includes nice stackable washer & dryer. Call the automated showing line at 407-499-8090 to schedule to see this property. Enter 200 when prompted to be sent a link to schedule to see the property. No Pets. HOA Approval required so allow for additional time for the HOA Process.

Days on market: 567

Available for immediate move in!! You will love living in this charming and unique condo in the heart of Winter Park This lovely two bedroom one and a half bathroom condo features beautiful ceramic tile floor throughout the living areas and carpet in the bedrooms. The Kitchen comes fully equipped with full appliance suite*, solid-surface countertops and cabinets with plenty of space. Enjoy the large living area that leads you to your own very private fenced in patio, perfect for relaxing or entertaining. Four Seasons community features 3 pools, tennis courts, clubhouse and large parks. This home is in prime location in Winter Park, conveniently located near SR436 shopping and dining, Hospitals and the University of Central Florida. All applicants are required to do a credit and background check. Renters insurance is required.

Days on market: 359

Available July 2025!! You will love living in this charming and unique condo in the heart of Winter Park . This lovely two-bedroom one-and-a-half-bathroom condo features fresh paint, brand new vinyl laminate in the living areas and bedrooms. The spacious kitchen has solid wood cabinets with tons of storage space. Enjoy the large living area that leads you to your own very private fenced-in patio, perfect for relaxing or entertaining. Four Seasons community features 3 swimming pools, a tennis court, a clubhouse, and several coin-operated laundry facilities. This unit does not have washer/dryer hookups. This home is in a prime location in Winter Park, conveniently located near SR436 shopping and dining, Hospitals, and the University of Central Florida. All applicants are required to do a credit and background check. Renters insurance is required.

Listed by Amy Spano

Days on market: 1047

A VIRTUAL VIDEO TOUR IS AVAILABLE ON OUR WEBSITE! 2-bedroom, 2-bath first floor condo in Four Seasons Condos of Winter Park. This 1st-floor condo has a small back porch, which houses stack-able washer/dryer unit (no warranty). Water, sewer, and landscaping are included. The Four Seasons Condos are located within the city limits of Winter Park. Three community pools, tennis court and laundry facilities are gated and keyed. Close to shopping, restaurants, the Winter Park Medical Center, Cady Way recreational trail and more. Living and total square feet is approximately 987. Additional HOA application & approval is required. DIRECTIONS: FROM THE INTERSECTION OF LAKEMONT & ALOMA IN WINTER PARK, GO E. ON ALOMA TO THE TRAFFIC LIGHT, TURN R. ONTO ST. ANDREWS BLVD.& GO TO THE END, TURN L. INTO FOUR SEASONS THEN IMMEDIATELY R. & LOOK FOR BLDG1900- UNIT #1906 IS DOWNSTAIRSAll information deemed reliable, but not guaranteed. Wilson Management Group does not discriminate on the basis of race, color, religion, national origin, sex, disability or familial status. Animals By Owner Approval. Additional Security Deposit: $300 per approved animal Nonrefundable Animal Fee: $200 per approved animal Property Manager: Amy Spano 407-896-1200 ext 224 **** TO APPLY ONLINE, please go to our Home page and click the Apply Online link at the top left corner of the page. APPLY NOW: https wmgi quickleasepro com d apply 103802View All Listings: www wilsonmanagementgroup com

Listed by Leasing Department

Days on market: 997

---- SCHEDULE A SHOWING ONLINE AT: http showmojo com lre 2074fd0021 ---- AVAILABLE NOW! Please call or text 407.863.8625 to schedule a showing. This lovely 2 bedroom, 2 bathroom ground floor unit in the Four Seasons community 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 vinyl plank flooring throughout, spacious bedrooms, two newly renovated bathrooms, and screened patio. The Four Seasons community amenities include 3 sparkling swimming pools, a tennis court, shuffle board, fitness center, and on-site laundry. At RPM Realty, we're here to make your time in the home as enjoyable and convenient as possible. We offer a safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, 24/7 emergency maintenance response team, and well-maintained homes. Please note the listed amenities may not be accurate. Please consult with an RPM Realty leasing agent to confirm the property will meet your individual needs. Some HOAs may have an additional application approval process.

Listed by Erin Eichler

Days on market: 549

Recently updated 2/2 condo in Winter Park! This second floor condo has recently had a facelift and is ready for your decor. Newer laminate flooring makes cleaning a breeze and helps keep allergies at bay. NO CARPET! Step inside and you'll discover an open, bright floorplan with living/dining combo, spacious kitchen with new range, and ample bedrooms with plenty of storage. Two full bathrooms mean you'll never fight for counter space! Newer interior paint will make it easy to display your artwork. Outside you'll discover a laundry closet with washer/dryer. This unit is pet friendly and close to Ward Park. Rollins College, Park Avenue, and Full Sail are only minutes away. Four Seasons Condo has 3 pools, tennis courts, on-site manager, on-site maintenance staff, fitness room, clubhouse, 3 laundry rooms, and lots of parking. Rent includes water, sewer, and trash. HOA approval required. Available December 7!

Listed by Available NOW! Charming 2

Days on market: 426

Welcome to 200 St Andrews Blvd, Unit 3201, a spacious 2-bedroom, 1.5-bathroom condo nestled in the desirable Four Seasons community in Winter Park, FL. This 1,266 sq. ft. home offers a bright and open layout, perfect for comfortable living. Enjoy a well-appointed kitchen, ample storage, and generous-sized bedrooms. The primary bedroom features a large closet and easy access to the full bathroom. As a resident of this HOA-managed community, you’ll have access to fantastic amenities, including a sparkling community pool, tennis courts, and clubhouse. Conveniently located near shopping, dining, and major roadways, this condo offers easy access to all that Winter Park has to offer. **HOA APPROVAL IS REQUIRED UP TO 30 DAYS FOR APPROVAL $100 PER APPLICANT OR MARRIED COUPLE Don’t miss this opportunity—schedule your showing today! Please visit The Realty Medics website (www.therealtymedics.com) to schedule a showing and apply or give us a call! Frequently Asked Questions: How can I get started? Go to The Realty Medics website! Select the property you want on the Rentals page, click the blue “Schedule A Showing” button above the property address, and complete the page accordingly. Once you’re ready to apply, click the blue “Apply Now” button to apply from our website and complete the online application form. Pet restrictions? Yes: No Aggressive or Dangerous Dog Breeds (Including but not limited to Dobermans, Rottweilers, Chows, German Shepherds, Staffordshire Terriers, and American Pit Bull Terriers). Additional HOA limits may apply. Application requirements www therealtymedics com rental-requirements and Move-in fees, Deposit information, and Pet Fees/Rent can be found at www therealtymedics com tenant-faq

Listed by Shari McClanahan

Days on market: 374

Property Id: 1840592 Beautiful 2/2 freshly renovated condo in the well maintained Four Seasons community of Winter Park Corner unit on 2nd floor. Internet and water included. VIRTUAL TOUR: https youtube com shorts jGTKxps-224 Community features mature, well maintained landscaping, Fitness center, several pools, tennis court and business center. Desirable Winter Park location near Rollins, upscale shops and restaurants. New appliances and designer finishes in bathrooms and kitchen. Walk to Ward Park with walking trails, sports fields, and playground! Don't miss this opportunity!

Listed by Leasing Office

Days on market: 855

3 Bedroom Winter Park Condo - Second Story Updated Condo, Rear Screened Porch, 3 Bedrooms and 2 Baths. Laminate Floors in Living areas, Carpet in Bedrooms. Washer Dryer in Kitchen. Water Included. Community Pool Right Across Parking Lot, Great Location. Near Buses, Shopping, Restaurants. No Pets Allowed