Apartments for Rent Near Winter Park High in Orlando - 26 rentals

Remarks: Nestled along picturesque tree-lined streets, this is a beautifully renovated 4-bedroom, 2-bathroom rental home that perfectly blends comfort and functionality. As you step inside, the spacious living room offers a welcoming ambiance, ideal for both relaxation and entertaining. To your right, the recently updated kitchen features elegant quartz countertops, sleek shaker-style cabinetry, and a classic subway tile backsplash, making it a dream for any home chef. Adjacent to the kitchen, a convenient mudroom provides indoor laundry hookups and ample storage while leading to a versatile fourth bedroom that can easily serve as an office or craft room. On the left side of the home, the serene primary bedroom boasts an ensuite bathroom and a walk-in closet, while two additional bedrooms share a well-appointed guest bathroom. A sliding glass door off the kitchen opens to a screen-enclosed porch, offering the perfect spot to enjoy Florida’s sunshine year-round. Beyond the porch, a fully fenced backyard with mature trees provides a peaceful retreat with plenty of space for outdoor activities. Situated in a quiet, family-friendly neighborhood, this home is zoned for top-rated schools, including Aloma Elementary, Glenridge Middle, and Winter Park High, with school bus pickup and drop-off conveniently located right outside the home. Its prime location offers quick access to Highway 417, UCF, Full Sail University, Rollins College, Downtown Orlando, and more, making daily commutes and errands a breeze. An expanded concrete driveway with a double gate runs along the side of the property, offering ample space for boat or RV storage, and with no HOA restrictions, you have the flexibility to make the space your own. Income verification/credit score check and background check are to be completed as a part of the application process. No pets. If interested in applying, contact the listing agent directly.

Listing is courtesy of: FLORIDA DREAMS PROPERTIES INC (386-675-0888)

Listing Agent: Java Sahler Llc (347-925-8983)

Remarks: NEWLY UPDATED, 3-STORY TOWNHOUSE w/ELEVATOR, FRONTING PARK! Discover this exceptional three-story townhouse featuring an elevator in vibrant Baldwin Park. The owner has just completed a full kitchen renovation and installed elegant white oak engineered hardwood flooring throughout the entire residence. Additionally, you will be just steps away from Grace Hopper Hall, which boasts a Junior Olympic Pool and a fitness center. The home overlooks a picturesque, tree-lined park, and the Village Center is conveniently located just a block away. As you step inside, you will be greeted by custom wood flooring and stylish wrought iron stair railings. Your private elevator provides easy access to each floor. The first floor features a two-car oversized garage and includes a bedroom with an ensuite bathroom and a walk-in closet. The second floor is the main living area with an open floor plan. The kitchen seamlessly connects to the family and dining rooms, complete with an eat-in space and access to the rear balcony. The third level is home to the Primary Suite and an additional separate bedroom which also has an ensuite bathroom, each offering granite counters, luxurious soaker tubs, and spacious closets. Baldwin Park offers convenient access to AdventHealth, Orlando Health, downtown Orlando, Winter Park, and Orlando International Airport.

Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)

Listing Agent: Brian Cirillo (321-231-1068)

Remarks: Wow, you've found this hidden GEM! Tree lined streets lead you to this Ranch Style, Front porch Move-in Ready home on a HUGE corner lot with no HOA. Super Clean- 3 Bed + office / 2 Bath / Covered Parking with a Fenced Yard - ALL TILE Floors throughout. Great Room plan in the front of the home and Kitchen overlooking the backyard. You’ll love the Kitchen- Maple Cabinets, GRANITE counters, Refrigerator, GAS Range, dishwasher and window above the sink for view of the patio and backyard. Master Suite has an office/ work-out room/ extra space/ room attached. Renovated Master Bathroom features HUGE Walk-in Shower, linen closet and access to the outdoor patio. Additional bedrooms share the remodeled bathroom. Plus- two storage closets in the hallway. Spacious covered Screened Enclosed Patio to enjoy the outdoors. Bring on the BBQs and outdoor games! Bonus- Lawn service is included, inside Laundry Room w/ W&D included and programable thermostat. Just minutes to the Little Econ trail to go for a jog or bike ride on this nature trail. Great Location- less than 5 minutes from Publix, Target, Restaurants and around the corner from the 417 Expressway. -Landlord requests tenants to apply with credit score 650+

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Jody Deabenderfer (407-312-3604)

Remarks: Welcome home! This fantastic 3 bedroom, 2 bath. Available on July 7th! Located conveniently close to the highly-desired Baldwin Park, this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with a full appliance suite, lots of counters, and cabinet space. Minutes from restaurants, and entertainment. Act now! This one won’t last long! All applicants are required to do a credit and background check. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: This well-maintained residence features spacious living areas, wood flooring, an eat-in kitchen, central air conditioning, and a large private backyard. Conveniently located near Downtown Orlando, Baldwin Park, Winter Park, restaurants, shopping, parks, and major highways. Excellent opportunity for tenants seeking comfort and convenience in a prime Orlando location.

Listing is courtesy of: HOMECOIN.COM (888-400-2513)

Listing Agent: Jonathan Minerick (888-400-2513)

Remarks: Available July 1, 2026. Enjoy a beautifully updated and furnished turn key home! A rare find in the highly sought after Baldwin Park neighborhood offering 2 furnished bedrooms and an office with a day bed 2 full bathrooms and a spacious open floor plan. The living area has engineered hardwood flooring, built in beverage bar with fridge and completed with a quartz countertop. The kitchen is updated with a Quartz backsplash, new stainless steel appliances, stainless steel farmhouse sink, gorgeous Quartz countertops, and has a bar with seating. The primary bedroom offers 2 large custom walk in closets, a gorgeous bathroom ensuite offering 2 sinks, a large soaking tub and a large walk-in newly tiled shower with a rainwater shower system, and updated lighting with dimmers. There is also a private balcony off of the primary bedroom. The secondary bathroom has also been fully updated. There is also a large storage closet and a spacious attached garage with a covered carport. Wonderful location -just minutes away from the community center of Grace Hopper Hall which offers an olympic sized pool with swimming lanes, childs pool, sunbathing area and inside has a state of the art work out facility. Baldiwn Park has amazing walking and biking trails, parks and playgrounds and a fabulous downtown area with many restaurants, water front dining, boutiques, CVS and Publix. All applicants are requred to do a credit and background check. No pets please.

Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)

Listing Agent: Kimberley Gernert Llc (423-381-5701)

Remarks: Welcome home to this charming 2-bedroom, 1-bath first-floor condo with 832 sq ft of comfortable living space, located in a peaceful, friendly community. Enjoy the convenience of being just minutes (about 0.5 miles) from Colonial Plaza and Coytown Market—giving you easy access to groceries, shopping, and everyday essentials. This home is zoned for top-rated schools, including Audubon Park School K-8 and Winter Park High School, making it a great option for families. You’ll also love being close to Winter Park and Baldwin Park, where you can enjoy weekend strolls, family-friendly activities, local restaurants, and a vibrant community atmosphere. If you’re looking for a comfortable home in a convenient and welcoming location, this condo is a must-see!

Listing is courtesy of: ZEAL REALTY (407-789-2051)

Listing Agent: Rocio Cobian (407-865-2671)

Remarks: Fantastic rental opportunity at 5405 Old Cheney Hwy! This unique property features two complete homes in one, making it ideal for extra privacy or multi-generational living. The entire property is completely new and move-in ready. The main home offers a bright, functional layout with 3 bedrooms, 2 full bathrooms, its own independent kitchen, and private laundry. The second home features 2 comfortable bedrooms, 1 full bathroom, also equipped with its own fully independent kitchen and laundry setup. Enjoy an unbeatable location just minutes from the vibrant dining, lakeside trails, and shopping at Baldwin Park, as well as Downtown Orlando. Perfect for anyone looking for an easy commute and a vibrant lifestyle. Schedule your tour today!

Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)

Listing Agent: Dayana Perez Moreno (786-384-0070)

Remarks: Fully-furnished, partial, or unfurnished. Discover your dream home in beautiful Baldwin Park! This stunning home boasts 4 bedrooms, 3.5 baths, & a 2-car garage. This home sits on a corner lot in front of a serene pond. As you approach this two-story home, you will be greeted by a charming front porch adorned with ceiling fans, rocking chairs, & a patio table with chairs. Step inside and experience the open floor plan with elevated ceilings and plantation shutters throughout. The great room features custom draped windows, a comfortable red leather couch, and a high-top table with chairs for casual dining. The gourmet kitchen is complete with stainless steel appliances, granite countertops with breakfast bar, R.O. filter, and a beverage center. It is the perfect space to create culinary masterpieces. Ceramic tile flooring in wet areas, and wood laminate flooring in the downstairs and upstairs loft. This home is perfect for entertaining guests with ceiling speakers installed throughout the downstairs living area, including even the front porch & garage. Relax and unwind in the sunroom. The study with a French door (with frosted windows for privacy) is perfect for those who work from home. There is also a powder room with a pedestal sink downstairs. Upstairs, the loft connects the 4 bedrooms and 3 full baths. It features a white leather couch and loveseat. The 19’ wide primary bedroom suite has a large built-in dresser and breathtaking views of the pond. The primary bathroom features a shower, a garden tub, double cultured marble vanities, compartmented commode, and walk-in closet with built-ins and cubby storage. There is a small patio on the rear of the home with a gas and charcoal grill, and a table with 2 chairs. The location is unbeatable - less than a mile walk to downtown Baldwin Park with numerous restaurants, shops, and Publix grocery. The subdivision amenities include 3 pools, 2 fitness centers, and endless trails and parks.

Listing is courtesy of: SOTERA LIVING (407-725-9660)

Listing Agent: Benjamin Cole Iv (407-399-0629)

Remarks: Welcome partial furnished home! This fantastic 4-bedroom, 3-bath home is available for move in on July 10th, 2026! Located conveniently in the desirable community of Enclave at Lake Jean, this property features a comfortable layout with well apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act now! This one won't last long! All applicants are required to pass a credit and background check. **Pets are accepted on a case by case basis** Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: Newly remodeled elegant estate home in the highly sought-after Baldwin Park community. This stunning residence features 5 bedrooms, 4.5 bathrooms, and a private office, offering an ideal blend of luxury, comfort, and functionality. Perfectly situated overlooking the park, the home is within walking distance to community amenities, shops, and dining. Inside, you’ll find high-end designer lighting and custom window treatments throughout. The spacious primary suite is conveniently located on the first floor and offers peaceful views of the backyard. A downstairs guest suite provides added flexibility, while upstairs includes three additional bedrooms and two full bathrooms. Additional highlights include newly finished epoxy garage flooring, a spacious three-car garage (3rd bay is smaller perfect for a golf cart), and an indoor laundry room with utility sink. The fenced backyard features a brick paver patio and grassy yard space, perfect for relaxing or entertaining outdoors. Enjoy all that Baldwin Park has to offer, including 3 community pools, fitness facilities, walking trails, playgrounds and beautifully maintained green spaces.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Meg Dolan (321-948-0701)

Remarks: **ALL SERVICES INCLUDED** Welcome home to this charming 2-bedroom, 1-bath residence located in the desirable Conway area of Orlando. This home offers a comfortable layout with spacious bedrooms, a functional kitchen with ample cabinet and counter space, and the convenience of an in-unit washer and dryer. Enjoy the added value of utilities included in the rent, including electricity, water, and Wi-Fi. Conveniently located near shopping, dining, major highways, Downtown Orlando, and the Orlando International Airport, this property provides both comfort and accessibility. All applicants are required to complete a credit and background screening. Renters insurance is required.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: “Beautiful, well-maintained condo that shows like new! The owner has taken great pride in keeping this home in excellent condition. Conveniently located near Baldwin Park Elementary, Glenridge Middle, and Winter Park High School. Enjoy easy access to downtown dining, shopping. You can also enjoy the same and and all that Winter Park has to offer. This desirable corner unit features a one-car garage and a wraparound covered porch—perfect for relaxing or entertaining. Nearby fitness options include Crunch Fitness and LA Fitness. Owner purchased with many upgrades to include updated cabinets, new carpet, and modern flooring. Lawn care is included for low-maintenance living. Don’t miss this opportunity—schedule your showing today!”

Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)

Listing Agent: Courtney James (321-228-6181)

Remarks: Studio on right side of this one-story-single-family home completely remodeled and move in ready within a few minutes to Baldwin Park, Winter Park, and Downtown Orlando! NO HOA! Excellent schools on "A" list. Bike, walking, and/or running paths. Walking distance to Cady Way Trail. Also close to Audubon Park, Milk District, and Lake Druid Mountain biking park. Easy access to 408 and I-4. Remodeled / beautifully updated flooring throughout the studio with laundry room. NO HOA! Call today for more information and appointments

Listing is courtesy of: THE KEYES COMPANY (305-371-3592)

Listing Agent: Jorge Bacallao, Jr (786-728-2656)

Remarks: Conveniently located studio apartment in the heart of Baldwin Park. The award-winning shopping (even a neighborhood Publix), dining, and entertainment of downtown Baldwin Park are all steps away from your door as well as three community pools, a fitness center, numerous parks and miles of beautiful walking trails. The apartment is located on the second level to provide great privacy and a quiet environment. Everything inside the 600 sq ft studio feels bright and airy including the kitchen equipped with a refrigerator, dishwasher, range / oven, and microwave. The home also includes the ease of an in-unit washer and dryer. Because the home is located in sought-after Baldwin Park, access to downtown Orlando, Winter Park, I-4, and SR 408 is a breeze. Professionally managed and pet friendly. Background and Credit check needed. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: Brand-new construction, be the first to live in this beautiful 3-bedroom, 2-bath unit featuring a modern open-concept design. Enjoy a bright and spacious living area that flows seamlessly into the kitchen, perfect for entertaining or everyday living. Each unit includes a private lanai for outdoor relaxation and a 1-car garage for added convenience. The thoughtfully designed layout maximizes space and functionality, offering walk-in closets and a dedicated laundry area. Built with modern finishes and practical features throughout, this home combines comfort, style, and efficiency. Ideal for families, roommates, or anyone seeking a fresh start in a newly built home. Conveniently located near major roads, shopping, dining, and more. Move-in ready don’t miss the opportunity to be the first occupant!

Listing is courtesy of: ALTIS REALTY (407-401-7447)

Listing Agent: Alfredo Meyer (407-990-2341)

Remarks: Perfectly situated in the premier Colonialtown neighborhood and just steps away from the vibrant Mills 50 District, this charming 2-bedroom, 1-bathroom bungalow is a cozy gem. The home features a versatile Florida Room/Den and has been meticulously updated with a new kitchen boasting butcher-block counters, with an enclave dining area, a remodeled bathroom, and freshly painted walls, along with newer double-pane windows that fill the space with natural light and offer utility savings. Step through to your massive, fully fenced, and shaded backyard—an ideal setting for outdoor activities or gathering around a fire pit. This adorable home puts you within walking distance of Mills Avenue and minutes from the East End Market, Lake Ivanhoe, and Downtown Orlando. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: Second floor 2 bedroom, 2 bath condominium in the vibrant Audubon Park Community. High quality wood-laminate floors stretch from the foyer at the main entry, all the way to the screened and covered balcony with interior courtyard views and an extra storage closet. The kitchen is fully equipped with dishwasher, refrigerator/freezer, oven, range and built-in microwave. Wood cabinets and a closet pantry provide plenty of storage space and breakfast bar rounds out the space. The master bedroom is privately located in the rear of the condo with a private bath and walk-in shower plus linen closet. The 2nd bedroom has spacious closets and shares a bathroom located next to the washer/dryer included in the rent. Audubon Place City Condos is loaded with amenities including a pool, fitness center and clubhouse. On-site management keeps the property well-maintained and makes this a great place to live.

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: Douglas Prince (407-448-6649)

Remarks: Rare opportunity to rent a beautiful single-family home in Baldwin Park. This stunning two-story Craftsman-style residence features a charming front porch overlooking a private mews and is just steps from the community pool. The home offers three bedrooms plus a spacious media or playroom, two and a half bathrooms, and a desirable first-floor primary suite. Interior highlights include gorgeous wood flooring and a well-appointed kitchen with wood cabinetry, granite countertops, stainless steel appliances, and a glass backsplash. The primary suite features a tray ceiling, a large walk-in closet, and a luxurious bathroom with an oversized shower, separate soaking tub and water closet. Upstairs, both bedrooms include walk-in closets, with a built-in desk between them, along with a generous bonus room that can easily function as a media room, playroom, or even a fourth bedroom. The home also offers abundant storage and is wired for surround sound both upstairs and downstairs. Step outside to a spacious patio in the back, perfect for entertaining. The property also includes an oversized two-car garage and a full driveway. Rent includes high-speed 1GB internet and landscaping for added convenience. Enjoy the Baldwin Park lifestyle with access to top rated schools, in addition to three community pools, two fitness centers, a recreation building, and scenic walking and jogging trails around Lake Baldwin. Ideally located near the Village Center, offering a variety of shopping, dining, and everyday conveniences.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Carolina Brum (407-450-9167)

Remarks: Wow. What a wonderful home to return to everyday! This home is light and bright with new solid surface floors throughout and fresh paint. The home has lots of windows which provides a light and airy feel plus you have a wrap around porch giving you wonderful views of Enders Park, Clubhouse and Pool. The home has a huge kitchen with stainless steel appliances. The bedrooms are split with the master having spectacular views of the park as well. The home has full size washer and dryer and comes with a 1 car detached garage with garage door opener. You will love this home from the moment you see it. Located in the heart of Baldwin Park where you can stroll to the Village Center and enjoy dinner or an evening coffee. This home comes with the Baldwin Park amenities which give you access to the 3 pools, 2 fitness centers, playgrounds, parks and meeting spaces. Available IMMEDIATELY! Welcome Home.

Listing is courtesy of: PARKSIDE PROPERTIES, LLC (407-376-6635)

Listing Agent: Kristin Haughwout-Osorio (407-376-6635)