Winter Park Single Family Homes For Rent - 43 homes

Remarks: Welcome home to the heart of Winter Park's coveted Tree Streets. This beautifully remodeled single-family home sits on an oversized lot just moments from Interlachen Country Club and Winter Park Racquet Club, and is zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. Inside, natural light pours through windows in every room, giving the home a bright, airy feel throughout. The main living areas feature classic plantation shutters, while all bedrooms are fitted with blinds, a thoughtful touch that makes every space feel finished and move-in ready. Warm engineered hardwood floors, recessed lighting, and a flowing open layout connect the living room, dining area, and family room with ease. The chef's kitchen is the heart of the home, featuring granite countertops, a large center island, rich wood cabinetry, stainless steel appliances, and a professional-grade range hood, all opening into the spacious family room with its slate tile floors, wood-burning fireplace, built-in shelving, and French doors to the backyard. The primary suite overlooks the pool and rear yard, offering a serene and private feel. Its spa-inspired en suite bath features a dual-sink vanity, a walk-in tiled shower, and a private access directly to the backyard and pool, making it ideal for those who love to start or end the day outdoors. The second bedroom enjoys its own en suite bath. A third full bath serves the remaining bedrooms, beautifully updated with designer gold fixtures, modern vanity, and stylish lighting. The split bedroom layout offers privacy and flexibility for families, guests, or a dedicated home office. Out back, your private oasis awaits with a sparkling pool, concrete deck, lush lawn, and towering mature oaks creating that quintessential Winter Park canopy. Pool and lawn maintenance are included in rent, so you can simply enjoy. The attached 2-car garage includes laundry. No pets. No exceptions.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Drew Henner (407-406-0662)

Remarks: Available for rent! Tucked onto a desirable corner lot just steps from Lake Killarney, this beautifully updated 3 bedroom, 2 bath single-family home puts you in one of the area's most sought-after spots. Walkable, quiet, and moments from the water. Inside, the home is move-in ready with a full suite of brand-new appliances (dishwasher, range, and refrigerator) plus washer/dryer hookups ready for your setup. Three comfortable bedrooms, two full baths, and bright, livable spaces make it easy to settle in from day one. Easy parking thanks to a covered carport and private driveway. Pets welcome on a case-by-case basis. Available now. Security deposit equal to one month's rent; move-in total is first month + security deposit. Tenant responsible for all utilities and minor maintenance (bulbs, filters); landlord handles major repairs and pest control.

Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)

Listing Agent: Zach Mitchell (407-920-6440)

Remarks: Beautiful 4 Bedroom Furnished House with a Pool! This home has an Eat-In Updated Kitchen. There are 3 bedrooms and a bathroom on one side and a large master suite on the other side with a fireplace. The master bathroom has an extra large walk-in shower with a double mirrored dressing area. There is a family room/ FLex Space/ Office Area with a Roku TV, Desk, and Wi-Fi. There is no garage. It has 2 sheds for storage in the back. The neighborhood is nice and quiet. It is conveniently located near Hospitals, Businesses, Restaurants, Schools and Shopping.

Listing is courtesy of: A +ROI PROPERTY (407-718-7994)

Listing Agent: Rene Fossey (407-718-7994)

Remarks: Nestled along a quiet brick-lined street in Winter Park’s coveted Via’s neighborhood, 1041 Tuscany Place offers a rare blend of elegance, comfort, and breathtaking natural beauty. From nearly every room, this exceptional residence captures tranquil views of the private backyard and picturesque Lake Temple beyond. Inside, a thoughtfully designed open floor plan is enhanced by soaring vaulted ceilings and an abundance of natural light, creating a warm yet sophisticated atmosphere. The gourmet kitchen is beautifully appointed with premium Wolf appliances, a Sub-Zero refrigerator, quartz countertops, imported Italian cabinetry, and a striking mother-of-pearl mosaic backsplash. The primary suite serves as a peaceful retreat, complete with serene landscape views and a spa-inspired bath featuring a spacious walk-in shower with skylights, body jets, and an oversized 40-inch rainfall showerhead. Upstairs, two generously sized bedrooms share a well-appointed Jack-and-Jill bath, offering comfort and privacy for family or guests. Outdoor living is just as impressive. A spacious deck invites you to relax and entertain while overlooking the sparkling pool and hot tub, while the lower decks bring you into nature with an inviting fire pit overlooking the water. The expansive, beautifully landscaped backyard provides a private setting to enjoy the best of Florida living. Ideally located just minutes from the Winter Park Racquet Club, Interlachen country club, Lake Maitland, and the shops and dining of Park Avenue, this home offers an extraordinary lifestyle in one of Winter Park’s most desirable settings.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Bradford Barnett (407-227-0647)

Remarks: Lawn and pool maintenance included in rent! Welcome to this beautifully upgraded Winter Park pool home, designed for effortless living and exceptional entertaining. This 3-bedroom, 2-bath residence offers an open, inviting floor plan with a spacious kitchen featuring updated countertops and cabinetry, stainless steel appliances, beautiful bathroom finishes and updated flooring throughout. The home truly shines outdoors, offering an abundance of entertaining space. Enjoy a screened-in pool, covered patio, and multiple seating areas including a tiled lounge space with a firepit, all set within a large, fenced backyard with both lush grass and low-maintenance turf. Whether hosting guests or enjoying a quiet evening, this home provides the perfect setting. Inside, the light-filled dining room overlooks the backyard from three sides, while the primary suite features a spacious closet and private en-suite bath. All bedrooms include newer carpet, and a generous utility room off the carport offers ample space for laundry and storage. Located in a highly rated school zone and just minutes from Rollins College, parks, shopping, dining, and everything Winter Park has to offer, this home delivers both lifestyle and convenience in one exceptional rental opportunity.

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

Listing Agent: Lianna Dangelo (321-446-3509)

Remarks: 3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and lawn service included. *Bonus Amenity Included* -All 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.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Shawn Beard (407-739-7722)

Remarks: Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step outside to your own private oasis — a fully fenced backyard with a sparkling private pool, perfect for relaxing or entertaining year-round. The property also includes an attached 2½-car garage and 4 additional driveway parking spaces, providing plenty of room for vehicles. Located in a prime Winter Park neighborhood, this home is close to parks, shopping, dining, and top-rated schools. Pets are welcome, making this a perfect home for the whole family. Don’t miss this opportunity to enjoy privacy, space, and convenience in one of Central Florida’s most sought-after areas.

Listing is courtesy of: THE REALTY MEDICS (321-947-7653)

Listing Agent: Jason Hamilton (321-947-7653)

Remarks: newly updated 3 bedroom 2 bath with flex room for home office. new appliances and ready for move-in.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Mike Wang (631-748-6708)

Remarks: Welcome to this beautifully updated 3-bedroom, 2-bath home located in the heart of Winter Park. Filled with abundant natural light throughout and thoughtful upgrades, this home offers a warm and inviting atmosphere that would be perfect for your family. Highlights: -Primary suite featuring a walk-in closet and private ensuite bathroom -Classic terrazzo flooring -Recently remodeled kitchen with brand-new appliances -Solid wood cabinetry -Fully fenced backyard -2-car parking space -Washer and dryer included -Lawn Service Included Enjoy living in a prime Winter Park location close to shopping, dining, parks, and top-rated schools. This home blends modern updates with timeless charm, definitely a must-see! 12-month Minimum Lease $85 Non-Refundable Application Fee (18+) All Belmont Management Group residents are enrolled in the Resident Benefits Package (RBP) for $50.00/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. Please note, that we require all applicants to have - a combined monthly, net household income of 3X the monthly rent, - good standing credit - minimum score of 650, No accounts in collections - and no prior evictions or collections from any apartment complexes Along with your application, please include a copy of your photo ID as well as two consecutive months of your most recent pay stubs or other proof of income. We will not accept W2s as proof of income. The application includes full background, credit check as well as eviction judgments Pets are allowed on a case-by-case basis via the owner's instructions.

Listing is courtesy of: BELMONT REALTY (407-745-0696)

Listing Agent: Summer Hornburg (407-495-8134)

Remarks: Exceptional Lease Opportunity | The Vias, Winter Park $13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available Now Rarely 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 combination of scale, sophistication, and livability across three thoughtfully designed levels. Rich hardwood floors anchor the main living areas, setting a tone of warmth and understated elegance throughout. The open-concept floor plan transitions effortlessly between spaces, equally suited to quiet evenings at home and large-scale entertaining. At the center of it all is a chef's kitchen appointed with 42-inch cabinetry, quartz countertops, a professional gas range, and double ovens. An oversized eat-in bar and adjacent dining area connect seamlessly to the family room, ensuring the cook is always part of the conversation. The home offers two expansive primary suites, each a serene private retreat. The main floor — along with the second level — encompasses 4,500 SF and five bedrooms with four baths. The main suite is a true sanctuary, complete with a spa-caliber bath and a custom walk-in closet. A gas fireplace anchors the family room, while French doors open to the covered rear patio and pool deck. Upstairs, four additional bedrooms are served by two Jack-and-Jill baths, a generous laundry room, and a versatile studio or playroom. Custom loft stairs climb to a third-floor bonus space, ideal for creative pursuits or kids' play. The lower level is an exceptional offering in its own right — a fully appointed 2,500 SF in-law suite with a private living area, kitchenette and breakfast bar, a spacious primary bedroom with ensuite bath, two secondary bedrooms, a full hallway bath, gym, workshop, and a game room with pool table. Generous window wells flood the space with natural light, and direct access to the back patio and pool deck makes the transition between levels completely seamless. Zoned for the highly regarded Dommerich/Maitland/Winter Park High School district, and just minutes from the shops and dining of Park Avenue and a short stroll to the Winter Park Racquet Club — this is Winter Park living at its finest. All measurements and dimensions should be independently verified.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Kelly Price (407-645-4321)

Remarks: 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, and a sunken family room with walls of windows overlooking the pool and backyard. The primary suite enjoys its own private bath, while three guest bedrooms share a hall bath. A full pool bath with walk-in shower off the family room adds everyday convenience. An attached 2-car garage offers additional parking or storage. Step outside to your private backyard oasis, where a sparkling pool, heated spa, and generous yard space are ideal for effortless Florida living. Situated on a nicely sized lot, this home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School. Lawn care and pool care are included. Available May 1, 2026. 4 bedrooms, 3 bathrooms, 2,207 SF at $5,895 per month. Security deposit of $7,500 required. Renters insurance is required. Pets are considered on a case-by-case basis, subject to owner approval.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Kelly Price (407-645-4321)

Remarks: Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , 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 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: Gorgeous single-family home in the "tree streets" of Winter Park now available for rent or purchase. Private pool, two car garage, fabulous location and newer construction! Don't wait! Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for today’s lifestyle. The open-concept main floor features a beautifully appointed kitchen, a spacious dining area, and a light-filled living room complete with a designer fireplace and custom built-in shelving. The stunning kitchen boasts quartz counters, spacious cabinetry, KitchenAid appliances, and designer lighting. A fourth bedroom (currently used as a study) is also located on the main level. From the great room, expansive sliding glass doors lead out to the covered lanai, where you'll find an in-ground pool, a fully fenced yard, tongue-in-groove wood ceiling, and pre-plumbing in place for your dream summer kitchen—ideal for entertaining year-round. Upstairs, the luxurious primary suite provides a peaceful retreat with an oversized balcony overlooking the pool and rear yard. Two additional bedrooms are also featured on the second level, along with a second full bath. The first-floor office doubles as a fourth bedroom, with an adjacent full bath for guests or multi-generational living. This home boasts well-thought-out upgrades, including beautiful wood inlays in niches, open shelving, quartz countertops, slat wall features, and stunning light fixtures throughout. The work has been done for you in this like-new home! Located just steps from Phelps Park and minutes from the shops and dining of Park Avenue and the Winter Park Chain of Lakes, this home offers the perfect blend of modern design, comfort, and convenience. Don't miss your chance to rent or own this exceptional home in the heart of Winter Park!

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Sue Silberbusch (407-252-3157)

Remarks: Check out this Winter Park gem near Lake Sue! This 3BR/2BA home features a modern kitchen with granite and stainless steel, wood floors, and a private backyard oasis (landscaping included). Perfect for commuters or remote workers, it boasts an oversized 3rd bedroom/office and is minutes from Park Ave and Audubon Park. Zoned for Audubon K-8 and Winter Park High. Every applicant should apply separately. 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: One or more photo(s) has been virtually staged. Welcome to this beautifully refreshed 3-bedroom, 2-bath home nestled in a highly desirable Winter Park location — offering comfort, style, and convenience with no HOA restrictions. With 1,676 square feet of thoughtfully designed living space, this home is the perfect blend of modern updates and timeless character. Step inside to discover brand-new wood-look tile flooring throughout, providing both durability and a clean, contemporary feel. Fresh interior paint enhances the bright and airy atmosphere, while vaulted ceilings with exposed wood beams add warmth and architectural charm to the main living area — creating a space that feels both open and inviting. The kitchen is equipped with stainless steel appliances and offers a functional layout ideal for everyday living and entertaining. Both bathrooms have been updated, including a new sink in the primary bath, adding a fresh and polished touch. Enjoy Florida living at its best on the screened-in back porch, perfect for morning coffee or evening relaxation. The spacious backyard offers endless possibilities — whether you envision a garden, play area, or outdoor entertaining space. Additional features include a 2-car garage for convenience and extra storage, as well as a prime location just minutes from shopping, dining, and major roadways — making daily commutes and errands a breeze. This well-maintained home offers a wonderful opportunity to live in an established neighborhood with character, space, and flexibility. A perfect place to call your dream home!

Listing is courtesy of: AMERICAN DREAM HOMES INC (407-382-8100)

Listing Agent: Jenny Forest Lin (407-780-6065)

Remarks: Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are welcomed by an abundance of natural light filling the entryway, dining room and formal living room. The inviting family room includes a stylish wood burning fireplace and French doors that lead out to the backyard. Cook and enjoy your favorite meals in the home’s gourmet kitchen and dinette area. Right off the large 2-car garage is a walk-in laundry room and a lovely half bathroom. Upstairs is the spacious master bedroom and master bathroom including a large soaker tub and walk-in shower. Experience gorgeous Florida outdoor living in the impressive second floor deck that can be accessed through the master bedroom or backyard. Enjoy the lime and pineapple trees in this well-maintained backyard. The home is conveniently located in close proximity to Winter Park’s Park Avenue restaurants and shops and incredible schools. Landscaping/Lawn Care will be provided by landlord.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Lisa Gould (407-721-7612)

Remarks: Updated Charming 4 Bed/2 Bath mid-century home located in Northwood Terrace/Audubon Park (just across the street from Baldwin Park). You will love the large lot .34 Acres with it botanical garden, meditation area, a patio with a raised HOT Tub (perfect for a starry night) and plenty of privacy with all the lush foliage. The front door opens to a great room where the kitchen, living area, dining room, and family room are all open to each other. The Hurricane resistant double panned windows offer gorgeous outdoor views, and invite natural light into each room. The kitchen features granite counters, a breakfast bar, pantry, and an additional combo utility & storage room with Washer/Dryer. The kitchen also has a reverse osmosis water filtration system to produce alkaline water for healthy living. The large family room has a wood-burning fireplace & sliding doors to the scenic backyard. The Master suite also has access to the backyard an impressive walk-in closet. The Master Bath has separate areas or the toilet/sink and bath/shower sink. All closets are cedar lined. Zoned for Winter Park Highschool and K-8 Audubon Park school! No HOA! Steps away from Baldwin Park, East End Market, and just a bike ride away from Downtown Winter Park!

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: John Goggin (321-332-3000)

Remarks: This beautiful 2 bed / 1 bath 1,029 square foot home in Winter Park is totally refurbished and available for immediate occupancy. Newer kitchen cabinets. Newer bathroom. With a single car carport. This property features wood floors throughout, tile floors in the kitchen, dining room and bathroom, large open yard. Washer/dryer, shed & lawn care included! Application Fee: $50 each adult (18+) **Full Credit/Skip/Eviction/Background check is done on all applicants. **Please have the following documents ready to attach as JPEG or PDF: - Drivers License - (3) Pay Stubs

Listing is courtesy of: PREMIER MANAGEMENT GROUP INC (407-370-4400)

Listing Agent: Ken Warren (407-370-4400)

Remarks: Rarely available neighborhood for rentals, this 2 bedroom 1 and a half bath house is surrounded by multi-million dollar homes. Large back yard is totally fenced for kids or pets. Zoned for Winter Park's finest schools and located just off Park Avenue for easy access to shopping and restaurants. Shorter term lease is negotiable. All appliances are in place, including washer/dryer. Don't miss this quaint home on a picturesque brick lined street.

Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)

Listing Agent: Jacob Johnson (407-353-0106)

Remarks: Experience the rare luxury of a high-performance, meticulously updated 3-bedroom sanctuary in a quiet Winter Park cul-de-sac, offering the perfect blend of modern utility and suburban serenity. Zoned for Winter Park High School, this versatile floor plan features both a dedicated private office for the remote professional and an expansive game room for premier entertaining. Every major system has been addressed for total peace of mind, including a BRAND NEW ROOF (2026), high-efficiency AC (2025), and a fresh 2026 interior refresh. The heart of the home is a light-filled living area anchored by a magnificent wood-burning stone fireplace, leading to a chef’s kitchen outfitted with premium Quartz countertops, new cabinetry, and a new dishwasher. Experience a seamless flow with brand-new luxury vinyl plank flooring throughout—no carpet—and spa-inspired bathrooms featuring a new walk-in primary shower and pristine guest bath updates. Situated on an oversized .33-acre lot, this property provides exceptional privacy and space rarely found in a rental. Enjoy the convenience of being just 5 minutes from Costco and major retail hubs, 15 minutes from Park Avenue’s world-class dining, and offering swift access to UCF and the 417. This is more than a rental; it is a meticulously modernized retreat ready for immediate move-in.

Listing is courtesy of: NEXTHOME NEIGHBORHOOD REALTY (407-377-7735)

Listing Agent: Brenden Rendo (407-710-8720)