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WINTER PARK PINES - S5152775 - 2828 SCARLET RD, WINTER PARK, FL 32792 Just Added on 06/30/2026 2:20PM
$2,350 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Available Now! This charming 3/2 Home located in the heart of Winter Park features a practical flow between the living, dining, and kitchen spaces. Large windows bring in natural light, Ceramic tile flooring, stainless steel appliances, and stone kitchen countertops. A convenient inside laundry room with washer and dryer provided as convenience only. The covered porch and outdoor space adds additional value, providing room for relaxation, gardening. Pets accepted (Dogs up to 35lb and Cats) with required application, fees, and rents. Conveniently located near top-rated schools, shopping, dining, parks, and major roadways, this home offers both comfort and accessibility in one of Winter Park’s desirable residential areas. A great opportunity to enjoy the best of Central Florida living. Don't miss out on this opportunity to make this beautiful house your home sweet home. Schedule a showing today! All our residents are enrolled in our Resident Benefits Package for $55.00 per month, charged as additional rent. This package includes Pest Assurance powered by Pest Share, access to an online resident portal, and availability of a dedicated 24/7 maintenance portal. Additionally, it offers monthly reporting of rental payments to Experian RentBureau, bi-monthly home delivery of replacement HVAC filters, and the use of resident-completed inspection technology. Residents are entitled to one late fee waiver during their residency and have access to concierge utility services.
Listing is courtesy of: ALLEGIANT MANAGEMENT GROUP INC
ORANGE TERRACE - O6421116 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 Just Added on 06/30/2026 10:35AM
$3,000 | Single Family Home | 4 beds | 2.0 baths
Spacious 4 bedroom, 2 bath home in a quiet neighborhood just minutes from I-4 and Fairbanks. Convenient to downtown Orlando, Winter Park Village, shopping, dining, and schools. Open split floor plan, with three comfortable bedrooms on one side and a large master suite on the other. Inside laundry room, ample parking spaces, fenced in side yard, all updated with modern finishes and move in ready.
Listing is courtesy of: A+ REALTY PROFESSIONALS, INC
HIDDEN OAKS CONDO PH 11 - S5150258 - 3220 OAK LAWN PLACE PL #210, WINTER PARK, FL 32792 1 Day on yellowkey
$1,900 | Townhouse | 3 beds | 2.5 baths
This beautiful corner-unit townhouse offers comfort, space, and convenience in a highly desirable location. This home features 3 bedrooms and 2.5 bathrooms, providing plenty of space for families and professionals. The kitchen flows seamlessly into the living, dining áreas and private patio offering a practical design for everyday living. All bedrooms are located upstairs for added privacy, including a comfortable primary suite with its own private bathroom.Conveniently situated near shopping, dining, schools, colleges and roadways, this property offers both comfort and accessibility to everything you need while still providing a peaceful residential setting.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION
WRENWOOD CONDO - O6420610 - 4812 TANGERINE AVE #4812, WINTER PARK, FL 32792 1 Day on yellowkey
$1,700 | Half Duplex | 2 beds | 2.0 baths | 3 car
Enjoy comfortable living in this well-maintained condo in a highly desirable Winter Park location. The home offers 2 spacious bedrooms and 2 full bathrooms, making it a great fit for families, professionals, or roommates. The bright open living and dining area creates a welcoming space for relaxing or entertaining. The kitchen includes all appliances, plus a washer and dryer for added convenience. Water is included in the rent, adding extra value. Both bedrooms offer generous space, natural light, and ample closet storage. The thoughtful layout provides privacy between the bedrooms, which is ideal for remote work or shared living. Located near Full Sail University, UCF, major highways, shopping, and everyday conveniences, the condo also offers easy access to Downtown Orlando. Residents can enjoy a community pool and fitness center in a quiet, private community. This property combines comfort, convenience, and a great location. It is an excellent rental opportunity in Winter Park.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC
VISTAS AT LAKE HOWELL - O6420636 - 2529 GALLIANO CIR, WINTER PARK, FL 32792 2 Days on yellowkey
$2,350 | Townhouse | 3 beds | 2.5 baths | 1 gar
Fantastic end corner unit with Seminole County Winter Park address. Gated community, 3/2.5 - 2 story townhome with open floor plan. Very convenient location just off Semoran Blvd, with Walmart super center, Publix and abundant of shopping and dining facilities nearby.
Listing is courtesy of: HONEST REAL ESTATE COMPANY
- O6416050 - 301 S CAPEN AVE, WINTER PARK, FL 32789 4 Days on yellowkey
$2,500 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue. Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage. Down the hall, you'll find three bedrooms with brand-new carpeting and easy access to the spacious backyard, offering plenty of room to relax or entertain outdoors.
Listing is courtesy of: CORCORAN PREMIER REALTY
AUTRYS PARK - WINTER PARK, FL 32789 4 Days on yellowkey
$7,500 | Single Family Home | 4 beds | 4.0 baths | 2 gar
Virtually Staged. Brand-New Luxury Home for Lease in Winter Park's Most Walkable Neighborhood Live in one of Central Florida's most desirable communities without compromising on space, style, or location. This brand-new, never-lived-in home by Nautilus Homes offers 4 bedrooms, 4 full bathrooms, a private office, and over 3,000 square feet of refined living, all in the heart of Winter Park, steps from everything that makes this city special. The moment you walk in, the difference is obvious. Crème Brûlée wide-plank wood flooring flows throughout, setting a warm, elevated tone that carries into every room. The open-concept living area is anchored by a built-in wine and coffee bar, perfect for morning routines and evening wind-downs alike. The chef's kitchen is the heart of the home, featuring custom ceiling-height cabinetry, a handcrafted wood range hood, and high-end finishes designed for serious cooking and effortless entertaining. Just off the kitchen, a beautifully appointed butler's pantry finished in statement Kit-Kat tile connects seamlessly to the formal dining room, a layout that makes hosting feel natural, not stressful. The floor plan gives everyone their own space. A private office and a full en-suite bedroom on the main level offer flexibility for working from home, hosting guests, or accommodating multigenerational living. Upstairs, three additional bedroom suites each feature walk-in closets and their own beautifully finished bathrooms, no sharing, no compromising. The primary suite is in a category of its own. A spa-inspired bathroom with a freestanding soaking tub, an oversized 9-foot walk-in shower with dual sprayers, a frameless glass enclosure, and sleek linear drainage make every morning feel intentional. The walk-in closet is generously sized and thoughtfully designed. Additional features include a 2-car attached garage, central air and heating, an irrigation system, wood flooring throughout, and electric dryer hookup, everything you'd expect in a home at this level, with nothing left out. Outside, you're minutes from Park Avenue, Winter Park Village, East End Market, and a tight-knit community known for tree-lined streets, top-rated schools, and a pace of life that feels a world away from the rest of Orlando. This is the rare rental that actually lives up to the photos. Reach out today, homes like this don't stay available long.
Listing is courtesy of: REAL BROKER, LLC
CONWILL ESTATES - O6420234 - 1791 SPRUCE AVE, WINTER PARK, FL 32789 4 Days on yellowkey
$4,900 | Single Family Home | 3 beds | 2.0 baths
Beautifully renovated 3 bedroom, 2 bath pool home in one of Winter Park's most desirable neighborhoods. Designed with an open floor plan, this home features wood flooring throughout the main living areas, crown molding, and an incredible chef's kitchen with Quartz countertops, a large breakfast bar, custom cabinetry, floating wood shelves, gas range, stainless steel appliances, and abundant storage. The spacious Florida room overlooks a private backyard complete with a sparkling pool, expansive deck, covered seating area, mature landscaping, and a fully fenced yard. Mango and lime trees, landscape lighting, and a powered storage shed with workbench make the outdoor space just as enjoyable as the inside. Additional features include hurricane impact windows, plantation shutters, updated lighting and ceiling fans, a Nest thermostat, surround sound, and a circular paver driveway. Ideally located just minutes from Park Avenue, Rollins College, the Winter Park Racquet Club, Winter Park Golf Club, Phelps Park, and the YMCA, with easy access to top rated schools, dining, shopping, and everything charming about Winter Park.
EASTBROOK SUB - O6420055 - 887 EASTBROOK BLVD, WINTER PARK, FL 32792 5 Days on yellowkey
$2,650 | Single Family Home | 4 beds | 2.0 baths
Come see this 4 bedroom 2 bath in the beautiful Winter Park neighborhood of Eastbrook. This home is completely move in ready with granite counter-tops and stainless steel appliances in the kitchen and new microwave. Large open kitchen/living room. Spacious bedrooms with lots of closets and storage space. Updated modern light fixtures and fans adorn the rooms throughout the home. Home is tiled and has new laminate throughout. Fenced backyard with huge screened in back porch.
Listing is courtesy of: ABSOLUTE REALTY GROUP, LLC
WINDWARD SQUARE SEC 2 - O6418670 - 2657 EXUMA WAY, WINTER PARK, FL 32792 5 Days on yellowkey
$2,400 | Townhouse | 3 beds | 2.0 baths
Freshly remodeled and move-in ready, this 3-bedroom, 2-bath townhome offers comfortable living in a highly desirable Winter Park location. The open-concept living and dining areas create a welcoming space for everyday living and entertaining, while the convenient pass-through window connects the kitchen and dining room for added functionality. The brand-new kitchen remodel features granite countertops and all-new stainless steel appliances. The spacious primary suite includes a walk-in closet and private en suite bath with a walk-in shower. Two additional bedrooms and a full bath offer ample room for everyone. Tile flooring throughout provides easy maintenance and durability. Enjoy time relaxing outdoors on the covered patio in the privacy of the fenced backyard. Additional recent updates include a new roof, all-new Low-E energy-efficient windows, and a new vanity, toilet, and faucets in the guest bath. Residents enjoy access to the community pool and clubhouse, along with a prime location close to shopping, dining, entertainment, and major roadways. With its combination of recent upgrades, community amenities, and sought-after Winter Park address, this is the perfect place to call home.
Listing is courtesy of: HAVEN PROPERTY GROUP LLC
WATERFALL COVE - O6419704 - 1695 LEE RD #A101, WINTER PARK, FL 32789 6 Days on yellowkey
$1,695 | Condo | 3 beds | 2.0 baths
Vacant! 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.
Listing is courtesy of: CINO INTERNATIONAL INC
TANGLEWOOD SEC 3 REP - O6419550 - 5117 LAKE HOWELL RD, WINTER PARK, FL 32792 6 Days on yellowkey
$2,395 | Single Family Home | 3 beds | 1.0 baths | 1 car
3/1, Carport, Single Family Home, Living Room, Dining Room, Eat in Kitchen, Stainless Steel Appliances Included: Stove, Microwave, Refrigerator, Dishwasher, Disposal, Inside Utility Room with Washer and Dryer Hookups, Laminate Wood Flooring & Ceramic Tile Throughout, Fenced Backyard, Pets Ok Upon Owner's Approval, NO SMOKING, Year Built: 1957/1300 Sqft.
Listing is courtesy of: LEGENDS REALTY
LAUREL SPGS - O6419181 - 7522 LAUREL SPRINGS DR, WINTER PARK, FL 32792 7 Days on yellowkey
$2,200 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Located in the highly sought-after Winter Park High School district, this beautifully maintained 3-bedroom, 2-bath home in Laurel Springs provides comfort, space, and convenience. The bright and inviting living area features tile and an open, welcoming feel. Enjoy year-round indoor-outdoor living in the expansive 400+ sq. feet. enclosed patio overlooking a fully fenced backyard—perfect for entertaining, relaxing, or family gatherings. Ideally situated with easy access to shopping, dining, parks, and major highways. Move-in ready!!!!
Listing is courtesy of: JOY ESTATE ENTERPRISE INC
LAKE FOREST PARK S/20 LOT 26 BLK B - O6419042 - 2234 HOWARD DR, WINTER PARK, FL 32789 8 Days on yellowkey
$8,295 | Single Family Home | 4 beds | 5.5 baths | 2 gar
Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility. Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal entertaining and casual gatherings. The gourmet kitchen is a chef's dream, complete with an enormous walk-in pantry, high-end appliances, and seamless flow into the dining area. Entertain in style with a wet bar and food service station, perfect for hosting elegant dinners or festive celebrations. Master Suite is an expansive sanctuary that features a spa-like bathroom equipped with a soaker tub, walk-in shower, His and Her vanities Step outside to your private heated lap pool, perfect for fitness or relaxation. The backyard retreat is surrounded by lush landscapingan ideal oasis for quiet relaxation or sunny Florida afternoons. A first-floor bedroom with en-suite bath adds convenience for guests or multi-generational living. Perfectly situated near Audubon Park and Baldwin Park, this home offers unbeatable access to top-rated schools, including Audubon Park K-8 & Winter Park H.S. Ideally situated near Downtown Orlando, Rollins College, hospitals, renowned restaurants, and boutique shopping, making it a prime location for those seeking convenience and accessibility. Explore numerous community parks, perfect for those who enjoy an active outdoor lifestyle. An area rich in culture with nearby museums to explore and learn. This is more than just a homeit's a lifestyle. Experience the best of Winter Park living: elegant, elevated, and effortlessly connected. Pets negotiable with owner approval. Additional fees may apply.
Listing is courtesy of: COLDWELL BANKER REALTY
WRENWOOD CONDO - O6415325 - 4796 TANGERINE AVE #4796, WINTER PARK, FL 32792 8 Days on yellowkey
$1,600 | Condo | 2 beds | 2.0 baths
Cute 2 bedroom, 2 bathroom, freshly painted condo in Winter Park. Amenities include a swimming pool, fitness center, clubhouse/conference room, well-maintained grounds, and ample parking. This property offers easy access to Full Sail University, University of Central Florida, Rollins College, Downtown Winter Park, Baldwin Park, and Downtown Orlando. Shopping, dining, entertainment, parks and grocery stores are all nearby. Major highways SR-417 and SR-408 are easily accessible. There is a washer and dryer in the condo and new carpet throughout bedrooms and main living areas. There is a screened in back patio with storage closet.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES