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- S5151826 - 1000 S SEMORAN BLVD #103, WINTER PARK, FL 32792 2 Days on yellowkey
$1,750 | Condo | 3 beds | 2.0 baths
Virtually Staged. Stylish Winter Park Condo Living – Spacious 3-Bedroom Home in a Prime Location! Welcome to 1000 S. Semoran Blvd #103, a beautifully maintained 3-bedroom, 2-bath residence offering comfort, convenience, and an unbeatable Winter Park location. Featuring a bright and open floor plan, this home provides the perfect space for relaxing, entertaining, and enjoying everyday living. The well-designed layout includes spacious living and dining areas, generously sized bedrooms, and a private primary suite for added comfort. The kitchen offers ample cabinet and counter space, making meal preparation easy and enjoyable. Located in the heart of Winter Park, you'll enjoy convenient access to top-rated schools, shopping centers, restaurants, parks, entertainment, and major roadways. Whether you're commuting to work or exploring everything Central Florida has to offer, this location puts you close to it all. This inviting home combines spacious living with exceptional convenience, making it an outstanding rental opportunity. Don't miss your chance to call this Winter Park gem home—schedule your private tour today!
Listing is courtesy of: TRANSCEND REALTY
WINDWARD SQUARE SEC 3 - O6416235 - 2304 INAGUA WAY #2304, WINTER PARK, FL 32792 3 Days on yellowkey
$1,750 | Condo | 2 beds | 1.0 baths
Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the established community of Winward Square with access to a community pool and tennis courts, this home offers both convenience and comfort. Don't miss out on this opportunity to live in Seminole County in this lovely property. Sorry Pets are not permitted. *Washer and dryer are in as/is condition and for tenant convenience only *Tenant is required to carry Renters Insurance If approved for this home, new tenants must pay a $200.00 lease coordination fee due at the same time as the security deposit payment. *RESIDENTS BENEFIT PACKAGE* Residents are enrolled in the Resident Benefits Package (RBP). There is an additional $35.00 a month charge for this added to the advertised rent and is considered additional rent. RBP includes HVAC air filter delivery, utility concierge services making utility connection a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application
Listing is courtesy of: CT HOMES REALTY CORPORATION
PARK WEST CONDO - O6415216 - 350 CAROLINA AVE #407, WINTER PARK, FL 32789 3 Days on yellowkey
$2,895 | Condo | 2 beds | 2.0 baths | 1 gar
Experience maintenance-free living in this spacious 2-bedroom, 2-bath condominium offering 1,529 square feet in the gated Park West community in the heart of Winter Park. Located on the top floor, this spacious residence features vaulted ceilings, hardwood flooring, quartz countertops, stainless steel appliances, walk-in closets, a soaking tub, a stacking washer and dryer, and charming Juliet balconies. Residents enjoy exceptional amenities, including a community pool, tennis courts, clubhouse, and an assigned garage parking space. Water service is included in the rent. Park West is across the street from the weekly Winter Park Farmers' Market, and one block from Park Avenue; you'll have easy access to boutique shopping, highly renowned restaurants, the SunRail station, and everything that downtown Winter Park offers. Cats will be considered on a case by case basis with a non-refundable pet fee and monthly pet rent. Prospective tenants are subject to the Park West Condominium Association approval process and associated application fee.
Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC
COLONIES - S5150999 - 3045 AARON BURR AVE #12D, WINTER PARK, FL 32792 3 Days on yellowkey
$1,650 | Condo | 2 beds | 2.0 baths
Condominium 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 to everything Orlando. Featuring new flooring and a clean, fresh interior, it is ideal for any lifestyle.
Listing is courtesy of: LPT REALTY, LLC
WINTER PARK PINES UT 5 - O6415814 - 418 R GILBERT RD, WINTER PARK, FL 32792 3 Days on yellowkey
$4,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools.
Listing is courtesy of: SOTERA LIVING
LAKE KILLARNEY CONDO - O6415735 - 151 N ORLANDO AVE #238, WINTER PARK, FL 32789 4 Days on yellowkey
$2,750 | Condo | 2 beds | 1.0 baths
Experience lakefront living at its finest in this exceptional Winter Park condo overlooking beautiful Lake Killarney. Enjoy breathtaking sunset views from your private waterfront retreat, complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.
Listing is courtesy of: COLONIALTOWN REALTY
SYLVAN HEIGHTS - A4696508 - 1741 GOODRICH AVE, WINTER PARK, FL 32789 5 Days on yellowkey
$3,600 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Virtually Staged. Charming 3-bedroom, 2-bath home in highly desirable historic Winter Park, situated on a large fenced lot with mature oak canopy, lush landscaping, and inviting outdoor living spaces. This well-maintained home offers a spacious living room, separate dining area, screened rear patio, large wooden deck with lighting, and a private fenced backyard perfect for relaxing or entertaining. NOT FURNISHED! The primary suite features two walk-in closets, double vanity sinks, a Jacuzzi tub, and a double walk-in shower. A guest suite with a closet and shared bathroom. The 3rd room has a closet and can be used as a bedroom or office. Additional features include ceiling fans throughout, generous closet space, newer bedroom flooring, fresh interior and exterior paint, a security system ready for activation, washer and dryer in the two-car garage, utility sink, and newly finished epoxy garage flooring. Major updates include roof and A/C replaced in 2021, and the refrigerator, stove, and microwave replaced in 2022. Lawn maintenance, lawn spraying, and pest control are included in the monthly rent. Located near AdventHealth Winter Park, Casa Feliz, Leu Gardens, Rollins College, Park Avenue shopping and dining, Baldwin Park, East End Market, Winter Park Farmers Market, Enzian Theater, city parks, museums, Winter Park Racquet Club, Interlachen Golf & Country Club, YMCA, Winter Park Boat Tours, the Winter Park Chain of Lakes, and Downtown Orlando. Zoned for highly rated local schools, including Brookshire Elementary, Glenridge Middle, and Winter Park High, with many nearby school options. Surrounded by historic homes and multi-million dollar estates, this property offers an excellent opportunity to enjoy the Winter Park lifestyle in a prime location. Lease Terms: Owner pays for lawn maintenance, lawn spraying, and pest control. Tenant is responsible for utilities, cable, and internet. First month’s rent, last month’s rent, and security deposit required. Credit and background check required for each applicant on the lease. Small pets may be considered with owner approval and an additional non-refundable pet fee. No smoking or vaping permitted. Current tenant leaving 7/2026. 24-hour notice to schedule a showing.
Listing is courtesy of: JOHN HARDING REALTY
CARVER TOWN FIRST ADD - O6414744 - 648 W SWOOPE AVE, WINTER PARK, FL 32789 6 Days on yellowkey
$2,700 | Single Family Home | 3 beds | 1.0 baths
FOR RENT - 648 W. SWOOPE AVENUE, WINTER PARK | OFFERED AT $2,700/MO - Stunning Home, Completely Remodeled, and Professionally Designed! Super cute 3 bedroom, 1 bath home in downtown Winter Park. Updated flooring, paint, windows, newer HVAC unit, updated kitchen cabinets, stainless steel appliances, Quartz countertops, beautiful bathroom tile work & fixtures, and interior washer/dryer. Open floorplan. Living/Dining room combo. Designer light fixtures. Fenced backyard. Located within walking distance to Park Avenue, Hannibal Square, the Winter Park Village, Rollins College and more. No smoking. Pets will be considered with an additional, non-refundable pet deposit. Move-in ready and available for occupancy July 1, 2025. Background and Credit Check required. $50 application fee. First month's rent + $3,000 security deposit. Tenant must carry renter's insurance. Lawn care and pest control included. Owner will consider pets.
Listing is courtesy of: KELLY PRICE & COMPANY LLC
- O6414626 - 1137 SOUTH PENNSYLVANIA AVE, WINTER PARK, FL 32789 7 Days on yellowkey
$2,995 Reduced | Single Family Home | 3 beds | 2.0 baths | 1 gar
Location!! Walking distance to Rollins campus and to downtown Winter Park. Beautiful 3-bedroom 2-bathroom home. Recently renovated kitchen and freshly painted. Nearby schools include Audubon Park elementary, Glenridge Middle School, and Winter Park education center school. This house is in the perfect location, close to great restaurants and within walking distance to Winter Park farmer's market.
Listing is courtesy of: COLDWELL BANKER REALTY
J KRONENBERGER SUB - O6413560 - 1760 ALABAMA DR, WINTER PARK, FL 32789 10 Days on yellowkey
$10,900 | Single Family Home | 4 beds | 2.5 baths | 2 gar
Behind a gated courtyard entrance in the Vias of Winter Park, just around the corner from Kraft Azalea Garden on the shores of Lake Maitland, this move-in ready residence offers privacy, thoughtful design and exceptional indoor-outdoor living. Surrounded by mature landscaping and accessed from both front and rear driveways, the property provides a rare sense of seclusion while remaining minutes from Park Avenue, Winter Park Racquet Club, dining, shopping and top-rated schools. Designed to maximize natural light, the home features vaulted ceilings, skylights, walls of windows and seamless connections to multiple outdoor living areas. The main level includes formal living and dining rooms, a spacious family room, dedicated home office and powder bath. Custom built-ins, extensive storage and carefully planned living spaces support both everyday living and entertaining. The chef's kitchen is appointed with custom wood cabinetry, stone countertops, premium appliances, a large center island with seating and generous preparation space. Open sightlines and direct access to outdoor gathering areas create a natural flow throughout the home. Upstairs, three bedrooms and two full baths include a spacious primary suite featuring vaulted ceilings, hardwood flooring, private balcony access and a renovated bath with marble finishes and a walk-in shower. Additional storage throughout the second level enhances functionality and organization. Outdoor living is a defining feature of the property. Multiple gathering spaces include a welcoming front courtyard, fire pit area and a fully equipped outdoor kitchen and dining space featuring a Wolf grill, brick pizza oven and market lighting. Mature hedges and professionally designed landscaping create privacy throughout the grounds. Additional highlights include hardwood flooring, an oversized garage with substantial storage capacity, dedicated utility room with laundry and utility sink, rear motor court access and multiple outdoor entertaining areas designed for year-round enjoyment. Available for a one-year lease. Unfurnished. Pets considered on a case-by-case basis subject to landlord approval.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY
WINTER PARK PINES REP - O6413831 - 2730 PRINCE JOHN RD, WINTER PARK, FL 32792 10 Days on yellowkey
$2,495 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Fantastic 4 Bed 2 Bath Winter Park Home with 2-car garage! Located in a highly desirable Winter Park area. Large living room/dining room combo, a large separate den area. The home has a large fenced-in backyard. Lawn care is included. Walking distance to the Cady Way Trail. *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 Home (with approval and a non-refundable pet fee).
Listing is courtesy of: RE/MAX 200 REALTY