Multiple Cities, Zip Codes, Addresses, Streets, Neighborhoods, MLS IDs
(separate each with the word OR)
Ex.Miami OR Coral Springs OR Boca Raton 33319 OR 33321 OR 33467
ENCLAVE AT HAWKS CREST - O6396367 - 1530 BANTAM WAY, WINTER PARK, FL 32792 1 Day on yellowkey
$2,800 | Townhouse 3 bedrooms, 2.5 bathroom, 2 car garage
Beautiful townhouse in a pool community, near to supermarket and Costco, good school area. High and trey ceiling in the master bedroom with high loft and living room. Beautiful tile floor on first floor
This listing is courtesy of: U S GLORY REALTY
CONWILL ESTATES - O6396000 - 1711 CHESTNUT AVE, WINTER PARK, FL 32789 2 Days on yellowkey
$4,150 | Single Family Home 4 bedrooms, 3.0 bathroom, 2 car garage
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.
This listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY
KILLARNEY ESTATES - O6396001 - 438 LAKEVIEW AVE, WINTER PARK, FL 32789 2 Days on yellowkey
$3,400 | Single Family Home 2 bedrooms, 1.0 bathroom , 1 car carport
Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete with a cozy firepit and large privacy bushes that create a secluded, tranquil retreat—ideal for relaxing evenings or entertaining guests. With a deeded dock and boat lift, you’ll have direct access to the Lake Killarney lifestyle you’ve been dreaming of. Come see this special home and start enjoying the lake life you deserve!
This listing is courtesy of: COLONIALTOWN REALTY
PARKVIEW VILLAGE - O6395924 - 3032 ANTIQUE OAKS CIR #145, WINTER PARK, FL 32792 3 Days on yellowkey
$1,400 | Condo 1 bedrooms, 1.0 bathroom
1 Bedroom/1 Bath condo in Winter Park's Parkview Village! Situated just off of 436/South Semoran Blvd & so convenient to UCF, Full Sail University, 417 & more! The living room, dining & kitchen layout flows easily with sliding doors that lead to the screened patio! Fresh interior paint, washer & dryer. Parkview Village offers a pool, clubhouse. Take a look today!
This listing is courtesy of: MAINFRAME REAL ESTATE
GOLFSIDE VILLAS CONDO - R4910991 - 1000 S SEMORAN BLVD #815, WINTER PARK, FL 32792 3 Days on yellowkey
$1,650 | Condo 2 bedrooms, 2.0 bathroom
This newly update and freshly painted. First floor condo in Winter Park offers a perfect blend of comfort and style and outdoor access ..It features two spacious bedrooms and two bathrooms, providing ample space for relaxation and privacy. The open plan living room and updated kitchen create a welcoming atmosphere, ideal for both entertaining and everyday living.. A standout features of this home is the in-unit washer and dryer a rare item within the complex. Community also has an additional laundry facility of it own. From the living room you can Step outside onto the nice open patio….whether it's for morning coffee or evening cookouts with family and friends. The community pool is walking distance and accessible to all residents. Unit has two parking spaces and plenty of additional guest parking. The condo is ideally located, with plenty shopping and dining nearby. Full Sail University and a newly built HCA Emergency room are minutes away. Commuting is made easy with access onto 436, and the 408 which makes it easy to travel to Downtown Orlando or Winter Park
This listing is courtesy of: KIMBRIDGE REALTY, LLC
HIDDEN OAKS CONDO PH 06 - WINTER PARK, FL 32792 3 Days on yellowkey
$1,750 | Townhouse 2 bedrooms, 1.5 bathroom
Charming 2-bedroom, 1.5-bath townhouse located in the highly desirable Hidden Oaks community. This two-story home offers 990 sq ft of comfortable living space. The main floor features a spacious living area that flows into the dining area and kitchen, along with a convenient half bath for guests. Upstairs, you’ll find the primary bedroom with a spacious bathroom, as well as an additional comfortable bedroom. Enjoy a cozy private patio, perfect for relaxing or entertaining, and a low-maintenance. Two reserved parking spaces are conveniently located directly in front of the unit. Community amenities include a pool, sidewalks, and guest parking. Ideally located just minutes from FL-408 and FL-417, offering easy access to Orlando International Airport and Downtown Orlando. Close to shopping, dining, and excellent schools in the Winter Park area. A great opportunity to enjoy comfort, convenience, and community living—schedule your showing today!
This listing is courtesy of: EXP REALTY LLC
LAKE KNOWLES TERRACE ADD 02 - O6395705 - 1441 ONECO AVE, WINTER PARK, FL 32789 3 Days on yellowkey
$6,000 | Single Family Home 4 bedrooms, 3.5 bathroom, 2 car garage
Gorgeous Modern Home with 4 bedrooms + 3 and a half bath home with numerous upgrades throughout located in desirable Winter Park. This house has a large kitchen that opens to the family room for entertaining. Fantastic kitchen with solid wood cabinets, granite counters, walk-in pantry, stainless appliances, Gas 5 burner stove, built-in microwave, large island, big windows emanating a lot of natural light. The home features hardwood floors throughout the main living area, stairs, upstairs bonus loft, and Primary bedroom. The living room offers a gas decorative fire feature, a separate dining room and a large sliding glass door allowing additional natural light, that leads out to a covered patio and private fenced yard. The downstairs living space also has a fourth bedroom and full bath, an indoor laundry room, and a guest half bathroom. At the top of the stairs is a bonus loft for more living space, 2 bedrooms with a jack-and-jill bathroom, and closets with shelving. Upstairs also has the large primary bedroom with double door entrance, wood floors, plantation shutters on windows as well as the large sliding glass doors that lead out to the private balcony, the walk-in closet has custom built-in shelving, the big bathroom has two separate sinks, large walk-in shower and a separate soaking tub and a toilet closet. Wonderful home for the family and one of the best school districts. The surrounding area offers grocery stores, shopping, parks, easy access to highways, and moments away from Park Ave shopping and entertainment, farmers market, boat tours and so much more.
This listing is courtesy of: OLDE TOWN BROKERS INC
SOUTH LAKEMONT SHORES - O6395037 - 1814 BARKER DR, WINTER PARK, FL 32789 3 Days on yellowkey
$11,000 | Single Family Home 5 bedrooms, 4.0 bathroom, 2 car garage
Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a reclaimed Chicago brick fireplace and full-length sliders opening to a resort-style lanai with summer kitchen, wood ceiling, and recessed lighting. Step outside to a private backyard oasis with a sparkling pool, outdoor kitchen area, and no rear neighbors—perfect for entertaining. The first-floor primary suite offers complete privacy with a spa-inspired bath, soaking tub, walk-in shower, and dream closet. The main level also includes a private office, full bath, dining room, laundry room, and generous living spaces. Upstairs features a large loft, rumpus room, four additional bedrooms, and two beautifully designed baths. The oversized two-car garage provides high ceilings, storage, and a flex space ideal for bikes, fitness, or workshop use. Located minutes from Park Avenue dining, shopping, and entertainment, this home delivers luxury, comfort, and an unbeatable Winter Park lifestyle. Professionally managed with exceptional service.
This listing is courtesy of: REAL BROKER, LLC
LAWNDALE - O6394834 - 1555 MICHIGAN AVE, WINTER PARK, FL 32789 4 Days on yellowkey
$1,450 | Half Duplex 1 bedrooms, 1.0 bathroom
Are you looking for a spacious 1 bedroom 1 bathroom unit to call home? This home features its own washer and dryer, a large bedroom and living room, a spacious kitchen with ample countertop space, plenty of cabinets. The back sunroom would make a great office or a bright sitting area. The home is located 1 mile from Park Avenue. In addition, the home is located within walking distance of restaurants and shopping.
This listing is courtesy of: BHHS FLORIDA REALTY
GLENCOE SUB - O6394762 - 2420 EUSTON RD, WINTER PARK, FL 32789 4 Days on yellowkey
$1,775 | Single Family Home 2 bedrooms, 1.0 bathroom, 1 car garage
One or more photo(s) has been virtually staged. Beautifully mainted and move-in ready home available for rent in a convenient location. This property features a bright and inviting interior with functional layout, spacious living areas, and well-sized bed rooms. The home offers a clean feel with plenty of natural light throughout, creating a comfortable and welcoming environment. Enjoy a private outdoor space perfect for relaxing or entertaining. Conveniently located near major roadways, shopping, dining, and everyday amenities. Available for immediate occupancy! Schedule your showing today.
This listing is courtesy of: PRIMAC GROUP, INC
WATERFALL COVE - O6395336 - 1695 LEE RD #D116, WINTER PARK, FL 32789 5 Days on yellowkey
$1,800 | Condo 3 bedrooms, 2.0 bathroom
Welcome Home to Waterfall Cove in Winter Park! This spacious 3-bedroom, 2-bath ground floor corner unit is move-in ready with fresh paint and brand new carpet throughout. Corner placement means extra natural light and a layout that lives even larger than its generous footprint. Community Perks include a sparkling pool just in time for summer, secured building access, and a peaceful, park-like setting complete with mature landscaping. Tucked into the heart of Winter Park, one of Central Florida's most charming and sought-after communities. You're steps from Winter Park Village, a premier open-air lifestyle center with upscale shopping, Publix, Regal Cinemas, and top-tier dining. Basic internet and cable TV. Tenant responsible for water and electricity only. Easy showing — call us today and move in tomorrow!
This listing is courtesy of: ZEAL REALTY
WINTER PARK HEIGHTS - O6393263 - 1640 PALM AVE, WINTER PARK, FL 32789 7 Days on yellowkey
$5,250 | Single Family Home 4 bedrooms, 3.0 bathroom
Fully renovated with stylish charm, this four-bedroom, three-bath home is in one of the most desired neighborhoods in Winter Park, the Tree Streets. A brick drive and path welcome you into this open living plan on a large 75-foot by 150-foot lot with tons of room to grow. Warm wood floors throughout and this home enjoys an open kitchen family plan with spaces that are flexible for your needs. The kitchen has custom cabinetry, quartz countertops, subway glass tile, GE stainless appliances including natural gas range and loads of storage. French doors lead to spacious patio and generous backyard. The owner’s retreat was seamlessly added with 9-foot ceilings, large walk-in closet and beautiful primary bath retreat with dual vanities, separate soaking tub and water closet. The home has lovely natural light throughout. Other features include newer Trane air conditioning, electric panel in 2010, updated plumbing, level five dry wall finish, new paint inside and out, upgraded lighting package, all baths renovated, generous closets, updated garage door, updated windows and treatments, and mature landscaping. Just a short distance to the YMCA, Phelps Park, Lakemont Elementary School and zoned for Winter Park High School. Close to all the amenities Park Avenue offers and the perfect location.
BROOKSHIRE HEIGHTS - O6394600 - 2356 COLDSTREAM DR, WINTER PARK, FL 32792 7 Days on yellowkey
$2,825 | Single Family Home 3 bedrooms, 2.0 bathroom
One or more photo(s) has been virtually staged. Lovely home in Winter Park school district. Closet to downtown Winter Park. Updated kitchen and baths on a Quiet street. Lawncare included.
This listing is courtesy of: VIA PROPERTIES LLC
GREENVIEW AT WINTER PINES - O6393971 - 1317 MEDINAH CT, WINTER PARK, FL 32792 9 Days on yellowkey
$3,650 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Winter Park Pines home,4 bed/2 bath ready for a new resident. On a quiet cul-de-sac, this renovated home offers a blend of modern amenities with a fantastic location. It features a brand new kitchen & bathrooms with quartz countertops, updated brushed brass fixtures, with lots of custom touches. It features engineered wood flooring in the living areas and primary bedroom, a convenient indoor laundry room, new windows and sliding doors that let in tons of natural light. Other upgrades include new doors, trim, fresh interior and exterior paint, and a beautiful paver patio. Outside, enjoy all-new landscaping with fresh sod and a new irrigation system, lawncare is included in the rent. This home also has a new roof, garage door, and a HVAC system. This home is also next to the scenic Cady Way trail, ideal for biking, walking, and running. Zoned for highly rated Winter Park schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Call for your showing today! Sorry NO PETS.
This listing is courtesy of: FANNIE HILLMAN & ASSOCIATES
PARKVIEW VILLAGE CONDOMINIUM - O6393639 - 2929 ANTIQUE OAKS CIR #53, WINTER PARK, FL 32792 10 Days on yellowkey
$1,350 | Condo 1 bedrooms, 1.0 bathroom
Welcome to this fully renovated residence in the heart of Winter Park, where modern upgrades meet timeless charm in one of Central Florida’s most desirable communities. Thoughtfully updated throughout, this home offers a fresh, move-in-ready living experience with stylish finishes and enhanced comfort. Ideally situated near Full Sail University and Rollins College, this property is well-suited for students, faculty, and professionals alike. Zoned for highly regarded schools including Aloma Elementary, Glenridge Middle, and Winter Park High School. Enjoy a vibrant lifestyle with easy access to nearby parks and outdoor destinations such as Kraft Azalea Garden and Mead Botanical Garden perfect for relaxing walks and enjoying nature. The renowned Park Avenue is also just a short drive away, offering boutique shopping, dining, and cultural experiences. Conveniently located with quick access to major roadways, downtown Orlando, and Orlando International Airport, this home also places you within reach of Florida’s beautiful east coast beaches, including Cocoa Beach and New Smyrna Beach ideal for weekend getaways. This fully renovated home offers the perfect combination of location, lifestyle, and modern living, making it an exceptional leasing opportunity in Winter Park. Water is included in the rent. Apply here: https://apply.link/oQ8t72Y
This listing is courtesy of: KELLER WILLIAMS WINTER PARK
LANDINGS AT HAWKS CREST - O6393864 - 1430 LONE FEATHER TRL, WINTER PARK, FL 32792 10 Days on yellowkey
$3,895 | Single Family Home 4 bedrooms, 3.5 bathroom
Welcome to this newly built and well-maintained home in the fabulous Winter Park gated community of Hawk's Crest. A gorgeous open floor plan single-family home with 4 bedrooms, 3.5 bathrooms and office / den room on the first floor. Be amazed by the spacious bright entrance and soaring ceilings in the family room and loft open to below. Tile throughout living areas, carpet in all four bedrooms. Impeccable master suite which offers OVER SIZED walk-in closet, dual sinks, and walk-in shower. Spacious kitchen with beautiful countertops and backsplash, with stainless appliances. Cook and entertain overlooking the large family-living-dining area. The family room is prewired for surround sound speakers. The home is incredibly well laid out with the masterful kitchen being the heart and center point of the home, Master suite, office/den, 1/2 bath, and laundry room all on the first floor. The second floor contains a loft area, all guest bedrooms with a full bathroom. Additional features include a 2-car garage, and a covered lanai. Close to Winter Park shopping and dining, and beautiful Lake Howell. Hawks Crest resort style amenities include Clubhouse, swimming pool, walking trails, gym, dog park, canoe launch to Lake Howell to enjoy beautiful sunsets in Winter Parks gated community! Located only minutes from the iconic and historic Winter Park Avenue with plentiful shopping, amazing venues, epic events, dining and zoned for all excellent rated schools. Lawn care, Washer, and Dryer are 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.
This listing is courtesy of: RE/MAX 200 REALTY
EASTGATE SUB - O6393183 - 524 BYRON RD, WINTER PARK, FL 32792 12 Days on yellowkey
$2,890 | Single Family Home 4 bedrooms, 3.0 bathroom
One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home located in the heart of highly desirable Winter Park area. Offering a rare combination of space, comfort and prime location. This home offers a spacious and functional layout with multiple living areas, abundant natural light, and well-sized bedrooms. The flexible floor plan provides plenty of room for a variety of living arrangements, including space for a home office, guest room, or additional living area. Step outside to enjoy a spacious Patio, ideal for relaxing , entertaining or enjoying florida's year round sunshine. The home also features a 2 car garage and extended driveway offering plenty of parking and storage. Enjoy a prime location just minutes from: Park Avenue dining and shopping, Rollins College, AdventHealth Winter Park and Major roads, grocery stores, and everyday conveniences Property Highlights: 4 Bedrooms | 3 Bathrooms, Spacious interior layout, Large outdoor yard, 2-car garage + additional parking, Convenient access to shopping, dining, and major roadways This Home offers a unique opportunity to enjoy both space and convenience in one of Central Florida most sought-after areas. Schedule your private showing today- Homes in this location and condition lease quickly
This listing is courtesy of: SOUTHERN PRESTIGE REALTY INC
WATERFALL COVE - TB8489708 - 1695 LEE RD #C206, WINTER PARK, FL 32789 12 Days on yellowkey
$1,750 | Condo 2 bedrooms, 1.0 bathroom
Beautiful and move-in ready condo! Located on the second floor in a quiet community, perfect for families or professionals seeking comfort and convenience. 1.- Property Features 2 Bedrooms 1 Full Bathroom Second-floor unit (added privacy) Total area: 881 sqft 2.- Comfort & Interior Features Central Air Conditioning Central Heating Ceiling Fans High Ceilings Open Floor Plan Walk-in Closet(s) 3.- Kitchen & Appliances Included Refrigerator Range Microwave Dishwasher Garbage Disposal Washer & Dryer 4.- Laundry Inside laundry Laundry closet 5.- Community Amenities Swimming Pool Playground Quiet and well-maintained community 6.- Utilities Included Internet Cable TV 7.- Conveniently located near: Shopping centers & grocery stores Restaurants & cafés Parks & recreational areas Hospitals & clinics Easy access to major roads Call now to schedulle a tour.
This listing is courtesy of: ROSS RENTALS LLC
DUBSDREAD HEIGHTS - O6392773 - 668 OVERSPIN DR, WINTER PARK, FL 32789 13 Days on yellowkey
$4,200 | Single Family Home 4 bedrooms, 3.0 bathroom, 2 car garage
One or more photo(s) has been virtually staged. A contemporary, beautifully finished home offering standout value in one of Winter Park’s most coveted zip codes. With more than 2,500 square feet of bright, open living space, this property features a sleek fireplace, a large pantry area, a designer kitchen, and a massive two-car garage. The private primary suite sits upstairs along with additional bedrooms, a versatile loft, and a conveniently placed laundry room. A first-floor guest suite adds flexibility for visitors or a dedicated workspace. Outside, a spacious backyard and custom gazebo create an inviting place to unwind. Zoned for Princeton Elementary and positioned for quick, easy access to everything College Park and Winter Park have to offer, this home delivers rare quality and exceptional value for 32789. This home is available immediatly.
This listing is courtesy of: COMPASS FLORIDA LLC
KILLARNEY BAY CONDO - O6392456 - 110 KILLARNEY BAY CT #1, WINTER PARK, FL 32789 16 Days on yellowkey
$2,550 | Condo 2 bedrooms, 2.0 bathroom
Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer generous space, with a private primary suite that includes an en-suite bathroom and ample closet storage. Step outside to enjoy serene surroundings or take advantage of community amenities, all just moments from shopping, dining, and entertainment. Ideally located near Downtown Winter Park, Park Avenue, and with convenient access to Interstate 4, this condo offers the perfect blend of comfort, convenience, and lifestyle. Don’t miss your opportunity to call this charming property home!
This listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS
WINTER PARK - GC538622 - 540 W COMSTOCK AVE, WINTER PARK, FL 32789 16 Days on yellowkey
$2,900 | Single Family Home 3 bedrooms, 1.0 bathroom
Newly Renovated | Prime Winter Park Location | Move-In Ready Opportunity Positioned in one of Central Florida’s most desirable and high-demand areas, this newly renovated residence at 540 W Comstock Ave offers a rare opportunity for tenants seeking both location and lifestyle in the heart of Winter Park. Thoughtfully updated with modern finishes, the home features a clean, refreshed interior designed for today’s renter, delivering comfort, functionality, and style in a true turnkey living experience. Ideally located just minutes from Park Avenue, Rollins College, and Winter Park’s premier dining, shopping, and entertainment, this property places tenants in the center of one of Orlando’s most vibrant communities while still offering a sense of neighborhood charm and convenience. Its proximity to major roadways and local amenities makes it especially attractive for professionals, families, and relocation clients seeking both accessibility and quality living. This is a high-demand rental opportunity in a low-inventory pocket of Winter Park, and clean, updated homes in this location do not last. Agents are encouraged to bring qualified tenants ready to move quickly. Now accepting applications with expedited approvals available for well-qualified applicants.
This listing is courtesy of: KELLER WILLIAMS GAINESVILLE REALTY PARTNERS
LANDINGS AT HAWKS CREST - O6391620 - 1461 LONE FEATHER TRL, WINTER PARK, FL 32792 18 Days on yellowkey
$3,600 | Single Family Home 4 bedrooms, 3.5 bathroom
Beautiful newer two-story home in Winter Park’s exclusive Gated community of Hawk’s Crest. Community has lake access with canon launch. The home has a great floor plan that features open dining and living rooms. Mastered room is conveniently located on the first floor. also Study room. This gated community features a resort style swimming pool, fitness center, splash pad, clubhouse, playgrounds, dog park, and access to a dock on Lake Howell where you can enjoy fishing and kayaking. The HOA fee includes lawn care for the best of maintenance free living.
This listing is courtesy of: MARVIEW INTERNATIONAL REALTY LLC
FAIRBANKS SHORES 4TH ADD - S5145882 - 2846 EUSTON RD, WINTER PARK, FL 32789 19 Days on yellowkey
$2,500 | Single Family Home 3 bedrooms, 1.5 bathroom
Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes form I4, close to Park Avenue District, College Park, major shopping centers and many more. Big backyard with a nice sized paved courtyard and shed. Don't miss this opportunity!
This listing is courtesy of: 365 REALTY, INC.
WRENWOOD CONDO - O6391063 - 4818 TANGERINE AVE #4818, WINTER PARK, FL 32792 20 Days on yellowkey
One or more photo(s) has been virtually staged. The 1 bed, 1 bath unit is ideally located in Winter Park, close to Full Sail and UCF. Rent includes water, and all appliances including washer & dryer. A spacious Living/Dining space and a Huge bedroom make this the best one bed/one bath you'll find. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet community with plenty of privacy. Amenities include a pool and workout room.
This listing is courtesy of: BENCHMARK REAL ESTATE GRP INC
SANDALWOOD CREEK CONDO PH 01 - O6390263 - 295 SANDLEWOOD TRL, WINTER PARK, FL 32789 24 Days on yellowkey
$1,875 | Townhouse 2 bedrooms, 2.5 bathroom
This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a gorgeous kitchen with quartz countertops, stainless steel appliances, and breakfast bar, a lovely primary suite with custom bathroom finishes, laundry closet, and a rear patio. Community amenities include a pool. Sorry, no pets. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
This listing is courtesy of: REAL PROPERTY MANAGEMENT AND REALTY
MAGNOLIA GARDENS SUB - O6389767 - 870 CARVER ST #A, WINTER PARK, FL 32789 24 Days on yellowkey
$3,300 | Single Family Home 2 bedrooms, 2.0 bathroom
Welcome to 870 Carver Street, a thoughtfully designed two-bedroom, two-bath residence in the core of Winter Park. Offering more than 1,200 square feet, the newly constructed home features vaulted ceilings with exposed rafters, warm wood finishes and industrial-inspired black metal ductwork that define its architectural character. The primary suite includes a floating wall closet system, a laundry closet, and a bath with dual-sink floating vanity + glass-enclosed walk-in shower. The second bedroom features an en-suite full bath with a tub-shower combination and a floating wall closet system. The open living area is designed for entertaining and anchored by a well-appointed kitchen with solid wood cabinetry, under-cabinet lighting, and a substantial island with seating for four. Black aluminum-framed windows bring abundant natural light into the interiors and enhance the open-plan layout. Outdoor spaces include covered entries, an expansive front porch with warm wood architectural detailing, and a fully fenced yard with a rear garden courtyard. The garage offers oversized dimensions and additional depth for storage and is accessed via a sliding steel-framed, wood-clad gate along Railroad Avenue. Ideally located within short distance to Park Avenue, Winter Park Village, Whole Foods Market, the Winter Park Golf Course and the SunRail and Amtrak stations, the residence provides convenient access to shopping, dining and transportation in one of Winter Park’s established neighborhoods. **Lease includes water, sewer, electric, trash, grounds maintenance, and exterior pest control. The garage apartment may be available separately or the entire property may be leased together if desired.**
- O6382466 - 2936 ANTIQUE OAKS #70, WINTER PARK, FL 32792 24 Days on yellowkey
Call to schedule your private showing of this well-maintained 2 bedroom, 2 bathroom condo located on the second floor in the desirable Parkview Village Subdivision.This bright and open floor plan features a spacious living room with vaulted ceilings, perfectly positioned at the front of the home and open to the kitchen. The kitchen has all new appliances with a corner window that is perfect for an indoor herb garden. A formal dining area sits just off the kitchen, creating the perfect space for entertaining.Down the hallway, you’ll find a full-size washer and dryer — INCLUDED in the rent — along with a generously sized laundry room offering ample storage space. The guest bathroom is conveniently located next to the laundry area and the second bedroom. The primary suite features a private en-suite bathroom and a large walk-in closet for added comfort and privacy.Enjoy relaxing evenings on the screened porch just off the living room.Pet-friendly! Pets under 40 lbs are welcome with a $350 pet deposit. Limit one Pet.Residents of Parkview Village enjoy access to a community pool and a prime location just south of University off Semoran Boulevard (SR 436). Conveniently located:Winter park Village and Park ave Winter Park are under 10 minutes away. The unit is also 10 minutes to Florida State Road 417, 12 minutes to Florida State Road 408 (East/West Expressway) Making your downtown commute quick and easy!Don’t miss this opportunity — schedule your showing today!
This listing is courtesy of: JML REALTY INVESTMENTS LLC
TUSCANY TERRACE - O6388913 - 1235 VIA ESTRELLA, WINTER PARK, FL 32789 27 Days on yellowkey
$5,895 | Single Family Home 4 bedrooms, 3.0 bathroom
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.
This listing is courtesy of: KELLY PRICE & COMPANY LLC
TEMPLE TERRACE ANNEX - O6388411 - 1924 AZALEA AVE, WINTER PARK, FL 32792 30 Days on yellowkey
$1,995 | Single Family Home 3 bedrooms, 1.0 bathroom
Adorable mid century modern bungalow in Winter Park! This 3 bedroom, 1 bathroom home has been beautifully updated with new tile wood floors in the main living area. The kitchen features white appliances and tasteful white cabinetry. The updated bathroom features a new vanity and classic mosaic tile floor. Enjoy the spacious backyard with wooden deck! Washer, dryer and lawn care is included! This property is available May 2026.
This listing is courtesy of: GATE PROPERTIES & MANAGEMENT INC
GOLFSIDE SEC 03 - G5109152 - 952 FAIRWAY DR, WINTER PARK, FL 32792 31 Days on yellowkey
$3,300 | Single Family Home 3 bedrooms, 2.0 bathroom
A absolutely stunning 3 Bedroom 2 Bath single family home, with upgrades galore, this is not your typical rental home. The owners have totally transformed this very unique home into a stunning retreat. From the minute you pull up to this home, you are wowed by the great curb appeal, brick paver driveway and manicured garden. You are welcomed by gorgeous wooden double doors, leading into a reception area in the heart of the home. Which in turn leads into a formal living room, formal dining room and a stunning state of the art kitchen. This new kitchen has it all, beautiful stainless appliances, with built in oven and microwave, double door fridge, quartz counter tops, with eating space. All leading into the family room, with wood burning fireplace and French doors leading to a screened, Spanish tiled sunroom, which in turns leads to a large deck for entertaining and a meandering garden with such a calming surreal feel. Large Master bedroom with spa like bathroom, double sinks with quartz counters, one of a kind shower with seat. Two additional generous bedrooms and second upgraded bathroom with tub complete this unique home. Inside laundry room including washer & dryer, double garage with opener. Includes lawn care, pest control and alarm. This home is situated in the much sought after Brookshire school district, close to shopping, restaurants and major hwys. On a quiet low traffic street close to the Winter Park Pines Golf course. Home will be available for a June 1st move in.
This listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE
HOWELL HEIGHTS - O6386314 - 2743 SANBINA ST, WINTER PARK, FL 32789 32 Days on yellowkey
$2,500 | Single Family Home 3 bedrooms, 2.0 bathroom
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.
This listing is courtesy of: BELMONT REALTY
SANDALWOOD CREEK CONDO PH 01 - O6387188 - 307 SANDLEWOOD TRL, WINTER PARK, FL 32789 33 Days on yellowkey
This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a gorgeous kitchen with quartz countertops and breakfast bar, a lovely primary suite with custom bathroom finishes, laundry closet, and a rear patio. Community amenities include a pool. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
CAROLYN ESTATES - O6385498 - 1813 E CHERYL DR, WINTER PARK, FL 32792 38 Days on yellowkey
$2,650 | Single Family Home 4 bedrooms, 2.0 bathroom
Lovely 4 bed, 2 bath one story home in desirable Winter Park! Attached 2 car garage, GRANITE countertops in kitchen, walk in closet in primary bedroom. Patio has ceramic tile flooring, overlooking the FENCED backyard! This home features a spacious layout! Location is PERFECT! Convenient to shopping, dining, highways & more!
This listing is courtesy of: STRONG FOUNDATION REALTY LLC
KENILWORTH SHORES SEC 06 - O6385792 - 1850 WHITEHALL DR, WINTER PARK, FL 32789 39 Days on yellowkey
$3,475 | Single Family Home 3 bedrooms, 2.0 bathroom
This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The backyard also has a gazebo, is totally fenced in and has lots of room to roam. Conveniently located between Baldwin Park and Winter Parks Park Avenue. Winter Park School district. Sorry, no pets.
ENCLAVE AT HAWKS CREST - O6381661 - 1611 LITTLE WREN LN, WINTER PARK, FL 32792 41 Days on yellowkey
$2,695 | Townhouse 3 bedrooms, 2.5 bathroom
This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Hawks Crest along the southern shores of beautiful Lake Howell, this ideal location provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Avenue and Winter Park Village. The home has an open floor plan with tile flooring throughout the downstairs living area. The upgraded kitchen features 42" cabinets, granite counter tops, stainless steel appliances, island, and pantry with plenty of storage. Upstairs you will find the carpeted bedrooms and primary suite with dual sinks, walk in shower, and a walk-in closet. Additional features include a 2 car garage, patio with quiet backyard area, and utility closet for the washer/dryer. Community features include a pool and cabana, park, and playground. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
QUARTERS AT WINTER PARK CONDO - O6384586 - 1130 WASHINGTON AVE #11C, WINTER PARK, FL 32789 43 Days on yellowkey
$5,495 | Condo 3 bedrooms, 2.5 bathroom, 2 car garage
Unbeatable Location! Don't miss this very rare and exquisite 3 bedroom, 2.5 bath, two-story Executive-Style condo in Winter Park-ideally located just around the corner from N. Orange Avenue, Park Avenue and Rollins College. Nestled in a prime, tucked-away setting, this home has been extensively remodeled with all new plumbing, electrical, duct work, flooring, appliances, and a natural gas line. In addition, two newer HVAC systems were installed in November 2022, offering modern efficiency and reliability. The gated front courtyard, thoughtfully designed by a landscape architect, provides a serene and welcoming entrance, complete with lush foliage, a potted herb garden, wooden bench, and tranquil fountain—creating the perfect first impression for guests. Inside, you’ll find a spacious dining room filled with natural light from a wall of French doors that open directly to the courtyard. A built-in dry bar with two wine refrigerators makes this an ideal space for entertaining, while oak wood flooring throughout the home adds warmth and timeless character. The chef’s kitchen is both stylish and functional, featuring sleek concrete countertops, custom cabinetry, and a premium dual-fuel 6-burner Wolf range. A cozy dinette area includes a built-in terrazzo-topped table and banquette, while a breakfast bar offers additional seating. Just beyond, the living room showcases a clean-burning bioethanol fireplace and dramatic soaring windows with views of the interior screened two-story courtyard. Upstairs, the private primary suite offers multiple closets, a private balcony overlooking the interior courtyard, and a luxurious en-suite bathroom complete with a large walk-in shower with body sprays, towel warmer, and a dedicated laundry room with built-in storage. At the opposite end of the second floor, the front-facing bedroom can also serve as an ideal home office, featuring a custom built-in desk and shelving, along with a screened balcony overlooking the front courtyard—perfect for enjoying your morning coffee or tea. The second floor also includes a third bedroom, a second full bathroom, a linen closet, and a charming sitting area or nook. A private alleyway behind the building provides convenient access to the oversized two-car garage, which features a custom built-in workbench and sink, as well as two dedicated storage closets. This exceptional location allows you to walk to the pleathora of shops and eateries on N. Orange Avneie, Rollins College, Park Avenue, the Winter Park Tennis Center, Azalea Lane Playground, and the brand new Seven Oaks Park, as well as the shops and restaurants along Orange Avenue. Offering the perfect blend of sophistication, comfort, and practicality, this beautifully updated condo is ideal for those seeking a refined, low-maintenance lifestyle in the heart of Winter Park. Full Lawn care by the HOA are included in the rental rate. A small pet may be considered on a case-by case basis. Proof of a renters insurance policy is required to rent this property. Showings by Appointment Only. Must see to fully appreciate.
This listing is courtesy of: FUSILIER MANAGEMENT GROUP
WINTER PARK PINES - O6381254 - 2907 LITTLE JOHN RD, WINTER PARK, FL 32792 51 Days on yellowkey
$2,800 | Single Family Home 4 bedrooms, 3.0 bathroom
One Story home in Winter Park Pines with 4 bedrooms and 3 full baths! Large Screened Porch and fenced rear yard. Quiet street. Stainless steel appliances: Refrigerator, Smooth-top Range/Oven, Dishwasher. Lawn Care included! W/D hookups in Laundry room. A/C replaced in 2022. Home re-piped in 2022. Move-in Ready Home! Convenient Winter Park Location Only Minutes from Baldwin Park, Park Avenue, Winter Park High School, etc. Realtor is owner of the home. Interior repainted 2/2026. Fireplace in family room is not available for use.
This listing is courtesy of: SOTERA LIVING
WINTER PARK REP BLK 75 - O6381970 - 421 W FAIRBANKS AVE, WINTER PARK, FL 32789 51 Days on yellowkey
$3,750 | Apartment 3 bedrooms, 3.0 bathroom
Occupying the entire second floor of a landmark 1925 brick building in the heart of Winter Park, this fully reimagined residence offers a rare opportunity to lease a true designer 3 bedroom, 3 bathroom loft just two blocks from Park Avenue. The open concept interior features high ceilings, abundant natural light from skylights and brand new windows, and a refined industrial aesthetic anchored by hardwood flooring and sleek quartz countertops. A custom architectural lighting package with sculptural glass pendants and vertical LED sconces adds a distinctive, high end finish throughout. The thoughtfully designed layout provides three separate bedrooms, each with its own private ensuite bath, offering both flexibility and privacy for residents or guests. Located minutes from Rollins College, Lake Virginia, boutique shopping, dining, and SunRail access, this turnkey residence combines historic character with modern design in one of Winter Park’s most desirable corridors.
This listing is courtesy of: REALTY ONE GROUP MVP
EASTBROOK SUB UNIT 06 - O6382078 - 1724 PERUVIAN LN, WINTER PARK, FL 32792 52 Days on yellowkey
$2,095 Reduced | Single Family Home 3 bedrooms, 2.0 bathroom
Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *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. Pet friendly home (w. approval and non-refundable pet fee).
- O6377466 - 1695 LEE ROAD RD #C110, WINTER PARK, FL 32789 59 Days on yellowkey
Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.
This listing is courtesy of: EMPIRE NETWORK REALTY
HENKEL ADD - R4910620 - 1380 INDIANA AVE #3, WINTER PARK, FL 32789 60 Days on yellowkey
$1,395 Reduced | Condo 2 bedrooms, 1.0 bathroom
Winter Park at your door step! This is a second floor 2 bedroom unit, in secured building. Large open backyard with rear balcony and patio space and plenty of parking. Unit has full kitchen, and washer/dryer in unit! Two full bedrooms both with walk-in closets and a full bath. Living room is large open/bright. Only a few blocks walk to Orlando Ave with all its shopping, Publix and restaurants. Easy access to downtown Winter Park or Downtown Orlando without the need of I-4. Available today no HOA
SWOOPE PARK - O6368619 - 438 W SWOOPE AVE, WINTER PARK, FL 32789 86 Days on yellowkey
$3,995 | Townhouse 3 bedrooms, 2.5 bathroom
SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 3/31!! PRIME LOCATION! JUST STEPS FROM PARK AVENUE, WALKING DISTANCE TO EVERYTHING! This beautiful TOWNHOME is located in the exclusive 400 West community, just moments from Park Avenue. It offers a PERFECT COMBINATION OF SUPERIOR CRAFTSMANSHIP, ELEGANT INTERIORS, and GREAT WALKABILITY. You can enter via the PRIVATE GARAGE or the charming garden-style front path. The main level is BRIGHT and OPEN, with HIGH-END FINISHES like large porcelain tiles and designer lighting. The CHEF'S KITCHEN features POLISHED CHROME HARDWARE, QUARTZ COUNTERTOPS, and STAINLESS-STEEL APPLIANCES, including a Whirlpool French door refrigerator. Ample STORAGE, MOTORIZED Lutron window shades, and a STYLISH POWDER BATH with under-stair storage add FUNCTIONALITY. UPSTAIRS, TWO SPACIOUS PRIMARY SUITES with HARDWOOD FLOORS and LARGE WINDOWS fill the rooms with NATURAL LIGHT. Spa-like en-suite bathrooms have LARGE PORCELAIN TILES, FRAMELESS GLASS SHOWERS, and MODERN VANITIES with CHROME FIXTURES. The primary bath includes a DOUBLE-SINK VANITY, private water closet, and built-in shower bench. A large WALK-IN CLOSET and a full LAUNDRY ROOM with Samsung washer and dryer complete this level. The THIRD FLOOR offers FLEXIBILITY with two additional bedrooms or versatile spaces, each with walk-in closets and a JACK-AND-JILL BATHROOM—perfect for GUESTS, HOME OFFICES, GYMS, or STUDIOS. Recent updates include INTERIOR REPAINT (2025), BLACKOUT SHADES, CLEANED CARPETS AND TILE, and SMART HOME features like NEST THERMOSTAT and RING DOORBELL. Guest PARKING is convenient on-site and nearby. BLENDING TIMELESS QUALITY with MODERN AMENITIES, this LOW-MAINTENANCE, THREE-LEVEL HOME offers PRIVACY and FLEXIBILITY in a QUIET, LOW-DENSITY COMMUNITY. Located just STEPS from everything Winter Park has to offer, it’s an EXCEPTIONAL OPPORTUNITY for a permanent residence or a LOCK-AND-LEAVE retreat in the HEART OF THE CITY. This property is eligible for alternative coverage in lieu of a security deposit. Eligibility requirements apply. For details and enrollment, please contact our leasing team and enjoy a deposit-free renting experience! All Specialized Property Management residents are automatically enrolled in our Resident Benefits Package (RBP) for $49/month. This package includes tenant legal liability insurance, HVAC air filter delivery (where applicable), credit reporting, a renter rewards program, and more! Specialized Property Management residents are enrolled in the Resident Benefits Package (RBP) for $49.00/month which includes tenant legal liability insurance, HVAC air filter delivery (for applicable properties), credit reporting, renter rewards program, and much more! Additionally, most homes feature high-speed internetup to 1 Gigat a special group rate. This includes premium support and professional setup powered by Second Nature, ensuring youre connected quickly at move-in. The group-rate internet is $64/month and is a required part of the program. Full details will be provided during the application process
This listing is courtesy of: SPECIALIZED PROPERTY MANAGEMENT
FOUR SEASONS CONDO - O6371317 - 200 SAINT ANDREWS BLVD #1803, WINTER PARK, FL 32792 89 Days on yellowkey
$1,499 | Townhouse 2 bedrooms, 1.5 bathroom , 1 car carport
2-bedroom, 1.5-bathroom, two-story townhouse in Four Seasons Condos of Winter Park. This well maintained townhouse includes a French country kitchen, which has been renovated with a faux tiled backsplash, custom maple cabinets, and complimentary appliances. This unit includes a half bath downstairs and full bathroom upstairs. Windows are double-pane, double-hung with a Pella sliding glass door with built-in blinds that open to a fenced patio. You will find a neutral color palette throughout the townhouse. Open and fenced-in patio located in the back of the unit. The second floor includes both bedrooms, full bathroom, and rear door to exterior staircase. Water, sewer, and landscaping are included. This unit also comes with covered carport space. The Four Seasons Condos are located within the city limits of Winter Park. Community pool and laundry facilities available at the Clubhouse. Close to shopping, restaurants, the Winter Park Medical Center, Cady Way recreational trail and more. Approximate living and total sq ft is 1219. This is a non-smoking unit. Additional HOA application and approval is required. All tenants are enrolled in a Resident Benefit Package for an additional $50/month (details available below). Don’t miss out, contact us today! All information is deemed reliable, but not guaranteed. Listing Brokerage does not discriminate on the basis of race, color, religion, national origin, sex, disability or familial status. All residents are enrolled in the Resident Benefits Package (RBP) for $50.00/month as additional rent, which includes renters insurance, credit building to help boost your credit score with timely rent payments, our best-in-class resident rewards program, $1M Identity Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, online resident portal for easy online rent payments & maintenance reporting, HVAC air filter delivery (for applicable properties), and much more! More details available upon application.
This listing is courtesy of: WILSON MANAGEMENT GROUP
GRAYSON SQUARE - S5140643 - 1986 CANNY CV, WINTER PARK, FL 32792 102 Days on yellowkey
$2,650 Reduced | Townhouse 3 bedrooms, 2.5 bathroom, 1 car garage
FOR RENT in Winter Park! Experience comfortable living in this beautiful 3-bedroom, 2.5-bathroom townhome located in the gated community of Grayson Square. Rent includes high-speed internet and cable, offering great value and convenience. The home features a bright open floor plan with abundant natural light, a modern kitchen with quartz countertops and stainless steel appliances, and sliding glass doors leading to a covered patio. Enjoy peaceful views with water, fountain features, and no rear neighbors, creating a relaxing and private outdoor setting that can be enjoyed from the living room, kitchen, and primary bedroom. Upstairs, you will find the spacious primary suite with a walk-in closet and an en-suite bathroom with dual vanities and a glass-enclosed shower. Two additional bedrooms share a full bathroom on the second floor. A washer and dryer are included for added convenience. Residents of Grayson Square enjoy access to the community pool and playground. The property is conveniently located off Howell Branch Road, minutes away from downtown Winter Park, with easy access to major highways, shopping, dining, and entertainment.
This listing is courtesy of: RIVA REALTY GROUP LLC
GRAYSON SQUARE - S5140507 - 1994 CANNY CV, WINTER PARK, FL 32792 106 Days on yellowkey
$2,600 | Townhouse 3 bedrooms, 2.5 bathroom
This beautiful three bedroom, two and a half bath townhome is located in the newly developed Grayson Square, a gated community in Winter Park. High-speed Internet and cable are included. There are no rear neighbors, so you will enjoy relaxing on your back porch with a beautiful water view. As you enter the home, the entrance leads to the large kitchen and living area. The kitchen features stainless steel appliances, including a refrigerator, a dishwasher, a range, a microwave, and quarts countertops. The sliding glass doors in the living area open to the covered patio. The half bath is on the 1st floor for easy access for guests. Located on the second floor are the primary bedroom and both additional bedrooms. The primary suite has a large walk-in closet. The primary bathroom features dual vanities and a glass-enclosed standing shower. The other bedrooms allow easy access to the second full bathroom. The home also includes a laundry closet and a one-car garage. Enjoy the community pool and playground area—easy access to major roads, shopping, schools, and entertainment.
OLYMPIA HEIGHTS - O6362840 - 1891 OGLESBY AVE, WINTER PARK, FL 32789 115 Days on yellowkey
$2,970 | Single Family Home 3 bedrooms, 2.0 bathroom
Beautifully maintained home in the highly desirable Winter Park 32789 neighborhood. This charming property offers an inviting floor plan with abundant natural light, spacious living and dining areas, and a well-appointed kitchen with generous counter space and modern finishes. Comfortable bedrooms provide ample storage, and the primary suite offers a private and peaceful retreat. Flexible bonus space is ideal for a home office, playroom, or guest area. Enjoy outdoor living in the private, landscaped fenced in backyard featuring mature trees and plenty of room for entertaining, gardening, or relaxing. Situated on a quiet street just minutes from Park Avenue, top-rated Winter Park schools, Rollins College, shopping, dining, and community parks. A rare opportunity to rent a home in one of Central Florida’s most sought-after neighborhoods.
This listing is courtesy of: URBANISTA BROKERS
LAWNDALE - O6360479 - 1565 MICHIGAN AVE, WINTER PARK, FL 32789 142 Days on yellowkey
$1,500 | Half Duplex 2 bedrooms, 1.0 bathroom
Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.
PARK GREEN - O6352263 - 1148 PARK GREEN PL, WINTER PARK, FL 32789 173 Days on yellowkey
$2,195 | Single Family Home 3 bedrooms, 2.0 bathroom
Single family home in Winter Park! Close to shopping, theater, malls! Single family three bedroom two bath home Fully tiled interior, all appliances including washer and dryer. Fenced courtyard and patio. Two car garage with remote! Home is currently occupied. Call ahead for showing appointments
This listing is courtesy of: DON ASHER & ASSOCIATES, INC.
- O6390460 - 1500 GAY RD #18A, WINTER PARK, FL 32789
$1,750 | Condo 2 bedrooms, 2.0 bathroom
Winter Park Lakefront Community. Lakefront Deck, Dock, Grill, Community Building, Heated Pool and Sauna. Immaculate 2 Bedroom 2 Bath First Floor Unit. Upgraded Kitchen with Raised Ceiling, Maple Cabinets and Granite Counters. Cabinets (matching Kitchen Cabinets) and Counters built in Dining Room for extra Storage. Recently Painted. New Carpets in Bedrooms. Bathroom Vanities and Commodes have been replaced. New Storage Cabinet in Hall. Windows have been replaced. A/C approximately 10 years old with regular servicing. Walking Distance to shopping Centers. Minutes to Downtown Park Ave. Look no further! You have found the perfect unit for rent! Unit also available for sale! (See MLS#65376215)
This listing is courtesy of: REALCOM REAL ESTATE SERVICES INC
COLONIES - TB8482802 - 3035 GEORGE MASON AVE #D19, WINTER PARK, FL 32792
$1,350 | Apartment 1.0 bathroom
Fully renovated studio in Winter Park FL! Accept immigrant applications. This is an individual studio, and there are only 4 units per block in the condominium. Great location close to Costco, Sams, and 408 exit. There is a supermarket in the plaza next door and walking distance for quick shopping. This unit is a studio and its equipped with semi-new appliances like washer/dryer, refrigerator, stove, and more. The shower is a walk-in new shower. Great schools in the area. Accommodates up to 2 people. Water included
This listing is courtesy of: FRIENDS REALTY LLC