Displaying: For Rent
Location: Winter Park
Property Type(s): Condos
Living Area Square Feet: 1000 to 1499
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Winter Park - 11 properties found
2911 ANTIQUE OAKS CIR #12, WINTER PARK, FL 32792
$1,57512 Days on yellowkey MLS ID: O6400748
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1018 Built: 1984Community: Parkview VillageCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Beautifully Remodeled 2 Bed / 2 Bath Condo – Second Floor | Prime Location Charming and fully remodeled second-floor condo located just steps from the pool. Perfect for those seeking a low-maintenance lifestyle. This bright and inviting unit features fresh paint, new wood and ceramic tile flooring, and updated bathrooms and kitchen with granite countertops and new appliances, including a washer and dryer. The layout offers a comfortable living room, dining area, and a screened-in patio to relax and enjoy the outdoors. Community amenities include: Pool Sauna Clubhouse Ideally located within walking distance to Full Sail University and just minutes from UCF, Rollins College, and Valencia College, as well as shopping, dining, and major roadways. Note: Some images may be virtually staged.
Listing is courtesy of: CLARA HERRERA REALTY (407-921-1200)
Listing Agent: Clara Herrera (407-921-1200)
612 MONTEGO BAY CT #612, WINTER PARK, FL 32792
$1,85084 Days on yellowkey MLS ID: O6381197
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1037 Built: 1981Community: Winter Park Villas CondoCondo
Remarks: Cozy one-story villa located in desirable Winter Park. This home features two bedrooms and two full bathrooms, a bright living room–dining room combo, and a charming fireplace. Enjoy outdoor living on the private patio. Washer and dryer are included in the rent for added convenience. Pets are welcome (with some restrictions). Excellent location close to shopping, major highways, and local colleges.
Listing is courtesy of: JEXOR LLC (407-587-5701)
Listing Agent: Carolina Barriento (407-587-5701)
7429 DANIEL WEBSTER DR #14 (#C), WINTER PARK, FL 32792
$1,7405 Days on yellowkey MLS ID: O6403382
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1974Community: ColoniesSpa: NoCondo
Elementary School: Cheney Elem
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease! Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all within reach of central Florida's vibrant offerings. Strategically positioned minutes from the 408 expressway and downtown Orlando, this location is a commuter's dream, with nearby access to Full Sail University, UCF, and Valencia Colleges. Come inside to discover a beautifully maintained space featuring upgraded light fixtures, freshly painted walls, and abundant natural light that accentuates the spaciousness. The unit boasts generously sized bedrooms and a kitchen adorned with new granite countertops in the breakfast bar, along with an in-unit washer and dryer – just pack your bags and move in! As a resident of Keller Williams, you'll enjoy exclusive benefits through our Resident Benefits Package (RBP), including HVAC air filter delivery, renters insurance, and credit-building opportunities. Act swiftly – this home won't last long!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: David Drawdy, Jr. (407-629-4420)
612 TRINIDAD CT #612, WINTER PARK, FL 32792
$1,85084 Days on yellowkey MLS ID: O6381198
Remarks: Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area with small private courtyard. Cozy fireplace in the living room, lots of windows bring in the natural light of the Florida sunshine. Water/sewer is included in rent. Community pool and fitness room at the clubhouse only 2-3 minutes walking distance from the unit. Condo conveniently located near Colleges, Shopping and dining. Pets welcomed! (some restrictions apply)
409 SANDLEWOOD CV #3, WINTER PARK, FL 32789
$2,20028 Days on yellowkey MLS ID: O6395198
0 Days Off yellowkey (back on 4/27/2026)
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1413 Built: 1986Community: Sandalwood Creek Condo Ph 07Condo
Elementary School: Dommerich Elem
Middle School: Maitland Middle
Remarks: Welcome to this beautifully refreshed townhome nestled in a quiet cove community in the heart of Winter Park. Thoughtfully updated throughout, this light-filled home features new flooring downstairs, fresh carpet on the stairs, new paint throughout, and new light fixtures — move-in ready and waiting for you. The open floor plan flows seamlessly from the living and dining combination into the kitchen, where granite countertops, a charming bay window with bench seating, and a convenient pass-through to the dining area make everyday living a pleasure. A powder room is conveniently located on the main level, and the family room opens into an enclosed sunroom — a versatile bonus space perfect for a home office, playroom, or quiet retreat. A decorative fireplace and ceiling fans add warmth and comfort throughout. Upstairs, the spacious primary suite offers a private en suite with walk-in shower and a walk-out balcony — your own personal escape. A second bedroom on the upper level enjoys its own private bath with tub/shower combo. The third-floor bedroom is a standout, complete with a full bath featuring a walk-in shower and an oversized walk-in closet. High ceilings throughout give the entire home an airy, expansive feel. Residents enjoy access to a community pool and are zoned for an exceptional A-rated school corridor — Dommerich Elementary, Maitland Middle, and Winter Park High School. The location is equally impressive, with easy access to major roads, shopping, and dining, plus walking distance to Howell Branch Preserve Park. Available now at $2,200/month. Security deposit of $2,200 required. Application fee of $50 per adult. No pets. No smoking.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Dee Morgan (407-616-5526)
148 SANDLEWOOD TRL, WINTER PARK, FL 32789
$2,17528 Days on yellowkey MLS ID: O6396280
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1133 Built: 1985Community: Sandalwood Creek Condo Ph 05Condo
Remarks: Welcome to this charming and well-maintained rental located in a quiet, centrally situated community in the highly desirable Maitland/Winter Park area. This spacious 2-bedroom, 2.5-bathroom home offers comfort, convenience, and a low-maintenance lifestyle. Inside, you’ll find a bright and open floor plan with a generous living and dining area that flows seamlessly into the kitchen, which is equipped with brand new appliances. The layout provides plenty of natural light, along with ample closet space and storage throughout. Step outside to enjoy a private backyard space—perfect for relaxing or entertaining. Residents of this community enjoy access to a sparkling pool, beautifully maintained grounds, and the ease of included exterior and yard maintenance. Assigned parking is available, along with additional guest parking for visitors. Ideally located just minutes from Park Avenue, this home offers quick access to popular dining, shopping, grocery stores, and entertainment options, as well as nearby parks and major roadways for easy commuting. Zoned for top-rated schools including Dommerich Elementary, Maitland Middle, and Winter Park High School. This is a great opportunity to enjoy a comfortable rental with the feel of a townhome in a prime location—don’t miss it!
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
1500 GAY RD #18A, WINTER PARK, FL 32789
$1,75049 Days on yellowkey MLS ID: O6390460
0 Days Off yellowkey (back on 4/6/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972Condo
Remarks: 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)
Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)
Listing Agent: Janice Erickson (407-621-6856)
1000 S SEMORAN BLVD #815, WINTER PARK, FL 32792
$1,65032 Days on yellowkey MLS ID: R4910991
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1003 Built: 1969Community: Golfside Villas CondoCondo
Remarks: 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
Listing is courtesy of: KIMBRIDGE REALTY, LLC (407-755-7367)
Listing Agent: Scott Butts (321-239-8509)
1695 LEE RD #D116, WINTER PARK, FL 32789
$1,80034 Days on yellowkey MLS ID: O6395336
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1149 Built: 1966Community: Waterfall CoveCondo
Elementary School: Hungerford Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: 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!
Listing is courtesy of: ZEAL REALTY (407-789-2051)
Listing Agent: Ryan Hoppe (321-247-1098)
2936 ANTIQUE OAKS #70, WINTER PARK, FL 32792
$1,65053 Days on yellowkey MLS ID: O6382466
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1018 Built: 1984Condo
Remarks: 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!
Listing is courtesy of: JML REALTY INVESTMENTS LLC (407-921-9635)
Listing Agent: Jacqueline Ramos (407-921-9635)
110 KILLARNEY BAY CT #1, WINTER PARK, FL 32789
$2,55045 Days on yellowkey MLS ID: O6392456
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1140 Built: 1986Community: Killarney Bay CondoCondo
Remarks: 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!
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