Location: Winter Park
Keyword(s): Lake Howell High
Keyword(s) High School: Lake Howell High
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2028 SUSSEX RD, WINTER PARK, FL 32792
$2,90026 Days on yellowkey MLS ID: S5152229
0 Days Off yellowkey (back on 7/14/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1674 Built: 1973Community: Winter Woods Unit 04Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year:
Middle School: Tuskawilla Middle
Remarks: Welcome home to Winter Park living at its finest in this beautifully updated one-story home where comfort, convenience, and charm come together. From the moment you enter, you'll notice the bright, freshly painted interior, spacious layout, and modern touches throughout—including new updated bathrooms, landscaping enhancements and brand-new stainless-steel appliances. The attached two-car garage adds everyday ease, while the included washer and dryer. Step outside to your private backyard retreat, where a peaceful water view and inviting fire pit creates the perfect setting for morning coffee, weekend gatherings, or quiet evenings under the stars. Professional landscaping and pest control are also included, so you can spend less time on upkeep and more time enjoying your home. Ideally located near Downtown Winter Park, Park Avenue, local coffee shops, restaurants, grocery stores, entertainment, and daily conveniences, this home also offers quick access to Maitland, Casselberry, Orlando, I-4, and SR-417. Zoned for Seminole Country Schools. If you're searching for a stylish, low-maintenance rental in a prime location, this Winter Park home is ready to welcome you. Schedule your showing today!
Listing is courtesy of: CENTRAL FLORIDA REALTY MANAGEMENT LLC (407-542-4403)
Listing Agent: Kevan Patel (407-491-3559)
3463 ARNEL DR, WINTER PARK, FL 32792
$2,95063 Days on yellowkey MLS ID: O6407196
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1770 Built: 1967Community: Eastbrook Sub Unit 11Single Family
Elementary School: Eastbrook Elementary
Remarks: Beautiful pool home for rent in Winter Park located in the established Eastbrook community with NO HOA. This home offers 3 bedrooms plus a versatile bonus room, 2 bathrooms, approximately 1,770 sq ft of living space, a 2-car garage, extended driveway, and a private screened pool with fully fenced backyard. Inside, you’ll find a bright and functional layout with comfortable living and dining areas, updated kitchen with granite countertops and modern cabinetry, plus updated bathrooms with clean finishes. The bonus room offers flexibility for a home office, gym, playroom, or additional living space. Major updates include roof replaced in 2018, fully paid solar panels installed in 2020, water heater 2019, and A/C replaced in 2013. Conveniently located near Park Avenue, Rollins College, Full Sail University, University of Central Florida, shopping, dining, and major highways. First month’s rent, last month’s rent, and security deposit required prior to move in. Background and credit check required through RentSpree at tenant expense ($50 x adult over 18 years old). Preferred credit score 550+. No prior evictions. Pet restrictions apply.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
2657 EXUMA WAY, WINTER PARK, FL 32792
$2,10020 Days on yellowkey MLS ID: O6418670
REDUCED by $300 (12.5%) on 07/13/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1467 Built: 1978Community: Windward Square Sec 2Townhouse
Remarks: 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. EV parking with outlet for your charger. 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 (407-928-3894)
Listing Agent: Jerry Agan (678-873-4463)
5171 LAZY OAKS DR, WINTER PARK, FL 32792
$2,05043 Days on yellowkey MLS ID: O6412797
REDUCED by $50 (2.4%) on 07/11/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1236 Built: 1984Community: Lazy Oaks CondoSpa: NoCondo
Remarks: This Winter Park condo features two bedrooms and three bathrooms, with an attached garage for convenient parking. The entrance welcomes you with a charming foyer. At the heart of the spacious open great room is the kitchen—highlighted by custom cabinets, quartz countertops, and stainless-steel appliances, all thoughtfully arranged on the first floor. An oversized counter provides space for dining, and the combined dining and living area provide access through French doors to the enclosed rear porch. The living room is enhanced by a decorative built-in electric fireplace. Upstairs you'll find two bedrooms, each with en suite baths. The master bedroom stands out with custom closets, a large window that fills the space with natural light and raised ceilings that add dimension. Two-tone contrasting colors create a cozy and inviting atmosphere, and the master bath includes a double sink vanity, walk-in shower, and linen closet. The second bedroom also boasts raised ceilings, custom closets, and its own private bathroom. Lazy Oaks Condominium is a highly sought-after community in Winter Park, located off Old Howell Branch Road. Residents enjoy amenities such as monthly pest control, guest parking, curbside garbage collection, and private mailboxes.
Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC (407-695-7898)
Listing Agent: Joyce Gary (407-782-3276)
WINTER PARK, FL 32792
$2,3259 Days on yellowkey MLS ID: O6422736
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1628 Built: 2004Community: Vistas At Lake HowellTownhouse
Elementary School: Sterling Park Elementary
Remarks: MOVE-IN SPECIAL-$230 OFF THE 1ST MONTH'S RENT!!!! Welcome home to this beautiful 3-bedroom, 2.5-bath end-unit townhome with a one-car garage, located in the highly desirable gated community of Vistas at Lake Howell in Winter Park. This rare rental opportunity offers a spacious and inviting floor plan with a large living room featuring laminate flooring and a built-in entertainment center. The fully equipped kitchen includes stainless steel appliances, solid-surface countertops, and solid wood cabinetry. All bedrooms are located upstairs for added privacy. The spacious primary suite features a large walk-in closet. The versatile third bedroom can serve as a traditional bedroom, home office, guest room, or flex space to suit your lifestyle. The upstairs laundry closet adds everyday convenience by keeping everything on one level. All Keller Williams residents are enrolled in the Resident Benefits Package (RBP). The RBP includes HVAC air filter delivery, renters' insurance, credit building to help boost your credit score with timely rent payments, $1M Identity Protection, utility concierge service to make utility connections a breeze during your move-in, our best-in-class resident rewards program, and much more. More details are available upon application. Renters' insurance is required, and proof of coverage must be provided. Conveniently located near shopping, dining, Full Sail University, Rollins College, and UCF, with easy access to SR 408, SR 417, SR 426 (Aloma Avenue), and SR 436 (Semoran Boulevard), making commuting throughout Central Florida quick and convenient. This exceptional townhome won't last long!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Kelly Popchock (863-207-7552)
1351 MERRYDALE WAY, WINTER PARK, FL 32792
$2,87561 Days on yellowkey MLS ID: O6408378
REDUCED by $100 (3.4%) on 06/23/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1755 Built: 2018Community: Enclave At Hawks CrestTownhouse
Remarks: Fantastic, Modern townhome WITH 3 beds & 2.5 baths. Hawk's Crest is a gated community in Winter Park. This home is has a very spacious open floor plan with a water view! The kitchen has granite countertops and is fully equipped with stainless steel Whirlpool appliances; oven, stove, microwave, refrigerator, dishwasher, and garbage disposal. The kitchen area also has a large pantry! This energy star-certified home features , large two car garage and private driveway, tile flooring throughout the first floor, carpet on stairs and in bedrooms. The home has a large back patio that is partially covered and that overlooks the beautiful pond. The backyard is very private and quiet with no on-looking neighbors. The extra large primary is upstairs, features a walk-in closet. The primary bathroom boasts two sinks with beautiful granite countertops. The two guest bedrooms have large closets and views of the lake. The guest bathroom upstairs, has a shower/tub combo. The laundry room with a whirlpool washer and dryer. The home has a large two car garage with cabinets for extra storage. The garage entry way has a mudroom section for your jackets and coats. High-speed Spectrum Wifi is included in the rent. The community features a resort-style pool, outdoor grills, and a playground only one block away from the home. There is on-street parking for guests. Foxtail Coffee and Kelly's Ice Cream are a 5 minute walk away. Downtown Maitland and Park Avenue are both a quick 10 minute drive.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Jackie O'Leary (407-718-0887)
1951 CANNY CV, WINTER PARK, FL 32792
$2,70068 Days on yellowkey MLS ID: O6406363
0 Days Off yellowkey (back on 7/8/2026)
REDUCED by $100 (3.6%) on 06/25/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1782 Built: 2023Community: Grayson SquareTownhouse
Remarks: Enjoy comfortable Winter Park living in this freshly painted 3-bedroom, 2.5-bath townhome located in the gated community of Grayson Square. Thoughtfully designed for everyday living, this home features a spacious open-concept living and dining area, perfect for entertaining, with direct access to a covered lanai for relaxing outdoors. The kitchen offers stainless steel appliances, quartz countertops, and ample cabinet space for storage and functionality. Upstairs, the owner’s suite includes a large walk-in closet and a private bathroom with dual sinks, quartz counters, and a glass-enclosed shower. A washer and dryer are also included for added convenience. Additional highlights include a two-car garage with epoxy floors and ceramic tile flooring throughout the main living areas, providing both style and easy maintenance. Residents of Grayson Square enjoy gated access, a community pool with cabana, and 1GB high-speed fiber optic internet included in the rent, along with 75 streaming cable and music channels. Ideally located near downtown Winter Park, this home offers easy access to Howell Branch Road, 436, 434, and 417. Starbucks, Publix, and Walmart are just minutes away, while the shopping and dining of Park Avenue are approximately 15 minutes away. Top-rated Seminole County schools are also nearby. A wonderful opportunity to lease a well-maintained home in a convenient Winter Park location. ¡Hablo Español!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Denise Del Castillo (321-960-3110)
2304 INAGUA WAY #2304, WINTER PARK, FL 32792
$1,69534 Days on yellowkey MLS ID: O6416235
REDUCED by $55 (3.1%) on 07/07/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 854 Built: 1980Community: Windward Square Sec 3Condo
Remarks: 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 (407-578-6545)
Listing Agent: Francisco Nieves-Taranto (321-248-4149)
2817 BRIGHT BIRD LN, WINTER PARK, FL 32792
$2,70042 Days on yellowkey MLS ID: O6412306
0 Days Off yellowkey (back on 7/6/2026)
REDUCED by $100 (3.6%) on 06/26/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2024Community: Grayson SquareTownhouse
Remarks: Welcome to Grayson Square in Winter Park. This beautifully maintained 3-bedroom, 2.5-bath townhome is located in one of the area’s newer gated communities and shows like new throughout. Exceptionally clean and well cared for, this home is truly move-in ready. The open-concept living and dining area offers a comfortable layout for both everyday living and entertaining. The covered lanai overlooks a peaceful pond, providing a relaxing outdoor space with a serene view. The kitchen features stainless steel appliances, quartz countertops, ample cabinetry, and generous storage. Upstairs, the spacious owner’s suite includes a walk-in closet and a private bathroom with dual sinks, quartz countertops, and a glass-enclosed shower. The second full bathroom includes a tub with shower combination. A washer and dryer are included for added convenience. Residents enjoy gated entry, a resort-style pool, and cabana amenities. Rent includes 1GB fiber-optic internet service along with 75 streaming cable and music channels. Conveniently located just minutes from Downtown Winter Park and Park Avenue, with easy access to SR 436, SR 434, and SR 417. Close to shopping, dining, and everyday essentials including Publix, Walmart, and Starbucks. Zoned for highly regarded Seminole County schools.HABLO ESPANOL.
296 LEWFIELD CIR #296, WINTER PARK, FL 32792
$1,30063 Days on yellowkey MLS ID: O6407086
0 Days Off yellowkey (back on 6/17/2026)
REDUCED by $50 (3.7%) on 05/27/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973Community: Stratford A Winter Park CondoSpa: NoCondo
Remarks: Experience effortless Winter Park living in this stylish, top-floor condo in the charming Stratford community. This move-in-ready gem features modern wood-look tile, a private balcony with serene landscape views, and the convenience of an in-unit washer/dryer. Enjoy resort-style perks like a sparkling pool, fitness center, and tennis courts. Perfectly situated just 10 minutes from the upscale dining of Park Avenue and major campuses like Rollins and Full Sail, this home offers the ideal blend of relaxation and location. Schedule your showing today before this Winter Park beauty is gone! Credit and background check needed. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.
Listing is courtesy of: 407 PROPERTIES (407-545-2594)
Listing Agent: Steven Simpson (407-545-2594)
3486 BOUGAINVILLEA DR #A, WINTER PARK, FL 32792
$2,295381 Days on yellowkey MLS ID: R4909541
REDUCED by $100 (4.2%) on 04/28/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1650 Built: 1963Community: Eastbrook Sub Unit 06Half Duplex
Remarks: Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.
Listing is courtesy of: LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV (407-207-2220)
Listing Agent: Smith Salomon (407-724-9127)
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