Winter Park Townhomes For Rent - 15 townhouses

Remarks: Welcome home to this beautifully updated Cherokee Park townhome, where modern elegance meets comfort in the heart of highly desirable Winter Park. Perfectly situated near some of the area’s best dining, shopping, and entertainment, this home offers both luxury and convenience in one exceptional location. Step inside to a bright and airy open-concept living space featuring wood-style flooring, soaring vaulted ceilings, and a sleek modern fireplace that creates a warm yet contemporary focal point. Large windows throughout flood the home with natural light, including a stunning arched window overlooking lush greenery for a peaceful and inviting atmosphere. The thoughtfully updated kitchen and bathrooms feature clean contemporary finishes, stone countertops, designer lighting, and premium frameless glass showers. Fresh interiors, updated fixtures, and organized closet shelving make this home completely move-in ready with both style and functionality in mind. Upstairs, spacious bedrooms offer comfort and privacy with abundant natural light and spa-inspired bathrooms designed for relaxation. Step outside to your own private backyard retreat featuring low-maintenance luxury landscaping, pristine white stone accents, and premium artificial turf that keeps the outdoor space vibrant year-round. The fully fenced yard is perfect for relaxing evenings, entertaining guests, or enjoying peaceful mornings outdoors. Located just minutes from the renowned shops and restaurants of Park Avenue, residents will enjoy easy access to boutique shopping, fine dining, local cafés, and everyday conveniences including Trader Joe's. You’re also close to scenic parks, Lake Virginia, and Rollins College, making this location ideal for those seeking an active and connected lifestyle. Zoned for highly rated Winter Park schools and professionally managed by Atrium Management, this home offers the perfect combination of style, location, and convenience.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Raquel Elliott (407-921-3772)

Remarks: This property will not last long! Schedule a showing today! Winter Park Two Story 2/2.5 Townhome located in the Private - Gated Community of Vistas at Lake Howell. All Stainless Steel Kitchen Appliances Included (Dishwasher, Range, Refrigerator, and Microwave). Living & Dining Room Combo. All bedrooms are located on the second floor. Primary Bedroom has custom closet design and ensuite bathroom. Ceiling Fans in Many Rooms. Half Bathroom Downstairs. Screened in Private Back Patio/Porch. Attached One Car Garage. Convenient to SR-436 & I-4. Laundry Room is upstairs near bedrooms. Washer and Dryer Convenience Only. Separate HOA Application & Approval Required. Schedule a showing today! All our residents are enrolled in our Resident Benefits Package for $55.00 per month, charged as additional rent. This package includes Pest Assurance powered by Pest Share, access to an online resident portal, and availability of a dedicated 24/7 maintenance portal. Additionally, it offers monthly reporting of rental payments to Experian RentBureau, bi-monthly home delivery of replacement HVAC filters, and the use of resident-completed inspection technology. Residents are entitled to one late fee waiver during their residency and have access to concierge utility services

Listing is courtesy of: ALLEGIANT MANAGEMENT GROUP INC (407-557-3164)

Listing Agent: Elizabeth Santiago Moyet (321-231-2105)

Remarks: Stunning 3 beds/2.5 bath/1car garage townhome ready to move-in June at Grayson Square, Winter park. RENT INCLUDES high-speed 1GB fiber optic internet & 75 streaming cable and music channels. The first floor is efficiently laid out with the kitchen, powder room, and spacious gathering room perfect for entertaining with a sliding glass door that opens to the covered lanai and patio that overlooks a pond. Enjoy indoor/outdoor entertaining in your new home. Well-appointed kitchen with top-of-the-line stainless steel appliances and a large quartz countertop. Ample storage throughout. Upstairs you will find a master suite with a spacious walk-in closet. Luxurious ensuite bathroom with glass-door shower and quartz countertop and double sinks. 2 additional bedrooms and a laundry closet with washer and dryer. Grayson Squares offers: Community Pool with Cabana, Zoned for Seminole County Schools, Gated Entry, Near Major Roadways Providing Easy Daily Commutes, Minutes to Shopping and Dining Options on Park Ave. in Downtown Winter Park, 3 Miles to SR 417, 20 Minutes to Downtown Orlando and Orlando Area Attractions. Welcome Home! Equal Housing Opportunity

Listing is courtesy of: P & C PROPERTIES (407-233-1372)

Listing Agent: Fabian Berastegui (407-233-1372)

Remarks: In the heart of Winter Park on a quiet cobbled street, this Mediterranean style 3-bedroom, 3-bathroom house is available to rent today. With beautiful Travertine floors throughout the downstairs of the home, granite countertop kitchen, marble countertop bathrooms, and limestone ornate pillars throughout the home, this home boasts character. Upstairs the home enjoys three bedrooms, two bathrooms, two balconies, and an upstairs utility room. The powder room is downstairs, and patio and a nice size back garden that the tenant can tend to as their own. The front of the house is a brick courtyard. New stainless-steel fridge 2023. 0.9 miles from Rollins College. Perfect for three tenants. Call today Weeks and Months Available

Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)

Listing Agent: Moire Mckibbin (407-361-1139)

Remarks: Beautiful freshly painted and cleaned property in Winter park. This is a townhouse style condo (no neighbors above and only on one side)- end unit with rear patio and storage closet. The first floor is a large living space, kitchen, a half bath and laundry with a dining nook. While there are 3 bedrooms upstairs with 2 full baths. The first floor is fully tiled and the upstairs bedrooms have carpet. The primary bedroom is large with a private ensuite bathroom. There are three assigned parking spaces for this unit (directly in front of home) . The community is conveniently located with easy access to SR 436 and Colonial (50) with a great community pool. $68 Application fee per adult, 650 credit or higher, 3X rent as income.

Listing is courtesy of: EXIT REAL ESTATE RESULTS (352-933-0018)

Listing Agent: Kyle Petteway (407-461-9141)

Remarks: Welcome to this beautiful 3-bedroom, 2.5-bath townhome featuring modern finishes and a serene setting. Enjoy cooking in the kitchen with elegant granite countertops, durable tile flooring downstairs, and stylish luxury vinyl plank flooring upstairs. Step outside to your private fenced patio with peaceful conservation views, perfect for relaxing or entertaining. Water is included! Available NOW! **All Remi Emerson Residential tenants are enrolled in the Resident Benefits Package (RBP) for an additional $50 a month which includes your $100,000 tenant liability insurance, quarterly HVAC air filter delivery, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, plus on-demand pest control! If you have an animal/pet you must click on the Pet Screening link in the application.**Security deposit is due upon lease signing. The first full month's rent is due 1 week prior to move in date. The 2nd month of rent is prorated. Every person 18 yrs or older must fill out an application. Please upload your last 2 months of paystubs in your application. Only complete applications will be considered. A one time admin fee of $250 due upon approval. A lease renewal fee of $125 after 1 year.**

Listing is courtesy of: REMI EMERSON RESIDENTIAL (407-490-1848)

Listing Agent: Shelley Davis (407-625-3489)

Remarks: 3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and lawn service 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.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Shawn Beard (407-739-7722)

Remarks: Discover modern living in this beautifully designed townhome located in the heart of Winter Park. This residence has a spacious layout with contemporary finishes, high ceilings, modern light fixtures and shades, and abundant natural light. Enjoy the convenience of a well-appointed kitchen, an inviting living area, and a private patio for relaxing, and private access to the community pool! The property provides access to community amenities and is situated near local shops, dining, and entertainment venues. Experience the vibrant lifestyle Winter Park has to accord.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

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)

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)

Remarks: Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained unit is move in ready: two-story 3 Bedrooms 2.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this space. Just off the dining room you will find the kitchen and eat in kitchen area.few stainless steel appliances and tons of storage. The eat in kitchen space is highlighted with a decorative wall and sliders leading to your fully fenced private backyard space. Upstairs you will find hardwood flooring, three bedrooms and master bathroom with a single vanity . Hidden Oaks community features on-site security, community pool & fenced playground area. Near Full Sail, UCF, Valencia & Rollins College, with easy access to shopping, Winter Park schools, Medical Facilities, Downtown Orlando, Downtown Winter Park, FL-408, FL-417 and the airport. This wonderful unit has it all...the only thing missing is YOU!

Listing is courtesy of: APPLE REALTY (407-647-6766)

Listing Agent: Manoj Patel (407-451-5872)

Remarks: One or more photo(s) has been virtually staged. Welcome to Lake Killarney Townhomes, a modern luxury and new construction waterfront community. Nestled in the heart of Winter Park, just north of downtown Orlando, these exclusive townhomes offer a unique blend of urban contemporary design and comfort. This home features a private terrace perfect for relaxing in style with slight views of Lake Killarney. Bright, open interiors with expansive storefront-style windows and soaring 10'6" ceilings create an atmosphere of elegance and comfort. This home is a two-story concrete block construction complemented by woodgrain composite siding. The layout offers three spacious bedrooms on the second floor and three-and-a-half luxurious bathrooms. The modern kitchen includes sleek cabinetry, premium Samsung appliances with a natural gas cooktop and built-in wall oven, expansive quartz countertops, and a generous walk-in pantry. The bathrooms each showcase unique porcelain tile, modern backlit mirrors, frameless glass shower enclosures, undermount sinks, and custom-built closet systems. Step outside to your expansive outdoor patio, designed with glass railings and pre-plumbed for a future summer or cocktail kitchen, perfect for hosting gatherings or simply enjoying the outdoors. An inviting back patio is great for dining alfresco or enjoying the amazing central Florida weather this time of year. Every detail has been thoughtfully curated to ensure ultimate comfort and style. Enjoy the serene beauty of Lake Killarney from your side patio, or relax at the inviting lakefront pavilion. The location offers unparalleled convenience, being close to downtown Winter Park, Park Avenue, I-4, and just a short drive to neighboring towns like College Park and Maitland. The community also provides kayak, canoe, and paddle-board racks for a leisurely day on the water. Enjoy the perfect blend of luxury and convenience. This home is available for rent immediately.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Kris Kennedy (813-947-3509)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom townhome in the highly desirable area of Winter Park—perfect for renters seeking comfort, convenience, and a vibrant community lifestyle. Step inside to an open-concept layout designed for modern living, featuring stylish tile flooring and a spacious kitchen with granite countertops that flows effortlessly into the living and dining areas—ideal for entertaining or relaxing at home. The generous primary suite offers a private retreat with dual walk-in closets and an ensuite bathroom, while two additional bedrooms provide flexibility for roommates, guests, or a home office. Residents will love the resort-style community amenities, including tennis courts, pickleball courts, two sparkling pools, a playground, a putting green, and a clubhouse—giving you plenty of ways to unwind and stay active right at home. Location is everything, and this property delivers. You’ll be just 15 minutes from the shops, dining, and nightlife of Park Avenue, approximately 7 miles from University of Central Florida, and only 1.7 miles from Full Sail University—making it an excellent option for aspiring academics, faculty, or professionals alike. Don’t miss the opportunity to live in a well-appointed home with unbeatable amenities and a prime location!

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Samuel Kingsford (407-808-6633)

Remarks: Welcome to the Four Seasons Condominiums! This great PARTIALLY FURNISHED 2 bedroom, 1.5 bath townhouse condo has much to offer. This completely uniquely designed townhouse features a sunken living room with glass sliding door that open to the private covered patio area, dining room , generous modern kitchen with a colorful glass subway tile backsplash , stainless steel appliances and quartz countertops. First floor also features entry way and half bath for guest. Upstairs features a split bedroom floor plan with two ample bedrooms with loads of closet space. Also upstairs is the modern style full bath with a large vanity and back lit mirror.medicine cabinet. Added features are the washer/dryer combo, laminate floor through out, Ecobee thermostat, new windows and glass doors, window treatments, one assigned carport space with extra open parking, and designer color scheme. Tenant will have access to the pool areas, tennis courts etc. Walk out your door with steps away to the Ward Memorial Park. Association approval is required. Water , sewer and trash is included. Owner will consider pet. Looking for a minimum of a years lease. Available JUNE 2026 SHOWINGS BY APPOINTMENT ONLY. ADVANCED NOTICE NEEDED.

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: John Abbott, Jr (407-398-2330)

Remarks: Nestled in the heart of Winter Park just off Howell Branch Rd., in the gated community of VISTAS AT LAKE HOWELL awaits this charming, spacious well equipped 2bedroom/2.5bathroom/1car garage with a loft and screen enclosed patio. This townhome features a modern aesthetic from upgraded recessed lighting and ceiling fans, upgraded wall switches, granite counter-tops, stainless steel appliances, kitchen center island, breakfast nook, stone floors downstairs, and wood laminate upstairs, large loft, high ceilings, front loading washer & dryer, ample closets, 2/private baths on the 2nd floor, half bath on the 1st. The master bedroom has a walk-in closet, the master bath is equipped with his & her vessel sinks with granite counters, a step-in tub with shower, bedroom #2 has a private bath with access from the bedroom or the loft. Downstairs enjoy the intimacy of relaxing on the patio just off of the living room, open the sliding glass doors completely then tune out the world with the natural greenery designed to set the mood and enjoy the experience of suburban Living. Just minutes from Esporta fitness, the 436 highway & Rt 417, restaurants, shopping and charming downtown Winter Park, great schools and universities makes this residence and location an ideal place to call home.

Listing is courtesy of: REALTY HUB (407-900-1001)

Listing Agent: Barbarite Adams Llc (407-288-6712)