Remarks: Charming 3BR/2.5BA single-family home in desirable Winter Park! Interior features include ceramic tile & laminate flooring, ceiling fans, and a bright kitchen with breakfast bar/kitchen island and stainless-steel appliances. Washer/dryer and major kitchen appliances included. Conveniently located near Hannibal Square, Park Ave, Central Park, Rollins College, the Winter Park Community Center, and the Farmers’ Market. Enjoy classic Florida curb appeal with a welcoming front porch and balcony, plus a functional layout perfect for everyday living and entertaining. Lease term 12 months. $75 application fee each adult. Pets considered with owner approval (pet fees/deposit may apply). Renters Insurance required. Great opportunity to live in one of Central Florida’s most desirable areas. Schedule your showing today!

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Alessandra Oliveira (305-788-0825)

Remarks: Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals, airports, Winter Park's cultural gems, and the scenic Chain of Lakes, this home is perfect for professionals, creatives, and families seeking a refined long-term stay. The neighborhood offers an exceptional lifestyle with walking trails, pickleball and tennis courts, playgrounds, dog parks, proximity to Baldwin Park, and Winter Park Pines Golf Club.

Listing is courtesy of: SOTERA LIVING (407-725-9660)

Listing Agent: Benjamin Cole Iv (407-399-0629)

Remarks: Who wouldn’t want to live on a street called LOTAFUN? This one-story Winter Park home has 3-bedrooms, 2.5-baths with great access to Interstate-4 and both Winter Park and Orlando downtown areas. With all new interior spaces, this fantastic home is totally rebuilt with brand new electrical, plumbing, heating and air, ductwork, roof, flooring and Energy Star doors and windows. Located at the end of a dead end street, the privacy is just one of its best features; with partial views of Lake Killarney from the dining area, kitchen, family room, and side yard as a close second. Spacious bedrooms, interior laundry closet and large side yard are also special features offered. This 1,534 sqft of living space is perfect for the tenant who wants quality, style and convenient location. This one is MOVE IN READY AND WAITING FOR YOU. There is a $99 per adult application fee and once approved the first & last month’s rent will be due along with the security deposit and any applicable pet fee and pet deposit.

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

Listing Agent: Johnny Hurlburt (407-579-3168)

Remarks: Check out this Winter Park gem near Lake Sue! This 3BR/2BA home features a modern kitchen with granite and stainless steel, wood floors, and a private backyard oasis (landscaping included). Perfect for commuters or remote workers, it boasts an oversized 3rd bedroom/office and is minutes from Park Ave and Audubon Park. Zoned for Audubon K-8 and Winter Park High. Every applicant should apply separately. 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)

Remarks: STYLISH, STUNNING AND RENOVATED TO THE NINES. This 3-bedroom, 2.5-bath Winter Park home has great access to Interstate-4 and both Winter Park and Orlando downtown areas. With all new interior spaces, this fantastic home is almost totally rebuilt with brand new electrical, plumbing, heating and air, ductwork, roof, flooring and Energy Star doors and windows. In addition to the 3 upstairs bedrooms, the downstairs has a bonus room which is perfect for a den or playroom and a convenient interior laundry room. The lot is 6,750 sqft and is fenced and gated offering a nice new patio of clay pavers, a carport, and large backyard. This 1,774 sqft of living space is perfect for the tenant who wants quality, style and convenient location. This one is MOVE IN READY AND WAITING FOR YOU. There is a $99 per adult application fee and once approved the first & last month’s rent will be due along with the security deposit and any applicable pet fee and deposit.

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

Listing Agent: Johnny Hurlburt (407-579-3168)

Remarks: Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step outside to your own private oasis — a fully fenced backyard with a sparkling private pool, perfect for relaxing or entertaining year-round. The property also includes an attached 2½-car garage and 4 additional driveway parking spaces, providing plenty of room for vehicles. Located in a prime Winter Park neighborhood, this home is close to parks, shopping, dining, and top-rated schools. Pets are welcome, making this a perfect home for the whole family. Don’t miss this opportunity to enjoy privacy, space, and convenience in one of Central Florida’s most sought-after areas.

Listing is courtesy of: THE REALTY MEDICS (321-947-7653)

Listing Agent: Jason Hamilton (321-947-7653)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully refreshed 3-bedroom, 2-bath home nestled in a highly desirable Winter Park location — offering comfort, style, and convenience with no HOA restrictions. With 1,676 square feet of thoughtfully designed living space, this home is the perfect blend of modern updates and timeless character. Step inside to discover brand-new wood-look tile flooring throughout, providing both durability and a clean, contemporary feel. Fresh interior paint enhances the bright and airy atmosphere, while vaulted ceilings with exposed wood beams add warmth and architectural charm to the main living area — creating a space that feels both open and inviting. The kitchen is equipped with stainless steel appliances and offers a functional layout ideal for everyday living and entertaining. Both bathrooms have been updated, including a new sink in the primary bath, adding a fresh and polished touch. Enjoy Florida living at its best on the screened-in back porch, perfect for morning coffee or evening relaxation. The spacious backyard offers endless possibilities — whether you envision a garden, play area, or outdoor entertaining space. Additional features include a 2-car garage for convenience and extra storage, as well as a prime location just minutes from shopping, dining, and major roadways — making daily commutes and errands a breeze. This well-maintained home offers a wonderful opportunity to live in an established neighborhood with character, space, and flexibility. A perfect place to call your dream home!

Listing is courtesy of: AMERICAN DREAM HOMES INC (407-382-8100)

Listing Agent: Jenny Forest Lin (407-780-6065)

Remarks: Welcome to 870 Carver Street, a one-of-a-kind rental offering two distinct, private residences on a single fully fenced property in the heart of Winter Park. The main home is a 2 bedroom, 2 bath retreat featuring vaulted ceilings with exposed rafters, warm wood finishes, and industrial-inspired black metal ductwork. The open living area is 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 flood the space with natural light. The primary suite includes a floating wall closet system, in-suite laundry, and a spa-style bath with dual-sink floating vanity and glass-enclosed walk-in shower. The second bedroom features an en-suite full bath with a tub-shower combination. The second residence is a self-contained 1 bedroom, 1 bath unit with its own private entrance and dedicated driveway on Carver Street, completely separate from the main home. Inside, vaulted ceilings, tile flooring, a full kitchen, en-suite bath, private laundry, and white oak stairs lead to a bright, cohesive living and dining area. The two residences share a fully fenced yard with a rear garden courtyard but are otherwise independent, making this an ideal arrangement for roommates, a home office, a live-in guest, or simply extra space on your own terms. Outdoor spaces include covered entries and an expansive front porch with warm wood architectural detailing. An oversized garage with extra depth for storage is accessed via a sliding steel-framed, wood-clad gate along Railroad Avenue. Just a short distance from Park Avenue, Winter Park Village, Whole Foods Market, the Winter Park Golf Course, and the SunRail and Amtrak stations... everything Winter Park has to offer is right at your door!

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Drew Henner (407-406-0662)

Remarks: 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).

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

Listing Agent: Mo Jabr (407-571-1441)

Remarks: 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.

Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)

Listing Agent: Donna Peebles (321-229-6085)

Remarks: 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.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Jackie O'Leary (407-718-0887)