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Houses for Rent in Windsong, Winter Park, FL

Average rent

$3,300

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607 Dunblane Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

607 Dunblane Dr, Winter Park, FL 32792

In-unit laundry | Outdoor space | Storage

4 beds

2 baths

$3,950

House for rent

Description

Property Status: Active Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenue’s top dining and shopping. Thoughtfully updated from top to bottom, this move-in-ready home features a brand-new AC system, luxury vinyl plank flooring throughout, and a stunning chef’s kitchen with quartz waterfall countertops, custom cabinetry, and all-new stainless steel appliances. Each bathroom has been modernized with sleek, contemporary finishes, while the spacious primary suite offers a private retreat with a beautifully

2037 Shaw Ln - Photo 1 of 1

5d+ ago

Baldwin Park house for rent in Orlando

2037 Shaw Ln, Orlando, FL 32814

Outdoor space | Garage parking | Swimming pool

6 beds

4 baths

$6,500

House for rent

Description

This charming two story Baldwin Park home has expansive front porch that provides numerous designer selections inside the home including plantation shutters. Hardwood floors flow throughout the home, carpet in bedrooms. The spacious kitchen is the heart of the home with ample counter space and storage, a center island with seating, a separate eating area, a large pantry and wet bar to make entertaining easy. The kitchen flows into the formal living & dining rooms. Additional living space includes a cozy family room with lots of natural lighting. To ensure the master sui

502 Dunraven Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

502 Dunraven Dr, Winter Park, FL 32792

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$2,975

House for rent

Description

Property Status: Active Discover the perfect blend of comfort and convenience in this delightful 3-bedroom, 2-bathroom home nestled in the sought-after Kenilworth Shores neighborhood of Winter Park. With over 1,600 square feet of thoughtfully designed living space, this property offers everything you need for comfortable Florida living. The home features two separate living spaces that are perfect for entertaining or creating distinct areas, along with a modern kitchen complete with stainless steel appliances. You'll appreciate the convenience of a dedicated interior laund

2128 Sycamore Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

2128 Sycamore Dr, Winter Park, FL 32789

In-unit laundry | Garage parking | Walk-in closets

3 beds

2 baths

$3,300

House for rent

Description

Property Status: Active MOVE-IN READY! Don’t miss this fantastic opportunity to rent a beautiful 3-bedroom, 2-bathroom home situated on a spacious .23-acre corner lot. This property has undergone a complete upgrade inside and out, making it perfect for those looking for a fresh start. Key Features: • Newer Septic Tank: Ensures peace of mind and efficiency. • 2016 Roof: A reliable roof that adds to the home’s longevity. • New Gutters and Fascia: Enhance the exterior and protect your investment. This home is located in a highly sought-after school district, making it an exce

1661 Hillcrest Ave - Photo 1 of 1

5d+ ago

Virginia Heights house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1661 Hillcrest Ave, Winter Park, FL 32789

In-unit laundry | Outdoor space | Storage

4 beds

3 baths

$10,000

House for rent

Description

Property Status: Active This property is also listed for sale with MLS # O6343469. Owner open to 9+ month lease period. Luxurious Winter Park Retreat with Stunning Features! Welcome to 1661 Hillcrest Avenue, a masterpiece of coastal design nestled in the heart of the highly sought after Winter Park. This exceptional property presents an exclusive opportunity to rent a home crafted by the Parade of Home Winner, Lazarus Development Group. This elegant home boasts 4 bedrooms, 3.5 baths, and a 2 car garage. As you step inside, you are greeted by a bright open, airy ambiance th

2011 Meeting Pl - Photo 1 of 1

5d+ ago

Baldwin Park townhouse for rent in Orlando

2011 Meeting Pl, Orlando, FL 32814

In-unit laundry | Outdoor space | Swimming pool

3 beds

3 baths

$3,500

House for rent

Description

Luxury living at its finest! This 3 bedroom/3.5 bathroom, fully remodeled, 3-story townhome, located in the sought-after neighborhood of Baldwin Park, could be your family’s new home today! Home offers a completely split floor plan with all 3 bedrooms having their own bathroom, as well as a half bath on the main floor. The kitchen has been fully upgraded including all stainless appliances, 18” tile, dark cherry wood cabinetry, granite countertops, and all new light fixtures! There is new paint throughout, a view of the community pool from the terrace, and it is ready for y

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Nearby rental good for pet owners

1946 Strathaven Rd - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1946 Strathaven Rd, Winter Park, FL 32792

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$3,000

House for rent

Description

Property Status: Active $100 OFF THE FIRST 6 MONTHS For Rent – Spacious 3BR Home in Prime Winter Park Location! LOCATION, LOCATION, LOCATION! This spacious 3-bedroom, 2-bath home with a large den and cozy wood-burning fireplace sits on an oversized lot in Kenilworth Shores – Sec 7, with deeded access to Lake Berry. Zoned for Winter Park High, Glenridge Middle, and Brookshire Elementary, and just minutes from Cady Way Trail, Baldwin Park, Park Avenue, YMCA, Rollins College, Full Sail, and more—you’ll be at the center of it all. This home features separate livi

2817 Eastern Pkwy - Photo 1 of 1

5d+ ago

House for rent in Winter Park

2817 Eastern Pkwy, Winter Park, FL 32789

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$2,995

House for rent

Description

Discover the perfect blend of comfort and convenience in this inviting 3-bedroom, 2-bathroom single-family home in the heart of Winter Park. Zoned for top-rated schools, including K-8 Audubon Park and Winter Park High School, this home puts you close to Park Ave dining, East End Market, Winter Park YMCA, AdventHealth Hospitals, and endless shopping and entertainment options. Inside, enjoy a spacious layout with elegant wood floors, a separate dining area, cozy breakfast nook, and a primary suite featuring a walk-in closet with custom built-ins and an adjoining office or n

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3851 Ethan Ln #3851 - Photo 1 of 1

5d+ ago

Baldwin Park townhouse for rent in Orlando

Baldwin Park Townhome

3851 Ethan Ln #3851, Orlando, FL 32814

In-unit laundry | Outdoor space | Garage parking

2 beds

2 baths

$3,650

House for rent

Available Nov 1

Description

Light and bright 2 bedroom, 2.5 bathroom, detached 2 car garage townhouse in Orlando. Private brick patio. Amenities included: high speed internet, central air, central heat, refrigerator, dishwasher, black stainless steel appliance, touchless kitchen faucet, washer, dryer, yard, and 3 Baldwin Park community pools, 2 fitness centers, many green spaces. Dedicated 20 Amp circuit in garage which can be used for Tesla charging. Utilities not included. Date Available: Nov. 1 2025 (earlier availability possible) $3,650/month rent. $3,650 security deposit required. Please submit

2148 Fresco Aly - Photo 1 of 1

4d ago

Baldwin Park townhouse for rent in Orlando

Orlando (Baldwin Park community)

2148 Fresco Aly, Orlando, FL 32814

In-unit laundry | Garage parking | Swimming pool

4 beds

3 baths

$4,500

House for rent

Available May 10

Description

Property Id: 1179048 This 3 story townhouse is in the desirable Baldwin Park and is an end unit. It is steps away from beautiful Lake Baldwin and Blue Jacket Park. It boasts dark hardwood floors, 10-foot ceilings, 8-foot doors, built-in surround sound system and beautiful finishes throughout. This home has an abundance of windows and natural light. Upon 1st floor entry you will be greeted by a bedroom/office , an upgraded full bathroom, a mudroom and an attached 2-car garage. The 2nd floor has a large open floorplan with gourmet kitchen, bar, living room with window sea

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These rentals are 10%-30% cheaper than the local average price for similar rentals.

Listings within 5 miles
1865 Britlyn Aly - Photo 1 of 1

2d ago

Baldwin Park townhouse for rent in Orlando

3 BR / 3.5 BA Townhouse In Baldwin Park

1865 Britlyn Aly, Orlando, FL 32814

On-site laundry | Balcony | Walk-in closets

3 beds

3 baths

$3,795

House for rent

Description

AVAILABLE NOW! Please call or text 407.863.8625 to schedule a showing. This beautiful 3 bedroom, 3.5 bathroom townhouse is located in the heart of Baldwin Park between Winter Park and Downtown Orlando. Enjoy Baldwin Park's abundance of shops, restaurants, and highly rated schools and a true feeling of community with its gorgeous tree lined streets, parks, wide sidewalks, and bike paths. The spacious main living area features volume ceilings, a lovely open kitchen with stainless steel appliances featuring an induction stove, stone countertops, and island, a dining room, and

630 N Lakemont Ave - Photo 1 of 1

2d ago

Our team has verified this company

Verified

630 N Lakemont Ave, Winter Park, FL 32792

Storage | Swimming pool | Balcony

3 beds

2 baths

$2,600

$2,190

Price drop

House for rent

Description

Please note that the advertised price may exclude additional fees. These include a mandatory $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; fees for amenities like smart home or internet service; and optional conditional fees for services like self-guided tours with third-party provider Rently ($1.99 to $11.99), pet fees/rent, or pool maintenance, if applicable. HOA application and amenity fees, where applicable, are paid directly to the HOA. Get rewarded for rental payments and more through FirstKey Homes Rewards - a re

2631 Ambergate Rd - Photo 1 of 1

4d ago

Our team has verified this company

Verified

2631 Ambergate Rd Winter Park, FL 32792

2631 Ambergate Rd, Winter Park, FL 32792

3 beds

2 baths

$2,395

$2,295

Price drop

House for rent

Available Oct 16

Description

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2439.90. That covers your base rent, $2295.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet & Media ($85), Smart Home with video doorbell ($40), and Utility Billing Service Fee ($9.95). Base rent varies based on selected lease term. Who said the perfect house doesn't exi

749 Altaloma Ave - Photo 1 of 1

19h ago

Colonialtown North house for rent in Orlando

749 Altaloma Ave, Orlando, FL 32803

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$3,400

House for rent

Available Oct 17

Description

Property Id: 2178814 Located just MINUTES from Lake Highland Preparatory School, this stylish 3-bedroom home in Colonial Town North blends thoughtful design with unbeatable location. Features a spacious primary suite on the first floor, smart-home upgrades, and a low-maintenance fenced yard. There are TWO laundry areas (upstairs laundry room and laundry in the garage), first floor master with walk in closet and bathroom, two oversized bedrooms on the second floor, stainless steel appliances, and prime location. Less than 10 minute WALK to the nearest Starbucks, Publix,

1215 Lake Highland Dr - Photo 1 of 1

1d ago

Colonialtown North house for rent in Orlando

Outdoor space | On-site management | Package service

2 beds

1 bath

$1,899

House for rent

Available Oct 16

Description

Discover this spacious 2-bedroom, 2-bathroom home with a versatile flex room, located in the vibrant city of Orlando. The property features easy-to-maintain tile flooring throughout, making cleaning a breeze. The galley-style kitchen is equipped with a refrigerator, range, and dishwasher, complemented by a cozy breakfast nook perfect for morning meals. Enjoy relaxing on the inviting front porch or entertaining in the private, fenced backyard. This charming home offers comfort, functionality, and outdoor space for your lifestyle. VIRTUAL TOUR: To apply for this property

1701 Palmer Ave - Photo 1 of 1

1d ago

House for rent in Winter Park

1701 Palmer Ave, Winter Park, FL 32789

In-unit laundry | Outdoor space | Garage parking

4 beds

3 baths

$5,400

House for rent

Description

Property Status: Active Winter Park– Prime 32789 Location! Live in style in this spacious 4-bedroom, 3-bath home with a private pool, just steps from Phelps Park and minutes from Park Avenue dining, shopping, and Rollins College. Enjoy bright open living spaces, a large kitchen with wood cabinetry and wine fridge, and French doors leading to a courtyard and pool area — perfect for entertaining or relaxing. The primary suite features pool access, a modern ensuite bath, and a walk-in closet. Additional highlights include a detached 2-car garage, carport, fresh inter

1681 Woodland Ave #NA - Photo 1 of 1

1d ago

House for rent in Winter Park

1681 Woodland Ave #NA, Winter Park, FL 32789

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$4,100

House for rent

Available Oct 16

Description

Located on a cobble stone road in one of the most sought after historic Winter Park neighborhoods, this home is only minutes away from the Alfond Inn, Rollins College, and the historic shopping district . The house has been professionally renovated and includes an upscale chefs kitchen, stone and wood floors throughout, an electric fireplace, seperate living areas with both a large den and living room, as well as a large custom two car garage. The outside includes professionally designed gardens, a saltwater pool surrounded by stone flooring, and a lit patio with gas fitti

1835 Edwin Blvd - Photo 1 of 1

2d ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1835 Edwin Blvd, Winter Park, FL 32789

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$3,450

House for rent

Description

Property Status: Active Welcome to this charming bungalow located near the historic district of Winter Park, FL. This home boasts three spacious bedrooms and two fully renovated bathrooms, featuring beautiful tile finishes. The kitchen is a chef's dream with stainless steel appliances, granite countertops, travertine floors and a modern design. The living room and bedrooms are adorned with beautiful wood flooring, adding a touch of warmth and elegance. The property also includes an enclosed sunroom, perfect for enjoying Florida's sunny days in comfort. The exterior of the

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1641 Chestnut Ave - Photo 1 of 1

2d ago

House for rent in Winter Park

1641 Chestnut Ave, Winter Park, FL 32789

Hardwood floor | Outdoor space

3 beds

3 baths

$3,495

House for rent

Description

AVAILABLE NOW! Please call or text 407.863.8625 to schedule a showing. Welcome to your new home nestled along Winter Park’s coveted tree-lined Chestnut Avenue. This beautiful 3 bedroom, 3 bathroom home blends classic charm with modern updates and is perfectly situated near Park Avenue, Phelps Park, the YMCA, Winter Park golf course, and Lakemont Elementary School. Upon entering, you’ll be greeted by gleaming hardwood floors flowing through an inviting, light-filled layout. The heart of the home is the window-lined kitchen, thoughtfully refreshed with newer cabinetry, appli

1235 Ayrshire St - Photo 1 of 1

2d ago

Orwin Manor house for rent in Orlando

1235 Ayrshire St, Orlando, FL 32803

In-unit laundry | Outdoor space | Garage parking

4 beds

2 baths

$3,750

House for rent

Available Oct 7

Description

This inviting single-story, 4-bedroom, 2-bath home is nestled in a peaceful suburban neighborhood that includes areas like Audubon Park and portions of downtown Orlando, which offer a unique blend of historic charm and modern living. The exterior showcases a fresh, light-colored façade complemented by a welcoming front yard, featuring lush greenery, vibrant flowers, and a well maintained lawn. A majestic oak tree draped in Spanish moss creates a picturesque frame, adding a touch of classic Southern elegance. Inside, warm wood floors flow throughout the home, enhancing its

1166 Palmer Ave - Photo 1 of 1

4d ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1166 Palmer Ave, Winter Park, FL 32789

In-unit laundry | Outdoor space | Storage

3 beds

3 baths

$4,695

House for rent

Description

Property Status: Active 1166 Palmer Ave Winter Park, Fl 32789 - Available December 1st - March 31st! Welcome home to this absolutely stunning property boasting an exceptionally open floor plan with loads of character! Located in the heart of Winter Park minutes from Downtown you will not find this opportunity arise often. This must see spacious home features 3 bedrooms, 3 full bathrooms, and 2 half bathrooms. Gorgeous lot with an oversized yard and driveway access to both Palmer Ave and Via Bella. The backyard features a fantastic Chicago brick back porch area with loads o

755 Golden Sunshine Cir - Photo 1 of 1

4d ago

House for rent in Azalea Park

Villa - ORLANDO, FL

755 Golden Sunshine Cir, Azalea Park, FL 32807

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$1,875

House for rent

Description

Property Status: Active Charming and spacious 3 bedrooms and 2 bath's end unit villa! You will be blown away by the space this unit has! This split plan home has a living room, dining room, and bonus area! The ample kitchen has a pass-thru bar opening to the dining room and plenty of cabinets and counter space. Retreat to your private master bedroom with great closet storage and floor to wall tiled bath! with one car garage boasting over 1300 square feet! You will not be disappointed! Fenced yard with lawn care included! Conveniently located walking distance to Colonial

1310 Fairview Ave - Photo 1 of 1

4d ago

House for rent in Winter Park

1310 Fairview Ave, Winter Park, FL 32789

In-unit laundry | Outdoor space | Dishwasher

4 beds

2 baths

$2,995

House for rent

Description

Welcome home to this GORGEOUS 4 bedroom and 2.5 bath home FULLY RENOVATED in Winter Park! Bright and open kitchen overlooking a large living area, this unit is perfect for entertaining! Additional Office Space. The bedrooms have ample closet space, and the split floor plan provides great privacy and comfort. Also featured is a large backyard and porch. Laundry Room Outside with Washer and Dryer, Centrally located near restaurants, local shopping and more, Close to Assigned Schools Edgewater High School, Killarney Elementary School, Robert E Lee Middle School and Cornersto

5537 Decatur St - Photo 1 of 1

5d+ ago

Townhouse for rent in Orlando

5537 Decatur St, Orlando, FL 32807

In-unit laundry | Outdoor space | Storage

2 beds

1 bath

$1,725

House for rent

Available Oct 10

Description

Free application fee for Active and Retired Military. Situated just minutes from Full Sail University, UCF, Winter Pines Golf Club and some of Orlando's best dining and entertainment, this gorgeous townhome offers both comfort and convenience. The kitchen boasts sleek quartz countertops and white cabinetry, while the private enclosed backyard provides the perfect space to unwind or entertain. With it's prime location near Lake Baldwin, easy access to Baldwin Park and zoning for the desirable Winter Park School System, this home is an exceptional find. Schedule your tour to

920 N Hampton Ave - Photo 1 of 1

5d+ ago

Colonialtown North house for rent in Orlando

Single Family Residence - ORLANDO, FL

920 N Hampton Ave, Orlando, FL 32803

In-unit laundry | Outdoor space | Carpet

3 beds

2 baths

$2,200

House for rent

Description

Property Status: Pending Super cute two-story Victorian-style house. Features wood floors on the ground floor and new carpet upstairs, eat-in kitchen with all appliances including microwave and dishwasher, washer/dryer, front porch with a swing. Third bedroom is on main floor and is great as home office or guest room. Lawn care included, fenced in back yard. Off street parking in private driveway, room for 2 cars tandem parking. Owner may consider small pet, no dangerous breeds. Close to everything downtown! Walk to all the fabulous restaurants, bars, and shops in the Mill

Showing 1 - 25 of 25 results
Home > House Rentals in Winter Park > Windsong Houses For Rent
Updated: October 18, 2025

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💰Best rent deal502 Dunraven Dr
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