Homes with Garages for Sale in Winter Park, FL

181 homes

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NEW 8 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Home with Garage for sale in Winter Park, FL:
Welcome to this beautifully updated Winter Park home offering modern finishes, strong mechanical upgrades, and a spacious open layout. Major improvements include a brand-new roof installed in October 2025, new windows and sliding door (2024), and a new A/C system (2020), providing long-term comfort and efficiency. Inside you’ll find new porcelain tile flooring installed in 2022, neutral interior tones, and abundant natural light flowing through the main living areas. The kitchen was fully renovated in 2022 and features upgraded cabinetry, corian countertops, pantry storage, and stainless steel appliances. All bedrooms include walk-in closets, and the primary suite showcases an updated

$429,000

3 beds2 baths1,578 sq ft

3236 Knottypine Ave, Winter Park, FL 32792

0.27 acre lot • 2 garage spots • Built 1981

NEW 14 HRS AGO

ABOUT THIS HOME
Home with Garage for sale in Winter Park, FL:
Under Construction. Designed with intention and built with precision, this brand-new LUIH Luxury home exemplifies the elegance and livability Winter Park is known for. Every inch of this residence has been curated for those who demand extraordinary design, flawless craftsmanship, and a lifestyle that feels both elevated and effortless. Step through the front door and into a grand two-story foyer where natural light cascades from above, illuminating the level of detail that unfolds in every direction. The main living space is an elegant composition of scale, comfort, and style. A dramatic fireplace anchors the room, while expansive glass sliders dissolve the boundary between indoors and outd

$2,679,000

5 beds4.5 baths3,520 sq ft

426 Worthington Dr, Winter Park, FL 32789

Custom cabinetry • Dedicated office • Two story foyer

HOT HOME

ABOUT THIS HOME
Home with Garage for sale in Winter Park, FL:
Location Location Location!! This 3 bedroom 2 bath home is situated on a cul-de-sac and is waiting for its new owner. This home features a kitchen with solid surface countertops that is open to the family room. Primary bedroom has an en-suite bath and walk in closest. The back of the home features a screened patio and spacious fenced backyard. New electrical panel in 2024, HVAC system 2020. Separate workshop in the backyard with electric. This home is waiting for the new owner to make it their own!!

$340,000

3 beds2 baths1,534 sq ft

5117 Cypress Ct, Winter Park, FL 32792

Screened patio • Cul-de-sac • Separate workshop

NEW 9 HRS AGOVIDEO TOUR

ABOUT THIS HOME
Home with Garage for sale in Winter Park, FL:
Welcome to the best of Winter Park living, where luxury meets lifestyle and every day feels like a getaway. This stunning custom home, built by Lundev, sits on a quiet, tree-lined street just a mile from Park Avenue and only steps from beautiful Lake Osceola. Imagine walking to brunch on Park Ave, then coming home to launch your paddleboard from the end of your street. From the moment you pull up, the home makes an impression from its striking architecture to the curved driveway that feels both elegant and inviting. Inside, it’s designed for the way people actually live and entertain today. The chef’s kitchen is the heart of the home, featuring a massive marble island, sleek cus

$3,250,000

5 beds5.5 baths4,296 sq ft

473 Fletcher Pl, Winter Park, FL 32789

Tree lined street • Custom home • Paddleboard access

ABOUT THIS HOME
Home with Garage for sale in Winter Park, FL:
Welcome to this beautifully renovated 3-bedroom, 2-bath home located in Seminole County — a rare find in Winter Park with NO HOA OR CDD! This delightful residence offers a perfect blend of modern updates and practical features throughout. Enjoy bright, inviting living spaces, a functional layout, and a master suite featuring its own private exterior door, offering added convenience for guests, multigenerational living, or potential rental use. This home has been thoughtfully renovated from top to bottom, featuring modern appliances, fresh interior and exterior paint, and a new septic system (2025) — giving you peace of mind for years to come. Additional Upgrades Completed in 202

$404,990

3 beds2 baths1,356 sq ft

5357 Orange Ave, Winter Park, FL 32792

Master suite • Brand-new ac system • Modern appliances

Property at 1494 Westchester Ave, Winter Park, FL 32789, 5 beds, 4.5 baths

$2,990,000

5 beds4.5 baths3,711 sq ft

1494 Westchester Ave, Winter Park, FL 32789

Property at 1613 Oriole Ave, Orlando, FL 32803, 4 beds, 2 baths

$675,000

4 beds2 baths1,752 sq ft

1613 Oriole Ave, Orlando, FL 32803

Property at 2632 Mandan Trl, Winter Park, FL 32789, 4 beds, 2.5 baths

$799,900

4 beds2.5 baths2,441 sq ft

2632 Mandan Trl, Winter Park, FL 32789

Property at 2218 King Richards Ct, Winter Park, FL 32792, 3 beds, 2 baths

$460,000

3 beds2 baths1,562 sq ft

2218 King Richards Ct, Winter Park, FL 32792

Property at 1408 Chapman Cir, Winter Park, FL 32789, 4 beds, 4 baths

$1,525,000

4 beds4 baths3,237 sq ft

1408 Chapman Cir, Winter Park, FL 32789

Property at 5047 Ferncrest Dr, Winter Park, FL 32792, 4 beds, 2 baths

$349,000

4 beds2 baths1,242 sq ft

5047 Ferncrest Dr, Winter Park, FL 32792

Property at 2015 Summerfield Rd, Winter Park, FL 32792, 4 beds, 4 baths

$1,375,000

4 beds4 baths3,024 sq ft

2015 Summerfield Rd, Winter Park, FL 32792

Property at 1624 Barcelona Way, Winter Park, FL 32789, 3 beds, 3 baths

$2,380,000

3 beds3 baths3,828 sq ft

1624 Barcelona Way, Winter Park, FL 32789

Property at 1134 Washington Ave #13, Winter Park, FL 32789, 3 beds, 3.5 baths

$675,000

3 beds3.5 baths2,083 sq ft

1134 Washington Ave #13, Winter Park, FL 32789

Property at 1205 Mayfield Ave, Winter Park, FL 32789, 5 beds, 4 baths

$2,490,000

5 beds4 baths3,948 sq ft

1205 Mayfield Ave, Winter Park, FL 32789

Property at 1421 Sunnyside Dr, Maitland, FL 32751, 4 beds, 2.5 baths

$1,300,000

4 beds2.5 baths2,116 sq ft

1421 Sunnyside Dr, Maitland, FL 32751

Property at 1630 Chestnut Ave, Winter Park, FL 32789, 3 beds, 4.5 baths

$1,750,000

3 beds4.5 baths3,164 sq ft

1630 Chestnut Ave, Winter Park, FL 32789

Property at 5563 Garden Grove Cir, Winter Park, FL 32792, 3 beds, 2 baths

$409,999

3 beds2 baths1,436 sq ft

5563 Garden Grove Cir, Winter Park, FL 32792

Property at 1401 Green Cove Rd, Winter Park, FL 32789, 3 beds, 5.5 baths

$2,900,000

3 beds5.5 baths5,483 sq ft

1401 Green Cove Rd, Winter Park, FL 32789

Property at 1092 Wading Waters Cir, Winter Park, FL 32792, 4 beds, 3 baths

$1,195,000

4 beds3 baths3,057 sq ft

1092 Wading Waters Cir, Winter Park, FL 32792

Property at 2299 Via Tuscany, Winter Park, FL 32789, 4 beds, 3.5 baths

$2,345,000

4 beds3.5 baths3,986 sq ft

2299 Via Tuscany, Winter Park, FL 32789

Property at 1251 Arlington Pl, Winter Park, FL 32789, 3 beds, 3.5 baths

$845,000

3 beds3.5 baths2,116 sq ft

1251 Arlington Pl, Winter Park, FL 32789

Property at 2189 Sussex Rd, Winter Park, FL 32792, 4 beds, 2.5 baths

$535,000

4 beds2.5 baths1,776 sq ft

2189 Sussex Rd, Winter Park, FL 32792

Property at 1885 Temple Dr, Winter Park, FL 32789, 5 beds, 3.5 baths

$2,295,000

5 beds3.5 baths3,691 sq ft

1885 Temple Dr, Winter Park, FL 32789

Property at 2920 Abbey Ct, Winter Park, FL 32792, 5 beds, 3 baths

$650,000

5 beds3 baths2,312 sq ft

2920 Abbey Ct, Winter Park, FL 32792

Property at 7728 Glenmoor Ln, Winter Park, FL 32792, 3 beds, 2 baths

$389,900

3 beds2 baths1,676 sq ft

7728 Glenmoor Ln, Winter Park, FL 32792

Property at 210 Laurel Park Ct, Winter Park, FL 32792, 4 beds, 3 baths

$950,000

4 beds3 baths2,838 sq ft

210 Laurel Park Ct, Winter Park, FL 32792

Property at 1751 Glencoe Rd, Winter Park, FL 32789, 5 beds, 6 baths

$3,895,000

5 beds6 baths4,520 sq ft

1751 Glencoe Rd, Winter Park, FL 32789

Property at 2206 Bonanza Ave, Winter Park, FL 32792, 4 beds, 2 baths

$455,000

4 beds2 baths1,776 sq ft

2206 Bonanza Ave, Winter Park, FL 32792

Property at 1411 Nottingham St, Orlando, FL 32803, 5 beds, 4 baths

$2,885,000

5 beds4 baths4,118 sq ft

1411 Nottingham St, Orlando, FL 32803

Property at 5110 N Woodcrest Dr, Winter Park, FL 32792, 3 beds, 2 baths

$365,500

3 beds2 baths1,220 sq ft

5110 N Woodcrest Dr, Winter Park, FL 32792

Property at 240 E Lake Sue Ave, Winter Park, FL 32789, 2 beds, 2 baths

$1,107,750

2 beds2 baths1,329 sq ft

240 E Lake Sue Ave, Winter Park, FL 32789

Property at 870 Carver St, Winter Park, FL 32789, 3 beds, 3 baths

$975,000

3 beds3 baths1,875 sq ft

870 Carver St, Winter Park, FL 32789

Property at 660 Osceola Ave #101, Winter Park, FL 32789, 3 beds, 3.5 baths

$2,295,000

3 beds3.5 baths2,714 sq ft

660 Osceola Ave #101, Winter Park, FL 32789

Property at 311 E Morse Blvd Unit 6-3, Winter Park, FL 32789, 1 bed, 1 bath

$329,000

1 bed1 bath570 sq ft

311 E Morse Blvd Unit 6-3, Winter Park, FL 32789

Property at 1245 Wading Waters Cir, Winter Park, FL 32792, 4 beds, 3 baths

$1,065,000

4 beds3 baths3,050 sq ft

1245 Wading Waters Cir, Winter Park, FL 32792

Property at 1807 Yorkshire Dr, Winter Park, FL 32792, 4 beds, 4.5 baths

$1,450,000

4 beds4.5 baths3,565 sq ft

1807 Yorkshire Dr, Winter Park, FL 32792

Property at 1605 Puritan Ave, Winter Park, FL 32792, 3 beds, 2 baths

$340,000

3 beds2 baths1,285 sq ft

1605 Puritan Ave, Winter Park, FL 32792

Property at 2412 Chantilly Ave, Winter Park, FL 32789, 5 beds, 6.5 baths

$2,350,000

5 beds6.5 baths4,506 sq ft

2412 Chantilly Ave, Winter Park, FL 32789

Property at 2722 Eastern Pkwy, Winter Park, FL 32789, 5 beds, 4.5 baths

$2,289,000

5 beds4.5 baths3,334 sq ft

2722 Eastern Pkwy, Winter Park, FL 32789

Property at 5343 Brady Ln, Orlando, FL 32814, 3 beds, 2.5 baths

$775,000

3 beds2.5 baths1,838 sq ft

5343 Brady Ln, Orlando, FL 32814

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Based on information submitted to the MLS GRID as of Tue Dec 02 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Garages for Sale in Winter Park

There are currently 181 homes with garages for sale in Winter Park at a median listing price of $835K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winter Park stay on the market for 94 days and receive 5 offers. Popular neighborhoods include Audubon Park, College Park, Winter Park Pines, Baldwin Park, and Downtown Maitland. This map is refreshed with the newest listings in Winter Park every 15 minutes.

In the past month, 51 homes have been sold in Winter Park. In addition to houses in Winter Park, there were also 66 condos, 16 townhouses, and 2 multi-family units for sale in Winter Park last month. Winter Park is a minimally walkable city in Orange County with a Walk Score of 44. Winter Park is home to approximately 27,958 people and 25,253 jobs. Find your dream home in Winter Park using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Park are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Park. Our Winter Park real estate stats and trends will give you more information about home buying and selling trends in Winter Park. If you're looking to sell your home in the Winter Park area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Park with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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