Cheap homes for sale & real estate in Winter Park, FL

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NEW 29 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Cheap Home for sale in Winter Park, FL:
Get ready to fall in love with this stunning Winter Park home! Tucked away in a peaceful cul-de-sac, this fully renovated 3-bedroom, 2-bath beauty blends modern style with everyday comfort. Step into the family room and instantly feel the openness of the bright, airy layout. The open floor plan creates a seamless flow from the living area to the brand-new kitchen, making the entire space feel spacious and inviting. Luxury vinyl flooring runs throughout the home, while quartz countertops sit elegantly atop all-new cabinetry. The grand center island pairs perfectly with the custom-built dry bar, complete with open shelving and extra cabinet storage, an entertainer’s dream! All brand-new

$435,000

3 beds2 baths1,727 sq ft

1914 Bonanza Ct, Winter Park, FL 32792

Fully renovated • Open floor plan • Quartz countertops

3D WALKTHROUGH

ABOUT THIS HOME
Cheap Home 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

ABOUT THIS HOME
Cheap Home for sale in Winter Park, FL:
A Wonderful Opportunity Awaits!! Discover the ease of low-maintenance living in this well-maintained GROUND-FLOOR unit in the always-popular Four Seasons community. Currently leased for $1,800/month to an excellent tenant who would love to stay (month-to-month with 60-day notice), this condo offers built-in stability for investors or a smooth transition for future owner-occupants. Inside, enjoy luxury vinyl flooring throughout, an in-unit washer & dryer, an updated electrical panel, A/C replaced in 2016, and an updated primary bath. The primary bedroom features a spacious walk-in closet, adding great storage and functionality. Four Seasons residents enjoy a host of amenities, incl

$185,000

2 beds2 baths987 sq ft

200 Saint Andrews Blvd #1905, Winter Park, FL 32792

Updated primary bath • In-unit washer • Ground-floor unit

ABOUT THIS HOME
Cheap Home for sale in Winter Park, FL:
Fantastic 3-Bedroom, 2-Bathroom Condo Located in the Highly Desirable Winter Park Area! This Home Features an Open Galley Kitchen with a High Vaulted Ceiling and a Convenient Pantry. The Spacious Living/Dining Room Combination Also Boasts Vaulted Ceilings and Fills with Natural Light Through the Sliding Glass Doors, Creating an Inviting Yet Cozy Atmosphere. Beautiful Laminate Flooring Flows Throughout, and the Split Floor Plan Offers Ideal Privacy. Down One Hallway, You Will Find Two Well-Sized Bedrooms and a Shared Full Bathroom with a Shower/Tub Combo. Off The Family Room, The Master Suite Is Generously Sized and Includes Two Separate Sinks. A Large Walk-In Closet Provides Excellent Stora

$239,900

3 beds2 baths1,230 sq ft

7771 Country Pl #7, Winter Park, FL 32792

Natural light • Convenient pantry • Open galley kitchen

ABOUT THIS HOME
Cheap Home for sale in Winter Park, FL:
Welcome to Lake Killarney Living . .. Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separ

$298,000

2 beds1 bath710 sq ft

151 N Orlando Ave #115, Winter Park, FL 32789

Private pool • Community dock • Private patio space

Property at 714 Denton Rd, Winter Park, FL 32792, 3 beds, 3 baths

$449,900

3 beds3 baths1,786 sq ft

714 Denton Rd, Winter Park, FL 32792

Property at 5357 Orange Ave, Winter Park, FL 32792, 3 beds, 2 baths

$404,990

3 beds2 baths1,356 sq ft

5357 Orange Ave, Winter Park, FL 32792

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

$379,900

3 beds2 baths1,676 sq ft

7728 Glenmoor Ln, Winter Park, FL 32792

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 623 Saint Johns Ct #623, Winter Park, FL 32792, 2 beds, 2 baths

$225,000

2 beds2 baths1,120 sq ft

623 Saint Johns Ct #623, Winter Park, FL 32792

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 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 1033 Hamlet Dr, Maitland, FL 32751, 3 beds, 2 baths

$350,000

3 beds2 baths1,146 sq ft

1033 Hamlet Dr, Maitland, FL 32751

Property at 3021 Aaron Burr Ave #3, Winter Park, FL 32792, 2 beds, 2.5 baths

$145,000

2 beds2.5 baths1,090 sq ft

3021 Aaron Burr Ave #3, Winter Park, FL 32792

Property at 3651 N Goldenrod Rd Unit E102, Winter Park, FL 32792, 2 beds, 2 baths

$168,150

2 beds2 baths840 sq ft

3651 N Goldenrod Rd Unit E102, Winter Park, FL 32792

Property at 1695 Lee Rd Unit E211, Winter Park, FL 32789, 2 beds, 1 bath

$144,990

2 beds1 bath881 sq ft

1695 Lee Rd Unit E211, Winter Park, FL 32789

Property at 2905 Antique Oaks Cir #6, Winter Park, FL 32792, 1 bed, 1 bath

$162,000

1 bed1 bath749 sq ft

2905 Antique Oaks Cir #6, Winter Park, FL 32792

Property at 3028 George Mason Ave #7, Winter Park, FL 32792, 2 beds, 2 baths

$40,000

2 beds2 baths1,088 sq ft

3028 George Mason Ave #7, Winter Park, FL 32792

Property at 1229 Park Green Pl, Winter Park, FL 32789, 2 beds, 2 baths

$372,500

2 beds2 baths1,495 sq ft

1229 Park Green Pl, Winter Park, FL 32789

Property at 1601 Grove St #552, Maitland, FL 32751, 2 beds, 2 baths

$250,000

2 beds2 baths1,087 sq ft

1601 Grove St #552, Maitland, FL 32751

Property at 151 N Orlando Ave #226, Winter Park, FL 32789, 2 beds, 1 bath

$235,000

2 beds1 bath768 sq ft

151 N Orlando Ave #226, Winter Park, FL 32789

Property at Undisclosed address, Winter Park, FL 32792, 3 beds, 2 baths

$335,000

3 beds2 baths1,104 sq ft

Undisclosed address, Winter Park, FL 32792

Property at 311 Scottsdale Sq #311, Winter Park, FL 32792, 1 bed, 1 bath

$110,000

1 bed1 bath785 sq ft

311 Scottsdale Sq #311, Winter Park, FL 32792

Property at 1900 Erudite Way, Winter Park, FL 32792, 3 beds, 2.5 baths

$439,000

3 beds2.5 baths1,907 sq ft

1900 Erudite Way, Winter Park, FL 32792

Property at 2009 Cornell Ave, Winter Park, FL 32789, 2 beds, 1 bath

$269,000

2 beds1 bath762 sq ft

2009 Cornell Ave, Winter Park, FL 32789

Property at 7480 Woodburn Ct #39, Winter Park, FL 32792, 3 beds, 2.5 baths

$199,999

3 beds2.5 baths1,151 sq ft

7480 Woodburn Ct #39, Winter Park, FL 32792

Property at 1670 Clematis Ln, Winter Park, FL 32792, 3 beds, 2 baths

$399,900

3 beds2 baths1,401 sq ft

1670 Clematis Ln, Winter Park, FL 32792

Property at 2808 Bright Bird Ln, Winter Park, FL 32792, 3 beds, 2.5 baths

$436,900

3 beds2.5 baths1,916 sq ft

2808 Bright Bird Ln, Winter Park, FL 32792

Property at 609 Gallery Dr Unit B204, Winter Park, FL 32792, 2 beds, 2 baths

$298,000

2 beds2 baths893 sq ft

609 Gallery Dr Unit B204, Winter Park, FL 32792

Property at 1816 Ivy Ln, Winter Park, FL 32792, 4 beds, 2 baths

$435,000

4 beds2 baths1,725 sq ft

1816 Ivy Ln, Winter Park, FL 32792

Property at 740 Baffie Ave, Winter Park, FL 32789, 3 beds, 2 baths

$445,000

3 beds2 baths1,456 sq ft

740 Baffie Ave, Winter Park, FL 32789

Property at 615 Warrenton Rd, Winter Park, FL 32792, 2 beds, 2 baths

$320,000

2 beds2 baths1,221 sq ft

615 Warrenton Rd, Winter Park, FL 32792

Property at 1920 Carrigan Ave, Winter Park, FL 32792, 3 beds, 2 baths

$315,000

3 beds2 baths1,242 sq ft

1920 Carrigan Ave, Winter Park, FL 32792

Property at 121 Stefanik Rd, Winter Park, FL 32792, 3 beds, 2 baths

$337,500

3 beds2 baths1,392 sq ft

121 Stefanik Rd, Winter Park, FL 32792

Property at 1007 Early Ave, Winter Park, FL 32789, 3 beds, 2 baths

$425,000

3 beds2 baths1,721 sq ft

1007 Early Ave, Winter Park, FL 32789

Property at 7580 Aloma Pines Ct, Winter Park, FL 32792, 3 beds, 3.5 baths

$359,500

3 beds3.5 baths1,872 sq ft

7580 Aloma Pines Ct, Winter Park, FL 32792

Property at 1507 Grove St #557, Maitland, FL 32751, 3 beds, 2 baths

$239,900

3 beds2 baths1,256 sq ft

1507 Grove St #557, Maitland, FL 32751

Property at 1250 S Denning #122 St #00122, Winter Park, FL 32789, 1 bed, 1 bath

$179,900

1 bed1 bath653 sq ft

1250 S Denning #122 St #00122, Winter Park, FL 32789

Property at 3642 Periwinkle Dr, Winter Park, FL 32792, 5 beds, 3 baths

$445,000

5 beds3 baths1,945 sq ft

3642 Periwinkle Dr, Winter Park, FL 32792

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Based on information submitted to the MLS GRID as of Sun Dec 07 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.

Cheap Homes for Sale in Winter Park

There are currently 110 cheap homes for sale in Winter Park at a median listing price of $894K. 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 90 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, 38 homes have been sold in Winter Park. In addition to houses in Winter Park, there were also 62 condos, 14 townhouses, and 1 multi-family unit 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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