MLS Listings for Sale in Winter Park, FL

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LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
2024 ROOF! NO HOA!! This 3 bedroom, 2 bathroom property offers a split plan bedroom arrangement with walk-in closets in every room. There are ceiling fans in every bedroom & common area, and the floors throughout have tile or luxury vinyl plank (LVP) - no carpets! The primary suite and dining room both exit out onto a covered, screen-enclosed back porch with custom-built elevated hot tub deck. This sanctuary of relaxation is kept private inside a fenced backyard with mature trees, custom landscaping, and 2 sheds with electricity & lighting. The 2-car garage offers a wifi-enabled garage door opener to grant remote access for guests, deliveries, etc. Additionally, this home has a

$375,000

3 beds2 baths1,200 sq ft

3083 Crane Strand Dr, Winter Park, FL 32792

2024 roof • Walk-in closets • Fenced backyard

NEW 18 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome to 2189 Sussex Rd, a beautifully updated home in the Winter Woods community. From the moment you walk in, the home feels bright, open, and inviting. The living areas have a warm flow, the finishes feel modern, and the fresh paint gives the entire home a clean and comfortable atmosphere. The kitchen is functional and well designed for everyday living. The primary suite is one of the best features of the home, offering its own private balcony that overlooks the pool and spacious backyard. It is a quiet place to relax at the end of the day. The additional bedrooms have generous space and flex

$569,990

4 beds2.5 baths1,776 sq ft

2189 Sussex Rd, Winter Park, FL 32792

Private balcony • 8,400 sq ft lot • 2 garage spots

NEW 19 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
Newly updated 2 Bedrooms and 1 Bathroom conveniently located in Winter Park/Orlando next to all of shops and restaurants. With private lake access to launch and dock your watercraft within the community for boating and fishing. Walk to Trader Joes next door and Winter Park Village to enjoy great number of restaurants, movie theater, retail shops and grocery stores.

$235,000

2 beds1 bath768 sq ft

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

Corner unit • Private lake access • $483 HOA

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
Priced to sell! Welcome to this 4-bedroom, 3-bathroom home offering 1,829 sq. ft. of inviting living space in one of Winter Park’s most desirable neighborhoods. Inside, you’ll find a spacious family room with plenty of natural light from large windows, a cozy fireplace, and elegant French doors leading to the porch. The split floor plan of this home provides privacy and comfort for the primary suite that features its own set of French doors that open to the screened porch, along with an updated en-suite bathroom. Additional highlights include ceiling fans in all bedrooms, stylish window shutters throughout, and an updated guest bathroom. Outside, enjoy relaxing on the screened p

$449,900

4 beds3 baths1,829 sq ft

639 Friar Rd, Winter Park, FL 32792

Elegant french doors • Split floor plan • Ceiling fans

OPEN TODAY, 2PM TO 4PM

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
Charming Winter Park block home featuring 3 bedrooms, 2 bathrooms, and a versatile enclosed Florida room—perfect for a home office, playroom, or additional living space. Recently updated with a brand-new roof (June 2025), fresh paint, and remodeled interior, this home is move-in ready. Ideally located on the border of Winter Park and Orlando, just minutes from Park Avenue, boutiques, dining, and all the charm Winter Park is known for.

$347,500

3 beds2 baths1,285 sq ft

1605 Puritan Ave, Winter Park, FL 32792

Remodeled interior • Fresh paint • Brand-new roof

Property at 7470 Canford Ct #23, Winter Park, FL 32792, 3 beds, 2.5 baths

$249,900

3 beds2.5 baths1,580 sq ft

7470 Canford Ct #23, Winter Park, FL 32792

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 1445 Via Sangro Pl, Winter Park, FL 32792, 7 beds, 5.5 baths

$1,399,990

7 beds5.5 baths5,021 sq ft

1445 Via Sangro Pl, Winter Park, FL 32792

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

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 2074 Laurelwood Way, Winter Park, FL 32792, 4 beds, 3 baths

$785,000

4 beds3 baths2,192 sq ft

2074 Laurelwood Way, Winter Park, FL 32792

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 2941 Antique Oaks Cir #79, Winter Park, FL 32792, 2 beds, 2 baths

$185,000

2 beds2 baths1,018 sq ft

2941 Antique Oaks Cir #79, Winter Park, FL 32792

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

$369,000

3 beds2 baths1,220 sq ft

5110 N Woodcrest Dr, 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 1229 Park Green Pl, Winter Park, FL 32789, 2 beds, 2 baths

$395,000

2 beds2 baths1,495 sq ft

1229 Park Green Pl, 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 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 422 S Ranger Blvd, Winter Park, FL 32792, 4 beds, 2 baths

$535,000

4 beds2 baths1,680 sq ft

422 S Ranger Blvd, Winter Park, FL 32792

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

$409,900

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 3917 Lake Mira Dr, Orlando, FL 32817, 4 beds, 2 baths

$629,900

4 beds2 baths2,869 sq ft

3917 Lake Mira Dr, Orlando, FL 32817

Property at 1872 Biscayne Dr, Winter Park, FL 32789, 2 beds, 1 bath

$415,000

2 beds1 bath969 sq ft

1872 Biscayne Dr, Winter Park, FL 32789

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

$449,000

3 beds2.5 baths1,907 sq ft

1900 Erudite Way, 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 1450 Glencoe Rd, Winter Park, FL 32789, 4 beds, 3 baths

$1,625,000

4 beds3 baths2,785 sq ft

1450 Glencoe Rd, 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 1324 Indiana Ave, Winter Park, FL 32789, 4 beds, 2.5 baths

$745,000

4 beds2.5 baths1,692 sq ft

1324 Indiana Ave, Winter Park, FL 32789

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

$1,549,000

4 beds4 baths3,237 sq ft

1408 Chapman Cir, Winter Park, FL 32789

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 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 2612 Roxbury Rd, Winter Park, FL 32789, 5 beds, 3 baths

$825,000

5 beds3 baths2,472 sq ft

2612 Roxbury Rd, Winter Park, FL 32789

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

$3,200,000

5 beds4 baths4,118 sq ft

1411 Nottingham St, Orlando, FL 32803

Property at 2148 Blossom Ln, Winter Park, FL 32789, 3 beds, 2 baths

$449,900

3 beds2 baths1,685 sq ft

2148 Blossom Ln, Winter Park, FL 32789

Property at 4019 Quenita Dr, Winter Park, FL 32792, 4 beds, 2.5 baths

$689,000

4 beds2.5 baths2,824 sq ft

4019 Quenita Dr, Winter Park, FL 32792

Property at 2412 Middleton Ave, Winter Park, FL 32792, 3 beds, 2 baths

$599,000

3 beds2 baths1,340 sq ft

2412 Middleton Ave, Winter Park, FL 32792

Property at 2510 Boyd Ave, Orlando, FL 32803, 2 beds, 2 baths

$475,000

2 beds2 baths1,508 sq ft

2510 Boyd Ave, Orlando, FL 32803

Property at 1451 Cavendish Rd, Winter Park, FL 32789, 3 beds, 2 baths

$619,500

3 beds2 baths1,437 sq ft

1451 Cavendish Rd, Winter Park, FL 32789

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

$364,900

3 beds3.5 baths1,872 sq ft

7580 Aloma Pines Ct, Winter Park, FL 32792

Property at 8162 Lazy Bear Ln, Winter Park, FL 32792, 4 beds, 2 baths

$525,000

4 beds2 baths1,843 sq ft

8162 Lazy Bear Ln, Winter Park, FL 32792

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Based on information submitted to the MLS GRID as of Sun Nov 16 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.

MLS Listings for Sale in Winter Park

There are currently 295 mls listings for sale in Winter Park at a median listing price of $864K. 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, 50 homes have been sold in Winter Park. In addition to houses in Winter Park, there were also 66 condos, 15 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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