Pending Listings in Winter Park, FL

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ACCEPTING BACKUP OFFERS

ABOUT THIS HOME
Pending Listing in Winter Park, FL:
Two bedrooms, two bathrooms, two car garage CBS home in Country Lane with a BRAND NEW ROOF and freshly painted inside! Pay low association fees $46.33/month ( $556/yearly). This home also features a lovely front porch, spacious screened back porch that overlooks a fenced backyard, generous and bright living-dining area connected to the ample kitchen with lots of cabinets and space for a breakfast table, floors in common areas all tiled. Spacious carpeted rooms filled with light, generous closets, main room with en suite bathroom, huge vanity, separate shower. Both bedrooms overlook the back screened porch and and yard thru sliding doors. Country Lane community has beautiful lakes, playgrou

$316,000

2 beds2 baths1,126 sq ft

1405 Auburn Green Loop, Winter Park, FL 32792

Ample kitchen • Screened back porch • Generous closets

PENDING

ABOUT THIS HOME
Pending Listing in Winter Park, FL:
Under contract-accepting backup offers. Incredible opportunity to rebuild on this 95’ x 125’ prime Winter Park corner lot in Timberlane Shores. Surrounded by multi-million dollar homes, and across the street from Lake Virginia! This property will have lake views from the second story of your future new home! A+ location that will not last long!

$995,000

3 beds2 baths1,577 sq ft

620 Virginia Dr, Winter Park, FL 32789

Timberlane shores • Lake views • 0.27 acre lot

REDFIN PENDING3D & VIDEO TOUR

ABOUT THIS HOME
Pending Listing in Winter Park, FL:
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this stunning Winter Park pool home, offering 3 bedrooms and 2 bathrooms across 1,668 square feet of thoughtfully designed living space. Upon entering, you are greeted by a spacious, open living area where the living and dining rooms flow seamlessly together, creating a perfect space for entertaining or relaxing with family. The kitchen features stainless steel appliances, abundant cabinetry, and generous counter space, complemented by a breakfast nook that opens to the family room. A sliding glass door leads from the family room to the enclosed Florida room, providing a bright, versatile spac

$439,000

3 beds2 baths1,668 sq ft

1630 Gladiolas Dr, Winter Park, FL 32792

Landscaped backyard • Pergola • In ground pool

PENDING

ABOUT THIS HOME
Pending Listing in Winter Park, FL:
Under contract-accepting backup offers. Desired Winter Park address. A 1950s bungalow on a spacious lot surrounded by multi-million-dollar homes, this is the last untouched original home left on this block. Short distance to Lake Sue, Winter Park schools and many parks in the area. The value is in the land.

$1,000,500

3 beds1.5 baths1,431 sq ft

210 E Rockwood Way, Winter Park, FL 32789

Winter park schools • Many parks • Spacious lot

PENDING

ABOUT THIS HOME
Pending Listing in Winter Park, FL:
Under contract-accepting backup offers. 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, 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 rela

$449,900

4 beds3 baths1,829 sq ft

639 Friar Rd, Winter Park, FL 32792

Elegant french doors • Split floor plan • Ceiling fans

Property at 1010 Aragon Ave, Winter Park, FL 32789, 3 beds, 2 baths

$575,000

3 beds2 baths1,453 sq ft

1010 Aragon Ave, Winter Park, FL 32789

Property at 1691 Bomi Cir, Winter Park, FL 32792, 4 beds, 2 baths

$500,000

4 beds2 baths2,002 sq ft

1691 Bomi Cir, Winter Park, FL 32792

Property at 502 Dunblane Dr, Winter Park, FL 32792, 3 beds, 2 baths

$499,000

3 beds2 baths1,125 sq ft

502 Dunblane Dr, Winter Park, FL 32792

Property at 443 S Lakemont Ave, Winter Park, FL 32792, 3 beds, 2 baths

$450,000

3 beds2 baths1,364 sq ft

443 S Lakemont Ave, Winter Park, FL 32792

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 4892 Tangerine Ave #4892, Winter Park, FL 32792, 1 bed, 1 bath

$175,000

1 bed1 bath747 sq ft

4892 Tangerine Ave #4892, Winter Park, FL 32792

Property at 1651 N Park Ave, Winter Park, FL 32789, 3 beds, 2 baths

$505,000

3 beds2 baths1,263 sq ft

1651 N Park Ave, Winter Park, FL 32789

Property at 2065 Cocos Ln, Winter Park, FL 32792, 3 beds, 2 baths

$360,000

3 beds2 baths1,448 sq ft

2065 Cocos Ln, Winter Park, FL 32792

Property at 4991 Tangerine Ave, Winter Park, FL 32792, 4 beds, 2 baths

$530,000

4 beds2 baths2,124 sq ft

4991 Tangerine Ave, Winter Park, FL 32792

Property at 2573 Madeline Ave, Winter Park, FL 32789, 3 beds, 2.5 baths

$899,000

3 beds2.5 baths2,035 sq ft

2573 Madeline Ave, Winter Park, FL 32789

Property at 224 Overlook Rd, Winter Park, FL 32789, 2 beds, 1.5 baths

$665,000

2 beds1.5 baths1,399 sq ft

224 Overlook Rd, Winter Park, FL 32789

Property at 2020 Cocos Ct, Winter Park, FL 32792, 3 beds, 2 baths

$475,000

3 beds2 baths1,715 sq ft

2020 Cocos Ct, Winter Park, FL 32792

Property at 100 S Virginia Ave #314, Winter Park, FL 32789, 3 beds, 3 baths

$1,129,000

3 beds3 baths2,615 sq ft

100 S Virginia Ave #314, Winter Park, FL 32789

Property at 1860 Summerland Ave, Winter Park, FL 32789, 5 beds, 5 baths

$5,675,000

5 beds5 baths5,022 sq ft

1860 Summerland Ave, 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 2844 Stanfield Ave, Orlando, FL 32814, 3 beds, 2.5 baths

$995,000

3 beds2.5 baths2,486 sq ft

2844 Stanfield Ave, Orlando, FL 32814

Property at 1513 Nottingham St, Orlando, FL 32803, 4 beds, 3.5 baths

$1,799,000

4 beds3.5 baths2,907 sq ft

1513 Nottingham St, Orlando, FL 32803

Property at 2381 Roxbury Rd, Winter Park, FL 32789, 3 beds, 2 baths

$499,900

3 beds2 baths1,785 sq ft

2381 Roxbury Rd, Winter Park, FL 32789

Property at 1931 Aster Dr, Winter Park, FL 32792, 3 beds, 2 baths

$479,900

3 beds2 baths2,031 sq ft

1931 Aster Dr, Winter Park, FL 32792

Property at 1460 Via Sangro Pl, Winter Park, FL 32792, 7 beds, 4 baths

$1,560,000

7 beds4 baths5,111 sq ft

1460 Via Sangro Pl, Winter Park, FL 32792

Property at 2747 Dorell Ave, Orlando, FL 32814, 4 beds, 4.5 baths

$1,400,000

4 beds4.5 baths3,264 sq ft

2747 Dorell Ave, Orlando, FL 32814

Property at 200 Saint Andrews Blvd #1707, Winter Park, FL 32792, 2 beds, 1.5 baths

$215,000

2 beds1.5 baths1,219 sq ft

200 Saint Andrews Blvd #1707, Winter Park, FL 32792

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 917 Dupont Ave, Winter Park, FL 32789, 3 beds, 2 baths

$345,000

3 beds2 baths1,552 sq ft

917 Dupont Ave, Winter Park, FL 32789

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

Property at 780 Baffie Ave, Winter Park, FL 32789, 3 beds, 2 baths

$359,900

3 beds2 baths1,283 sq ft

780 Baffie Ave, Winter Park, FL 32789

Property at 5201 Ardmore Dr, Winter Park, FL 32792, 3 beds, 2 baths

$428,900

3 beds2 baths1,640 sq ft

5201 Ardmore Dr, Winter Park, FL 32792

Property at 1083 Eastbrook Blvd, Winter Park, FL 32792, 4 beds, 2 baths

$379,990

4 beds2 baths1,530 sq ft

1083 Eastbrook Blvd, 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 3227 Crown Jewel Ct, Orlando, FL 32807, 3 beds, 2.5 baths

$279,900

3 beds2.5 baths1,430 sq ft

3227 Crown Jewel Ct, Orlando, FL 32807

Property at 2634 Ultra Vista Dr, Maitland, FL 32751, 3 beds, 2 baths

$589,900

3 beds2 baths1,998 sq ft

2634 Ultra Vista Dr, Maitland, FL 32751

Property at 1612 Magnolia Ave, Winter Park, FL 32789, 4 beds, 4 baths

$1,995,000

4 beds4 baths3,153 sq ft

1612 Magnolia Ave, Winter Park, FL 32789

Property at 131 Stefanik Rd, Winter Park, FL 32792, 4 beds, 4 baths

$485,000

4 beds4 baths2,000 sq ft

131 Stefanik Rd, Winter Park, FL 32792

Property at 1386 Clay St, Winter Park, FL 32789, 2 beds, 1 bath

$479,000

2 beds1 bath1,182 sq ft

1386 Clay St, Winter Park, FL 32789

Property at 3214 Lowndes Dr, Winter Park, FL 32792, 3 beds, 2 baths

$390,000

3 beds2 baths1,200 sq ft

3214 Lowndes Dr, Winter Park, FL 32792

Property at 1752 Chestnut Ave, Winter Park, FL 32789, 4 beds, 4.5 baths

$1,995,000

4 beds4.5 baths3,314 sq ft

1752 Chestnut Ave, Winter Park, FL 32789

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Based on information submitted to the MLS GRID as of Mon Nov 24 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.

Pending Listings in Winter Park

There are currently 106 pending listings for sale in Winter Park at a median listing price of $840K. 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 93 days and receive 5 offers. Popular neighborhoods include Audubon Park, Virginia Heights, Garden Acres, Winter Park Downtown Historic District, College Park, Winter Park Pines, Windsong, Baldwin Park, Downtown Maitland, and Orwin Manor. 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, 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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