Homes with Pools for Sale in Winter Park, FL

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ABOUT THIS HOME
Home with a Pool for sale in Winter Park, FL:
Rare opportunity for a "Jewel of Park Lake" spacious 3 bedroom, 2 bath villa with beautiful wooded view in the desirable Park Lake community of Maitland. MOVE-IN READY!!! Assigned/dedicated Parking. Close to major transportation routes, employment centers, Park Avenue/Winter Park, Altamonte Springs and downtown Orlando. HVAC replaced in 2021. NEW Appliances flooring and paint in 2025. Exterior painted and replaced roof in 2024 and newly paved in 2025. Primary Suite with en suite bathroom. Private Courtyard accessible from Primary Suite and bedroom #2. Room features too numerous to mention but include window treatments, kitchen to dining pass-through, ceiling fans, stainless a

$249,000

3 beds2 baths1,256 sq ft

1503 Grove St #559, Maitland, FL 32751

Stainless appliances • Walk-in closets • Rain shower

ABOUT THIS HOME
Home with a Pool for sale in Winter Park, FL:
PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone fireplace and built in shelving for an elegant look in the Family Room. The kitchen has stainless steel appliances, wood cabinets with under cabinet lighting, and bar top seating. Primary Bedroom has a walk-in closet and a glass door shower with tile walls and built-in niches. The Primary bathroom has priv

$530,000

3 beds2 baths1,592 sq ft

346 S Ranger Blvd, Winter Park, FL 32792

No cdd • High rated schools • Prime location

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Winter Park, FL:
Welcome to this newer single-family home tucked away in the Karolina On Killarney section of Winter Park. Situated on a generously sized . 16 acre lot with no HOA, this property offers both privacy and optimal convenience. Enjoy hopping over to Park Avenue for shopping and restaurants or to the weekly Farmer's Market. Bustling College Park is a 5-minute jaunt down the road and I-4 is 2-minutes from the house. Walk to beautiful spring-fed Lake Killarney. Inside, the home features a thoughtfully designed floor plan with spacious living areas and thoughtful upgrades. The stunning kitchen is a true highlight, boasting modern finishes, quality cabinetry, quartz countertops and a breakfast bar wi

$560,000

4 beds2 baths2,036 sq ft

1875 Staunton Ave, Winter Park, FL 32789

Quartz countertops • Generously sized lot • Modern finishes

ABOUT THIS HOME
Home with a Pool for sale in Winter Park, FL:
Tucked away on the tree-lined streets of the Lost Creek community, this contemporary two-story residence offers a rare blend of serenity and sophistication. Ideally located in sought-after Winter Park, this exceptional property offers exclusive creek-to-lake access leading to the sparkling waters of Lake Howell—just minutes away from vibrant city life and top-tier amenities. From the moment you arrive, the home makes a striking first impression with its stately architecture and bold navy double doors, creating a grand sense of arrival. Inside, a warm, welcoming foyer introduces an elegant layout, with a private office to one side and a formal dining room on the other—both adorne

$625,827

4 beds3 baths2,672 sq ft

3102 Heartleaf Pl, Winter Park, FL 32792

15 foot boat permit • Gourmet kitchen • 1.4 acre lot

ABOUT THIS HOME
Home with a Pool for sale in Winter Park, FL:
Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the community’s heated pool, putting green, manicured gardens and Lake Osceola. Unlike many residences in the community, this property retains its original open balcony design, offering outdoor living rarely found in this floor plan. Inside, every surface has been thoughtfully remodeled. The

$879,000

2 beds2 baths1,143 sq ft

100 S Interlachen Ave #503, Winter Park, FL 32789

Solid wood cabinetry • Manicured gardens • Putting green

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 825 Palmer Ave, Winter Park, FL 32789, 3 beds, 3 baths

$1,799,000

3 beds3 baths3,297 sq ft

825 Palmer Ave, Winter Park, FL 32789

Property at 2215 Marsh Sedge Ln, Winter Park, FL 32792, 5 beds, 2.5 baths

$799,000

5 beds2.5 baths2,646 sq ft

2215 Marsh Sedge Ln, Winter Park, FL 32792

Property at 1275 Michigan Ave, Winter Park, FL 32789, 3 beds, 2.5 baths

$679,000

3 beds2.5 baths1,866 sq ft

1275 Michigan Ave, Winter Park, FL 32789

Property at 1914 Bonanza Ct, Winter Park, FL 32792, 3 beds, 2 baths

$437,500

3 beds2 baths1,727 sq ft

1914 Bonanza Ct, Winter Park, FL 32792

Property at 2330 Coldstream Dr, Winter Park, FL 32792, 4 beds, 2 baths

$649,900

4 beds2 baths1,750 sq ft

2330 Coldstream Dr, Winter Park, FL 32792

Property at 1525 Granville Dr, Winter Park, FL 32789, 5 beds, 5.5 baths

$4,750,000

5 beds5.5 baths5,211 sq ft

1525 Granville Dr, Winter Park, FL 32789

Property at 2948 Antique Oaks Cir #94, Winter Park, FL 32792, 1 bed, 1 bath

$150,000

1 bed1 bath749 sq ft

2948 Antique Oaks Cir #94, Winter Park, FL 32792

Property at 1842 Puritan Ave, Winter Park, FL 32792, 4 beds, 2 baths

$439,000

4 beds2 baths1,836 sq ft

1842 Puritan Ave, Winter Park, FL 32792

Property at 1695 Lee Rd Unit D113, Winter Park, FL 32789, 2 beds, 1 bath

$158,000

2 beds1 bath881 sq ft

1695 Lee Rd Unit D113, Winter Park, FL 32789

Property at 1166 Oaks Blvd, Winter Park, FL 32789, 4 beds, 3.5 baths

$1,649,999

4 beds3.5 baths2,860 sq ft

1166 Oaks Blvd, Winter Park, FL 32789

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

$455,000

5 beds3 baths1,945 sq ft

3642 Periwinkle Dr, Winter Park, FL 32792

Property at 1174 Wildmeadow Run, Winter Park, FL 32792, 3 beds, 2.5 baths

$689,000

3 beds2.5 baths1,770 sq ft

1174 Wildmeadow Run, Winter Park, FL 32792

Property at 702 Via Bella, Winter Park, FL 32789, 4 beds, 5.5 baths

$4,250,000

4 beds5.5 baths3,720 sq ft

702 Via Bella, Winter Park, FL 32789

Property at 1362 Tierra Cir, Winter Park, FL 32792, 4 beds, 3 baths

$399,000

4 beds3 baths2,179 sq ft

1362 Tierra Cir, Winter Park, FL 32792

Property at 616 Ellendale Dr, Winter Park, FL 32792, 3 beds, 2 baths

$409,900

3 beds2 baths1,405 sq ft

616 Ellendale Dr, Winter Park, FL 32792

Property at 2500 Lee Rd #232, Winter Park, FL 32789, 1 bed, 1 bath

$189,000

1 bed1 bath645 sq ft

2500 Lee Rd #232, Winter Park, FL 32789

Property at 720 W Webster Ave, Winter Park, FL 32789, 3 beds, 2 baths

$575,000

3 beds2 baths1,356 sq ft

720 W Webster Ave, Winter Park, FL 32789

Property at 311 E Morse Blvd Unit 7-11, Winter Park, FL 32789, 1 bed, 1 bath

$329,900

1 bed1 bath570 sq ft

311 E Morse Blvd Unit 7-11, Winter Park, FL 32789

Property at 2458 Grand Teton Cir #2458, Winter Park, FL 32792, 2 beds, 2 baths

$310,000

2 beds2 baths1,457 sq ft

2458 Grand Teton Cir #2458, Winter Park, FL 32792

Property at 100 S Interlachen Ave #404, Winter Park, FL 32789, 2 beds, 2 baths

$1,195,000

2 beds2 baths1,220 sq ft

100 S Interlachen Ave #404, Winter Park, FL 32789

Property at 3019 Antique Oaks Cir #124, Winter Park, FL 32792, 1 bed, 1 bath

$161,500

1 bed1 bath749 sq ft

3019 Antique Oaks Cir #124, Winter Park, FL 32792

Property at 1981 Blue Ridge Rd, Winter Park, FL 32789, 4 beds, 2 baths

$1,199,900

4 beds2 baths2,750 sq ft

1981 Blue Ridge Rd, Winter Park, FL 32789

Property at 1161 Valencia Ave, Winter Park, FL 32789, 4 beds, 4.5 baths

$4,545,000

4 beds4.5 baths4,181 sq ft

1161 Valencia Ave, Winter Park, FL 32789

Property at 805 Nottingham St, Orlando, FL 32803, 3 beds, 2 baths

$750,000

3 beds2 baths2,296 sq ft

805 Nottingham St, Orlando, FL 32803

Property at 675 Overspin Dr, Winter Park, FL 32789, 4 beds, 3.5 baths

$815,000

4 beds3.5 baths3,062 sq ft

675 Overspin Dr, Winter Park, FL 32789

Property at 915 Garden Dr, Winter Park, FL 32789, 3 beds, 3 baths

$900,000

3 beds3 baths2,456 sq ft

915 Garden Dr, Winter Park, FL 32789

Property at Lot #21 Karolina Ave, Winter Park, FL 32789, 4 beds, 3.5 baths

$916,050

4 beds3.5 baths2,662 sq ft

Lot #21 Karolina Ave, Winter Park, FL 32789

Property at 2514 Tuscarora Trl, Maitland, FL 32751, 4 beds, 2.5 baths

$849,000

4 beds2.5 baths3,000 sq ft

2514 Tuscarora Trl, Maitland, FL 32751

Property at 1447 Broad Wing Ln, Winter Park, FL 32792, 3 beds, 2.5 baths

$450,000

3 beds2.5 baths2,308 sq ft

1447 Broad Wing Ln, Winter Park, FL 32792

Property at 2774 Banchory Rd, Winter Park, FL 32792, 3 beds, 2 baths

$490,000

3 beds2 baths1,560 sq ft

2774 Banchory Rd, Winter Park, FL 32792

Property at 3370 Cedar Springs Pl #156, Winter Park, FL 32792, 2 beds, 2.5 baths

$198,500

2 beds2.5 baths1,031 sq ft

3370 Cedar Springs Pl #156, Winter Park, FL 32792

Property at 7444 Woodburn Ct #29, Winter Park, FL 32792, 2 beds, 2.5 baths

$195,000

2 beds2.5 baths1,031 sq ft

7444 Woodburn Ct #29, Winter Park, FL 32792

Property at 1713 W Cheryl Dr, Winter Park, FL 32792, 4 beds, 2 baths

$525,000

4 beds2 baths2,030 sq ft

1713 W Cheryl Dr, Winter Park, FL 32792

Property at 1849 Viburnum Ln, Winter Park, FL 32792, 4 beds, 2 baths

$425,000

4 beds2 baths1,627 sq ft

1849 Viburnum Ln, Winter Park, FL 32792

Property at 2222 Marsh Sedge Ln, Winter Park, FL 32792, 4 beds, 3 baths

$799,000

4 beds3 baths2,192 sq ft

2222 Marsh Sedge Ln, Winter Park, FL 32792

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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 Pools for Sale in Winter Park

There are currently 349 homes with pools 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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