Winter Park, FL Homes

/14
$1,100,000
- Land
- 0.32 Acre
- $3,437,500 per Acre
901 Palmer Ave, Winter Park, FL 32789

This expansive .32-acre lot (13,732 sq ft) offers exceptional potential for either a brand-new custom build or a renovation with room to expand. Ideally located in the heart of Winter Park, the property sits across the street from several grand estates on the Winter Park Chain of Lakes, offering both prestige and endless possibilities. The existing 1960’s residence features original wood floors,

Sharon Helsby FANNIE HILLMAN & ASSOCIATES

901 Palmer Ave, Winter Park, FL 32789
/17

$1,300 - $1,855 per month

La Aloma

1 - 3 Beds

3040 Aloma Ave, Winter Park, FL 32792

La Aloma Apartments offers the ideal blend of comfort, convenience, and tranquility in the heart of Central Florida. Perfectly situated just minutes from downtown Winter Park, this centrally located community provides easy access to everything Orlando has to offer—including top attractions, dining, shopping, and entertainment. Whether you're a student or professional, you'll appreciate being just

3040 Aloma Ave, Winter Park, FL 32792
/2
$560,000 Sold Aug 19, 2025
- 789 Sq Ft
- $710/SF
- 46 Days On Market
- 2 Beds
- 1 Bath
- Built 1953
1339 Orchid Ave, Winter Park, FL 32789

A rare find in Winter Park: A charming Bungalow with 3-Car Garage (24x36) and detached finished Shed (10x14) for office & or additional Storage! Walking distance to Mead Gardens and the new Seven Oaks Park. Convenient to Rollins College, Park Avenue and Winter Park Village, featuring multiple local eateries and restaurants. Just one mile to Hospital, Science Center and Museum. Easy access to

Barbara Allen ABIDE REALTY

1339 Orchid Ave, Winter Park, FL 32789

/24
Est $379,300 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,426 Sq Ft
172 Balfour Dr Unit 2, Winter Park, FL 32792

172 Balfour Dr Unit 2, Winter Park, FL 32792

/33
$150,000
- 1 Bed
- 1 Bath
- 749 Sq Ft
2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792

Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of

SANTIAGO SILVA THE PAMPAS REAL ESTATE GROUP, LLC.

2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
/17
$2,500 per month
- 2 Beds
- 2.5 Baths
- 1,204 Sq Ft
- Townhouse for Rent
645 Huntington Ave Unit 7, Winter Park, FL 32789

Live in style in this renovated 2-bedroom, 2.5-bath townhome located in the heart of Winter Park. The modern kitchen features stainless steel appliances, granite counters, and upscale finishes. Both bedrooms have private balconies, and the master includes a versatile loft space, great for a workspace or lounge. The home also comes equipped with a front-load washer and dryer. Outside, enjoy a

Summer Hornburg BELMONT REALTY

645 Huntington Ave Unit 7, Winter Park, FL 32789
/2
$485,000 Sold Aug 18, 2025
- 2,171 Sq Ft
- $223/SF
- 11 Days On Market
- 4 Beds
- 2 Baths
- Built 1971
1921 Japonica Rd, Winter Park, FL 32792

Welcome to 1921 Japonica Rd – Your Winter Park Retreat AwaitsTucked away on a quiet street just minutes from the heart of Winter Park, this beautifully maintained 4-bedroom, 2-bath home offers the perfect blend of comfort, character, and potential. From the moment you arrive, you'll notice how lovingly this home has been cared for, offering peace of mind with newer roof (2021) and a

Jose Gabriel Rodriguez COLDWELL BANKER RESIDENTIAL RE

1921 Japonica Rd, Winter Park, FL 32792

/18
Est $450,547 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
2786 Bright Bird Ln, Winter Park, FL 32792

2786 Bright Bird Ln, Winter Park, FL 32792

/80
$499,000
- 4 Beds
- 2 Baths
- 2,200 Sq Ft
1339 Monte Ln, Winter Park, FL 32792

Lovely home with an expanded floor plan in Casa Aloma—one of Winter Park’s most walkable and established neighborhoods! Featuring approx. 2,200 sq ft of living space (permitted addition, buyer to verify), this 3/2 offers a spacious, flexible layout and a relaxing backyard oasis. Enjoy a sparkling pool, screened patio, and mature palm landscaping—perfect for entertaining! Fresh exterior paint,

Rod Banks ANCHOR FLORIDA REALTY LLC

1339 Monte Ln, Winter Park, FL 32792
/27

$1,236 - $2,599 per month

Village Park Senior

1 - 3 Beds

550 W Denning Dr, Winter Park, FL 32789

WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

550 W Denning Dr, Winter Park, FL 32789
/2
$450,000 Sold Aug 18, 2025
- 2,076 Sq Ft
- $217/SF
- 139 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2021
1522 Bantam Way, Winter Park, FL 32792

Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood. The corner townhouse has huge living room with a high ceiling when you walk into the house, screen patio with the tile floor, one half bathroom downstairs. 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy

He Gao U S GLORY REALTY

1522 Bantam Way, Winter Park, FL 32792

/29
Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,393 Sq Ft
7482 Canford Ct Unit 7482, Winter Park, FL 32792

7482 Canford Ct Unit 7482, Winter Park, FL 32792

/51
$1,799,000
- 3 Beds
- 3 Baths
- 3,297 Sq Ft
825 Palmer Ave, Winter Park, FL 32789

825 Palmer Avenue, Winter Park | $1,799,000 - A Rare Venetian Canal Treasure Awaits Your Vision! Discover an extraordinary opportunity on one of Winter Park's most coveted waterways. This exceptional single-story estate on Palmer Avenue presents over 3,200 square feet of pure potential, perfectly positioned on an oversized .35-acre lot (85x173') with exclusive boathouse access to the prestigious

Kelly Price KELLY PRICE & COMPANY LLC

825 Palmer Ave, Winter Park, FL 32789
/34
$2,375 per month
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
- Townhouse for Rent
2891 Clever Ln, Winter Park, FL 32792

Welcome home to 2891 Clever Lane, a three bedroom, two and a half bath town home with a one car garage! The kitchen overlooks the main living area and features a full suite of stainless steel appliances including the refrigerator, range, over the range microwave and dishwasher as well as plenty of cabinetry and counter top space. The half bath is located on the first floor, easily accessible for

Justin Recca INNOVATIVE REALTY, LLC

2891 Clever Ln, Winter Park, FL 32792
/2
$470,000 Sold Aug 18, 2025
- 2,122 Sq Ft
- $221/SF
- 226 Days On Market
- 4 Beds
- 2 Baths
- Built 1979
4026 Tenita Dr, Winter Park, FL 32792

One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available at closing.Welcome to this stunning property where elegance meets comfort. The neutral color paint scheme and fresh interior paint provide a modern and clean feel. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, equipped with stainless steel

Karen Albright OPENDOOR BROKERAGE LLC

4026 Tenita Dr, Winter Park, FL 32792

/11
Est $445,110 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,782 Sq Ft
2711 Bright Bird Ln, Winter Park, FL 32792

2711 Bright Bird Ln, Winter Park, FL 32792

/49
$439,000
- 4 Beds
- 2 Baths
- 1,836 Sq Ft
1842 Puritan Ave, Winter Park, FL 32792

Modern design, Open concept layout, Sleek quartz counter top, All new appliances, New luxury vinyl plank flooring, New lanai upgrade. This beautiful 4 bedrooms and 2 full bath is situated on a 8,250 square feet lot was newly fenced in 2024 which gives a sense of privacy and spaciousness as you enter into the lanai. There is two detached sheds for your storage convenience. This beautiful done was

Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

1842 Puritan Ave, Winter Park, FL 32792
/27

$1,250 - $1,680 per month

Westmount at Winter Park

Studio - 3 Beds

1701 Lee Rd, Winter Park, FL 32789

Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

1701 Lee Rd, Winter Park, FL 32789
/2
$3,000,000 Sold Aug 18, 2025
- 4,080 Sq Ft
- $735/SF
- 313 Days On Market
- 5 Beds
- 5.5 Baths
- Built 2024
1730 Winchester Dr, Winter Park, FL 32789

Welcome to this exquisite 5-bedroom, 5.5-bathroom home built by Lundev, perfectly situated in the highly sought-after Timberlane Shores neighborhood of Winter Park. Spanning 4,080 square feet, this property offers the ultimate blend of luxury and comfort. Thoughtfully designed for both entertaining and everyday living, this home features high-end finishes and top-quality craftsmanship

Nickolas McKee KELLER WILLIAMS WINTER PARK

1730 Winchester Dr, Winter Park, FL 32789

/27
Est $172,937 Not Listed For Sale
- 1 Bed
- 1 Bath
- 759 Sq Ft
603 Saint Johns Ct Unit S, Winter Park, FL 32792

603 Saint Johns Ct Unit S, Winter Park, FL 32792

/34
$158,000
- 2 Beds
- 1 Bath
- 881 Sq Ft
1695 Lee Rd Unit D113, Winter Park, FL 32789

Welcome to this charming 2-bedroom, 1-bathroom first-floor condo conveniently located in the heart of Winter Park. This home offers a spacious open layout with plenty of natural light, NO CARPET, and a functional floor plan perfect for comfortable living.The kitchen features ample cabinet space and next to it you will find the laundry closet (washer and dryer included). Both bedrooms are

Gisela Gaztambide Balzac EMPIRE NETWORK REALTY

1695 Lee Rd Unit D113, Winter Park, FL 32789
/26
$2,400 per month
- 2 Beds
- 2.5 Baths
- 1,495 Sq Ft
- Condo for Rent
2340 Sun Valley Cir Unit 2340, Winter Park, FL 32792

Welcome to 2340 Sun Valley Circle, Winter Park, FL 32792, a stylish 2-bedroom, 2-bath condo featuring a bonus loft that’s perfect for a office or guest space. Step into an updated layout boasting vaulted ceilings, modern luxury flooring, a remodeled kitchen, and a sleek, refreshed bathroom that feels both contemporary and timeless. In-unit laundry, two dedicated parking spaces, and smart,

Melissa Johnson EXP REALTY LLC

2340 Sun Valley Cir Unit 2340, Winter Park, FL 32792
/2
$298,000 Sold Aug 15, 2025
- 1,776 Sq Ft
- $168/SF
- 9 Days On Market
- 4 Beds
- 2 Baths
- Built 1971
2206 Bonanza Ave, Winter Park, FL 32792

This Winter Park BLOCK home offers 4 bedrooms, 2 full bathrooms and all with no HOA. This home features a SPLIT FLOOR PLAN and NEW ROOF (2022). The oversized enclosed porch is perfect for entertaining or relaxing after a long day of work. Front screened in patio to enjoy as well. Storage will not be an issue, as there is a 2 CAR GARAGE You're also located in a very established community that's

Hannah Thompson FLORIDA REALTY INVESTMENTS

2206 Bonanza Ave, Winter Park, FL 32792

/44
Est $900,585 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,513 Sq Ft
1403 Michigan Ave, Winter Park, FL 32789

1403 Michigan Ave, Winter Park, FL 32789

/43
$1,799,000
- 4 Beds
- 3.5 Baths
- 2,860 Sq Ft
1166 Oaks Blvd, Winter Park, FL 32789

Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxury features throughout its expansive 2,860 square feet of thoughtfully designed living space.Relax on the charming front covered

Kevin Kelly FANNIE HILLMAN & ASSOCIATES

1166 Oaks Blvd, Winter Park, FL 32789
/35

$1,500 - $2,750 per month

Hannibal Square

Studio - 2 Beds

433 W New England Ave, Winter Park, FL 32789

We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

433 W New England Ave, Winter Park, FL 32789
/2
$5,225,000 Sold Aug 15, 2025
- 3,738 Sq Ft
- $1,398/SF
- 6 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2023
1333 Alberta Dr, Winter Park, FL 32789

An architectural triumph, this one-of-a-kind modern masterpiece was custom designed and built in 2023 by the award-winning Z Properties and is ideally sited on the shores of Lake Osceola, part of the Winter Park Chain of Lakes. Radiating bold sophistication and contemporary elegance, the residence is a curated work of art, where floor-to-ceiling glass walls and striking steel windows and doors

Mick Night PREMIER SOTHEBY'S INTL. REALTY

1333 Alberta Dr, Winter Park, FL 32789

/43
Est $1,081,789 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,310 Sq Ft
1780 Mondrian Cir, Winter Park, FL 32789

1780 Mondrian Cir, Winter Park, FL 32789

/31
$475,000
- 3 Beds
- 2 Baths
- 1,671 Sq Ft
1932 Houndslake Dr, Winter Park, FL 32792

Newly renovated 3 Bedroom 2 Bath in a well establish community of Cedar Ridge. Conveniently located in Winter Park Seminole County Pool home. The office can easily turn into a 4th bedroom if needed. New tile floors throughout. Open, airy and bright. Updated kitchen with quartz countertop. New stainless steel appliances. New roof, new water heater and most of the windows are newly

Trung Nguyen LA ROSA REALTY LLC

1932 Houndslake Dr, Winter Park, FL 32792
/27
$6,995 per month
- 4 Beds
- 5 Baths
- 3,948 Sq Ft
- House for Rent
1205 Mayfield Ave, Winter Park, FL 32789

Great rental opportunity in Winter Park, FL! This two-story residence is located in the TEMPLE HEIGHTS neighborhood. This large well maintained family home comes with 5 bedrooms and 4 baths in the main home with over 3,900 sqft. The home also features a separate large pool home or in-law suite. The Pool home / In-Law Suite comes with its own bathroom and kitchenette. The home has wood / vinyl

Mo Jabr RE/MAX 200 REALTY

1205 Mayfield Ave, Winter Park, FL 32789
/2
$2,125,000 Sold Aug 15, 2025
- 2,450 Sq Ft
- $867/SF
- 20 Days On Market
- 2 Beds
- 3 Baths
- Built 2007
140 E Morse Blvd Unit C, Winter Park, FL 32789

When you enter through the secure and elegant wrought iron gates and walk into in the private central courtyard, you'll feel the sophistication of The Landmark Winter Park. Take the elevator to the second floor and your private entrance balcony overlooking the courtyard. Inside, this spacious corner unit you'll find 2 bedrooms, 3 full bathrooms and a spacious media room/office. From the foyer

Sue Gilman KELLER WILLIAMS WINTER PARK

140 E Morse Blvd Unit C, Winter Park, FL 32789

/18
Est $447,537 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
2809 Bright Bird Ln, Winter Park, FL 32792

2809 Bright Bird Ln, Winter Park, FL 32792

/33
$450,000
- 3 Beds
- 2 Baths
- 1,727 Sq Ft
1914 Bonanza Ct, Winter Park, FL 32792

Welcome to your winter Park retreat!Step into this beautifully renovated 3 bedroom, 2 bathroom home where modern meets timeless comfort. Designed with an open floor plan, the living space flows seamlessly, making it perfect for both entertaining and everyday living.The brand new kitchen shines with contemporary finishes, while the new flooring throughout the home adds warmth and

William Moxey WYNNMORE REALTY LLC

1914 Bonanza Ct, Winter Park, FL 32792
/15
$2,995 per month
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
- House for Rent
5417 Ferrol Dr, Winter Park, FL 32792

Beautifully Remodeled 3 Bed, 2 Bath Home Energy Efficient & Prime Location!Welcome to your dream rental! This stunning newly remodeled 3-bedroom, 2-bath home offers modern comfort with a touch of elegance. Featuring an open floor concept, the spacious living area is perfect for entertaining, complete with a cozy fireplace and abundant natural light from double-glazed windows.The

5417 Ferrol Dr, Winter Park, FL 32792
/2
$140,000 Sold Aug 15, 2025
- 793 Sq Ft
- $177/SF
- 31 Days On Market
- 1 Bed
- 1 Bath
- Built 1970
200 St Andrews Blvd Unit 911, Winter Park, FL 32792

One or more photo(s) has been virtually staged. Here is an amazing 1-bedroom, 1-bath condo in Winter Park's beautiful Four Seasons. It's on the 2nd floor, so you won't have to worry about noisy neighbors above you! The garden views are lovely, and it has a huge walk-in closet along with really spacious rooms. Plus, there's a nice screened balcony that's perfect for those cool summer

Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

200 St Andrews Blvd Unit 911, Winter Park, FL 32792

/18
Est $443,382 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
2805 Bright Bird Ln, Winter Park, FL 32792

2805 Bright Bird Ln, Winter Park, FL 32792

/32
$480,000
- 3 Beds
- 2 Baths
- 1,978 Sq Ft
2831 Lion Heart Rd, Winter Park, FL 32792

Welcome to your Winter Park retreat! This spacious single-story ranch offers nearly 2,000 sq. ft. of living space with 3 bedrooms, 2 baths, and a versatile bonus room. The updated kitchen boasts granite counters, stainless steel appliances, and a cozy breakfast area, opening into a bright Florida room perfect for entertaining. The split floor plan ensures privacy, with a generous primary suite

Joyce Tang JOY ESTATE ENTERPRISE INC

2831 Lion Heart Rd, Winter Park, FL 32792
/18
$2,000 per month
- 3 Beds
- 3.5 Baths
- 1,413 Sq Ft
- Townhouse for Rent
235 Sandlewood Trail Unit 5, Winter Park, FL 32789

WINTER PARK: Sandlewood Creek Community - AVAILABLE NOW!! Welcome home to this great 3 bedroom, 3.5 bath, 3 story townhome in Winter Park. The kitchen is open, light and bright with all appliances, a breakfast bar and is open to the living room/dining area. The living room features a fireplace and sliding glass doors that open out onto the screened porch. Downstairs you will also find the half

Kelly Carr CFRP REALTY LLC

235 Sandlewood Trail Unit 5, Winter Park, FL 32789
/2
$999,999 Sold Aug 15, 2025
- 2,348 Sq Ft
- $426/SF
- 43 Days On Market
- 4 Beds
- 3 Baths
- Built 1957
2112 Fosgate Dr, Winter Park, FL 32789

Welcome to 2112 Fosgate Drive, a beautifully updated home nestled on a quiet, tree-lined street in Winter Park. With 4 bedrooms, 3 bathrooms, and just under 2,400 square feet, this residence offers a thoughtful layout with plenty of space to fit your lifestyle. Fully remodeled in 2018, it’s move-in ready with a blend of charm and modern comfort.Step inside and you’ll be welcomed by real

Nickolas McKee KELLER WILLIAMS WINTER PARK

2112 Fosgate Dr, Winter Park, FL 32789

/18
Est $462,477 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,782 Sq Ft
2821 Bright Bird Ln, Winter Park, FL 32792

2821 Bright Bird Ln, Winter Park, FL 32792

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