Homes in ZIP Code 32789

/25
$395,000

$15K PRICE DROP
- 3 Beds
- 2 Baths
- 1,201 Sq Ft
2568 Lotafun Ave, Winter Park, FL 32789

Virtually Staged. Conveniently located just minutes from I-4, downtown Orlando, and Winter Park, this versatile home offers the perfect blend of comfort, flexibility, and location. The upper level features two bedrooms and one full bath, while the lower level includes one bedroom and one full bath. Each floor has its own private entrance and full kitchen, making it ideal for multi-generational

Randall Wolber SIMPLE FEE LISTINGS LLC

2568 Lotafun Ave, Winter Park, FL 32789
/13
$1,600 Per Month
- 2 Beds
- 1 Bath
- 881 Sq Ft
- Condo for Rent
1695 Lee Rd Unit A113, Winter Park, FL 32789

Welcome to this updated first-floor condo in the Waterfall Cove community of Winter Park. This 2-bedroom, 1-bath residence features new luxury vinyl plank flooring throughout, a bright and open living area, and a well-maintained air-conditioning system. The unit also offers an inside laundry area with washer and dryer. Community amenities include a swimming pool and playground. Conveniently

Yigit Orer EMPIRE NETWORK REALTY

1695 Lee Rd Unit A113, Winter Park, FL 32789
/2
$3,200,000

Sold Nov 04, 2025

1900 W Fawsett Rd, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 4,600 Sq Ft
- Built 1969
Last Sold Summary
- 4% Below List Price
- $696/SF
- 6 Days On Market
Current Estimated Value $3,268,249

Last Listing Agent Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

1900 W Fawsett Rd, Winter Park, FL 32789

/18
Not Listed For Sale

1411 Miller Ave, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 1,813 Sq Ft
- Built 2023
1411 Miller Ave, Winter Park, FL 32789

Last Sold Summary
- 30 Days On Market
Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

/26
$235,000

$15K PRICE DROP
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
1500 Gay Rd Unit 3C, Winter Park, FL 32789

NEW PRICE/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring

Heather Frazee FANNIE HILLMAN & ASSOCIATES

1500 Gay Rd Unit 3C, Winter Park, FL 32789
/26
$8,900 Per Month
- 3 Beds
- 3.5 Baths
- 2,714 Sq Ft
- Condo for Rent
660 Osceola Ave Unit 101, Winter Park, FL 32789

Experience the best of Winter Park waterfront living in this beautifully updated ground-floor residence at Perle du Lac, ideally located just a short stroll from the boutiques, restaurants, and cafés of Park Avenue. Even more rare, this exceptional residence includes a private covered boat slip on the pristine waters of Lake Virginia, offering direct access to the renowned Winter Park Chain of

Jennifer King CORCORAN PREMIER REALTY

660 Osceola Ave Unit 101, Winter Park, FL 32789
/2
$879,000

Sold Nov 14, 2025

451 Fairfax Ave, Winter Park, FL 32789
- 3 Beds
- 3 Baths
- 2,227 Sq Ft
- Built 2003
Last Sold Summary
- 2% Below List Price
- $395/SF
- 5 Days On Market
Current Estimated Value $885,646

Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

451 Fairfax Ave, Winter Park, FL 32789

/2
Est $534,444

Not Listed For Sale

1051 Aragon Ave Unit 1051, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 1,669 Sq Ft
- Built 1987
1051 Aragon Ave Unit 1051, Winter Park, FL 32789

Last Sold Summary
- 104 Days On Market
Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

/61
$2,394,500

New Construction Pending
- 5 Beds
- 6.5 Baths
- 4,506 Sq Ft
2412 Chantilly Ave, Winter Park, FL 32789

Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This

Tab Bish LLC REAL BROKER, LLC

2412 Chantilly Ave, Winter Park, FL 32789
/21
$3,150 Per Month
- 3 Beds
- 2.5 Baths
- 1,803 Sq Ft
- Townhouse for Rent
1409 Michigan Ave, Winter Park, FL 32789

Move-in ready and freshly painted inside and out, this spacious 3-bedroom, 2.5-bathroom Winter Park townhome features a private 2-car garage and a prime location.The bright, open-concept floor plan features a generous main living area alongside a versatile front flex room - ideal for a formal dining room or a dedicated home office. At the heart of the home is a well-appointed kitchen boasting

Kyle Li UNIONE REALTY INC

1409 Michigan Ave, Winter Park, FL 32789
/2
$2,185,000

Sold May 21, 2026

2722 Eastern Pkwy, Winter Park, FL 32789
- 5 Beds
- 4.5 Baths
- 3,334 Sq Ft
- Built 2026
Last Sold Summary
- 5% Below List Price
- $655/SF
- 105 Days On Market
Current Estimated Value $1,997,486

Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

2722 Eastern Pkwy, Winter Park, FL 32789

/2
Est $810,523

Not Listed For Sale

1818 Mondrian Cir, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,265 Sq Ft
- Built 2018
1818 Mondrian Cir, Winter Park, FL 32789

Last Sold Summary
- 189 Days On Market
Last Listing Agent Brian Teach COLDWELL BANKER REALTY

/27
$660,000

$15K PRICE DROP
- 3 Beds
- 1 Bath
- 1,243 Sq Ft
1416 Border Dr, Winter Park, FL 32789

An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer to design from the ground up on a street where redevelopment is already underway. Within a half mile, seven custom single-family homes are in their final phase of construction, most starting near $1.5 million. Border Drive

Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

1416 Border Dr, Winter Park, FL 32789
/9
$2,200 Per Month
- 3 Beds
- 2 Baths
- 1,068 Sq Ft
- House for Rent
1751 Westchester Ave, Winter Park, FL 32789

Move-in ready 3-bedroom, 2-bath home in a convenient Winter Park location just off Orange Avenue and minutes from Park Avenue. The home features updated vinyl flooring, fresh interior paint and fixtures, a kitchen with new appliances included, comfortable single-story layout, screened lanai, covered carport, and private backyard. Enjoy quick access to Downtown Winter Park, Park Avenue’s shops,

Ahmad Hassan COMPASS FLORIDA LLC

1751 Westchester Ave, Winter Park, FL 32789
/2
$975,000

Sold Feb 10, 2026

1150 Kenwood Ave, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 2,557 Sq Ft
- Built 1988
Last Sold Summary
- 24% Below List Price
- $381/SF
- 97 Days On Market
Current Estimated Value $1,051,714

Last Listing Agent JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

1150 Kenwood Ave, Winter Park, FL 32789

/2
Est $2,445,048

Not Listed For Sale

1010 N Pennsylvania Ave, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 4,074 Sq Ft
- Built 2017
1010 N Pennsylvania Ave, Winter Park, FL 32789

Last Sold Summary
- 94 Days On Market
Last Listing Agent Dana Laing BHHS FLORIDA REALTY

/38
$810,000

$69K PRICE DROP
- 3 Beds
- 3.5 Baths
- 2,030 Sq Ft
1265 Arlington Place, Winter Park, FL 32789

Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood

Erika Beerbower FANNIE HILLMAN & ASSOCIATES

1265 Arlington Place, Winter Park, FL 32789
/2
$2,200 Per Month
- 3 Beds
- 2 Baths
- 1,156 Sq Ft
- House for Rent
128 Oak Grove Rd, Winter Park, FL 32789

Charming 3-bedroom, 2-bathroom home in a desirable Winter Park location, within walking distance of the new Life Time Fitness. This bright and inviting residence features an open floor plan, tile flooring, large windows, and a well-appointed kitchen with granite countertops. The fenced backyard provides a private space for relaxing or entertaining, while the attached one-car garage offers added

Lafa Britto NOVA REAL ESTATE SERVICES INC

128 Oak Grove Rd, Winter Park, FL 32789
/2
$475,000

Sold May 14, 2026

665 W Lyman Ave, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,119 Sq Ft
- Built 1994
Last Sold Summary
- 6% Above List Price
- $424/SF
- 6 Days On Market
Current Estimated Value $471,517

Last Listing Agent Jonathan Nakhnoukh CENTRAL FLORIDA PRIME REAL ESTATE LLC

665 W Lyman Ave, Winter Park, FL 32789

/2
Est $673,432

Not Listed For Sale

782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 2,354 Sq Ft
- Built 1988
782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

Last Sold Summary
- 81 Days On Market
Last Listing Agent Richard Palmano PALMANO GROUP RE BROKERAGE LLC

/4
$1,750,000
- Land
- 16,117 Sq Ft
- $4,729,730 per Acre
313L Sylvan Dr, Winter Park, FL 32789

Exceptional opportunity to build on beautiful Lake Sylvan with this 0.37-acre (approximately 16,603-square-foot) lakefront homesite. Offering a picturesque waterfront setting, the property is ideally positioned just minutes from Park Avenue's shops and restaurants, major roadways, leading hospitals and top private schools. Create a custom lakefront residence tailored to your vision in one of

Mick Night PREMIER SOTHEBY'S INTL. REALTY

313L Sylvan Dr, Winter Park, FL 32789
/20
$2,300 Per Month
- 3 Beds
- 2 Baths
- 1,536 Sq Ft
- House for Rent
2823 Wright Ave, Winter Park, FL 32789

Enjoy lakefront living at 2823 Wright Avenue in Winter Park. Set on more than half an acre, this three-bedroom home offers a spacious yard with mature trees, privacy, and peaceful water views. Remodeled throughout the interior, the home features wood flooring, large windows that bring in natural light, and an updated kitchen with high-end appliances, custom cabinetry, and designer finishes. The

Juliana Jard Souza NOVA REAL ESTATE SERVICES INC

2823 Wright Ave, Winter Park, FL 32789
/2
$475,000

Sold Feb 02, 2026

1740 Anzle Ave, Winter Park, FL 32789
- 4 Beds
- 2 Baths
- 1,808 Sq Ft
- Built 1956
Last Sold Summary
- 40% Below List Price
- $263/SF
- 109 Days On Market
Current Estimated Value $563,676

Last Listing Agent Freddy DeCoster GOYAL & DECOSTER REALTY

1740 Anzle Ave, Winter Park, FL 32789

/50
Est $2,038,743

Not Listed For Sale

270 E Lake Sue Ave, Winter Park, FL 32789
- 5 Beds
- 4.5 Baths
- 3,151 Sq Ft
- Built 2023
270 E Lake Sue Ave, Winter Park, FL 32789

Last Sold Summary
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

/11
$4,299,000
- Land
- 8.23 Acres
- $522,357 per Acre
2403 Euston Rd, Winter Park, FL 32789

Fly In. Unwind. Build Your Dream on Lake Killarney. Bring your seaplane and envision the lakefront estate of your dreams on one of Winter Park’srarest offerings. Tucked away on a private peninsula surrounded by multi-million-dollar homes, this extraordinary property spans approximately432 feet of shoreline along the spring-fed, crystal-clear waters of Lake Killarney. With 1.514 buildable

Marie Ledbetter COLDWELL BANKER REALTY

2403 Euston Rd, Winter Park, FL 32789
/38
$3,200 Per Month
- 3 Beds
- 2 Baths
- 1,782 Sq Ft
- House for Rent
450 W Canton Ave, Winter Park, FL 32789

450 Canton Avenue — Winter Park, FL | $3,200/moCharming and spacious, this beautifully located rental sits just 2 blocks from Park Avenue, offering walking-distance access to Winter Park's best restaurants, boutique shopping, and Winter Park Village — plus easy access to the Winter Park Train Station for effortless commuting.Step inside to find a thoughtfully laid-out floor plan

Kelly Price KELLY PRICE & COMPANY LLC

450 W Canton Ave, Winter Park, FL 32789
/2
$2,750,000

Sold Jun 18, 2026

151 Oakwood Way, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 4,129 Sq Ft
- Built 2023
Last Sold Summary
- 14% Below List Price
- $666/SF
- 113 Days On Market
Current Estimated Value $2,781,381

Last Listing Agent Matthew Burks CORCORAN PREMIER REALTY

151 Oakwood Way, Winter Park, FL 32789

/49
Est $2,353,011

Not Listed For Sale

180 Whipple Ave, Winter Park, FL 32789
- 4 Beds
- Built 2025
180 Whipple Ave, Winter Park, FL 32789

Last Sold Summary
- 353 Days On Market
Last Listing Agent Adam Cole COLEDEV REAL ESTATE LLC

/45
$965,000

Coming Soon
- 3 Beds
- 2.5 Baths
- 1,957 Sq Ft
1256 S Pennsylvania Ave Unit 9, Winter Park, FL 32789

Positioned in Winter Park’s Virginia Heights neighborhood, just moments from Park Avenue and Seven Oaks Park, this Mediterranean-inspired townhome-style condominium offers three bedrooms, two and a half baths and nearly 2,000 square feet of conditioned living space. A rare private driveway, gated entry and paver walkway establish a distinct sense of arrival, while wrought-iron details introduce

Drew Henner PREMIER SOTHEBY'S INTL. REALTY

1256 S Pennsylvania Ave Unit 9, Winter Park, FL 32789
/25
$7,995 Per Month
- 4 Beds
- 5.5 Baths
- 3,295 Sq Ft
- House for Rent
2234 Howard Dr, Winter Park, FL 32789

Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility. Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal

Raquel Elliott COLDWELL BANKER REALTY

2234 Howard Dr, Winter Park, FL 32789
/2
$1,725,000

Sold Mar 05, 2026

617 Worthington Dr, Winter Park, FL 32789
- 5 Beds
- 4.5 Baths
- 3,533 Sq Ft
- Built 2018
Last Sold Summary
- 13% Below List Price
- $488/SF
- 215 Days On Market
Current Estimated Value $1,780,985

Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

617 Worthington Dr, Winter Park, FL 32789

/17
Not Listed For Sale

700 Melrose Ave Unit K, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,074 Sq Ft
- Built 1964
700 Melrose Ave Unit K, Winter Park, FL 32789

Last Sold Summary
- 188 Days On Market
Last Listing Agent Scott Butts KIMBRIDGE REALTY, LLC

/13
$1,275,000
- 3 Beds
- 2.5 Baths
- 1,329 Sq Ft
240 Killarney Dr, Winter Park, FL 32789

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just

Shandy Ortiz PREMIER SOTHEBYS INT'L REALTY

240 Killarney Dr, Winter Park, FL 32789
/2
$2,835,000

Sold Nov 24, 2025

255 Stirling Ave, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 3,635 Sq Ft
- Built 1982
Last Sold Summary
- 14% Below List Price
- $780/SF
- 25 Days On Market
Current Estimated Value $2,930,153

Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

255 Stirling Ave, Winter Park, FL 32789

/2
Est $1,223,162

Not Listed For Sale

242 W Lyman Ave, Winter Park, FL 32789
- 3 Beds
- 3 Baths
- 2,199 Sq Ft
- Built 2014
242 W Lyman Ave, Winter Park, FL 32789

Last Sold Summary
- 12 Days On Market
Last Listing Agent Jill Henry COLDWELL BANKER REALTY

/22
$1,795,000

New Construction Pending
- 4 Beds
- 4 Baths
- 2,819 Sq Ft
2501 Lafayette Ave, Winter Park, FL 32789

Virtually Staged. A rare new construction offering in the heart of Winter Park — 2501 Lafayette Ave is a 2,810 sq ft architectural residence crafted by curated design firm - Catalyst Design, with 25-year experience and Parade of Homes judge across Naples, Daytona & Southwest Florida. 4 bed | 4 bath | office | 2-car garage | saltwater pool. Every detail built to a single standard: the highest one.

Michael Elias CHARLES RUTENBERG REALTY ORLANDO

2501 Lafayette Ave, Winter Park, FL 32789
/2
$625,000

Sold Mar 27, 2026

1500 Berkshire Ave, Winter Park, FL 32789
- 3 Beds
- 1.5 Baths
- 1,485 Sq Ft
- Built 1925
Last Sold Summary
- $421/SF
- 51 Days On Market
Current Estimated Value $631,472

Last Listing Agent Lianna D'Angelo SOTERA LIVING

1500 Berkshire Ave, Winter Park, FL 32789

/2
Est $1,084,101

Not Listed For Sale

625 N Interlachen Ave Unit A, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,718 Sq Ft
- Built 1981
625 N Interlachen Ave Unit A, Winter Park, FL 32789

Last Sold Summary
- 196 Days On Market
Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

/33
$1,350,000
- 4 Beds
- 4 Baths
- 2,998 Sq Ft
1320 Orchid Ave, Winter Park, FL 32789

Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Orlando. Offering nearly 3,000 square feet of thoughtfully designed living space, this 4-bedroom, 4-bath home combines contemporary architecture, abundant natural light, and elevated finishes in one of Central Florida’s most

Isis Sarcos EXP REALTY LLC

1320 Orchid Ave, Winter Park, FL 32789
/2
$1,430,000

Sold Nov 10, 2025

1011 Mckean Cir, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 2,230 Sq Ft
- Built 1955
Last Sold Summary
- $641/SF
- 0 Days On Market
Current Estimated Value $1,496,120

Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

1011 Mckean Cir, Winter Park, FL 32789

Showing Results 241 - 280, Page 7 of 18

Florida Orange County Winter Park

How to Buy a Home How to Finance a Home How to Sell a Home

Properties in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage