Homes in ZIP Code 32789

/43
$550,000 Open Thu 3PM - 7PM
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
720 W Webster Ave, Winter Park, FL 32789

One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends modern updates with timeless character

Vincent Cordaro

SERHANT

(321) 341-3712

720 W Webster Ave, Winter Park, FL 32789
/103

$1,807 - $6,390 per month

Paseo at Winter Park Village

1 - 3 Beds

940 W Canton Ave, Winter Park, FL 32789

Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

940 W Canton Ave, Winter Park, FL 32789
/2
$1,590,000 Sold Mar 06, 2026

1166 Oaks Blvd, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,860 Sq Ft
- Built 2018
Last Sold Summary
- 12% Below List Price
- $556/SF
- 153 Days On Market
Current Estimated Value $1,580,246

Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

1166 Oaks Blvd, Winter Park, FL 32789

/2
Est $791,970 Not Listed For Sale

1375 Suffolk Rd, Winter Park, FL 32789
- 4 Beds
- 2.5 Baths
- 2,548 Sq Ft
- Built 1940
1375 Suffolk Rd, Winter Park, FL 32789

Last Sold Summary
- 6% Above List Price
- $292/SF
- 30 Days On Market
Last Sold Price $745,000

Last Listing Agent Beth Hobart MAINFRAME REAL ESTATE

/66
$2,395,000
- 4 Beds
- 5.5 Baths
- 4,392 Sq Ft
1760 Legion Dr, Winter Park, FL 32789

Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect

Steven Looper CHARLES RUTENBERG REALTY ORLANDO

1760 Legion Dr, Winter Park, FL 32789
/16
$1,895 per month
- 2 Beds
- 2.5 Baths
- 959 Sq Ft
- Townhouse for Rent
295 Sandlewood Trail, Winter Park, FL 32789

This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a

Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

295 Sandlewood Trail, Winter Park, FL 32789
/2
$1,335,000 Sold Jul 15, 2025

1077 Minnesota Ave, Winter Park, FL 32789
- 4 Beds
- 4 Baths
- 3,046 Sq Ft
- Built 2025
Last Sold Summary
- 1% Below List Price
- $438/SF
- 75 Days On Market
Current Estimated Value $1,312,562

Last Listing Agent Jake Johnson SHORES REAL ESTATE

1077 Minnesota Ave, Winter Park, FL 32789

/42
Est $1,581,353 Not Listed For Sale

1805 Harland Park Dr, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 3,052 Sq Ft
- Built 2014
1805 Harland Park Dr, Winter Park, FL 32789

Last Sold Summary
- 7% Above List Price
- $483/SF
- 12 Days On Market
Last Sold Price $1,475,000

Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

/43
$3,295,000
- 5 Beds
- 5.5 Baths
- 4,955 Sq Ft
1761 Legion Dr, Winter Park, FL 32789

One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

Brian Scanlon SCANLON REALTY GROUP LLC

1761 Legion Dr, Winter Park, FL 32789
/50

$1,550 - $3,136 per month

Seven41 Winter Park

Studio - 2 Beds

741 Clay St, Winter Park, FL 32789

Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

741 Clay St, Winter Park, FL 32789
/2
$580,000 Sold Apr 21, 2025

3006 Northwood Blvd, Winter Park, FL 32789
- 4 Beds
- 2 Baths
- 1,710 Sq Ft
- Built 1953
Last Sold Summary
- 2% Below List Price
- $339/SF
- 1 Day On Market
Current Estimated Value $656,461

Last Listing Agent Chris Creegan CREEGAN GROUP

3006 Northwood Blvd, Winter Park, FL 32789

/2
Est $436,076 Not Listed For Sale

1761 Indiana Ave Unit F, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 1,598 Sq Ft
- Built 2008
1761 Indiana Ave Unit F, Winter Park, FL 32789

Last Sold Summary
- 6% Above List Price
- $258/SF
Last Sold Price $413,000

Last Listing Agent Brock Stocksett HOMEVEST REALTY

/41
$2,249,900 Pending
- 5 Beds
- 4 Baths
- 3,948 Sq Ft
1205 Mayfield Ave, Winter Park, FL 32789

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This two-story property is located in the highly desired Temple Heights neighborhood in the heart of Winter Park, where the true value is in the prime location and expansive double lot. The property includes a main residence plus a separate pool home/in-law suite, offering flexibility for redevelopment,

Abby Nelson RE/MAX 200 REALTY

1205 Mayfield Ave, Winter Park, FL 32789
/39
$3,300 per month
- 2 Beds
- 2 Baths
- 1,209 Sq Ft
- House for Rent
870 Carver St Unit A, Winter Park, FL 32789

Welcome to 870 Carver Street, a thoughtfully designed two-bedroom, two-bath residence in the core of Winter Park. Offering more than 1,200 square feet, the newly constructed home features vaulted ceilings with exposed rafters, warm wood finishes and industrial-inspired black metal ductwork that define its architectural character. The primary suite includes a floating wall closet system, a laundry

Drew Henner PREMIER SOTHEBY'S INTL. REALTY

870 Carver St Unit A, Winter Park, FL 32789
/2
$890,000 Sold Jun 12, 2025

1762 Mondrian Cir, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,265 Sq Ft
- Built 2024
Last Sold Summary
- 4% Below List Price
- $393/SF
- 114 Days On Market
Current Estimated Value $922,502

Last Listing Agent Brian Teach COLDWELL BANKER REALTY

1762 Mondrian Cir, Winter Park, FL 32789

/2
Est $2,919,257 Not Listed For Sale

1618 Holts Grove Cir, Winter Park, FL 32789
- 5 Beds
- 8 Baths
- 4,807 Sq Ft
- Built 2014
1618 Holts Grove Cir, Winter Park, FL 32789

Last Sold Summary
- 1% Above List Price
- $603/SF
- 173 Days On Market
Last Sold Price $2,900,000

Last Listing Agent Shirley Jones COLDWELL BANKER REALTY

/51
$2,800,000 New Construction
- 4 Beds
- 3.5 Baths
- 3,553 Sq Ft
541 W Canton Ave, Winter Park, FL 32789

Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood

Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

541 W Canton Ave, Winter Park, FL 32789
/50

$1,510 - $5,399 per month

Berkshire Winter Park

Studio - 3 Beds

1874 Harmon Ave, Winter Park, FL 32789

Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

1874 Harmon Ave, Winter Park, FL 32789
/2
$1,575,000 Sold Aug 14, 2025

1394 Grove Terrace, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,958 Sq Ft
- Built 2002
Last Sold Summary
- $532/SF
- 5 Days On Market
Current Estimated Value $1,577,588

Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

1394 Grove Terrace, Winter Park, FL 32789

/43
Est $1,778,783 Not Listed For Sale

1809 Harland Park Dr, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 3,660 Sq Ft
- Built 2014
1809 Harland Park Dr, Winter Park, FL 32789

Last Sold Summary
- 15% Above List Price
- $423/SF
- 8 Days On Market
Last Sold Price $1,550,000

Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC

/54
$1,974,000 Open Thu 12PM - 2PM
- 4 Beds
- 3.5 Baths
- 3,307 Sq Ft
2614 Parkland Dr, Winter Park, FL 32789

Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of

Ryan Gaston JW GASTON LLC

2614 Parkland Dr, Winter Park, FL 32789
/37
$5,900 per month
- 4 Beds
- 3 Baths
- 2,741 Sq Ft
- House for Rent
220 W Reading Way, Winter Park, FL 32789

Welcome to your dream home! This recently renovated gem in the highly coveted Forrest Hills area of Winter Park is now available for rent. Surrounded by enchanting brick streets and majestic trees, this charming residence has been thoughtfully upgraded by the new owner, offering a perfect blend of modern amenities and classic charm. As you step onto the inviting front covered porch, you'll be

Thomas Hewitt HEWITT RESIDENTIAL, LLC

220 W Reading Way, Winter Park, FL 32789
/2
$325,000 Sold Dec 30, 2025

520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,160 Sq Ft
- Built 1986
Last Sold Summary
- 7% Below List Price
- $280/SF
- 6 Days On Market
Current Estimated Value $323,555

Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

520 Killarney Bay Ct Unit 2, Winter Park, FL 32789

/2
Est $1,875,506 Not Listed For Sale

1411 Border Dr, Winter Park, FL 32789
- 4 Beds
- 6 Baths
- 4,638 Sq Ft
- Built 2019
1411 Border Dr, Winter Park, FL 32789

Last Sold Summary
- 11% Above List Price
- $364/SF
- 195 Days On Market
Last Sold Price $1,690,000

Last Listing Agent Ana Scarlato CORCORAN PREMIER REALTY

/29
$1,925,000
- 4 Beds
- 4 Baths
- 2,653 Sq Ft
721 Pansy Ave, Winter Park, FL 32789

Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From

Drew Henner PREMIER SOTHEBY'S INTL. REALTY

721 Pansy Ave, Winter Park, FL 32789
/18

$1,330 - $1,750 per month

Park East - Park Knowles Apartments

Studio - 2 Beds

311 N Knowles Ave, Winter Park, FL 32789

Park East Apartments, a charming community of studio, one, and two bedroom homes in the heart of Winter Park, FL. Spacious, modern interiors welcome you inside, as a collection of convenient resident amenities allows you to relax and enjoy residential life in style.Choose from a wide array of floor plans and layouts to find the home that meets your needs. Your fully equipped kitchen opens

311 N Knowles Ave, Winter Park, FL 32789
/2
$690,000 Sold May 08, 2025

1806 Mondrian Cir, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,016 Sq Ft
- Built 2018
Last Sold Summary
- 1% Below List Price
- $342/SF
- 61 Days On Market
Current Estimated Value $708,223

Last Listing Agent Brian Teach COLDWELL BANKER REALTY

1806 Mondrian Cir, Winter Park, FL 32789

/44
Est $854,896 Not Listed For Sale

436 W Swoope Ave, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,602 Sq Ft
- Built 2014
436 W Swoope Ave, Winter Park, FL 32789

Last Sold Summary
- 10% Above List Price
- $298/SF
- 170 Days On Market
Last Sold Price $775,000

Last Listing Agent Delora Credle COLDWELL BANKER REALTY

/57
$1,825,000 Pending
- 5 Beds
- 4.5 Baths
- 3,746 Sq Ft
501 Henkel Cir, Winter Park, FL 32789

Walk to Park Avenue from this stylish and impeccably maintained Winter Park home, tucked along a charming brick street just minutes from the shops, dining, and vibrant energy of downtown Winter Park. Designed for both effortless living and entertaining, the main residence offers 3,410 SF with 4 bedrooms and 3.5 baths, while a detached studio apartment sits above the two-car garage, adding 300+ SF

MaryStuart Day FANNIE HILLMAN & ASSOCIATES

501 Henkel Cir, Winter Park, FL 32789
/90
$13,500 per month
- 8 Beds
- 6 Baths
- 7,000 Sq Ft
- House for Rent
1860 Via Contessa, Winter Park, FL 32789

Exceptional Lease Opportunity | The Vias, Winter Park$13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available NowRarely does a home of this caliber come to market for lease. Set on a quiet cul-de-sac in one of Winter Park's most prestigious enclaves — the coveted Vias neighborhood — this magnificent 7,000 SF residence delivers an unmatched

Kelly Price KELLY PRICE & COMPANY LLC

1860 Via Contessa, Winter Park, FL 32789
/2
$550,000 Sold May 08, 2025

2906 Rapidan Trail, Winter Park, FL 32789
- 4 Beds
- 2.5 Baths
- 2,326 Sq Ft
- Built 1965
Last Sold Summary
- $236/SF
- 4 Days On Market
Current Estimated Value $620,188

Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

2906 Rapidan Trail, Winter Park, FL 32789

/2
Not Listed For Sale

700 Melrose Ave Unit G, Winter Park, FL 32789
- 1 Bed
- 1 Bath
- 687 Sq Ft
- Built 1964
700 Melrose Ave Unit G, Winter Park, FL 32789

Last Sold Summary
- $281/SF
- 73 Days On Market
Last Sold Price $193,000

Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

/3
$1,950,000 New Construction
- 4 Beds
- 4 Baths
- 2,810 Sq Ft
2501 Lafayette Ave, Winter Park, FL 32789

Under Construction. Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 4 bedroom, 4 bath home offers over 2,800 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom pivot front door into the foyer leading to your main living area featuring sliding glass walls for indoor-outdoor living.

Tab Bish LLC REAL BROKER, LLC

2501 Lafayette Ave, Winter Park, FL 32789
/35

$1,695 - $1,825 per month

The Lofts of Winter Park Village

1 Bed

520 N Orlando Ave, Winter Park, FL 32789

Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban

520 N Orlando Ave, Winter Park, FL 32789
/2
$720,000 Sold Jan 20, 2026

2955 Lolissa Ln, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 3,538 Sq Ft
- Built 1969
Last Sold Summary
- 4% Below List Price
- $204/SF
- 47 Days On Market
Current Estimated Value $737,384

Last Listing Agent Catherine Williams COLDWELL BANKER REALTY

2955 Lolissa Ln, Winter Park, FL 32789

/60
Est $1,652,755 Not Listed For Sale

1318 Chapman Cir, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 3,105 Sq Ft
- Built 2014
1318 Chapman Cir, Winter Park, FL 32789

Last Sold Summary
- 3% Above List Price
- $519/SF
- 162 Days On Market
Last Sold Price $1,612,000

Last Listing Agent Lance Kotowski Properties By Lanko, Inc

/50
$2,298,000
- 4 Beds
- 2.5 Baths
- 2,841 Sq Ft
1760 Alabama Dr, Winter Park, FL 32789

Welcome to 1760 Alabama Drive, a striking mid-century residence where architectural character, thoughtful modernization, and exceptional livability come together in one of Winter Park’s most desirable neighborhoods. Spanning 2,841 square feet, this distinctive home celebrates authentic mid-century design with clean lines, intentional geometry, and expansive walls of glass that bring the outdoors

Brian Ruth DAILLAND REAL ESTATE

1760 Alabama Dr, Winter Park, FL 32789
/14
$5,895 per month
- 4 Beds
- 3 Baths
- 2,207 Sq Ft
- House for Rent
1235 Via Estrella, Winter Park, FL 32789

Rare opportunity to lease a spacious 4-bedroom, 3-bath home in one of Winter Park's most coveted enclaves — The Vias. Spanning 2,207 SF, this sun-drenched residence sits just a short stroll from the prestigious Winter Park Racquet Club. Flooded with natural light, the open-concept living spaces feature beautiful bamboo wood floors, a well-appointed kitchen with white cabinetry and a large island,

Kelly Price KELLY PRICE & COMPANY LLC

1235 Via Estrella, Winter Park, FL 32789
/2
$2,285,000 Sold Nov 19, 2025

521 S Phelps Ave, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 3,883 Sq Ft
- Built 2015
Last Sold Summary
- 7% Below List Price
- $588/SF
- 118 Days On Market
Current Estimated Value $2,243,307

Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

521 S Phelps Ave, Winter Park, FL 32789

/14
Est $557,876 Not Listed For Sale

1821 Hammerlin Ave Unit A, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 1,818 Sq Ft
- Built 2006
1821 Hammerlin Ave Unit A, Winter Park, FL 32789

Last Sold Summary
- 1% Above List Price
- $303/SF
- 0 Days On Market
Last Sold Price $550,000

Last Listing Agent nicoletta buonaccordo ALTIS REALTY

Showing Results 41 - 80, Page 2 of 18

Florida Orange County Winter Park 32789

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

Homes in ZIP Code 32789

Real Estate & Homes

Properties in Nearby Zip Codes