Homes in ZIP Code 32789

/38
$825,000

$25K PRICE DROP
- 2 Beds
- 2 Baths
- 1,540 Sq Ft
1431 Palm Ave, Winter Park, FL 32789

Welcome to this beautifully maintained 1960s home nestled in one of Winter Park’s desirable neighborhoods, where classic charm meets thoughtful modern updates. Set along picturesque brick streets shaded by mature trees, this inviting home offers a warm, light-filled interior and a private backyard oasis. From the moment you enter, you’ll notice the abundance of natural light and the large windows

Kelsey Payton ALL REAL ESTATE & INVESTMENTS

1431 Palm Ave, Winter Park, FL 32789
/46
$4,295 Per Month
- 4 Beds
- 3 Baths
- 2,134 Sq Ft
- 4/3 WINTER PARK POOL HOME WITH WINTER PARK SCHOOLS! (Orange County Winter Park Schools)
1625 Tioga Trail, Winter Park, FL 32789

A RARE FIND IN WINTER PARK!! 4 BEDROOMS, 3 BATHROOMS, POOL, AND FENCED BACKYARD.Welcome home to this beautifully updated 4-bedroom, 3-bath pool home nestled on a quiet cul-de-sac in Winter Park Hills. Surrounded by million-dollar homes and zoned for excellent Winter Park schools (Dommerich Elementary, Maitland Middle and Winter Park High), this exceptional rental offers the perfect

1625 Tioga Trail, Winter Park, FL 32789
/24
$649,000

Sold Oct 17, 2025

2304 Depauw Ave, Orlando, FL 32804
- 3 Beds
- 2.5 Baths
- 1,668 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $389/SF
- 199 Days On Market
Current Estimated Value $687,000

David Weekley Homes Central Living - Downtown

2304 Depauw Ave, Orlando, FL 32804

/2
Est $1,441,948

Not Listed For Sale

1077 Minnesota Ave, Winter Park, FL 32789
- 4 Beds
- 4 Baths
- 3,046 Sq Ft
- Built 2025
1077 Minnesota Ave, Winter Park, FL 32789

Last Sold Summary
- 75 Days On Market
Last Listing Agent Jake Johnson SHORES REAL ESTATE

/27
$424,400

$51K PRICE DROP Pending
- 1 Bed
- 1 Bath
- 767 Sq Ft
644 N Knowles Ave Unit 3, Winter Park, FL 32789

Virtually Staged. LOCATION! LOCATION! LOCATION! Welcome to Knowles Manor...a charming 11 unit condo perched on quiet brick street in the heart of Olde Winter Park...just steps from the Winter Park 9 golf course, Casa Feliz, and the boutiques, restaurants, and vibrant lifestyle of Park Avenue, this location is hard to beat. This delightful first-floor residence is the perfect place to call home or

Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

644 N Knowles Ave Unit 3, Winter Park, FL 32789
/82
$1,850 Per Month
- 3 Beds
- 2 Baths
- 1,149 Sq Ft
- Condo for Rent
1695 Lee Rd Unit E215, Winter Park, FL 32789

Discover your ideal home in this newly renovated 3-bedroom, 2-bathroom condo at Waterfall Cove in Winter Park, FL. Enjoy fresh paint, modern stainless steel appliances, and a fully upgraded kitchen that makes cooking a delight. Each spacious room offers plenty of natural light and comfort. This condo comes equipped with a washer and dryer, and includes cable and internet for your convenience. The

Jenaia Fowlkes FOWLKES REALTY CO

1695 Lee Rd Unit E215, Winter Park, FL 32789
/2
$500,000

Sold May 27, 2026

720 W Webster Ave, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
- Built 1950
Last Sold Summary
- 9% Below List Price
- $369/SF
- 54 Days On Market
Current Estimated Value $501,470

Last Listing Agent Vincent Cordaro SERHANT

720 W Webster Ave, Winter Park, FL 32789

/2
Est $789,667

Not Listed For Sale

2320 Janice Ave, Winter Park, FL 32789
2320 Janice Ave, Winter Park, FL 32789

Last Sold Summary
- 2 Days On Market
Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES

/12
$1,699,000

New Construction
- 4 Beds
- 3.5 Baths
- 2,530 Sq Ft
2308 Mulbry Dr, Winter Park, FL 32789

Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balances contemporary grandeur with effortless livability. Spanning 2,500 square feet of open-concept living space, the home features four bedrooms and three-and-a-half lavish bathrooms. Framed by hand-selected architectural stone, the elegant entryway reveals a luminous interior anchored by wide-plank light oak

Brandon Geers COMPASS FLORIDA LLC

2308 Mulbry Dr, Winter Park, FL 32789
/27
$2,200 Per Month
- 3 Beds
- 2 Baths
- 1,158 Sq Ft
- House for Rent
301 S Capen Ave, Winter Park, FL 32789

Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue.Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage.Down the hall, you'll find three

301 S Capen Ave, Winter Park, FL 32789
/2
$160,000

Sold Jun 05, 2026

2500 Lee Rd Unit 122, Winter Park, FL 32789
- 1 Bed
- 1 Bath
- 645 Sq Ft
- Built 1969
Last Sold Summary
- 11% Below List Price
- $248/SF
- 60 Days On Market
Current Estimated Value $161,423

Last Listing Agent Andrea Aylett-Hosch PINEAPPLE PLACE REALTY, LLC

2500 Lee Rd Unit 122, Winter Park, FL 32789

/2
Est $1,021,011

Not Listed For Sale

1975 Biscayne Dr, Winter Park, FL 32789
- 5 Beds
- 4 Baths
- 3,270 Sq Ft
- Built 2020
1975 Biscayne Dr, Winter Park, FL 32789

Last Sold Summary
- 68 Days On Market
Last Listing Agent nana Ahn SOGO REAL ESTATE SERVICES LLC

/32
$1,300,000
- 3 Beds
- 2.5 Baths
- 2,563 Sq Ft
504 W Swoope Ave, Winter Park, FL 32789

Enjoy luxury living and premium sought-after location at Vilasa Homes, the newest construction in Winter Park, FL 32789. Walk to Park Avenue lifestyle, arts and culture- a mini-version of Manhattan’s Central Park, brick streets, historic neighborhoods, area’s hottest restaurants, shopping and the prestigious Rollins College. The finishes for this 2-estory townhome personally selected by one of

Jennifer Sloan COMPASS FLORIDA LLC

504 W Swoope Ave, Winter Park, FL 32789
/33
$9,900 Per Month
- 5 Beds
- 6 Baths
- 2,735 Sq Ft
- House for Rent
1442 Palm Ave, Winter Park, FL 32789

Gorgeous 5-bedroom /6-bathroom Luxury Estate with Guest House & Pool in Winter ParkThis stunning two-story home offers the perfect blend of luxury and comfort right in the heart of Winter Park. At the center of the home is a beautiful open kitchen outfitted with high-end appliances, solid wood cabinets, and granite countertops . A true chef’s layout that flows into the living spaces. You'll

Magdalena Cuprys KELLER WILLIAMS REALTY AT THE PARKS

1442 Palm Ave, Winter Park, FL 32789
/2
$145,000

Sold Apr 23, 2026

2500 Lee Rd Unit 243, Winter Park, FL 32789
- 1 Bed
- 1 Bath
- 645 Sq Ft
- Built 1969
Last Sold Summary
- 28% Below List Price
- $225/SF
- 286 Days On Market
Current Estimated Value $146,596

Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

2500 Lee Rd Unit 243, Winter Park, FL 32789

/2
Est $1,737,235

Not Listed For Sale

643 Balmoral Rd, Winter Park, FL 32789
643 Balmoral Rd, Winter Park, FL 32789

Last Sold Summary
- 17 Days On Market
Last Listing Agent Laura Hope COMPASS FLORIDA LLC

/59
$2,195,000

Open Sun 1PM - 3PM $100K PRICE DROP
- 5 Beds
- 3.5 Baths
- 3,691 Sq Ft
1885 Temple Dr, Winter Park, FL 32789

Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich

Jennifer Sloan COMPASS FLORIDA LLC

1885 Temple Dr, Winter Park, FL 32789
/2
$1,800 Per Month
- 1 Bed
- 1 Bath
- House for Rent
759 Antonette Ave, Winter Park, FL 32789

Wonderful 1 bedroom, 1 bathroom half of a duplex for rent in the College Quarter neighborhood of Winter Park. The location is walking distance to Park Ave and Rollins College. Inside the property there is a spacious living and bedroom, kitchen with a stackable washer/ dryer and a bathroom. There are charming wood floors and a spacious closet. Outside there is a detached shed, perfect for storing

759 Antonette Ave, Winter Park, FL 32789
/2
$850,000

Sold Mar 31, 2026

1929 S Lakemont Ave, Winter Park, FL 32792
- 3 Beds
- 3.5 Baths
- 2,160 Sq Ft
- Built 2023
Last Sold Summary
- 10% Below List Price
- $394/SF
- 91 Days On Market
Current Estimated Value $788,997

Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

1929 S Lakemont Ave, Winter Park, FL 32792

/2
Est $287,440

Not Listed For Sale

311 E Morse Blvd Unit 7-15, Winter Park, FL 32789
- 1 Bed
- 1 Bath
- 482 Sq Ft
- Built 1960
311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

Last Sold Summary
- 3 Days On Market
Last Listing Agent Susan Logan LOGAN LAND & HOMES, INC.

/5
$2,700,000

New Construction
- 5 Beds
- 4.5 Baths
- 3,588 Sq Ft
648 Worthington Dr, Winter Park, FL 32789

Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable pocket of Winter Park. A sophisticated modern farmhouse façade creates an impressive first impression, framed by a sweeping double-entry curved driveway that gives the home a commanding yet welcoming presence. Inside, the

Christopher Christensen ONE LUXURY INTERNATIONAL LLC

648 Worthington Dr, Winter Park, FL 32789
/17
$2,095 Per Month
- 3 Beds
- 1.5 Baths
- 1,514 Sq Ft
- House for Rent
2028 Albert Lee Pkwy, Winter Park, FL 32789

This charming 3 bedroom, 2 bathroom home is located in the heart of Winter Park. Enjoy the best of Downtown Winter Park, Park Avenue's shops and restaurants, Winter Park Village, 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, a lovely kitchen, dining room, large bedrooms, a cozy

Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

2028 Albert Lee Pkwy, Winter Park, FL 32789
/2
$510,000

Sold Jul 21, 2026

641 W Lyman Ave, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 2003
Last Sold Summary
- $455/SF
- 12 Days On Market
Current Estimated Value $506,872

Last Listing Agent Ted Moseley REAL BROKER, LLC

641 W Lyman Ave, Winter Park, FL 32789

/2
Est $1,064,140

Not Listed For Sale

1782 Mondrian Cir, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,377 Sq Ft
- Built 2023
1782 Mondrian Cir, Winter Park, FL 32789

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

/26
$370,000
- 3 Beds
- 2 Baths
- 1,283 Sq Ft
780 Baffie Ave, Winter Park, FL 32789

Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

Melissa Woodman FANNIE HILLMAN & ASSOCIATES

780 Baffie Ave, Winter Park, FL 32789
/29
$2,495 Per Month
- 2 Beds
- 2 Baths
- 1,140 Sq Ft
- House for Rent
720 Killarney Bay Ct, Winter Park, FL 32789

LAKE KILLARNEY CONDO IN WINTER PARK! Enjoy the best of Winter Park living in this beautiful 2-bedroom, 2-bath corner condo in the private lakefront community of Killarney Bay. Featuring an open floor plan, stone and wood flooring, high ceilings, quartz kitchen countertops, stainless-steel appliances, generous storage, and a stunning stone-accented fireplace. Plus a utility room with a full size

720 Killarney Bay Ct, Winter Park, FL 32789
/2
$3,020,000

Sold Oct 02, 2025

1820 Englewood Rd, Winter Park, FL 32789
- 5 Beds
- 5.5 Baths
- 4,263 Sq Ft
- Built 2015
Last Sold Summary
- 8% Below List Price
- $708/SF
- 70 Days On Market
Current Estimated Value $3,112,433

Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

1820 Englewood Rd, Winter Park, FL 32789

/2
Est $1,372,383

Not Listed For Sale

1733 Harmon Ave, Winter Park, FL 32789
- 5 Beds
- 4.5 Baths
- 3,267 Sq Ft
- Built 2025
1733 Harmon Ave, Winter Park, FL 32789

Last Sold Summary
- 27 Days On Market
Last Listing Agent Jordan Freeland SOUTH REALTY, INC

/66
$3,265,000
- 5 Beds
- 5.5 Baths
- 4,924 Sq Ft
1761 Legion Dr, Winter Park, FL 32789

One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, and an unbeatable location. Completed in 2017 and first sold in 2018, this 5-bedroom, 5.5-bath home has been meticulously maintained by its original owner and enhanced with high-end designer finishes. Much of the interior was

Harry Pool, III COLDWELL BANKER REALTY

1761 Legion Dr, Winter Park, FL 32789
/50
$4,677 Per Month
- 4 Beds
- 3 Baths
- 2,267 Sq Ft
- House for Rent
350 N Phelps Ave, Winter Park, FL 32789

Beautifully updated home in the heart of Winter Park - available November 1! Welcome to 350 North Phelps Avenue. This move-in-ready home offers four bedrooms, three full bathrooms, an open split floor plan, a bonus room with French doors, and a large fenced backyard, blending modern elegance with timeless charm. The house has a Tesla Level 2 fast charger and a state-of-the-art reverse osmosis

AJ Lash GOYAL & DECOSTER REALTY

350 N Phelps Ave, Winter Park, FL 32789
/67
$4,000,000

Sold Sep 14, 2026

1180 Via Lugano, Winter Park, FL 32789
- 5 Beds
- 5.5 Baths
- 4,961 Sq Ft
- Built 2006
Last Sold Summary
- 18% Below List Price
- $806/SF
- 47 Days On Market
Current Estimated Value $4,822,693

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

1180 Via Lugano, Winter Park, FL 32789

/2
Est $392,539

Not Listed For Sale

740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789
- 2 Beds
- 2.5 Baths
- 1,536 Sq Ft
- Built 1986
740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

Last Sold Summary
- 171 Days On Market
Last Listing Agent Michael O'Shaughnessy MICHAEL O'SHAUGHNESSY, INC.

/10
$1,749,000

New Construction
- 4 Beds
- 3.5 Baths
- 2,715 Sq Ft
2525 Lafayette Ave, Winter Park, FL 32789

Under Construction. Currently under construction by LUIH Luxury Homes, this exceptional new construction residence is anticipated for completion in November 2026 and brings contemporary design and elevated living to one of Winter Park's most desirable neighborhoods. Offering 4 bedrooms, 3.5 bathrooms, and 2,715 square feet of thoughtfully designed living space, the home blends clean architectural

Matt Tomaszewski CORCORAN PREMIER REALTY

2525 Lafayette Ave, Winter Park, FL 32789
/11
$1,795 Per Month
- 3 Beds
- 1.5 Baths
- 1,024 Sq Ft
- House for Rent
731 W Comstock Ave, Winter Park, FL 32789

Close to downtown Winter Park, Winter Park Village, and Park Avenue - Charming 3 bedroom 1.5 bath home, with single carport, fenced backyard, ceiling fans and blinds. Tile floors in main living areas and NEW carpet in bedrooms. Additional sun room located off the kitchen with entry to/from carport. This home is available for immediate move in. PETS NEGOTIABLE. Please call to schedule an

731 W Comstock Ave, Winter Park, FL 32789
/2
$2,150,000

Sold Aug 13, 2026

2361 Mulbry Dr, Winter Park, FL 32789
- 4 Beds
- 4 Baths
- 3,130 Sq Ft
- Built 2026
Last Sold Summary
- 10% Below List Price
- $687/SF
- 77 Days On Market
Current Estimated Value $1,953,802

Last Listing Agent Ahmad Hassan COMPASS FLORIDA LLC

2361 Mulbry Dr, Winter Park, FL 32789

/2
Est $666,000

Not Listed For Sale

1632 Haven Dr, Orlando, FL 32803
- 3 Beds
- 2.5 Baths
- 1,772 Sq Ft
- Built 2025
1632 Haven Dr, Orlando, FL 32803

Last Sold Summary
- 110 Days On Market
Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

/18
$130,000
- 1 Bed
- 1 Bath
- 645 Sq Ft
2500 Lee Rd Unit 143, Winter Park, FL 32789

It doesn't get much better than this: Living in a Lakefront and Winter Park community, that is convenient to I-4 providing easy access to points north and south, downtown Winter Park, shopping, fine dining, and the price can't be beat. The HOA dues includes water, trash pickup, a full package from Spectrum including internet. Lakeside Manor is situated on the north side of Lake Killarney, a 239

Carol Wittman PALMANO GROUP RE BROKERAGE LLC

2500 Lee Rd Unit 143, Winter Park, FL 32789
/46
$7,250 Per Month
- 4 Beds
- 2.5 Baths
- 2,394 Sq Ft
- House for Rent
1368 Hibiscus Ave, Winter Park, FL 32789

Discover refined living in the heart of Winter Park in this beautifully appointed 4-bedroom, 2.5-bathroom single-family pool home. Immediately to the right of the entryway, a beautiful private office provides a convenient and quiet space for working from home or studying.Filled with natural light, the home features an inviting open layout, and a spacious living area centered around a cozy

Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

1368 Hibiscus Ave, Winter Park, FL 32789
/2
$389,900

Sold Mar 18, 2026

700 Melrose Ave Unit M4, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,074 Sq Ft
- Built 1964
Last Sold Summary
- 1% Below List Price
- $363/SF
- 7 Days On Market
Current Estimated Value $381,022

Last Listing Agent Mary Harmening ROAM FLORIDA REALTY LLC

700 Melrose Ave Unit M4, Winter Park, FL 32789

/2
Not Listed For Sale

1630 Haven Dr, Orlando, FL 32803
- 3 Beds
- 2.5 Baths
- 1,668 Sq Ft
- Built 2024
1630 Haven Dr, Orlando, FL 32803

Last Sold Summary
- 53 Days On Market
Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

Showing Results 121 - 160, Page 4 of 18

Florida Orange County Winter Park

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