Homes in ZIP Code 32789

/89
$8,950,000
- 7 Beds
- 11 Baths
- 11,255 Sq Ft
1120 Preserve Point Dr, Winter Park, FL 32789

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths.

Hal George PREMIER SOTHEBY'S INTL. REALTY

1120 Preserve Point Dr, Winter Park, FL 32789
/2
$600,000 Sold Oct 17, 2025

2812 Woodside Ave, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,842 Sq Ft
- Built 1952
Last Sold Summary
- 4% Below List Price
- $326/SF
- 50 Days On Market
Current Estimated Value $589,359

Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

2812 Woodside Ave, Winter Park, FL 32789

/2
Est $272,876 Not Listed For Sale

700 Melrose Ave Unit M33, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,074 Sq Ft
- Built 1964
700 Melrose Ave Unit M33, Winter Park, FL 32789

Last Sold Summary
- 3% Above List Price
- $247/SF
- 155 Days On Market
Last Sold Price $265,000

Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

/65
$4,295,000
- 4 Beds
- 4.5 Baths
- 4,181 Sq Ft
1161 Valencia Ave, Winter Park, FL 32789

Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a

Lisa Mahjoub THE REAL ESTATE COLLECTION LLC

1161 Valencia Ave, Winter Park, FL 32789
/2
$2,594,550 Sold May 09, 2025

254 Sylvan Blvd, Winter Park, FL 32789
- 3 Beds
- 3 Baths
- 3,653 Sq Ft
- Built 2000
Last Sold Summary
- 4% Below List Price
- $710/SF
- 8 Days On Market
Current Estimated Value $2,537,253

Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

254 Sylvan Blvd, Winter Park, FL 32789

/2
Est $2,077,499 Not Listed For Sale

660 Osceola Ave Unit 104, Winter Park, FL 32789
- 3 Beds
- 3 Baths
- 2,632 Sq Ft
- Built 1999
660 Osceola Ave Unit 104, Winter Park, FL 32789

Last Sold Summary
- 8% Below List Price
- $855/SF
- 21 Days On Market
Last Sold Price $2,250,000

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

/27
$495,000
- 1 Bed
- 2 Baths
- 1,149 Sq Ft
300 Carolina Ave Unit 207C, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Enjoy the best of downtown Winter Park living in this spacious 1-bedroom, 2-bathroom condominium located in the highly sought-after Park West Condominiums. This well designed residence offers comfortable living with the rare convenience of two full bathrooms. Park West is a gated community known for its exceptional amenities, including a

Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

300 Carolina Ave Unit 207C, Winter Park, FL 32789
/2
$1,025,000 Sold Jun 27, 2025

2680 Oglesby Ave, Winter Park, FL 32789
- 4 Beds
- 2.5 Baths
- 2,546 Sq Ft
- Built 2019
Last Sold Summary
- 2% Below List Price
- $403/SF
- 55 Days On Market
Current Estimated Value $1,022,742

Last Listing Agent Kris Kennedy COMPASS FLORIDA LLC

2680 Oglesby Ave, Winter Park, FL 32789

/22
Est $214,047 Not Listed For Sale

700 Melrose Ave Unit L33, Winter Park, FL 32789
- 1 Bed
- 1 Bath
- 917 Sq Ft
- Built 1964
700 Melrose Ave Unit L33, Winter Park, FL 32789

Last Sold Summary
- 3% Below List Price
- $240/SF
- 76 Days On Market
Last Sold Price $220,000

Last Listing Agent Mary Harmening ROAM FLORIDA REALTY LLC

/61
$1,795,000 Open Sat 1PM - 3PM
- 5 Beds
- 3.5 Baths
- 3,304 Sq Ft
2501 Winter Park Rd, Winter Park, FL 32789

A masterfully crafted custom residence in the heart of Winter Park, this 2014 Barefoot Brothers home blends timeless architecture with modern functionality just moments from Park Avenue and the Audubon Park Garden District. Designed for both refined entertaining and active everyday living, this 5-bedroom + office home offers a flexible, family-focused floor plan plus an expansive second floor

Jill Healey KELLER WILLIAMS WINTER PARK

2501 Winter Park Rd, Winter Park, FL 32789
/2
$5,250,000 Sold Mar 31, 2025

210 Chelton Cir, Winter Park, FL 32789
- 5 Beds
- 5.5 Baths
- 5,264 Sq Ft
- Built 2024
Last Sold Summary
- 8% Below List Price
- $997/SF
- 125 Days On Market
Current Estimated Value $5,457,476

Last Listing Agent Laura Earl CORCORAN PREMIER REALTY

210 Chelton Cir, Winter Park, FL 32789

/18
Est $310,473 Not Listed For Sale

700 Melrose Ave Unit K33, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,074 Sq Ft
- Built 1964
700 Melrose Ave Unit K33, Winter Park, FL 32789

Last Sold Summary
- 11% Above List Price
- $260/SF
- 1 Day On Market
Last Sold Price $279,000

Last Listing Agent Michael Ford FANNIE HILLMAN & ASSOCIATES

/53
$949,900 New Construction
- 3 Beds
- 3 Baths
- 1,875 Sq Ft
870 Carver St, Winter Park, FL 32789

Welcome to 870 Carver Street, a versatile three-bedroom, three-bath residence offering privacy, thoughtful design, and two distinct living experiences in the heart of Winter Park. With 1,875 square feet under air, the property includes a 1,209-square-foot, two-bedroom, two-bath main home and a 666-square-foot, one-bedroom, one-bath garage apartment, ideal for multigenerational living, rental

Drew Henner PREMIER SOTHEBY'S INTL. REALTY

870 Carver St, Winter Park, FL 32789
/2
$2,400,000 Sold Mar 28, 2025

1010 N Pennsylvania Ave, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 4,074 Sq Ft
- Built 2017
Last Sold Summary
- 14% Below List Price
- $589/SF
- 94 Days On Market
Current Estimated Value $2,495,844

Last Listing Agent Dana Laing BHHS FLORIDA REALTY

1010 N Pennsylvania Ave, Winter Park, FL 32789

/39
Est $279,269 Not Listed For Sale

700 Melrose Ave Unit K3, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,074 Sq Ft
- Built 1964
700 Melrose Ave Unit K3, Winter Park, FL 32789

Last Sold Summary
- 5% Above List Price
- $247/SF
- 62 Days On Market
Last Sold Price $265,000

Last Listing Agent Julie Glass KEYSEEKERS REAL ESTATE

/22
$399,999 Pending
- 2 Beds
- 1 Bath
- 987 Sq Ft
3505 Corrine Dr, Orlando, FL 32803

Under contract-accepting backup offers. Live steps from everything that makes the Audubon Park Garden District one of Orlando’s most sought-after neighborhoods. Located along Corrine Drive, this mid-century home in Audubon Park offers unbeatable shopping, dining, and local favorites including the beloved East End Market. As you arrive, the classic mid-century character and welcoming curb appeal

Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

3505 Corrine Dr, Orlando, FL 32803
/2
$1,050,000 Sold Jul 14, 2025

795 W Canton Ave, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,374 Sq Ft
- Built 2017
Last Sold Summary
- 9% Below List Price
- $442/SF
- 23 Days On Market
Current Estimated Value $1,053,889

Last Listing Agent Margo Rochelle WEICHERT REALTORS HALLMARK PROPERTIES

795 W Canton Ave, Winter Park, FL 32789

/2
Est $177,719 Not Listed For Sale

700 Melrose Ave Unit G34, Winter Park, FL 32789
- Studio
- 1 Bath
- 624 Sq Ft
- Built 1964
700 Melrose Ave Unit G34, Winter Park, FL 32789

Last Sold Summary
- 5% Below List Price
- $300/SF
- 0 Days On Market
Last Sold Price $187,500

Last Listing Agent Luly Cueto-Lauridsen PARK PLACE REAL ESTATE

/8
$800,000 Pending
- Land
- 0.19 Acre
- $4,210,526 per Acre
1760 Bryan Ave, Winter Park, FL 32789

Under contract-accepting backup offers. Discover a truly unique offering in the heart of Winter Park! This property, located at 1760 Bryan Avenue, is being offered along with the adjoining lots at 1770 and 1780 Bryan Avenue. While available together as a rare collection of three consecutive parcels, each lot is also being sold separately at individual prices, giving buyers the flexibility to

Nickolas McKee KELLER WILLIAMS WINTER PARK

1760 Bryan Ave, Winter Park, FL 32789
/2
$1,480,000 Sold Sep 19, 2025

1742 Barcelona Way, Winter Park, FL 32789
- 5 Beds
- 8 Baths
- 3,626 Sq Ft
- Built 1973
Last Sold Summary
- 18% Below List Price
- $408/SF
- 81 Days On Market
Current Estimated Value $1,494,204

Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

1742 Barcelona Way, Winter Park, FL 32789

/20
Est $362,279 Not Listed For Sale

700 Melrose Ave Unit C2, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 1,448 Sq Ft
- Built 1964
700 Melrose Ave Unit C2, Winter Park, FL 32789

Last Sold Summary
- 11% Above List Price
- $224/SF
- 35 Days On Market
Last Sold Price $325,000

Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

/21
$550,000 Pending
- 2 Beds
- 2 Baths
- 986 Sq Ft
535 N Interlachen Ave Unit 203, Winter Park, FL 32789

Under contract-accepting backup offers. Experience effortless luxury living just blocks from iconic Park Avenue in this stunning, fully renovated condo located in the heart of downtown Winter Park. Perfectly designed for a lock-and-leave lifestyle, this beautifully upgraded residence blends timeless elegance with modern convenience. Step into a beautifully designed foyer entry that opens to

Mary Colton FANNIE HILLMAN & ASSOCIATES

535 N Interlachen Ave Unit 203, Winter Park, FL 32789
/2
$1,500,000 Sold May 14, 2025

1741 Pine Ave, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 3,297 Sq Ft
- Built 2002
Last Sold Summary
- $455/SF
- 7 Days On Market
Current Estimated Value $1,560,876

Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

1741 Pine Ave, Winter Park, FL 32789

/44
Est $2,176,138 Not Listed For Sale

200 S Interlachen Ave Unit 400, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 3,074 Sq Ft
- Built 2001
200 S Interlachen Ave Unit 400, Winter Park, FL 32789

Last Sold Summary
- 7% Below List Price
- $764/SF
- 40 Days On Market
Last Sold Price $2,350,000

Last Listing Agent Lisa Shear FANNIE HILLMAN & ASSOCIATES

/29
$949,000
- 2 Beds
- 2 Baths
- 1,086 Sq Ft
560 Ololu Dr, Winter Park, FL 32789

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this

Tiffany Yates COMPASS FLORIDA LLC

560 Ololu Dr, Winter Park, FL 32789
/2
$560,000 Sold Aug 19, 2025

1339 Orchid Ave, Winter Park, FL 32789
- 2 Beds
- 1 Bath
- 789 Sq Ft
- Built 1953
Last Sold Summary
- 12% Below List Price
- $710/SF
- 46 Days On Market
Current Estimated Value $551,301

Last Listing Agent Barbara Allen ABIDE REALTY

1339 Orchid Ave, Winter Park, FL 32789

/2
Est $2,641,245 Not Listed For Sale

315 E New England Ave Unit 30, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 3,130 Sq Ft
- Built 2008
315 E New England Ave Unit 30, Winter Park, FL 32789

Last Sold Summary
- 6% Below List Price
- $895/SF
- 1 Day On Market
Last Sold Price $2,800,000

Last Listing Agent Michelle Daniels COLDWELL BANKER REALTY

/41
$115,000
- 2 Beds
- 1 Bath
- 881 Sq Ft
1695 Lee Rd Unit C214, Winter Park, FL 32789

Charming 2-bedroom, 1-bath condo located in the heart of Winter Park. This well-maintained unit offers comfortable living with an open layout, ample natural light, and convenient access to shopping, and dining. Enjoy the community pool and beautifully landscaped grounds, perfect for relaxing or entertaining. Ideal for first-time buyers, investors, or anyone looking to enjoy the Winter Park

Diana Perez PROFESSIONAL REAL ESTATE TEAM

1695 Lee Rd Unit C214, Winter Park, FL 32789
/2
$975,000 Sold Mar 25, 2026

456 Carolina Ave, Winter Park, FL 32789
- 3 Beds
- 3 Baths
- 1,615 Sq Ft
- Built 2004
Last Sold Summary
- 3% Below List Price
- $604/SF
- 9 Days On Market
Current Estimated Value $1,049,938

Last Listing Agent Heather Frazee FANNIE HILLMAN & ASSOCIATES

456 Carolina Ave, Winter Park, FL 32789

/2
Est $1,606,274 Not Listed For Sale

315 E New England Ave Unit 9, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,637 Sq Ft
- Built 2007
315 E New England Ave Unit 9, Winter Park, FL 32789

Last Sold Summary
- 3% Below List Price
- $1,008/SF
- 5 Days On Market
Last Sold Price $1,650,000

Last Listing Agent Anna Lohr URBANISTA BROKERS

/49
$180,000
- 2 Beds
- 2 Baths
- 956 Sq Ft
2500 Lee Rd Unit 208, Winter Park, FL 32789

This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents

Debbie Fussell KELLER WILLIAMS REALTY AT THE PARKS

2500 Lee Rd Unit 208, Winter Park, FL 32789
/2
$475,000 Sold Oct 14, 2025

621 Symonds Ave, Winter Park, FL 32789
- Land
- 0.13 Acre
- $3,653,846 per Acre
Last Sold Summary
- 12% Below List Price
- 147 Days On Market
Current Estimated Value $472,210

Last Listing Agent Emily Williams FANNIE HILLMAN & ASSOCIATES

621 Symonds Ave, Winter Park, FL 32789

/100
Est $3,178,137 Not Listed For Sale

300 S Interlachen Ave Unit 303, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 3,355 Sq Ft
- Built 2005
300 S Interlachen Ave Unit 303, Winter Park, FL 32789

Last Sold Summary
- 5% Below List Price
- $999/SF
- 11 Days On Market
Last Sold Price $3,350,000

Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

/30
$3,100,000
- 5 Beds
- 4.5 Baths
- 3,896 Sq Ft
457 E New England Ave, Winter Park, FL 32789

Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented

Mick Night PREMIER SOTHEBY'S INTL. REALTY

457 E New England Ave, Winter Park, FL 32789
/2
$230,000 Sold May 30, 2025

1500 Gay Rd Unit 10C, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
- Built 1972
Last Sold Summary
- 7% Below List Price
- $224/SF
- 75 Days On Market
Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

1500 Gay Rd Unit 10C, Winter Park, FL 32789

/24
Est $217,703 Not Listed For Sale

1250 S Denning Dr Unit 126, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 893 Sq Ft
- Built 1967
1250 S Denning Dr Unit 126, Winter Park, FL 32789

Last Sold Summary
- 1% Below List Price
- $245/SF
- 66 Days On Market
Last Sold Price $219,025

Last Listing Agent Shahram Sondi SHAHRAM SONDI + CO.

/41
$2,049,000 New Construction
- 5 Beds
- 3.5 Baths
- 2,964 Sq Ft
785 N Phelps Ave, Winter Park, FL 32789

Exquisite new construction in the heart of Winter Park, this LUIH Luxury Homes residence distinguishes itself through refined design, thoughtful efficiency, and an elevated level of craftsmanship. From the moment you enter, the home reveals itself with deliberate intention, clean architectural lines and a light-filled, open-concept layout create an effortless flow throughout. The main living

Christopher Christensen ONE LUXURY INTERNATIONAL LLC

785 N Phelps Ave, Winter Park, FL 32789
/2
$1,740,000 Sold Aug 29, 2025

443 Beloit Ave, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 2,964 Sq Ft
- Built 1983
Last Sold Summary
- 3% Below List Price
- $587/SF
- 0 Days On Market
Current Estimated Value $1,733,713

Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

443 Beloit Ave, Winter Park, FL 32789

/41
Est $1,041,484 Not Listed For Sale

100 S Virginia Ave Unit 316, Winter Park, FL 32789
- 3 Beds
- 3 Baths
- 2,599 Sq Ft
- Built 2008
100 S Virginia Ave Unit 316, Winter Park, FL 32789

Last Sold Summary
- 8% Above List Price
- $371/SF
- 140 Days On Market
Last Sold Price $965,000

Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

/24
$209,999
- 2 Beds
- 1 Bath
- 808 Sq Ft
851 Miles Ave Unit 13, Winter Park, FL 32789

Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready.As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to

Eric Campbell LPT REALTY, LLC

851 Miles Ave Unit 13, Winter Park, FL 32789

Showing Results 481 - 520, Page 13 of 18

Florida Orange County Winter Park 32789

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