Homes in ZIP Code 32789

/39
$474,000 Pending
- 2 Beds
- 1 Bath
- 925 Sq Ft
764 W Comstock Ave, Winter Park, FL 32789

Under contract-accepting backup offers. Welcome to this charming 1935 Winter Park bungalow that blends timeless character with smart, modern upgrades in one of the city’s most walkable locations. This 2-bedroom, 1-bath home offers 1,002 square feet of thoughtfully updated living space, including a remodeled kitchen and bathroom (2021), newer ROOF (2021), Carrier A/C (2020), new flooring, and a

Manny del Valle

KELLER WILLIAMS WINTER PARK

(321) 475-7512

764 W Comstock Ave, Winter Park, FL 32789
/26
$1,465 per month
- 1 Bed
- 1 Bath
- 645 Sq Ft
- Condo for Rent
2500 Lee Rd Unit 244, Winter Park, FL 32789

Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storageand an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped

Rustina Gibson

RE/MAX VANTAGE

(321) 336-5615

2500 Lee Rd Unit 244, Winter Park, FL 32789
/2
$130,000 Sold May 09, 2025

1695 Lee Rd Unit E205, Winter Park, FL 32789
- 2 Beds
- 1 Bath
- 881 Sq Ft
- Built 1966
Last Sold Summary
- 10% Below List Price
- $148/SF
- 25 Days On Market
Current Estimated Value $131,826

Last Listing Agent Joseph Pacholski KELLER WILLIAMS HERITAGE REALTY

1695 Lee Rd Unit E205, Winter Park, FL 32789

/46
Est $1,190,660 Not Listed For Sale

1778 Mondrian Cir, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,377 Sq Ft
- Built 2023
1778 Mondrian Cir, Winter Park, FL 32789

Last Sold Summary
- 5% Below List Price
- $526/SF
- 51 Days On Market
Last Sold Price $1,250,000

Last Listing Agent Brian Teach COLDWELL BANKER REALTY

/41
$245,000 Open Sun 2PM - 5PM
- 2 Beds
- 2 Baths
- 956 Sq Ft
2500 Lee Rd Unit 229, Winter Park, FL 32789

DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has

Janice Erickson

REALCOM REAL ESTATE SERVICES INC

(321) 252-5096

2500 Lee Rd Unit 229, Winter Park, FL 32789
/29
$1,799 per month
- 2 Beds
- 1 Bath
- 804 Sq Ft
- Condo for Rent
151 N Orlando Ave Unit 101, Winter Park, FL 32789

Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of theLake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & openlayout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining orcasual family meals. Granite

Elizabeth Fowler

THE FLORIDA PROPERTY SHOP SALE

(689) 588-1599

151 N Orlando Ave Unit 101, Winter Park, FL 32789
/2
$2,144,000 Sold Aug 21, 2025

1077 N Pennsylvania Ave, Winter Park, FL 32789
- 4 Beds
- 4 Baths
- 3,462 Sq Ft
- Built 2004
Last Sold Summary
- $619/SF
- 0 Days On Market
Current Estimated Value $2,127,094

Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

1077 N Pennsylvania Ave, Winter Park, FL 32789

/2
Est $1,100,764 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
- 4% Below List Price
- $666/SF
- 196 Days On Market
Last Sold Price $1,145,000

Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

/65
$1,150,000 Open Sat 12PM - 3PM
- 4 Beds
- 2.5 Baths
- 2,431 Sq Ft
1800 Magnolia Ave, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Experience refined living in this exquisitely renovated custom home, positioned on an oversized corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. Inside, soaring 10-foot ceilings

Kathy Summers

FLORIDA REALTY INVESTMENTS

(321) 306-4359

1800 Magnolia Ave, Winter Park, FL 32789
/65
$6,995 per month
- 5 Beds
- 4 Baths
- 2,918 Sq Ft
- House for Rent
2075 Jewell Ave, Winter Park, FL 32789

FULLY FURNISHED 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the perfect blend of charm, convenience, and lifestyle. Set on a

Paul Jimenez

URBANISTA BROKERS

(321) 483-3119

2075 Jewell Ave, Winter Park, FL 32789
/2
$675,000 Sold Jul 10, 2025

1511 Chestnut Ave, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,275 Sq Ft
- Built 1960
Last Sold Summary
- $529/SF
- 1 Day On Market
Current Estimated Value $668,030

Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

1511 Chestnut Ave, Winter Park, FL 32789

/26
Est $187,580 Not Listed For Sale

851 Miles Ave Unit 15, Winter Park, FL 32789
- 2 Beds
- 1 Bath
- 808 Sq Ft
- Built 1984
851 Miles Ave Unit 15, Winter Park, FL 32789

Last Sold Summary
- 1% Below List Price
- $235/SF
- 101 Days On Market
Last Sold Price $190,000

Last Listing Agent Chris Creegan CREEGAN GROUP

/41
$525,000
- 2 Beds
- 1 Bath
- 1,073 Sq Ft
1036 Aragon Ave, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just

Tim Veigle

WATSON REALTY CORP

(321) 516-0689

1036 Aragon Ave, Winter Park, FL 32789
/15
$2,975 per month
- 3 Beds
- 2 Baths
- 1,195 Sq Ft
- House for Rent
1891 Oglesby Ave, Winter Park, FL 32789

Beautifully maintained home in the highly desirable Winter Park 32789 neighborhood. This charming property offers an inviting floor plan with abundant natural light, spacious living and dining areas, and a well-appointed kitchen with generous counter space and modern finishes. Comfortable bedrooms provide ample storage, and the primary suite offers a private and peaceful retreat. Flexible bonus

Paul Jimenez

URBANISTA BROKERS

(321) 977-5674

1891 Oglesby Ave, Winter Park, FL 32789
/2
$955,000 Sold Feb 24, 2026

512 Clarendon Ave, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,824 Sq Ft
- Built 2001
Last Sold Summary
- 3% Below List Price
- $338/SF
- 21 Days On Market
Current Estimated Value $977,629

Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

512 Clarendon Ave, Winter Park, FL 32789

/2
Est $1,229,585 Not Listed For Sale

2258 Howard Dr, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 2,747 Sq Ft
- Built 1953
2258 Howard Dr, Winter Park, FL 32789

Last Sold Summary
- 2% Below List Price
- $457/SF
- 30 Days On Market
Last Sold Price $1,255,000

Last Listing Agent Greysy Ysea NAIM REAL ESTATE LLC

/40
$2,200,000
- 4 Beds
- 3.5 Baths
- 3,195 Sq Ft
872 Granville Dr, Winter Park, FL 32789

A rare offering in the highly sought-after Park Grove neighborhood, this expertly redesigned 4-bedroom residence blends elevated design with effortless everyday living. Originally renovated by award-winning interior designer John McClain and recognized with first-place honors in 2020, the home reflects a refined balance of style and functionality.??Ideally located just moments from Park Avenue

Jennifer King

CORCORAN PREMIER REALTY

(321) 485-7250

872 Granville Dr, Winter Park, FL 32789
/75

$1,465 - $3,341 per month

Bainbridge Winter Park

1 - 3 Beds

1400 Morgan Stanley Ave, Winter Park, FL 32789

Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.

1400 Morgan Stanley Ave, Winter Park, FL 32789
/2
$280,000 Sold Jul 30, 2025

700 Melrose Ave Unit A22, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,074 Sq Ft
- Built 1964
Last Sold Summary
- 11% Below List Price
- $261/SF
- 130 Days On Market
Current Estimated Value $275,942

Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

700 Melrose Ave Unit A22, Winter Park, FL 32789

/2
Est $886,530 Not Listed For Sale

533 Balmoral Rd, Winter Park, FL 32789
- 3 Beds
- 3 Baths
- 1,900 Sq Ft
- Built 1957
533 Balmoral Rd, Winter Park, FL 32789

Last Sold Summary
- 2% Below List Price
- $476/SF
- 3 Days On Market
Last Sold Price $905,000

Last Listing Agent Molly Nichols CHARLES RUTENBERG REALTY ORLANDO

/43
$550,000
- 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
/17
$1,750 per month
- 2 Beds
- 1 Bath
- 881 Sq Ft
- Condo for Rent
1695 Lee Rd Unit C206, Winter Park, FL 32789

Beautiful and move-in ready condo!Located on the second floor in a quiet community, perfect for families or professionals seeking comfort and convenience. 1.- Property Features2 Bedrooms1 Full BathroomSecond-floor unit (added privacy)Total area: 881 sqft 2.- Comfort & Interior FeaturesCentral Air ConditioningCentral HeatingCeiling FansHigh CeilingsOpen

Yein Ross ROSS RENTALS LLC

1695 Lee Rd Unit C206, Winter Park, FL 32789
/2
$1,300,000 Sold Aug 28, 2025

1500 Mizell Ave, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 2,303 Sq Ft
- Built 1957
Last Sold Summary
- $564/SF
- 2 Days On Market
Current Estimated Value $1,298,029

Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

1500 Mizell Ave, Winter Park, FL 32789

/6
Est $522,059 Not Listed For Sale

2613 Lafayette Ave, Winter Park, FL 32789
- 2 Beds
- Built 1956
2613 Lafayette Ave, Winter Park, FL 32789

Last Sold Summary
- $586/SF
- 148 Days On Market
Last Sold Price $520,000

Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC

/21
$255,000
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
1500 Gay Rd Unit 18A, Winter Park, FL 32789

REDUCED! Lakefront Community on beautiful Lake Killarney. 2 Bedroom/2 Bath First Floor Unit with Courtyard and Lake Views. Lovingly updated and meticulously maintained. Kitchen has raised ceilings, Maple Cabinets and Granite Counters. Dining Room has Cabinets matching those in Kitchen and Counters with pull-out Drawers for additional Storage. Tile Floors in Living Areas. New Carpets in both

Janice Erickson

REALCOM REAL ESTATE SERVICES INC

(321) 449-7958

1500 Gay Rd Unit 18A, Winter Park, FL 32789
/28

$1,674 per month

Elon Winter Park

1 Bed

712 Nicolet Ave, Winter Park, FL 32789

Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

712 Nicolet Ave, Winter Park, FL 32789
/2
$2,295,000 Sold Dec 16, 2025

1661 Palm Ave, Winter Park, FL 32789
- 4 Beds
- 6 Baths
- 3,570 Sq Ft
- Built 2025
Last Sold Summary
- 12% Below List Price
- $643/SF
- 26 Days On Market
Current Estimated Value $2,222,050

Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

1661 Palm Ave, Winter Park, FL 32789

/2
Est $475,995 Not Listed For Sale

1937 Eland Ave, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
- Built 1957
1937 Eland Ave, Winter Park, FL 32789

Last Sold Summary
- 3% Above List Price
- $295/SF
- 22 Days On Market
Last Sold Price $460,000

Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

/40
$2,650,000 Open Sun 1PM - 3PM
- 5 Beds
- 3.5 Baths
- 4,011 Sq Ft
1130 Park North Place, Winter Park, FL 32789

Located on a quiet cul-de-sac in the heart of Winter Park, this traditional two-story home offers a functional, well-designed floorplan for both everyday living and entertaining. From the moment you step inside, the home has an inviting warmth that you can immediately feel. The main level features a spacious primary suite along with connected living spaces that flow easily from room to room. The

Jennifer King

CORCORAN PREMIER REALTY

(321) 257-9480

1130 Park North Place, Winter Park, FL 32789
/12
$2,550 per month
- 2 Beds
- 2 Baths
- 1,140 Sq Ft
- Condo for Rent
110 Killarney Bay Ct Unit 1, Winter Park, FL 32789

Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer generous space, with a private primary suite

David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

110 Killarney Bay Ct Unit 1, Winter Park, FL 32789
/2
$2,700,000 Sold Oct 30, 2025

1020 Mayfield Ave, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 2,663 Sq Ft
- Built 1989
Last Sold Summary
- 15% Below List Price
- $1,014/SF
- 149 Days On Market
Current Estimated Value $2,594,633

Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

1020 Mayfield Ave, Winter Park, FL 32789

/2
Est $355,252 Not Listed For Sale

829 W New England Ave, Winter Park, FL 32789
- 3 Beds
- Built 1930
829 W New England Ave, Winter Park, FL 32789

Last Sold Summary
- 4% Above List Price
- $324/SF
- 16 Days On Market
Last Sold Price $340,000

Last Listing Agent Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

/22
$262,000
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
1500 Gay Rd Unit 20D, Winter Park, FL 32789

LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE.BRIGHT SUN-FILLED

Janice Erickson

REALCOM REAL ESTATE SERVICES INC

(689) 399-5336

1500 Gay Rd Unit 20D, Winter Park, FL 32789
/53

$1,635 - $9,294 per month

Juno Winter Park

Studio - 3 Beds

1305 Morgan Stanley Ave, Winter Park, FL 32789

Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

1305 Morgan Stanley Ave, Winter Park, FL 32789
/2
$4,100,000 Sold Apr 18, 2025

1691 Chestnut Ave, Winter Park, FL 32789
- 5 Beds
- 4.5 Baths
- 4,582 Sq Ft
- Built 2024
Last Sold Summary
- 15% Below List Price
- $895/SF
- 1 Day On Market
Current Estimated Value $4,040,574

Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC

1691 Chestnut Ave, Winter Park, FL 32789

/49
Est $1,667,650 Not Listed For Sale

1781 Goodrich Ave, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,701 Sq Ft
- Built 2024
1781 Goodrich Ave, Winter Park, FL 32789

Last Sold Summary
- 1% Above List Price
- $611/SF
- 88 Days On Market
Last Sold Price $1,650,000

Last Listing Agent Laura Hope COMPASS FLORIDA LLC

/21
$264,000
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
1500 Gay Rd Unit 24B, Winter Park, FL 32789

ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS!Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters,

Janice Erickson

REALCOM REAL ESTATE SERVICES INC

(321) 450-8960

1500 Gay Rd Unit 24B, Winter Park, FL 32789
/25
$2,500 per month
- 3 Beds
- 1.5 Baths
- 1,279 Sq Ft
- House for Rent
2846 Euston Rd, Winter Park, FL 32789

Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes form I4, close to Park Avenue District, College Park, major shopping centers and many more. Big backyard with a nice sized paved courtyard and

Vanessa Laboy 365 REALTY, INC.

2846 Euston Rd, Winter Park, FL 32789
/2
$775,000 Sold May 21, 2025

1818 Mondrian Cir, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,265 Sq Ft
- Built 2018
Last Sold Summary
- 6% Below List Price
- $342/SF
- 189 Days On Market
Current Estimated Value $797,659

Last Listing Agent Brian Teach COLDWELL BANKER REALTY

1818 Mondrian Cir, Winter Park, FL 32789

/2
Est $3,396,363 Not Listed For Sale

443 Lakewood Dr, Winter Park, FL 32789
- 3 Beds
- 5 Baths
- 2,803 Sq Ft
- Built 1954
443 Lakewood Dr, Winter Park, FL 32789

Last Sold Summary
- 4% Below List Price
- $1,267/SF
- 0 Days On Market
Last Sold Price $3,550,000

Last Listing Agent Jenny Lake FANNIE HILLMAN & ASSOCIATES

Showing Results 1 - 40, Page 1 of 18

Florida Orange County Winter Park 32789

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