Homes in ZIP Code 32789

/52
$1,150,000
- 4 Beds
- 2 Baths
- 2,750 Sq Ft
1981 Blue Ridge Rd, Winter Park, FL 32789

Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and

Thomas Nickley

KELLER WILLIAMS REALTY AT THE PARKS

1981 Blue Ridge Rd, 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

2500 Lee Rd Unit 244, Winter Park, FL 32789
/2
$400,000

Sold Jun 24, 2026

721 Dunbar St, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,018 Sq Ft
- Built 1950
Last Sold Summary
- $393/SF
- 4 Days On Market
Current Estimated Value $475,488

Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

721 Dunbar St, Winter Park, FL 32789

/2
Est $2,159,282

Not Listed For Sale

301 Rippling Ln, Winter Park, FL 32789
- 4 Beds
- 6 Baths
- 3,694 Sq Ft
- Built 1958
301 Rippling Ln, Winter Park, FL 32789

Last Sold Summary
- 98 Days On Market

/48
$625,000

Open Sun 1AM - 3PM $55K PRICE DROP
- 3 Beds
- 2 Baths
- 1,287 Sq Ft
1830 Edwin Blvd, Winter Park, FL 32789

Virtually Staged. *** JUST REDUCED TO $625,000 | 1830 Edwin Blvd, Winter Park, FL 32789*** This is your moment. One of Winter Park's most beautifully RENOVATED and MOVE-IN READY homes has just been repriced, and at $625,000, it will not last long. From the moment you step inside, you are welcomed by an open, airy layout with soaring VAULTED CEILINGS that make the home feel expansive and inviting.

Nydia Marrero

ZEN LIVING HOMES LLC

1830 Edwin Blvd, Winter Park, FL 32789
/28
Starting at $1,599 Per Month
- 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

Elon Winter Park

712 Nicolet Ave, 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 $2,128,691

Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

1077 N Pennsylvania Ave, Winter Park, FL 32789

/2
Est $900,086

Not Listed For Sale

1832 Magnolia Ave, Winter Park, FL 32789
- 5 Beds
- 3.5 Baths
- 2,910 Sq Ft
- Built 1954
1832 Magnolia Ave, Winter Park, FL 32789

Last Sold Summary
- 25 Days On Market

/31
$380,000

Pending
- 2 Beds
- 1 Bath
- 988 Sq Ft
440 Cambridge Blvd, Winter Park, FL 32789

Under contract-accepting backup offers. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer

Thomas Nickley

KELLER WILLIAMS REALTY AT THE PARKS

440 Cambridge Blvd, Winter Park, FL 32789
/23
$2,450 Per Month
- 2 Beds
- 2 Baths
- 1,137 Sq Ft
- Townhouse for Rent
1440 Michigan Ave, Winter Park, FL 32789

Live in the heart of Winter Park, just steps from the city’s most loved restaurants, cafés, yoga studios, and boutique shops. This beautifully renovated unit offers the perfect blend of walkability, comfort, and style. Zoned for top-rated Winter Park schools and within walking distance to a renowned private school, the location alone makes this an exceptional find. Inside, the home features a

Farzana Zalil

CHARLES RUTENBERG REALTY ORLANDO

1440 Michigan 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 $681,645

Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

1511 Chestnut Ave, Winter Park, FL 32789

/42
Est $1,597,726

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
- 12 Days On Market

/65
$995,000

Open Sat 12AM - 2PM $155K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,431 Sq Ft
1800 Magnolia Ave, Winter Park, FL 32789

Virtually Staged. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a 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. With soaring 10-foot ceilings throughout and a stately

Kathy Summers

FLORIDA REALTY INVESTMENTS

1800 Magnolia Ave, Winter Park, FL 32789
/75
Starting at $1,443 Per Month
- 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.

Bainbridge Winter Park

1400 Morgan Stanley 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 $965,643

Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

512 Clarendon Ave, Winter Park, FL 32789

/2
Est $2,789,534

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
- 173 Days On Market

/24
$134,900

$5K PRICE DROP
- 2 Beds
- 1 Bath
- 881 Sq Ft
1695 Lee Rd Unit E103, Winter Park, FL 32789

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the

Jason Price

RE/MAX SELECT GROUP

1695 Lee Rd Unit E103, Winter Park, FL 32789
/49
$6,600 Per Month
- 5 Beds
- 4 Baths
- 2,918 Sq Ft
- House for Rent
2075 Jewell Ave, Winter Park, FL 32789

FULLY FURNISHED and move in ready elegant home.A rare find in Winter Park. 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

Paul Jimenez

URBANISTA BROKERS

2075 Jewell 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 $285,523

Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

700 Melrose Ave Unit A22, Winter Park, FL 32789

/33
Est $799,170

Not Listed For Sale

1316 Fountain Hills Ct, Winter Park, FL 32792
- 4 Beds
- 3.5 Baths
- 2,823 Sq Ft
- Built 2018
1316 Fountain Hills Ct, Winter Park, FL 32792

Last Sold Summary
- 138 Days On Market

/38
$259,900
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
1500 Gay Rd Unit 17D, Winter Park, FL 32789

Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates include: Water Heater in

Janice Erickson

REALCOM REAL ESTATE SERVICES INC

1500 Gay Rd Unit 17D, Winter Park, FL 32789
/50
Starting at $1,930 Per Month
- 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

Paseo at Winter Park Village

940 W Canton Ave, 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 $1,279,216

Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

1500 Mizell Ave, Winter Park, FL 32789

/2
Est $1,855,793

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
- 195 Days On Market

/28
$199,900
- 2 Beds
- 1 Bath
- 851 Sq Ft
2500 Lee Rd Unit 220, Winter Park, FL 32789

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms

Thomas Nickley

KELLER WILLIAMS REALTY AT THE PARKS

2500 Lee Rd Unit 220, Winter Park, FL 32789
/50
Starting at $1,585 Per Month
- 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.

Seven41 Winter Park

741 Clay St, 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 $2,201,722

Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

1661 Palm Ave, 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
- 73 Days On Market

/22
$258,000

$4K PRICE DROP
- 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

1500 Gay Rd Unit 20D, Winter Park, FL 32789
/50
Starting at $1,593 Per Month
- 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

Berkshire Winter Park

1874 Harmon Ave, 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 $2,787,254

Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

1020 Mayfield Ave, Winter Park, FL 32789

/60
Est $1,621,122

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
- 162 Days On Market

/23
$259,500

$16K PRICE DROP Pending
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
1500 Gay Rd Unit 24B, Winter Park, FL 32789

Under contract-accepting backup offers. 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

Janice Erickson

REALCOM REAL ESTATE SERVICES INC

1500 Gay Rd Unit 24B, Winter Park, FL 32789
/50
Starting at $1,852 Per Month
- 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,

Juno Winter Park

1305 Morgan Stanley Ave, Winter Park, FL 32789
/2
$4,250,000

Sold Jun 01, 2026

1336 College Point, Winter Park, FL 32789
- 4 Beds
- 5 Baths
- 3,181 Sq Ft
- Built 1926
Last Sold Summary
- 8% Below List Price
- $1,336/SF
- 109 Days On Market
Current Estimated Value $4,442,314

Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

1336 College Point, Winter Park, FL 32789

/14
Est $533,300

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
- 0 Days On Market

/41
$2,495,000

$155K PRICE DROP
- 5 Beds
- 3.5 Baths
- 4,011 Sq Ft
1130 Park North Place, Winter Park, FL 32789

Half-acre lot just steps from Park Avenue shopping and dining, tucked on a quiet cul-de-sac in the heart of Winter Park.This traditional two-story home offers a well-designed floorplan for both everyday living and entertaining. From the moment you enter, the home feels warm and inviting. The main level features a spacious primary suite along with connected living spaces that flow easily from

Jennifer King

CORCORAN PREMIER REALTY

1130 Park North Place, Winter Park, FL 32789
/18
Starting at $1,330 Per Month
- 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

Park East - Park Knowles Apartments

311 N Knowles 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 $1,621,179

Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

1166 Oaks Blvd, Winter Park, FL 32789

/2
Est $697,471

Not Listed For Sale

2602 Winter Park Rd, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,966 Sq Ft
- Built 1975
2602 Winter Park Rd, Winter Park, FL 32789

Last Sold Summary
- 4 Days On Market

Showing Results 1 - 40, Page 1 of 18

Florida Orange County Winter Park 32789

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