Homes in ZIP Code 32789

/37
$650,000 Pending
- 5 Beds
- 3 Baths
- 1,917 Sq Ft
352 Cambridge Blvd, Winter Park, FL 32789

Under contract-accepting backup offers. This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from three separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a

Karen Jacobs COLDWELL BANKER REALTY

352 Cambridge Blvd, Winter Park, FL 32789
/23
$1,425 per month
- 2 Beds
- 1 Bath
- 920 Sq Ft
- Condo for Rent
1380 Indiana Ave Unit 3, Winter Park, FL 32789

Winter Park at your door step! This is a second floor 2 bedroom unit, in secured building. Large open backyard with rear balcony and patio space and plenty of parking. Unit has full kitchen, and washer/dryer in unit! Two full bedrooms both with walk-in closets and a full bath. Living room is large open/bright. Only a few blocks walk to Orlando Ave with all its shopping, Publix and restaurants.

Scott Butts KIMBRIDGE REALTY, LLC

1380 Indiana Ave Unit 3, Winter Park, FL 32789
/2
$1,002,000 Sold May 31, 2025

1265 Park Pointe Ln, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 2,295 Sq Ft
- Built 1989
Last Sold Summary
- 3% Above List Price
- $437/SF
- 4 Days On Market
Current Estimated Value $995,846

Last Listing Agent Frances Speights KELLER WILLIAMS ADVANTAGE III

1265 Park Pointe Ln, Winter Park, FL 32789

/89
Est $1,313,042 Not Listed For Sale

3629 Midiron Dr, Winter Park, FL 32789
- 5 Beds
- 4.5 Baths
- 3,252 Sq Ft
- Built 2024
3629 Midiron Dr, Winter Park, FL 32789

Last Sold Summary
- 3% Below List Price
- $417/SF
- 13 Days On Market
Last Sold Price $1,355,000

Last Listing Agent Amanda Wood RE/MAX

/39
$599,900
- 3 Beds
- 2 Baths
- 1,269 Sq Ft
1354 Indiana Ave, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle.The beautifully

Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO

1354 Indiana Ave, Winter Park, FL 32789
/52
$8,950 per month
- 3 Beds
- 3 Baths
- 2,462 Sq Ft
- Condo for Rent
311 E Morse Blvd Unit 1-5, Winter Park, FL 32789

Enjoy elevated lakeside living in this top-floor residence overlooking tranquil Lake Osceola in downtown Winter Park. Located on the top level of the Whispering Waters condominium community, this fully remodeled home features three spacious bedrooms (one currently used as a den), three full baths and an open layout designed to showcase expansive water views. The primary suite features an

Drew Henner PREMIER SOTHEBY'S INTL. REALTY

311 E Morse Blvd Unit 1-5, Winter Park, FL 32789
/2
$1,975,000 Sold Mar 27, 2025

140 Dana Way, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 3,441 Sq Ft
- Built 2011
Last Sold Summary
- 6% Below List Price
- $574/SF
- 16 Days On Market
Current Estimated Value $2,007,732

Last Listing Agent Maria Blanchard OLDE TOWN BROKERS INC

140 Dana Way, Winter Park, FL 32789

/2
Est $358,053 Not Listed For Sale

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

Last Sold Summary
- 16% Above List Price
- $202/SF
- 53 Days On Market
Last Sold Price $310,000

Last Listing Agent Carol van den Berg VAN DEN BERG REAL ESTATE GROUP

/76
$6,895,000 New Construction
- 5 Beds
- 6.5 Baths
- 5,939 Sq Ft
550 Palmer Ave, Winter Park, FL 32789

Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff

John McDade FANNIE HILLMAN & ASSOCIATES

550 Palmer Ave, Winter Park, FL 32789
/50
$3,150 per month
- 3 Beds
- 2 Baths
- 1,436 Sq Ft
- House for Rent
1835 Edwin Blvd, Winter Park, FL 32789

Charming bungalow on a brick street in beautiful Winter Park, available March 1, 2026. This 3-bedroom, 2-bathhome offers a great split floorplan and newer finishes. The kitchen and both primary en-suite and secondary bathroomshave been completely remodeled with premium finishes. The home boasts a newer roof, hardwood and stone floorsthroughout, with granite counters, white cabinetry,

Vincent Scarlatos CORCORAN PREMIER REALTY

1835 Edwin Blvd, Winter Park, FL 32789
/2
$230,000 Sold Aug 29, 2025

1500 Gay Rd Unit 7A, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
- Built 1972
Last Sold Summary
- 6% Below List Price
- $224/SF
- 205 Days On Market
Last Listing Agent Sean McCartney PRISTINE FLORIDA PROPERTIES LLC

1500 Gay Rd Unit 7A, Winter Park, FL 32789

/44
Not Listed For Sale

1250 Formosa Ave, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 1,937 Sq Ft
- Built 2022
1250 Formosa Ave, Winter Park, FL 32789

Last Sold Summary
- 3% Above List Price
- $307/SF
- 50 Days On Market
Last Sold Price $595,000

Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

/88
$8,500,000
- 5 Beds
- 6 Baths
- 6,502 Sq Ft
1112 Preserve Point Dr, Winter Park, FL 32789

Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2-acre lakefront estate, is absolutely gorgeous and is available for the first time! Custom built by Phil Kean Design Group and located within Windsong's Preserve Point, this extraordinary Lake Berry home has it all including 1.97 acres of land adjacent to the historic Genius Preserve

Kelly Price KELLY PRICE & COMPANY LLC

1112 Preserve Point Dr, Winter Park, FL 32789
/27
$3,995 per month
- 3 Beds
- 2.5 Baths
- 2,317 Sq Ft
- Townhouse for Rent
438 W Swoope Ave, Winter Park, FL 32789

SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 3/31!! PRIME LOCATION! JUST STEPS FROM PARK AVENUE, WALKING DISTANCE TO EVERYTHING! This beautiful TOWNHOME is located in the exclusive 400 West community, just moments from Park Avenue. It offers a PERFECT COMBINATION OF SUPERIOR CRAFTSMANSHIP, ELEGANT INTERIORS, and GREAT WALKABILITY. You can enter via the PRIVATE GARAGE or the charming

Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

438 W Swoope Ave, Winter Park, FL 32789
/2
$3,450,000 Sold Jul 25, 2025

182 N Phelps Ave, Winter Park, FL 32789
- 4 Beds
- 5 Baths
- 4,812 Sq Ft
- Built 2025
Last Sold Summary
- 4% Below List Price
- $717/SF
- 61 Days On Market
Current Estimated Value $3,340,418

Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

182 N Phelps Ave, Winter Park, FL 32789

/44
Est $868,596 Not Listed For Sale

1403 Michigan Ave, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,513 Sq Ft
- Built 2024
1403 Michigan Ave, Winter Park, FL 32789

Last Sold Summary
- 6% Below List Price
- $369/SF
- 65 Days On Market
Last Sold Price $927,000

Last Listing Agent Amanda Wood RE/MAX

/8
$849,000
- 4 Beds
- 2 Baths
- 1,617 Sq Ft
1780 Bryan Ave, Winter Park, FL 32789

Discover a truly unique offering in the heart of Winter Park! This property, located at 1780 Bryan Avenue, is being offered along with theadjoining lots at 1760 and 1770 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 purchase one, two, or all three.

Nickolas McKee KELLER WILLIAMS WINTER PARK

1780 Bryan Ave, Winter Park, FL 32789
/17
$3,850 per month
- 3 Beds
- 2.5 Baths
- 1,880 Sq Ft
- House for Rent
1302 Michigan Ave, Winter Park, FL 32789

This is a unique opportunity to live in this glamorous, impeccably maintained 3 bedrooms, 2.5 baths in the heart of Winter Park (Unfurnished). This beautiful home features formal living and dining rooms that open to the impressive gourmet kitchen fitted with wood cabinetry, stainless steel appliances, granite countertops, a breakfast bar, there is also room for a breakfast nook. Through the

Mo Jabr RE/MAX 200 REALTY

1302 Michigan Ave, Winter Park, FL 32789
/2
$1,950,000 Sold Sep 16, 2025

141 Oakwood Way, Winter Park, FL 32789
- 5 Beds
- 4 Baths
- 3,909 Sq Ft
- Built 2015
Last Sold Summary
- 14% Below List Price
- $499/SF
- 170 Days On Market
Current Estimated Value $1,967,770

Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

141 Oakwood Way, Winter Park, FL 32789

/88
Est $1,986,652 Not Listed For Sale

1661 Hillcrest Ave, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 3,161 Sq Ft
- Built 2017
1661 Hillcrest Ave, Winter Park, FL 32789

Last Sold Summary
- 10% Above List Price
- $569/SF
- 21 Days On Market
Last Sold Price $1,800,000

Last Listing Agent Domenique Lombardo ROYALTY R E BOUTIQUE INC

/25
$179,000
- 1 Bed
- 1 Bath
- 645 Sq Ft
2500 Lee Rd Unit 122, Winter Park, FL 32789

PRICE IMPROVEMENT! Welcome home to this updated 1-bedroom 1-bathroom GROUND FLOOR condo, ideally positioned toward the desirable rear of the sought-after Lakeside Manor community. The move-in-ready residence features a spacious, open floor plan enhanced by ceramic tile throughout, elegant crown molding and a thoughtfully updated kitchen complete with modern countertops, soft-close cabinetry, and

Andrea Aylett-Hosch PINEAPPLE PLACE REALTY, LLC

2500 Lee Rd Unit 122, Winter Park, FL 32789
/24
$1,650 per month
- 3 Beds
- 2 Baths
- 1,149 Sq Ft
- Condo for Rent
1695 Lee Rd Unit C216, Winter Park, FL 32789

Available for immediate move-in, this comfortable second-floor corner condo offers a peaceful setting with playground and pool views. The home features a fully carpeted interior, a spacious kitchen with a pantry closet, and a newer refrigerator. Washer and dryer are included for added convenience. Great balcony for relaxing on the cooler Florida days! Located in desirable Winter Park, you'll

Yarmmys Vargas ZEN LIVING HOMES LLC

1695 Lee Rd Unit C216, Winter Park, FL 32789
/45
$1,100,000 Sold May 29, 2025

708 Balmoral Rd, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 2,786 Sq Ft
- Built 1960
Last Sold Summary
- 4% Below List Price
- $395/SF
- 130 Days On Market
Current Estimated Value $1,154,852

Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

708 Balmoral Rd, Winter Park, FL 32789

/39
Est $816,307 Not Listed For Sale

1770 Mondrian Cir, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,193 Sq Ft
- Built 2023
1770 Mondrian Cir, Winter Park, FL 32789

Last Sold Summary
- 1% Below List Price
- $376/SF
- 18 Days On Market
Last Sold Price $825,000

Last Listing Agent Brian Teach COLDWELL BANKER REALTY

/28
$145,000 Pending
- 1 Bed
- 1 Bath
- 645 Sq Ft
2500 Lee Rd Unit 243, Winter Park, FL 32789

Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living

Sue Gilman KELLER WILLIAMS WINTER PARK

2500 Lee Rd Unit 243, Winter Park, FL 32789
/36
$4,495 per month
- 4 Beds
- 2.5 Baths
- 2,406 Sq Ft
- House for Rent
1580 Oakhurst Ave, Winter Park, FL 32789

Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are

Lisa Gould KELLER WILLIAMS WINTER PARK

1580 Oakhurst Ave, Winter Park, FL 32789
/2
$699,000 Sold Jun 30, 2025

1632 Haven Dr, Orlando, FL 32803
- 3 Beds
- 2.5 Baths
- 1,772 Sq Ft
- Built 2025
Last Sold Summary
- 3% Below List Price
- $394/SF
- 110 Days On Market
Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

1632 Haven Dr, Orlando, FL 32803

/25
Est $2,020,397 Not Listed For Sale

1925 Killarney Dr, Winter Park, FL 32789
1925 Killarney Dr, Winter Park, FL 32789

Last Sold Summary
- 1% Above List Price
- 33 Days On Market
Last Sold Price $2,000,000

Last Listing Agent Cathy Marino CATHY S. MARINO REALTY, INC.

/32
$915,000 Pending
- 3 Beds
- 3.5 Baths
- 2,160 Sq Ft
1929 S Lakemont Ave, Winter Park, FL 32792

This modern Winter Park townhome sits in a quiet pocket between Lake Spier and Lake Compton, offering a rare mix of style, comfort, and convenience. This home feels tucked away while still keeping you close to everything you love about Winter and Baldwin Park. Inside, the layout is open and easy to live in. The kitchen features stone countertops, stainless steel appliances, and a large island

Brandon Geers COMPASS FLORIDA LLC

1929 S Lakemont Ave, Winter Park, FL 32792
/39
$7,900 per month
- 4 Beds
- 3 Baths
- 2,476 Sq Ft
- House for Rent
300 Killarney Dr, Winter Park, FL 32789

Exceptional Lakefront Living in the Heart of Winter ParkWelcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle.Property Highlights:Situated on an oversized lot with coveted Lake Killarney

Kelly Price KELLY PRICE & COMPANY LLC

300 Killarney Dr, 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 $3,022,056

Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

1820 Englewood Rd, Winter Park, FL 32789

/2
Est $1,050,626 Not Listed For Sale

311 E Morse Blvd Unit 6-18, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 2,096 Sq Ft
- Built 1960
311 E Morse Blvd Unit 6-18, Winter Park, FL 32789

Last Sold Summary
- 5% Above List Price
- $477/SF
- 102 Days On Market
Last Sold Price $1,000,000

Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

/47
$1,100,000
- 3 Beds
- 2.5 Baths
- 2,578 Sq Ft
1541 Westchester Ave, Winter Park, FL 32789

Set on over half an acre in Winter Park’s coveted Orwin Manor, this 1935 French Provincial estate offers a rare blend of architectural character, modern system updates, and extraordinary future potential. The property offers the unique opportunity to own an estate in a beautifully historic Winter Park neighborhood. Whether thoughtfully renovated, expanded, or reimagined, this property stands as a

Lisa Gould KELLER WILLIAMS WINTER PARK

1541 Westchester Ave, Winter Park, FL 32789
/12
$1,500 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Townhouse for Rent
1565 Michigan Ave, Winter Park, FL 32789

Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

Troy Hensley BHHS FLORIDA REALTY

1565 Michigan Ave, Winter Park, FL 32789
/2
$799,000 Sold Apr 30, 2025

2320 Janice Ave, Winter Park, FL 32789
- Land
- 0.28 Acre
- $2,853,571 per Acre
Last Sold Summary
- 2 Days On Market
Current Estimated Value $793,000

Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES

2320 Janice Ave, Winter Park, FL 32789

/36
Est $1,373,494 Not Listed For Sale

1405 Chapman Cir Unit OR, Winter Park, FL 32789
- 3 Beds
- 4 Baths
- 2,950 Sq Ft
- Built 2007
1405 Chapman Cir Unit OR, Winter Park, FL 32789

Last Sold Summary
- 7% Above List Price
- $436/SF
- 2 Days On Market
Last Sold Price $1,285,000

Last Listing Agent William Maroon MAROON REALTY GROUP LLC

/17
$185,000
- 1 Bed
- 1 Bath
- 732 Sq Ft
1500 Gay Rd Unit 5, Winter Park, FL 32789

Welcome to Chateaux du Lac, a lakefront community in the heart of Winter Park, FL, offering an active and convenient lifestyle. Residents enjoy an impressive array of amenities including a heated community pool, clubhouse, lakefront community deck, BBQ area, resident-only boat ramp, community laundry facilities, and two on-site saunas. This second-floor one-bedroom, one-bath apartment features

Jacob Hara TRANSCEND REALTY

1500 Gay Rd Unit 5, Winter Park, FL 32789
/42
$2,950 per month
- 3 Beds
- 2 Baths
- 1,747 Sq Ft
- House for Rent
1807 N Park Ave, Winter Park, FL 32789

Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step

Jason Hamilton THE REALTY MEDICS

1807 N Park 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 $384,173

Last Listing Agent Mary Harmening ROAM FLORIDA REALTY LLC

700 Melrose Ave Unit M4, Winter Park, FL 32789

/55
Est $1,024,175 Not Listed For Sale

1772 Mondrian Cir, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,193 Sq Ft
- Built 2023
1772 Mondrian Cir, Winter Park, FL 32789

Last Sold Summary
- 18% Below List Price
- $570/SF
- 83 Days On Market
Last Sold Price $1,250,000

Last Listing Agent Brian Teach COLDWELL BANKER REALTY

Showing Results 161 - 200, Page 5 of 18

Florida Orange County Winter Park 32789

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