$375,000
$25K PRICE DROP
Pending
- 2 Beds
- 1 Bath
- 913 Sq Ft
2482 Roxbury Rd, Winter Park, FL 32789
Gary Cohl COLDWELL BANKER REALTY
11,849
Homes in ZIP Code 32789
-
2482 Roxbury Rd, Winter Park, FL 32789
-
Starting at $1,675 Per Month
- 1 Bed
520 N Orlando Ave, Winter Park, FL 32789
520 N Orlando Ave, Winter Park, FL 32789Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban
The Lofts of Winter Park Village
-
$2,050,000
Sold Apr 30, 20261205 Mayfield Ave, Winter Park, FL 32789
- Land
- 23,958 Sq Ft
- $3,727,273 per Acre
Last Sold Summary
- 18% Below List Price
- 89 Days On Market
Current Estimated Value $2,208,348
Last Listing Agent Abby Nelson RE/MAX 200 REALTY
1205 Mayfield Ave, Winter Park, FL 32789 -
Est $5,501,810
Not Listed For Sale300 S Interlachen Ave Unit 601, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 5,430 Sq Ft
- Built 2005
Last Sold Summary
- 0 Days On Market
-
$2,650,000
New Construction $150K PRICE DROP- 4 Beds
- 3.5 Baths
- 3,553 Sq Ft
541 W Canton Ave, Winter Park, FL 32789
541 W Canton Ave, Winter Park, FL 32789Bianca Rey PREMIER SOTHEBY'S INTL. REALTY
-
Starting at $1,600 Per Month
- Studio - 3 Beds
433 W New England Ave, Winter Park, FL 32789
433 W New England Ave, Winter Park, FL 32789We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,
Hannibal Square
-
$261,000
Sold May 13, 20261500 Gay Rd Unit 8D, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
- Built 1972
Last Sold Summary
- 2% Below List Price
- $254/SF
- 19 Days On Market
Current Estimated Value $264,210
Last Listing Agent Trevor Laug. Realtor SOLID OAK REAL ESTATE LLC
1500 Gay Rd Unit 8D, Winter Park, FL 32789 -
Est $2,738,184
Not Listed For Sale1737 Lookout Landing Cir, Winter Park, FL 32789
- 5 Beds
- 5.5 Baths
- 5,066 Sq Ft
- Built 2013
Last Sold Summary
- 232 Days On Market
-
$1,995,000
- 4 Beds
- 3 Baths
- 3,696 Sq Ft
2261 Mulbry Dr, Winter Park, FL 32789
2261 Mulbry Dr, Winter Park, FL 32789Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY
-
$3,000
Total Monthly Price
- 2 Beds
- 2.5 Baths
- 1,100 Sq Ft
- Townhouse for Rent
1144 Washington Ave, Winter Park, FL 32789
1144 Washington Ave, Winter Park, FL 32789Fully remodeled 2 BR, 2.5 BA townhouse in a wonderful location of Winter Park. 1 block from the Winter Park Tennis Center, walking distance to Rollins College and Park Ave. The townhouse is tucked into a quiet neighborhood known as The Quarters. New Kitchen, Appliances, cabinets and fixtures. New carpeting, and hard wood floors throughout. All three bathrooms have been remodel with new vanities
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$800,000
Sold Apr 30, 2026737 N Capen Ave, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,930 Sq Ft
- Built 2021
Last Sold Summary
- 13% Below List Price
- $415/SF
- 99 Days On Market
Current Estimated Value $883,096
Last Listing Agent Jenn Carlisle LPT REALTY, LLC
737 N Capen Ave, Winter Park, FL 32789 -
Est $691,474
Not Listed For Sale311 E Morse Blvd Unit 6-21, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 1960
Last Sold Summary
- 75 Days On Market
-
$1,800,000
$200K PRICE DROP- 4 Beds
- 4 Baths
- 3,065 Sq Ft
723 Symonds Ave, Winter Park, FL 32789
723 Symonds Ave, Winter Park, FL 32789Nickolas McKee KELLER WILLIAMS WINTER PARK
-
Starting at $1,154
Total Monthly Price
- Studio - 3 Beds
1701 Lee Rd, Winter Park, FL 32789
1701 Lee Rd, Winter Park, FL 32789There's no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the
Westmount at Winter Park
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$640,000
Sold Jun 05, 2026352 Cambridge Blvd, Winter Park, FL 32789
- 5 Beds
- 3 Baths
- 1,917 Sq Ft
- Built 1920
Last Sold Summary
- 2% Below List Price
- $334/SF
- 46 Days On Market
Current Estimated Value $631,911
Last Listing Agent Karen Jacobs COLDWELL BANKER REALTY
352 Cambridge Blvd, Winter Park, FL 32789 -
Est $1,308,458
Not Listed For Sale345 W Welbourne Ave Unit 104, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,734 Sq Ft
- Built 2009
Last Sold Summary
- 3 Days On Market
-
$184,900
- 1 Bed
- 1 Bath
- 645 Sq Ft
2500 Lee Rd Unit 222, Winter Park, FL 32789
2500 Lee Rd Unit 222, Winter Park, FL 32789Christine Bouchard HOMESMART
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Starting at $3,200 Per Month
- 2 Beds
1886 Demetree Dr, Winter Park, FL 32789
1886 Demetree Dr, Winter Park, FL 32789Beautifully Remodeled Ground-Floor Townhome — Available Now in Winter ParkWelcome home to this stylish, move-in-ready townhome located in the heart of Winter Park. Enjoy the perfect balance of convenience and comfort—just a short walk to Winter Park Dog Park and Baldwin Park, and minutes from Rollins College, Park Avenue, downtown Orlando, and major hospitals.This thoughtfully
Waterbridge Subdivision
-
$1,575,000
Sold Aug 14, 20251394 Grove Terrace, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,958 Sq Ft
- Built 2002
Last Sold Summary
- $532/SF
- 5 Days On Market
Current Estimated Value $1,595,861
Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC
1394 Grove Terrace, Winter Park, FL 32789 -
Est $972,329
Not Listed For Sale1245 Wisconsin Ave, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,610 Sq Ft
- Built 2013
Last Sold Summary
- 51 Days On Market
-
$1,890,000
$405K PRICE DROP- 4 Beds
- 3.5 Baths
- 3,307 Sq Ft
2614 Parkland Dr, Winter Park, FL 32789
2614 Parkland Dr, Winter Park, FL 32789Ryan Gaston JW GASTON LLC
-
$3,300 Per Month
- 3 Beds
- 1 Bath
- 820 Sq Ft
- House for Rent
853 W Lyman Ave, Winter Park, FL 32789
853 W Lyman Ave, Winter Park, FL 32789Property Id: 1403118Our home is convenient for your extended friends and family, remote workers, traveling nurses, Rollins College parents and alum, snowbirds, conference attendees, or exploring travelers who prefer to stay in our home away from home.Three bedrooms (one queen and two double beds) accommodate three couples, Living room has large sectional and flat screen TV (bring
-
$325,000
Sold Dec 30, 2025520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,160 Sq Ft
- Built 1986
Last Sold Summary
- 7% Below List Price
- $280/SF
- 6 Days On Market
Current Estimated Value $324,182
Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK
520 Killarney Bay Ct Unit 2, Winter Park, FL 32789 -
Est $1,529,956
Not Listed For Sale101 S New York Ave Unit 303, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 3,174 Sq Ft
- Built 2009
Last Sold Summary
- 129 Days On Market
-
$1,250,000
New Construction- 4 Beds
- 3.5 Baths
- 2,525 Sq Ft
1870 Staunton Ave, Winter Park, FL 32789
1870 Staunton Ave, Winter Park, FL 32789Vinny Lay COMPASS FLORIDA LLC
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$2,390 Per Month
- 3 Beds
- 2.5 Baths
- 1,277 Sq Ft
- House for Rent
2866 Euston Rd, Winter Park, FL 32789
2866 Euston Rd, Winter Park, FL 32789Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,
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$720,000
Sold Jan 20, 20262955 Lolissa Ln, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 3,538 Sq Ft
- Built 1969
Last Sold Summary
- 4% Below List Price
- $204/SF
- 47 Days On Market
Current Estimated Value $812,250
Last Listing Agent Catherine Williams COLDWELL BANKER REALTY
2955 Lolissa Ln, Winter Park, FL 32789 -
Est $3,045,520
Not Listed For Sale140 E Morse Blvd Unit G, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 3,367 Sq Ft
- Built 2008
Last Sold Summary
- 3 Days On Market
-
$699,000
$20K PRICE DROP- 4 Beds
- 2 Baths
- 1,877 Sq Ft
2333 Westminster Ct, Winter Park, FL 32789
2333 Westminster Ct, Winter Park, FL 32789Ernest Middleton CHARLES RUTENBERG REALTY ORLANDO
-
$1,300
Total Monthly Price
- 2 Beds
- 1 Bath
- 713 Sq Ft
- Condo for Rent
1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789
1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789Centrally located 2/1 apartment. Near Shopping, gas, churches, golf, convenience store, park and much more. Across the street is Orlando. Hardwood floors. Over 100 restaurants within 1 mile. Easy on and off I-4. Good neighbors. No pets.
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$2,285,000
Sold Nov 19, 2025521 S Phelps Ave, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 3,883 Sq Ft
- Built 2015
Last Sold Summary
- 7% Below List Price
- $588/SF
- 118 Days On Market
Current Estimated Value $2,276,166
Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC
521 S Phelps Ave, Winter Park, FL 32789 -
Est $1,535,503
Not Listed For Sale311 E Morse Blvd Unit 1-1, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 2,066 Sq Ft
- Built 1960
Last Sold Summary
- 0 Days On Market
-
$779,000
Pending- 4 Beds
- 2.5 Baths
- 2,391 Sq Ft
1826 Banchory Rd, Winter Park, FL 32789
1826 Banchory Rd, Winter Park, FL 32789Karen Jacobs COLDWELL BANKER REALTY
-
$2,950
Total Monthly Price
- 3 Beds
- 3.5 Baths
- 1,400 Sq Ft
- Townhouse for Rent
223 Sandlewood Trail, Winter Park, FL 32789
223 Sandlewood Trail, Winter Park, FL 32789The townhouse has been renovated, including updates to the kitchen with modern countertops, cabinetry, and stainless steel appliances. The bathrooms are renovated with updated vanities, fixtures, and finishes. Includes community pool access and directly behind the property is a recreational area offering various amenities.
-
$4,772,500
Sold Sep 18, 2025765 Via Lugano, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 4,319 Sq Ft
- Built 2019
Last Sold Summary
- $1,105/SF
- 1 Day On Market
Current Estimated Value $4,778,066
Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY
765 Via Lugano, Winter Park, FL 32789 -
Est $360,155
Not Listed For Sale1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
- 1 Bed
- 1 Bath
- 864 Sq Ft
- Built 1983
Last Sold Summary
- 36 Days On Market
-
$589,900
$10K PRICE DROP- 3 Beds
- 2 Baths
- 1,269 Sq Ft
1354 Indiana Ave, Winter Park, FL 32789
1354 Indiana Ave, Winter Park, FL 32789Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO
-
$3,200 Per Month
- 1 Bed
- 1 Bath
- 673 Sq Ft
- Condo for Rent
640 N Park Ave Unit 5, Winter Park, FL 32789
640 N Park Ave Unit 5, Winter Park, FL 32789One or more photo(s) has been virtually staged. Welcome to Park Aire, a small iconic condo community located on Park Avenue by the WP9 golf course. 1st floor unit with oversized window views of the golf course and Casa Feliz. This one bedroom unit has an updated kitchen and bath. Amenities include a covered parking space, swimming pool, social room, a guest room for rent, open air patios on the
Andy Holland PREMIER SOTHEBY'S INTL. REALTY
-
$3,100,000
Sold Jun 27, 2025731 Williams Dr, Winter Park, FL 32789
- 5 Beds
- 6 Baths
- 4,260 Sq Ft
- Built 2025
Last Sold Summary
- 6% Below List Price
- $728/SF
- 45 Days On Market
Current Estimated Value $2,885,321
Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES
731 Williams Dr, Winter Park, FL 32789 -
Est $819,333
Not Listed For Sale2320 Janice Ave, Winter Park, FL 32789
Last Sold Summary
- 2 Days On Market
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