Winter Park, FL Homes

/26
$197,500
- 2 Beds
- 2.5 Baths
- 1,031 Sq Ft
3370 Cedar Springs Place Unit 156, Winter Park, FL 32792

Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. No rear neighbors. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own

Qing Lin SPRINGHILL PROPERTIES LLC

3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
/16
$2,295 per month
- 3 Beds
- 2 Baths
- 1,496 Sq Ft
- House for Rent
1557 Nottingham Dr, Winter Park, FL 32792

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2439.90. That covers your base rent, $2295.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

1557 Nottingham Dr, Winter Park, FL 32792
/2
$800,200 Sold Oct 03, 2025

4107 Gabriella Ln, Winter Park, FL 32792
- 4 Beds
- 3.5 Baths
- 3,074 Sq Ft
- Built 1998
Last Sold Summary
- 33% Below List Price
- $260/SF
- 112 Days On Market
Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

4107 Gabriella Ln, Winter Park, FL 32792

/2
Est $198,356 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,219 Sq Ft
200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

/11
$130,000
- 3 Beds
- 2 Baths
- 1,250 Sq Ft
334 Scottsdale Square Unit 334, Winter Park, FL 32792

CASH ONLY. Desirable Winter Park Location with highly rated schools! Down the street Full Sail University, close to famous Park Ave, Rollins College, short drive to UCF and International Airport. Leased until 09/30/2026 to Long term tenant paying $1600 a month willing to stay. This spacious well maintained property features an amazing open floor plan with a full bedroom and bathroom downstairs,

John Sheynkman CHARLES RUTENBERG REALTY ORLANDO

334 Scottsdale Square Unit 334, Winter Park, FL 32792
/31
$2,795 per month
- 3 Beds
- 2 Baths
- 1,240 Sq Ft
- House for Rent
2717 Scarlet Rd, Winter Park, FL 32792

Stunning - beautifully upgraded 3 bedroom, 2 bath home with 2 car garage and oversized backyard in prime location of Winter Park. Enjoy direct access to CADY WAY TRAIL and the CADY WAY PARK with its nearly 70 acres and amenities of various ball fields, picnic tables, tennis courts, playgrounds and Olympic sized swimming pool. This light and bright home features an open split floor plan for

Andreas Kunert KUNERT REALTY INC

2717 Scarlet Rd, Winter Park, FL 32792
/2
$350,000 Sold Feb 12, 2025

535 N Interlachen Ave Unit 304, Winter Park, FL 32789
- 1 Bed
- 1.5 Baths
- 726 Sq Ft
- Built 1972
Last Sold Summary
- 11% Below List Price
- $482/SF
- 82 Days On Market
Current Estimated Value $356,524

Last Listing Agent Jennifer Cornette HOLT REAL ESTATE LLC

535 N Interlachen Ave Unit 304, Winter Park, FL 32789

/2
Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,079 Sq Ft
3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

/18
$499,000
- 4 Beds
- 2 Baths
- 1,827 Sq Ft
1422 Tierra Cir, Winter Park, FL 32792

PRICE IMPROVEMENT! INCREDIBLE OPPORTUNITY! 5.75% ASSUMABLE MORTGAGE Interest Rate Available, making it an excellent opportunity for qualified Buyers. Welcome to 1422 Tierra Circle, beautifully refreshed immaculate pool home located in the well-established community of Casa Aloma, featuring 4 bedrooms, 2 full bathrooms and open floor plan. You will notice the enhanced curb appeal from the moment

Jennifer Conrado CHARLES RUTENBERG REALTY ORLANDO

1422 Tierra Cir, Winter Park, FL 32792
/16
$1,880 per month
- 3 Beds
- 1 Bath
- 1,520 Sq Ft
- House for Rent
1915 Carrigan Ave, Winter Park, FL 32792

Welcome to 1915 Carrigan Avenue! This charming 3-bedroom, 1-bathroom home offers a generous 1,520 square feet of well-designed space. The heart of the home is the newly updated kitchen, that features sleek stainless steel appliances, abundant white cabinetry, and ample counter space that runs along a functional layout. Enjoy added convenience with in-home washer and dryer hookups. Step outside

1915 Carrigan Ave, Winter Park, FL 32792
/2
$151,000 Sold Jan 08, 2025

2541 Leeward Way, Winter Park, FL 32792
- 2 Beds
- 2 Baths
- 1,020 Sq Ft
- Built 1977
Last Sold Summary
- 4% Above List Price
- $148/SF
- 2 Days On Market
Current Estimated Value $282,863

Last Listing Agent Michael Kara CORBELO LLC

2541 Leeward Way, Winter Park, FL 32792

/2
Est $431,472 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
Unlisted Address

Unlisted Address

/16
$158,500
- 1 Bed
- 1 Bath
- 749 Sq Ft
3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792

Investment Opportunity calling you!! Are you looking to start a portfolio of properties with monthly income? Now's your chance. Are you tired of paying rent and want to become a homeowner? This unit is exceptionally located in a great community. Prime Location and Zip Code are key! Low HOA! with minimal stress. Welcome home to 3019 Antique Oaks Circle Unit 124 at Parkview Village Winter Park, FL.

Kelly Flores COLDWELL BANKER REALTY

3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
/18
$1,999 per month
- 3 Beds
- 2 Baths
- 1,136 Sq Ft
- House for Rent
Unlisted Address

Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 1 car garage and approximately 1,136 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool

Cathy Behe TAH FLORIDA LLC

Unlisted Address
/2
$380,000 Sold Mar 27, 2025

3877 Waterview Loop, Winter Park, FL 32792
- 3 Beds
- 2.5 Baths
- 1,527 Sq Ft
- Built 1988
Last Sold Summary
- $249/SF
Current Estimated Value $375,470

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

3877 Waterview Loop, Winter Park, FL 32792

/2
Est $435,673 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
2838 Bright Bird Ln, Winter Park, FL 32792

2838 Bright Bird Ln, Winter Park, FL 32792

/27
$129,900
- 2 Beds
- 1 Bath
- 881 Sq Ft
1695 Lee Rd Unit E204, Winter Park, FL 32789

Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom.

Brandy Ray LOKATION

1695 Lee Rd Unit E204, Winter Park, FL 32789
/18
$2,335 per month
- 3 Beds
- 2 Baths
- 1,467 Sq Ft
- House for Rent
4967 N Magnolia Ave, Winter Park, FL 32792

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2479.90. That covers your base rent, $2335.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

4967 N Magnolia Ave, Winter Park, FL 32792
/2
$396,477 Sold May 20, 2025

7543 Dockside St, Winter Park, FL 32792
- 3 Beds
- 2 Baths
- 1,434 Sq Ft
- Built 1973
Last Sold Summary
- 3% Above List Price
- $276/SF
- 7 Days On Market
Current Estimated Value $395,245

Last Listing Agent Juan Matias LPT REALTY, LLC

7543 Dockside St, Winter Park, FL 32792

/35
Est $220,114 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,037 Sq Ft
656 Saint Johns Ct Unit S, Winter Park, FL 32792

656 Saint Johns Ct Unit S, Winter Park, FL 32792

/69
$1,750,000
- 4 Beds
- 2.5 Baths
- 3,263 Sq Ft
446 Alberta Dr, Winter Park, FL 32789

Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows residents to have walking access to Lake

Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

446 Alberta Dr, Winter Park, FL 32789
/20
$1,895 per month
- 2 Beds
- 1.5 Baths
- 1,219 Sq Ft
- Condo for Rent
200 Saint Andrews Blvd Unit 2903, Winter Park, FL 32792

Experience the best of Winter Park living in this highly sought-after 2-bedroom, 1.5-bathroom 2-story condo located in the Four Seasons community! This beautiful unit features modern light fixtures, stainless steel appliances, and upgraded flooring throughout. Enjoy the convenience of an included washer and dryer. Unwind on your private, fenced porch, perfect for entertaining. Four Seasons offers

Carissa Lawhun FLORIDA REALTY INVESTMENTS

200 Saint Andrews Blvd Unit 2903, Winter Park, FL 32792
/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
Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

1820 Englewood Rd, Winter Park, FL 32789

/2
Est $385,321 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,536 Sq Ft
230 Killarney Bay Ct Unit 3, Winter Park, FL 32789

230 Killarney Bay Ct Unit 3, Winter Park, FL 32789

/15
$160,000
- 3 Beds
- 2 Baths
- 1,149 Sq Ft
1695 Lee Rd Unit E215, Winter Park, FL 32789

Move-in Ready Renovated Condo – Prime Location!This beautifully renovated condo offers both style and convenience, situated right next to the community pool and playground. Enjoy modern upgrades throughout, along with the added assurance of a Home Warranty America coverage plan, valued up to $500, for extra peace of mind. Plus, you'll be just minutes from restaurants, shopping, major roads,

Kerem Munoz- Franquiz LA ROSA REALTY CENTRAL FLORIDA

1695 Lee Rd Unit E215, Winter Park, FL 32789
/15
$2,760 per month
- 4 Beds
- 2 Baths
- 1,534 Sq Ft
- House for Rent
2045 Houndslake Dr, Winter Park, FL 32792

We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

2045 Houndslake Dr, Winter Park, FL 32792
/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 $790,000

Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES

2320 Janice Ave, Winter Park, FL 32789

/24
Est $317,514 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,426 Sq Ft
172 Balfour Dr Unit 2, Winter Park, FL 32792

172 Balfour Dr Unit 2, Winter Park, FL 32792

/45
$460,000
- 3 Beds
- 2 Baths
- 1,694 Sq Ft
2152 Conifer Ave, Winter Park, FL 32792

This POOL home is amazing in every way and is truly a must see! Original Owner with incredible pride of ownership. Brand NEW Roof, Brand NEW Water Heater, HVAC 2020, entire replumb and newer windows throughout. Nestled in the highly coveted community of Eastbrook in Winter Park. A perfect location just minutes to everything. This residence boasts an array of desirable features. As you stroll down

Denise Korrey KORR REALTY CORP

2152 Conifer Ave, Winter Park, FL 32792
/13
$1,795 per month
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
- House for Rent
918 Gloriosa Ave, Winter Park, FL 32789

**HOLIDAY SPECIAL, If you take occupancy by January 1st 2026 receive $800.00 off your first months rent** Discover the charm of Winter Park living in this beautiful 3-bedroom, 2-bath rental home! Nestled in a peaceful neighborhood, this property offers a bright and open floor plan perfect for both relaxing and entertaining. Enjoy a spacious kitchen with modern appliances, a comfortable living

David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

918 Gloriosa Ave, Winter Park, FL 32789
/2
$235,000 Sold Apr 29, 2025

2529 Leeward Way, Winter Park, FL 32792
- 2 Beds
- 1 Bath
- 912 Sq Ft
- Built 1977
Last Sold Summary
- $258/SF
- 26 Days On Market
Current Estimated Value $237,046

Last Listing Agent Chris Creegan CREEGAN GROUP

2529 Leeward Way, Winter Park, FL 32792

/18
Est $420,201 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
2786 Bright Bird Ln, Winter Park, FL 32792

2786 Bright Bird Ln, Winter Park, FL 32792

/99
$5,495,000
- 5 Beds
- 6.5 Baths
- 7,278 Sq Ft
2211 Azalea Place, Winter Park, FL 32789

Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all

Maggie Walas FORTUNE INTERNATIONAL REALTY

2211 Azalea Place, Winter Park, FL 32789
/16
$2,505 per month
- 3 Beds
- 2 Baths
- 1,896 Sq Ft
- House for Rent
5133 Oak Hill Dr, Winter Park, FL 32792

Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month’s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

5133 Oak Hill Dr, Winter Park, FL 32792
/2
$423,000 Sold Aug 07, 2025

2812 Bright Bird Ln, Winter Park, FL 32792
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
- Built 2024
Last Sold Summary
- 8% Below List Price
- $222/SF
- 87 Days On Market
Current Estimated Value $425,480

Last Listing Agent Jessica Snyder LPT REALTY, LLC

2812 Bright Bird Ln, Winter Park, FL 32792

/29
Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,393 Sq Ft
7482 Canford Ct Unit 7482, Winter Park, FL 32792

7482 Canford Ct Unit 7482, Winter Park, FL 32792

/26
$625,000
- 3 Beds
- 3 Baths
- 1,890 Sq Ft
1360 Formosa Ave, Winter Park, FL 32789

Discover a rare and lucrative opportunity at 1360 Formosa Ave, a corner lot triplex in the highly sought-after Winter Park market. This income-generating property features three fully rented one-bedroom, one-bathroom units, providing a strong and steady return on investment. With 100% occupancy, this property is already a cash-flowing asset, but its value-add potential makes it even more enticing

Salvison Dickson TOP FLORIDA HOMES

1360 Formosa Ave, Winter Park, FL 32789
/16
$2,300 per month
- 3 Beds
- 2 Baths
- 1,280 Sq Ft
- House for Rent
2111 Biscayne Dr, Winter Park, FL 32789

Remodeled Winter Park 3 Bedroom Home For RentPriced Low, Call Now! This Property Has Been Professionally Refurbished And Features A 1-car Garage, Screened-in Patio, Fenced-in Yard, And Large Private Backyard. Enjoy Granite Countertops, An Upgraded Kitchen, Fresh Paint, And Beautiful Wood Plank Tile Flooring Throughout. Blinds Are Included. Located Just 10 Minutes To Downtown Orlando And 30

Jay Myers ORLANDO REALTY & PROPERTY MGNT

2111 Biscayne Dr, Winter Park, FL 32789
/2
$760,000 Sold Jul 17, 2025

2159 Marsh Sedge Ln, Winter Park, FL 32792
- 4 Beds
- 3 Baths
- 2,192 Sq Ft
- Built 2019
Last Sold Summary
- 4% Below List Price
- $347/SF
- 42 Days On Market
Current Estimated Value $757,514

Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

2159 Marsh Sedge Ln, Winter Park, FL 32792

/11
Est $411,524 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,782 Sq Ft
2711 Bright Bird Ln, Winter Park, FL 32792

2711 Bright Bird Ln, Winter Park, FL 32792

Showing Results 401 - 440, Page 11 of 18

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