Winter Park, FL Homes

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  /33

  $375,000

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft

  1307 Formosa Ave, Winter Park, FL 32789

  Charming 2-bed home in Winter Park located in the Golfview subdivision offering approximately 1,150 square feet of living space on a 6,414 square foot lot. Built in 1946, this single family residence features a functional layout with a blend of original character and updated interior finishes. The home includes original pine flooring in the main living areas, ceramic tile in the kitchen and

  Tyler Gibson LPT REALTY, LLC

  1307 Formosa Ave, Winter Park, FL 32789
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  /23

  $3,500 Per Month

  • 4 Beds
  • 2 Baths
  • 2,099 Sq Ft
  • House for Rent

  2115 Sycamore Dr, Winter Park, FL 32789

  Updated Charming 4 Bed/2 Bath mid-century home located in Northwood Terrace/Audubon Park (just across the street from Baldwin Park). You will love the large lot .34 Acres with it botanical garden, meditation area, a patio with a raised HOT Tub (perfect for a starry night) and plenty of privacy with all the lush foliage. The front door opens to a great room where the kitchen, living area, dining

  John Goggin STOCKWORTH REALTY GROUP

  2115 Sycamore Dr, Winter Park, FL 32789
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  $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 $383,763

  Last Listing Agent Mary Harmening ROAM FLORIDA REALTY LLC

  700 Melrose Ave Unit M4, Winter Park, FL 32789
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  /2

  Est $143,287 Not Listed For Sale

  160 Lewfield Cir Unit 160, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft
  • Built 1973

  160 Lewfield Cir Unit 160, Winter Park, FL 32792

  Last Sold Summary

  • 15% Below List Price
  • $249/SF
  • 18 Days On Market

  • Last Sold Price $169,000
  • Oct 21, 2024

  Last Listing Agent Luis Cancel GLOBAL BROKERS RLTY OF FLORIDA
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  $2,395,000 New Construction

  • 4 Beds
  • 4 Baths
  • 3,111 Sq Ft

  2361 Mulbry Dr, Winter Park, FL 32789

  *** Parade of Homes Showcase This Weekend | Open House Saturday & Sunday 10 AM – 6 PM ***Casa Noir — Brand new construction custom home selected as a 2026 Parade of Homes showcase in Winter Park. 4 bedrooms. 4 full baths. Dedicated office. Loft. 2-car garage. Approximately 3,200 sq ft living space. Custom finishes done to perfection throughout. Inside, the foyer delivers on every promise made

  Ahmad Hassan COMPASS FLORIDA LLC

  2361 Mulbry Dr, Winter Park, FL 32789
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  /20

  $3,995 Per Month

  • 3 Beds
  • 3 Baths
  • 1,715 Sq Ft
  • House for Rent

  1667 Mizell Ave, Winter Park, FL 32789

  Minimum Deposit $3995. Monthly Rent $3995. Available June 1st!Contact Polina at or email to schedule your private showing. Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been established.Welcome to your dream Winter Park home! This charming 3-bedroom, 3 full bathroom gem is the epitome of comfort and

  1667 Mizell Ave, Winter Park, FL 32789
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  $605,000 Sold Dec 22, 2025

  2478 Whitehall Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 1965

  Last Sold Summary

  • 19% Below List Price
  • $268/SF
  • 123 Days On Market

  Current Estimated Value $612,149

  Last Listing Agent Erica Magtira LPT REALTY, LLC

  2478 Whitehall Cir, Winter Park, FL 32792
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  /2

  Est $852,512 Not Listed For Sale

  1905 S Lakemont Ave, Winter Park, FL 32792

  • 3 Beds
  • 3.5 Baths
  • 2,066 Sq Ft
  • Built 2024

  1905 S Lakemont Ave, Winter Park, FL 32792

  Last Sold Summary

  • $411/SF
  • 251 Days On Market

  • Last Sold Price $850,000
  • Apr 03, 2025

  Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK
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  $1,949,999 New Construction

  • 4 Beds
  • 4 Baths
  • 2,810 Sq Ft

  2501 Lafayette Ave, Winter Park, FL 32789

  Under Construction. GENEROUSLY APPOINTED LUXURY HOME at $1,875.000 with sound and water walls at $1,950,000.Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 4-bedroom, 4-bath home offers over 2,800 square feet of bright, open living space, designed for both comfort and functionality. Enter through your custom pivot front door into the foyer

  Tab Bish LLC REAL BROKER, LLC

  2501 Lafayette Ave, Winter Park, FL 32789
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  /17

  $1,350 Per Month

  • 1 Bed
  • 1 Bath
  • 753 Sq Ft
  • Condo for Rent

  4818 Tangerine Ave Unit 4818, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. The 1 bed, 1 bath unit is ideally located in Winter Park, close to Full Sail and UCF. Rent includes water, and all appliances including washer & dryer. A spacious Living/Dining space and a Huge bedroom make this the best one bed/one bath you'll find. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet

  Torey Eisenman BENCHMARK REAL ESTATE GRP INC

  4818 Tangerine Ave Unit 4818, Winter Park, FL 32792
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  $260,000 Sold Apr 03, 2026

  3580 Wilde Ave, Winter Park, FL 32792

  • Land
  • 35,283 Sq Ft
  • $320,988 per Acre

  Last Sold Summary

  • 340 Days On Market

  Current Estimated Value $257,181

  Last Listing Agent Gwendolen Flynn COLDWELL BANKER REALTY

  3580 Wilde Ave, Winter Park, FL 32792
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  /2

  Est $442,307 Not Listed For Sale

  2953 Clever Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  2953 Clever Ln, Winter Park, FL 32792

  Last Sold Summary

  • 6% Below List Price
  • $246/SF
  • 7 Days On Market

  • Last Sold Price $469,190
  • Aug 18, 2024

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  /65

  $549,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,513 Sq Ft

  1018 Bradford Dr, Winter Park, FL 32792

  LOCATION LOCATION! Welcome to this beautifully Updated and Meticulously Maintained Split 5-Bedroom, 3-Full Bathroom Floor Plan, Pool Home with No HOA in highly desirable Winter Park in Seminole County. Situated on an almost one-half-acre lot, this exceptional, spacious residence offers the perfect blend of comfort, privacy, and functionality. Enter the welcoming Foyer into the home's flexible

  Janie Harris UNITED REAL ESTATE PREFERRED

  1018 Bradford Dr, Winter Park, FL 32792
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  /11

  $1,495 Per Month

  • 2 Beds
  • 2 Baths
  • 1,045 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 806, Winter Park, FL 32792

  LB/O - Nice 2 bedroom 2 bathrooms, 2nd Floor Unit, Open Floor Concept, Living Area, Breakfast Area, Community Pool, Water Included! Apply Today!TO SCHEDULE A SHOWING YOU MUST EMAIL US WITH YOUR CONTACT INFORMATION AND THE PROPERTY YOU WISH TO SEE AT AND AN AGENT WILL RESPOND BACK WITH THE AVAILABLE SHOW TIMES.HOW TO APPLY/ABOUT OUR APPLICATION PROCESS: Our application process

  1000 S Semoran Blvd Unit 806, Winter Park, FL 32792
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  $417,100 Sold Nov 24, 2025

  690 Osceola Ave Unit 502, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1969

  Last Sold Summary

  • 26% Below List Price
  • $298/SF
  • 196 Days On Market

  Current Estimated Value $437,105

  Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

  690 Osceola Ave Unit 502, Winter Park, FL 32789
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  /18

  Est $194,371 Not Listed For Sale

  3351 River View Way Unit 41, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft
  • Built 1983

  3351 River View Way Unit 41, Winter Park, FL 32792

  Last Sold Summary

  • 15% Below List Price
  • $231/SF
  • 53 Days On Market

  • Last Sold Price $229,000
  • Oct 31, 2023

  Last Listing Agent My Hien Domeika Coldwell Banker Realty
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  /17

  $170,000

  • 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
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  /17

  $2,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789
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  $435,800 Sold Apr 27, 2026

  5418 Ardmore Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $279/SF
  • 5 Days On Market

  Current Estimated Value $427,547

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  5418 Ardmore Dr, Winter Park, FL 32792
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  /42

  Est $475,432 Not Listed For Sale

  2444 Firstlight Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft
  • Built 2020

  2444 Firstlight Way, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $204/SF
  • 11 Days On Market

  • Last Sold Price $485,000
  • Jun 17, 2024

  Last Listing Agent Patrick Pixley THE AGENCY FL
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  /68

  $825,000

  • 5 Beds
  • 3 Baths
  • 2,242 Sq Ft

  1927 Eland Ave, Winter Park, FL 32789

  *Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental

  Ryan Leitter CHARLES RUTENBERG REALTY ORLANDO

  1927 Eland Ave, Winter Park, FL 32789
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  /15

  $2,195 Per Month

  • 3 Beds
  • 2 Baths
  • 1,324 Sq Ft
  • House for Rent

  704 Carnation Dr, Winter Park, FL 32792

  Welcome to 704 Carnation Drive in Winter Park! This amazing home is located on a quiet street in the Eastbrook subdivision off Aloma Ave and was just freshly painted inside and out. The single-story home features an open concept living room/dining room/kitchen floorplan with stainless steel appliances, granite countertops, ceiling fan and ceramic tile flooring throughout. There is plenty of

  704 Carnation Dr, Winter Park, FL 32792
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  $1,200,000 Sold Mar 20, 2026

  950 Aragon Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 2020

  Last Sold Summary

  • $463/SF
  • 5 Days On Market

  Current Estimated Value $1,184,514

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  950 Aragon Ave, Winter Park, FL 32789
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  Not Listed For Sale

  3069 Aaron Burr Ave Unit D, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Built 1974

  3069 Aaron Burr Ave Unit D, Winter Park, FL 32792

  Last Sold Summary

  • $187/SF
  • 53 Days On Market

  • Last Sold Price $112,000
  • Aug 14, 2024

  Last Listing Agent Kristen Ackley Chowdhury ACKLEY FLORIDA PROPERTY MANAGEMENT INC
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  /16

  $790,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft

  521 Fairfax Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. A rare opportunity awaits at 519 & 521 Fairfax Avenue in the highly sought-after Virginia Heights neighborhood. This rare mid-century duplex features two well-designed units, each offering 2 bedrooms, 2 bathrooms, and spacious interior utility rooms large enough to accommodate a washer and dryer, an additional refrigerator, and ample storage. Filled with

  Jennifer Sloan COMPASS FLORIDA LLC

  521 Fairfax Ave, Winter Park, FL 32789
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  /24

  $2,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 118, Winter Park, FL 32789

  Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 118, Winter Park, FL 32789
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  $1,206,400 Sold Oct 15, 2025

  4048 Gilder Rose Place, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 3,321 Sq Ft
  • Built 1992

  Last Sold Summary

  • $363/SF
  • 101 Days On Market

  Current Estimated Value $1,183,591

  Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

  4048 Gilder Rose Place, Winter Park, FL 32792
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  /2

  Est $212,751 Not Listed For Sale

  200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $180/SF
  • 44 Days On Market

  • Last Sold Price $220,000
  • Jul 23, 2024

  Last Listing Agent Marion Thacker RED BIRD REALTY OF FLORIDA INC
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  /38

  $1,199,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,618 Sq Ft

  1807 Magnolia Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Positioned as one of the best values currently available for new construction in Winter Park, this exceptional residence by Hamilton Homes seamlessly blends timeless character with the ease and efficiency of modern living. From the moment you arrive, the home makes a lasting impression with its inviting front porch and classic gas lantern, setting a tone

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1807 Magnolia Ave, Winter Park, FL 32789
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  /11

  $1,695 Per Month

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Condo for Rent

  3011 George Mason Ave Unit 1-2E, Winter Park, FL 32792

  Great location! Spacious SECOND FLOOR 2 bedroom + 2 full bath condo featuring an open living room/dining room combo and large kitchen. Conveniently located across from the pool. Stackable washer/dryer in unit. NEW CARPET in bedrooms! Parking permit required. Two pet max permitted. Available now! NOTE: Petscreening required on all applications, whether tenant has a pet or not. . $30 per pet to

  3011 George Mason Ave Unit 1-2E, Winter Park, FL 32792
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  $487,500 Sold Mar 26, 2026

  275 N Ranger Blvd, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 1,864 Sq Ft
  • Built 1965

  Last Sold Summary

  • 2% Below List Price
  • $262/SF
  • 2 Days On Market

  Current Estimated Value $542,268

  Last Listing Agent David Augello ON POINT REALTY LLC

  275 N Ranger Blvd, Winter Park, FL 32792
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  Est $181,818 Not Listed For Sale

  200 Saint Andrews Blvd Unit 2703, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,127 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 2703, Winter Park, FL 32792

  Last Sold Summary

  • 17% Above List Price
  • $138/SF
  • 276 Days On Market

  • Last Sold Price $156,000
  • Feb 28, 2025

  Last Listing Agent Jodie Lutz COLDWELL BANKER REALTY
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  /50

  $2,198,000

  • 4 Beds
  • 2.5 Baths
  • 2,841 Sq Ft

  1760 Alabama Dr, Winter Park, FL 32789

  Welcome to 1760 Alabama Drive, a striking mid-century residence where architectural character, thoughtful modernization, and exceptional livability come together in one of Winter Park’s most desirable neighborhoods. Spanning 2,841 square feet, this distinctive home celebrates authentic mid-century design with clean lines, intentional geometry, and expansive walls of glass that bring the outdoors

  Brian Ruth DAILLAND REAL ESTATE

  1760 Alabama Dr, Winter Park, FL 32789
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  /15

  $1,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit D116, Winter Park, FL 32789

  Welcome Home to Waterfall Cove in Winter Park! This spacious 3-bedroom, 2-bath ground floor corner unit is move-in ready with fresh paint and brand new carpet throughout. Corner placement means extra natural light and a layout that lives even larger than its generous footprint. Community Perks include a sparkling pool just in time for summer, secured building access, and a peaceful, park-like

  Ryan Hoppe ZEAL REALTY

  1695 Lee Rd Unit D116, Winter Park, FL 32789
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  $72,000 Sold Jun 24, 2025

  273 Scottsdale Square Unit 273, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 785 Sq Ft
  • Built 1974

  Last Sold Summary

  • 24% Below List Price
  • $92/SF
  • 4 Days On Market

  Current Estimated Value $75,230

  Last Listing Agent Erin Tompkins COLDWELL BANKER REALTY

  273 Scottsdale Square Unit 273, Winter Park, FL 32792
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  /2

  Est $411,930 Not Listed For Sale

  620 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,214 Sq Ft
  • Built 1986

  620 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  Last Sold Summary

  • 3% Below List Price
  • $349/SF
  • 188 Days On Market

  • Last Sold Price $423,750
  • Dec 02, 2024

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES
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  /32

  $775,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,062 Sq Ft

  675 Overspin Dr, Winter Park, FL 32789

  Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatile layout, and the best of Winter Park at your doorstep! With Dubsdread Golf Course just around the corner and Fairbanks Avenue minutes away, this 4-bedroom, 3.5-bath CUSTOM BUILT HOME puts you in the center of it all – NO HOA required! Major systems have been well maintained; including a NEW A/C UNIT with UV

  Jennifer Wemert WEMERT GROUP REALTY LLC

  675 Overspin Dr, Winter Park, FL 32789
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  /9

  $2,100 Per Month

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Nice 3 bedroom, 2 bath single family home

  3036 Patel Dr, Winter Park, FL 32792

  Available May 1st! 3/2 with open-concept kitchen. Your new home has an open and airy living room/kitchen area with easy-to-maintain tile. A HUGE screened patio looks out to a private wooded backyard. Privacy fence and attached one-car garage make this the perfect place to call home! The home is nestled on a cul-de-sac minutes from Full Sail.All ERA Grizzard Real Estate residents are

  3036 Patel Dr, Winter Park, FL 32792
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  /2

  $630,000 Sold Apr 16, 2026

  649 Berwick Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,943 Sq Ft
  • Built 1966

  Last Sold Summary

  • 3% Above List Price
  • $324/SF
  • 3 Days On Market

  Current Estimated Value $608,599

  Last Listing Agent Caroline Fiore MAINFRAME REAL ESTATE

  649 Berwick Dr, Winter Park, FL 32792
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  Est $546,599 Not Listed For Sale

  875 Miles Ave Unit 4, Winter Park, FL 32789

  • 18 Beds
  • 18 Baths
  • 1,852 Sq Ft
  • Built 2005

  875 Miles Ave Unit 4, Winter Park, FL 32789

  Last Sold Summary

  • 81% Below List Price
  • $1,579/SF
  • 123 Days On Market

  • Last Sold Price $2,925,000
  • Oct 25, 2024

  Last Listing Agent Moshe Sheffi HPL REALTY INVESTMENTS

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