Winter Park, FL Homes

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  $299,999 Open Fri 4PM - 7PM

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  3204 Netherwood Dr, Winter Park, FL 32792

  Discover this beautifully renovated 2-bedroom, 1.5 -bathroom villa in the heart of Winter Park! Nestled on a private cul-de-sac lot with no HOA, this home has been completely upgraded to offer modern comfort and style. Step inside to luxury vinyl flooring throughout, an open-concept living space, and a sleek kitchen with stainless steel appliances. The high-end bathroom remodel adds a spa-like

  Renee Anthony WATSON REALTY CORP.

  3204 Netherwood Dr, Winter Park, FL 32792
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  $850 per month

  • 1 Bed
  • 1 Bath
  • House for Rent

  2206 Bonanza Ave, Winter Park, FL 32792

  Property Id: 2445485Room for rent in a beautiful home located at 2206 Bonanza Ave, Winter Park, FL 32792, situated in a quiet and safe neighborhood—ideal for students or professionals. Features:•Private room with a digital lock •Clean home with a peaceful atmosphere•Shared kitchen, living room, and laundry facilities•WiFi and utilities included (water, electricity,

  2206 Bonanza Ave, Winter Park, FL 32792
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  $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 $431,251

  Last Listing Agent Jessica Snyder LPT REALTY, LLC

  2812 Bright Bird Ln, Winter Park, FL 32792
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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

  Last Listing Agent Kristen Ackley Chowdhury ACKLEY FLORIDA PROPERTY MANAGEMENT INC
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  $6,600,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,636 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 09/26/2025!! SELLER FINANCING AVAILABLE WITH VERY ATTRACTIVE TERMS Introducing a Unique, Stunning Modern Home A groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest building codes, this

  Prescilla Vazquez COMPASS FLORIDA LLC

  2661 Vía Tuscany, Winter Park, FL 32789
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  $1,950 per month

  • 2 Beds
  • 2.5 Baths
  • 1,236 Sq Ft
  • Townhouse for Rent

  5169 Lazy Oaks Dr, Winter Park, FL 32792

  Welcome to Lazy Oaks condominium. This townhome features two levels with an open floor plan that consist of 2 bedrooms, 2.5 bathrooms, and a Florida Room. Over 1200 sqft of living space awaits you with an upgraded laminate flooring, baseboards, lighting, and ceiling fans. A prime location that is nestled near Full Sail, UCF, Lynx bus stop, major shopping centers, restaurants, I-4, 408, & Orlando

  Damon Mayers MAYERS REAL ESTATE LLC

  5169 Lazy Oaks Dr, Winter Park, FL 32792
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  $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 $747,588

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

  2159 Marsh Sedge Ln, Winter Park, FL 32792
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  Est $204,180 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

  • 7% Below List Price
  • $180/SF
  • 44 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Marion Thacker RED BIRD REALTY OF FLORIDA INC
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  $645,000

  • 5 Beds
  • 3 Baths
  • 2,472 Sq Ft

  2612 Roxbury Rd, Winter Park, FL 32789

  SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!!Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with

  Laura Mcadams EXP REALTY LLC

  2612 Roxbury Rd, Winter Park, FL 32789
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  /19

  $2,420 per month

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft
  • House for Rent

  1891 Aster Dr, Winter Park, FL 32792

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  1891 Aster Dr, Winter Park, FL 32792
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  $450,000 Sold Jul 22, 2025

  1624 Little Wren Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $195/SF
  • 23 Days On Market

  Current Estimated Value $455,676

  Last Listing Agent Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

  1624 Little Wren Ln, Winter Park, FL 32792
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  Est $174,671 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

  • 12% Above List Price
  • $138/SF
  • 276 Days On Market

  Last Sold Price $156,000

  Last Listing Agent Jodie Lutz COLDWELL BANKER REALTY
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  $625,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft

  1500 Berkshire Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to this beautifully renovated historic home in the heart of Orwin Manor, one of Winter Park’s most treasured neighborhoods. Thoughtfully updated while preserving its timeless character, this 3 bedroom 1 and a half bath home blends classic architectural charm with today’s modern conveniences. Major system improvements include updated plumbing and

  Lianna D'Angelo SOTERA LIVING

  1500 Berkshire Ave, Winter Park, FL 32789
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  $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
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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 $384,173

  Last Listing Agent Mary Harmening ROAM FLORIDA REALTY LLC

  700 Melrose Ave Unit M4, Winter Park, FL 32789
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  Est $394,197 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

  • 7% Below List Price
  • $349/SF
  • 188 Days On Market

  Last Sold Price $423,750

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES
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  $475,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft

  1537 Bantam Way, Winter Park, FL 32792

  Under contract-accepting backup offers. There’s a certain feeling you get the moment you arrive in the secure, gated community of Enclave at Hawks Crest... a sense of calm, privacy, and understated luxury that immediately sets it apart. At 1537 Bantam Way, that feeling begins the second you pull up. The clean architectural lines, paver driveway, and polished contemporary exterior create a

  Jared Dunn LIVE MVRK LLC

  1537 Bantam Way, Winter Park, FL 32792
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  $2,695 per month

  • 3 Beds
  • 2.5 Baths
  • 1,886 Sq Ft
  • Townhouse for Rent

  7518 Aloma Pines Ct, Winter Park, FL 32792

  Welcome to 7518 Aloma Pines Ct, a modern 3-bedroom, 2.5-bath townhome in the heart of Winter Park, FL. Set in a quiet, gated community, this 1,872 sq ft residence blends upscale living with smart home features — including a built-in 5.1 surround sound system for a theater-quality experience.Interior Highlights:•Chef’s kitchen with granite countertops, 42” wood cabinetry, stainless

  7518 Aloma Pines Ct, Winter Park, FL 32792
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  $432,000 Sold May 08, 2025

  2472 Firstlight Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $208/SF
  • 53 Days On Market

  Current Estimated Value $436,660

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  2472 Firstlight Way, Winter Park, FL 32792
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  Est $576,457 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

  • 80% Below List Price
  • $1,579/SF
  • 123 Days On Market

  Last Sold Price $2,925,000

  Last Listing Agent Moshe Sheffi HPL REALTY INVESTMENTS
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  $1,375,000 Open Sat 1PM - 4PM

  • 4 Beds
  • 4 Baths
  • 3,024 Sq Ft

  2015 Summerfield Rd, Winter Park, FL 32792

  Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The

  Christina Fata REAL BROKER, LLC

  2015 Summerfield Rd, Winter Park, FL 32792
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  $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
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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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  Est $439,544 Not Listed For Sale

  2931 Clever Ln, Winter Park, FL 32792

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

  2931 Clever Ln, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $235/SF
  • 32 Days On Market

  Last Sold Price $448,190

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  $284,900

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  2335 Inagua Way, Winter Park, FL 32792

  Rare opportunity in beautiful Winter Park - Move in ready 3 bed 2 bath townhome for under $300,000. Super low HOA at only $92/month. Spacious split plan with new roof, newer AC, new carpet in bedrooms, freshly painted, tile, inside laundry, atrium off living room and open floor plan. Patio with storage room and shed. Front entrance & parking area with beautiful pavers. Townhome is on

  Marion McGrath ABSOLUTE REALTY GROUP, LLC

  2335 Inagua Way, Winter Park, FL 32792
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  $1,375 per month

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft
  • Condo for Rent

  2500 Lee Rd Unit 212, Winter Park, FL 32789

  Welcome to Lakeside Manor on beautiful Lake Killarney! This charming 2 bedroom, 1 bathroom second-floor condo offers tranquil living in one of Central Florida’s most desirable areas. Enjoy a serene, park-like setting right outside your door and access to breathtaking sunset views from the private community dock.Just minutes from Park Ave, Rollins College, Mills District, top dining,

  2500 Lee Rd Unit 212, Winter Park, FL 32789
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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 $428,343

  Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

  690 Osceola Ave Unit 502, Winter Park, FL 32789
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  Est $447,604 Not Listed For Sale

  2939 Clever Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2024

  2939 Clever Ln, Winter Park, FL 32792

  Last Sold Summary

  • 6% Below List Price
  • $268/SF
  • 8 Days On Market

  Last Sold Price $477,890

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  $664,000 Open Sat 12AM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft

  2087 Laurelwood Way, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Set within the serene gated community of Hawks Crest in Winter Park, this beautifully designed single-story home combines modern comfort with resort-style living. Featuring 4 bedrooms, 2 baths, and 1,920 sq. ft. of thoughtfully crafted space, it’s the perfect blend of style and function. Inside, an open-concept layout creates seamless flow between

  Brian Rotenberger COMPASS FLORIDA LLC

  2087 Laurelwood Way, Winter Park, FL 32792
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  $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
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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 $1,006,236

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

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

  3065 George Mason Ave Unit B, Winter Park, FL 32792

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

  3065 George Mason Ave Unit B, Winter Park, FL 32792

  Last Sold Summary

  • $190/SF
  • 168 Days On Market

  Last Sold Price $100,000

  Last Listing Agent Jacki Sandler SANDLER MANAGEMENT INC
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  $2,450,000

  • 4 Beds
  • 5 Baths
  • 5,051 Sq Ft

  2550 Venetian Way, Winter Park, FL 32789

  Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s

  Felicia Donateli PALM PROPERTIES OF CF, INC.

  2550 Venetian Way, Winter Park, FL 32789
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  $1,000 per month

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft
  • House for Rent

  5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792

  Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the 4 rooms has its own electronic keypad lock for your privacy and security. The extra large common areas provide the perfect space for dining and living. Spacious laundry and kitchen provide you with plenty of space

  5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792
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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 $1,174,078

  Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

  4048 Gilder Rose Place, Winter Park, FL 32792
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  Est $197,603 Not Listed For Sale

  608 Montego Bay Ct Unit S, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1981

  608 Montego Bay Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • 10% Below List Price
  • $196/SF
  • 5 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK
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  $149,990

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit E215, Winter Park, FL 32789

  Located in the heart of Winter Park, this charming condo stands ready to welcome you home. This three-bedroom, two-bathroom sanctuary offers a blend of comfort and modern elegance, perfect for those who cherish both relaxation and entertaining. As you step inside, the spacious living and dining areas greet you with an abundance of natural light, creating a warm and inviting atmosphere. Imagine

  Jenaia Fowlkes FOWLKES REALTY CO

  1695 Lee Rd Unit E215, Winter Park, FL 32789
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  $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
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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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  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

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