Winter Park, FL Homes

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  /21

  $562,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,778 Sq Ft

  5233 Lake Howell Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. NO HOA. Dual Master Suites. One main, and one mother-in-law or guest suite. All single story, no stairs. NEW POOL DECK. NEW POOL PUMP. POOL RESURFACED.NEW ROOF (installation in progress). Totally renovated. NEW HOT WATER HEATER. NEW FLOORS. POOL RESURFACED. NEW POOL DECK. NEW POOL PUMP. NEW ALL TURF BACK LAWN (NO Mowing). NEW PUTTING GREEN (for your

  Miranda Cady CADENCE LIFESTYLE REAL ESTATE

  5233 Lake Howell Rd, Winter Park, FL 32792
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  /24

  $1,282 - $2,730 per month

  Alvista Winter Park

  1 - 2 Beds

  3935 Sutton Place Blvd, Winter Park, FL 32792

  Live life better at Alvista Winter Park! Located in the sought-after neighborhood of Winter Park, Orlando, and just minutes from Full Sail University, Harbor Park and Winter Pines Golf Club, our community effortlessly blends the concepts of convenience and ease. Our collection of lifestyle amenities and interior details make our residents quickly feel right at home!Choose from spacious one and

  3935 Sutton Place Blvd, Winter Park, FL 32792
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  $420,000 Sold Jan 15, 2026

  1847 Azalea Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 1,477 Sq Ft
  • Built 1961

  Last Sold Summary

  • $284/SF
  • 1 Day On Market

  Current Estimated Value $414,196

  Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

  1847 Azalea Ave, Winter Park, FL 32789
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  /47

  Est $239,299 Not Listed For Sale

  200 Saint Andrews Blvd Unit 1203, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 1203, Winter Park, FL 32792

  Last Sold Summary

  • 18% Below List Price
  • $222/SF
  • 8 Days On Market

  Last Sold Price $293,455

  Last Listing Agent Steven Luppert COMPASS FLORIDA LLC
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  /35

  $750,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  676 Dunblane Dr, Winter Park, FL 32792

  This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds | 2 Baths | Bonus Room | This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room provides flexible use — ideal as

  Emma Kaplan BALDWIN PARK REALTY LLC

  676 Dunblane Dr, Winter Park, FL 32792
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  /32

  $2,950 per month

  • 4 Beds
  • 3 Baths
  • 2,070 Sq Ft
  • House for Rent

  2907 Little John Rd, Winter Park, FL 32792

  One Story home in Winter Park Pines with 4 bedrooms and 3 full baths! Large Screened Porch and fenced rear yard. Quiet street. Stainless steel appliances: Refrigerator, Smooth-top Range/Oven, Dishwasher. Lawn Care included! W/D hookups in Laundry room. A/C replaced in 2022. Home re-piped in 2022. Move-in Ready Home! Convenient Winter Park Location Only Minutes from Baldwin Park, Park Avenue,

  Benjamin Cole, IV SOTERA LIVING

  2907 Little John Rd, Winter Park, FL 32792
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  /2

  $199,900 Sold Nov 03, 2025

  2500 Lee Rd Unit 134, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Below List Price
  • $310/SF
  • 130 Days On Market

  Current Estimated Value $189,655

  Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

  2500 Lee Rd Unit 134, Winter Park, FL 32789
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  /64

  Est $658,459 Not Listed For Sale

  1327 Fountain Hills Ct, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,575 Sq Ft
  • Built 2017

  1327 Fountain Hills Ct, Winter Park, FL 32792

  Last Sold Summary

  • 1% Above List Price
  • $252/SF
  • 0 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Brannon Ogburn JPAR SOUTH FLORIDA LIVING
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  /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
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  $1,458 - $2,620 per month

  Stonecastle Apartment Homes

  1 - 3 Beds

  2015 New Stonecastle Terrace, Winter Park, FL 32792

  Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

  2015 New Stonecastle Terrace, Winter Park, FL 32792
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  /19

  $172,000 Sold May 23, 2025

  700 Melrose Ave Unit E24, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 787 Sq Ft
  • Built 1964

  Last Sold Summary

  • 14% Below List Price
  • $219/SF
  • 164 Days On Market

  Current Estimated Value $176,943

  Last Listing Agent Susan Dering HOMEVEST REALTY

  700 Melrose Ave Unit E24, Winter Park, FL 32789
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  /2

  Est $372,652 Not Listed For Sale

  1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 864 Sq Ft
  • Built 1983

  1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  Last Sold Summary

  • 12% Below List Price
  • $492/SF
  • 36 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Jenni Owens KELLER WILLIAMS WINTER PARK
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  /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
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  /21

  $3,750 per month

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft
  • Apartment for Rent

  421 W Fairbanks Ave, Winter Park, FL 32789

  Occupying the entire second floor of a landmark 1925 brick building in the heart of Winter Park, this fully reimagined residence offers a rare opportunity to lease a true designer 3 bedroom, 3 bathroom loft just two blocks from Park Avenue. The open concept interior features high ceilings, abundant natural light from skylights and brand new windows, and a refined industrial aesthetic anchored by

  Nicholas Cadwallader REALTY ONE GROUP MVP

  421 W Fairbanks Ave, Winter Park, FL 32789
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  /2

  $340,000 Sold Feb 26, 2026

  7580 Aloma Pines Ct, Winter Park, FL 32792

  • 3 Beds
  • 3.5 Baths
  • 1,872 Sq Ft
  • Built 2016

  Last Sold Summary

  • 7% Below List Price
  • $182/SF
  • 94 Days On Market

  Current Estimated Value $348,407

  Last Listing Agent Simon Colak USCO CAPITAL GROUP

  7580 Aloma Pines Ct, Winter Park, FL 32792
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  /2

  Est $1,543,351 Not Listed For Sale

  2185 Talman Ct, Winter Park, FL 32792

  • 5 Beds
  • 6 Baths
  • 4,760 Sq Ft
  • Built 2008

  2185 Talman Ct, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $328/SF
  • 5 Days On Market

  Last Sold Price $1,562,500

  Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES
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  /27

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,140 Sq Ft

  989 Eastbrook Blvd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. You’ve just found a Gem! Immaculate, move-in ready, and so conveniently located, you’ll love this turn-key home. Just painted inside and out, featuring brand new contemporary flooring, a 2025 AC, a newer tankless hot water heater, a brand new kitchen cooktop, all new light fixtures, switches, ceiling fans, and door hardware. A new roof was added in

  Jane Pedigree COLDWELL BANKER REALTY

  989 Eastbrook Blvd, Winter Park, FL 32792
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  /20

  $1,456 - $2,718 per month

  ARIUM Winter Park

  1 - 2 Beds

  3250 Bishop Park Dr, Winter Park, FL 32792

  Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

  3250 Bishop Park Dr, Winter Park, FL 32792
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  /2

  $600,000 Sold Apr 10, 2025

  7531 Lodge Pole Trail, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,141 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $280/SF
  • 20 Days On Market

  Current Estimated Value $576,618

  Last Listing Agent Austin Cummings NEXTDWELL

  7531 Lodge Pole Trail, Winter Park, FL 32792
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  /2

  Est $1,834,642 Not Listed For Sale

  643 Balmoral Rd, Winter Park, FL 32789

  643 Balmoral Rd, Winter Park, FL 32789

  Last Sold Summary

  • 4% Above List Price
  • 17 Days On Market

  Last Sold Price $1,767,500

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC
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  /11

  $128,500 Pending

  • 2 Beds
  • 2 Baths
  • 1,072 Sq Ft

  1000 S Semoran Blvd Unit 512, Winter Park, FL 32792

  Priced to sell! This 2 bedroom 2 bathroom condo located in the highly sought after Winter Park area is the perfect opportunity for an investor or a first time buyer. This unit has new luxury vinyl plank flooring throughout, recently upgraded kitchen cabinets, huge living room area and very spacious bedrooms. Located on the 2nd floor, and within steps of the community pool and laundry facility.

  Cristina Burgos REALSOURCE PROPERTY MANGNT LLC

  1000 S Semoran Blvd Unit 512, Winter Park, FL 32792
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  /15

  $2,195 per month

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft
  • House for Rent

  1724 Peruvian Ln, Winter Park, FL 32792

  Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *Bonus Amenity Included* - All residents are enrolled

  Mo Jabr RE/MAX 200 REALTY

  1724 Peruvian Ln, Winter Park, FL 32792
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  /2

  $266,000 Sold Nov 19, 2025

  1500 Gay Rd Unit 9B, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $259/SF
  • 5 Days On Market

  Current Estimated Value $262,337

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 9B, Winter Park, FL 32789
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  /18

  Est $237,506 Not Listed For Sale

  7781 Country Place Unit J-1, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,227 Sq Ft
  • Built 1988

  7781 Country Place Unit J-1, Winter Park, FL 32792

  Last Sold Summary

  • 5% Below List Price
  • $203/SF
  • 6 Days On Market

  Last Sold Price $249,000

  Last Listing Agent Rick Protheroe RE/MAX
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  /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
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  /7

  $2,425 per month

  • 3 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • House for Rent

  5206 Ardmore 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 $2569.90. That covers your base rent, $2425.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5206 Ardmore Dr, Winter Park, FL 32792
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  /2

  $470,000 Sold Jan 15, 2026

  3319 Ellwood Ct, Winter Park, FL 32792

  • 5 Beds
  • 3 Baths
  • 1,546 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $304/SF
  • 78 Days On Market

  Current Estimated Value $466,961

  Last Listing Agent Elena Sanchez BALDWIN PARK REALTY LLC

  3319 Ellwood Ct, Winter Park, FL 32792
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  /17

  Est $189,544 Not Listed For Sale

  7460 Swallow Run Unit 42, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft
  • Built 1974

  7460 Swallow Run Unit 42, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $140/SF
  • 10 Days On Market

  Last Sold Price $191,000

  Last Listing Agent Stephani Castro OLYMPUS EXECUTIVE REALTY INC
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  /6

  $99,000

  • Studio
  • 1 Bath
  • 537 Sq Ft

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792

  Attention investors! Take a look at this great opportunity to purchase a Cozy Condo located in Winter Park, FL. This studio condo features beautiful tile floors and lots of closet space. First-floor unit with open patio. Minutes away from Downtown Winter Park, expressway, downtown Orlando, Full Sail, and the University of Central Florida. This community offers a pool, tennis court, and clubhouse.

  Lynda Cheros OAKSTRAND REALTY

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
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  /12

  $1,850 per month

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Condo for Rent

  612 Trinidad Ct Unit 612, Winter Park, FL 32792

  Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area

  Carolina Barriento JEXOR LLC

  612 Trinidad Ct Unit 612, Winter Park, FL 32792
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  $245,900 Sold Aug 11, 2025

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,132 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $217/SF
  • 2 Days On Market

  Current Estimated Value $262,032

  Last Listing Agent Matt Merdian MERDIAN REALTY LLC

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789
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  /30

  Est $618,886 Not Listed For Sale

  1086 Azalea Ln Unit 1, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 1983

  1086 Azalea Ln Unit 1, Winter Park, FL 32789

  Last Sold Summary

  • 5% Above List Price
  • $332/SF
  • 5 Days On Market

  Last Sold Price $589,000

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES
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  /57

  $1,825,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,746 Sq Ft

  501 Henkel Cir, Winter Park, FL 32789

  Walk to Park Avenue from this stylish and impeccably maintained Winter Park home, tucked along a charming brick street just minutes from the shops, dining, and vibrant energy of downtown Winter Park. Designed for both effortless living and entertaining, the main residence offers 3,410 SF with 4 bedrooms and 3.5 baths, while a detached studio apartment sits above the two-car garage, adding 300+ SF

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  501 Henkel Cir, Winter Park, FL 32789
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  /18

  $2,345 per month

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

  7433 Betty St, 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 $2489.90. That covers your base rent, $2345.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7433 Betty St, Winter Park, FL 32792
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  /2

  $725,000 Sold May 13, 2025

  1570 Grove Terrace, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft
  • Built 1991

  Last Sold Summary

  • $436/SF

  Current Estimated Value $758,527

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

  1570 Grove Terrace, Winter Park, FL 32789
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  /2

  Est $269,567 Not Listed For Sale

  218 Balfour Dr Unit 12, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Built 1985

  218 Balfour Dr Unit 12, Winter Park, FL 32792

  Last Sold Summary

  • 9% Below List Price
  • $235/SF
  • 19 Days On Market

  Last Sold Price $295,000

  Last Listing Agent Dawn Romance FANNIE HILLMAN & ASSOCIATES
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  /29

  $499,999

  • 4 Beds
  • 3 Baths
  • 1,826 Sq Ft

  731 Bongart Rd, Winter Park, FL 32792

  Experience luxury living in this stunning, fully remodeled single-family home located in the heart of Winter Park, where modern sophistication meets exceptional functionality. This spectacular residence features a total of 4 spacious bedrooms and 3 modern bathrooms, boasting sleek laminate flooring throughout and a chef-inspired kitchen fully equipped with premium stainless steel appliances. A

  Maria Gomez Arevalo MY REALTY GROUP, LLC.

  731 Bongart Rd, Winter Park, FL 32792
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  /12

  $1,400 per month

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

  1695 Lee Rd Unit C110, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit C110, Winter Park, FL 32789
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  /2

  $1,300,000 Sold Sep 22, 2025

  1371 Lyndale Blvd, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,714 Sq Ft
  • Built 1949

  Last Sold Summary

  • 4% Below List Price
  • $479/SF
  • 8 Days On Market

  Current Estimated Value $1,273,815

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
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  /2

  Est $314,183 Not Listed For Sale

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $684/SF
  • 3 Days On Market

  Last Sold Price $329,900

  Last Listing Agent Susan Logan LOGAN LAND & HOMES, INC.

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