Winter Park, FL Homes

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  $435,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,002 Sq Ft

  1306 Merrydale Way, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. MERITAGE BUILDER HOME- PRICE IMPROVEMENT - OWNER MOTIVATED - WILLING TO HELP WITH CLOSING COSTS OR RATE BUY DOWN. Welcome to the Enclave at Hawks Crest, a newly built GATED luxury townhomecommunity in sought-after Winter Park, and this 3BD/2.5BA home with a bright open floor plan, UPGRADES throughout,

  Claire Sims LLC LPT REALTY, LLC

  1306 Merrydale Way, Winter Park, FL 32792
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  $2,550 Per Month

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Condo for Rent

  110 Killarney Bay Ct Unit 1, Winter Park, FL 32789

  **MOVE IN SPECIAL $500 off first months rent** Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  110 Killarney Bay Ct Unit 1, Winter Park, FL 32789
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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 $414,739

  Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

  1847 Azalea Ave, Winter Park, FL 32789
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  /2

  Est $325,756 Not Listed For Sale

  3167 Crown Jewel Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,406 Sq Ft
  • Built 2019

  3167 Crown Jewel Ct, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $238/SF
  • 54 Days On Market

  • Last Sold Price $335,000
  • May 05, 2025

  Last Listing Agent Amy Phillips CALL IT CLOSED INTL REALTY
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  $1,050,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,342 Sq Ft

  632 Country Club Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards

  Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

  632 Country Club Dr, Winter Park, FL 32789
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  /15

  $2,125 Per Month

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  1407 Chilean Ln, Winter Park, FL 32792

  We are currently making final preparations for this home to be available. 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

  1407 Chilean Ln, Winter Park, FL 32792
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  $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 $189,746

  Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

  2500 Lee Rd Unit 134, Winter Park, FL 32789
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  Est $1,517,124 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

  • 3% Below List Price
  • $328/SF
  • 5 Days On Market

  • Last Sold Price $1,562,500
  • Mar 03, 2025

  Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES
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  $189,500

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 222, Winter Park, FL 32789

  Lakefront access in Winter Park under $200K! One of the few condos at this price point offering direct access to Lake Killarney. This move-in ready 1-bedroom, 1-bath residence combines peaceful lakeside living with unbeatable proximity to Winter Park Village shopping, dining, and entertainment. The open-concept living and kitchen area features engineered wood flooring and abundant natural light,

  Christine Bouchard HOMESMART

  2500 Lee Rd Unit 222, Winter Park, FL 32789
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  /12

  $6,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Apartment for Rent

  301 W Comstock Ave, Winter Park, FL 32789

  Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.

  Sydney Brownlee THE SYDGAN CORP

  301 W Comstock Ave, Winter Park, FL 32789
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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 $180,280

  Last Listing Agent Susan Dering HOMEVEST REALTY

  700 Melrose Ave Unit E24, Winter Park, FL 32789
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  Est $423,726 Not Listed For Sale

  1496 Broad Wing Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Built 2021

  1496 Broad Wing Ln, Winter Park, FL 32792

  Last Sold Summary

  • 2% Above List Price
  • $236/SF
  • 52 Days On Market

  • Last Sold Price $415,000
  • Apr 03, 2025

  Last Listing Agent Michelle Deleon BHHS FLORIDA REALTY
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  /31

  $194,995 Pending

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  4790 Tangerine Ave Unit 4790, Winter Park, FL 32792

  Under contract-accepting backup offers. Move right into this beautifully two-bedroom, two-bath condominium located in desirable East Winter Park. The thoughtfully designed floor plan offers two spacious bedrooms, and bathrooms—one featuring a tub and the other a shower—providing comfort and privacy.The light-filled great room showcases attractive laminate wood flooring and sliding glass doors

  Sonny Manku SUNSHINE BROKERAGE, LLC

  4790 Tangerine Ave Unit 4790, Winter Park, FL 32792
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  $3,150

  Total Monthly Price

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Townhouse for Rent

  1351 Merrydale Way, Winter Park, FL 32792

  Modern townhome in a gated community in Winter Park. This energy star-certified home features 3 BED/2.5 BATH, large two car garage and private driveway, tile floors all throughout the first floor, granite countertops in the kitchen and bathroom, and all stainless steel appliances. The downstairs is an airy open concept with views of the lake. There's a 1/2 bath downstairs so you are never

  1351 Merrydale Way, Winter Park, FL 32792
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  $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 $348,697

  Last Listing Agent Simon Colak USCO CAPITAL GROUP

  7580 Aloma Pines Ct, Winter Park, FL 32792
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  Est $1,826,827 Not Listed For Sale

  643 Balmoral Rd, Winter Park, FL 32789

  643 Balmoral Rd, Winter Park, FL 32789

  Last Sold Summary

  • 3% Above List Price
  • 17 Days On Market

  • Last Sold Price $1,767,500
  • Mar 21, 2025

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC
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  /46

  $950,000

  • 3 Beds
  • 2 Baths
  • 2,114 Sq Ft

  250 Cortland Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy

  James Ferngren CREEGAN GROUP

  250 Cortland Ave, Winter Park, FL 32789
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  $3,900 Per Month

  • 4 Beds
  • 3 Baths
  • 2,130 Sq Ft
  • House for Rent

  1542 Sugarwood Cir, Winter Park, FL 32792

  Spacious, fully remodeled 4-bedroom, 2.5-bath single-family home located in the desirable Amberwood community in Winter Park. This one-story property offers approximately 2,130 sq ft of living space, featuring vaulted ceilings, a functional layout, and a bright living and dining area. The home showcases luxury finishes throughout, a brand-new roof, central A/C, and a 2-car attached garage. Enjoy

  Dayana Perez Moreno AROD PARTNERS REALTY

  1542 Sugarwood Cir, Winter Park, FL 32792
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  $250,000 Sold Apr 10, 2026

  1823 Maywood Rd, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,232 Sq Ft
  • Built 1956

  Last Sold Summary

  • $203/SF
  • 1 Day On Market

  Current Estimated Value $220,273

  Last Listing Agent Abby Nelson RE/MAX 200 REALTY

  1823 Maywood Rd, Winter Park, FL 32792
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  /18

  Est $240,197 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

  • 4% Below List Price
  • $203/SF
  • 6 Days On Market

  • Last Sold Price $249,000
  • Nov 29, 2023

  Last Listing Agent Rick Protheroe RE/MAX
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  $1,149,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,153 Sq Ft

  2922 Reef Knot Place, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Incredible Value!!! Major price reduction! Private Lakefront Living! Move-in Ready! Wake up to water views, quiet mornings and the kind of lifestyle that rarely becomes available in the Winter Park/Howell Branch area. Set along the shores of a private ski lake- Lake Florence, this single-level lakefront

  Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO

  2922 Reef Knot Place, Winter Park, FL 32792
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  /13

  $1,522

  Total Monthly Price

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

  1500 Gay Rd Unit 1D, Winter Park, FL 32789

  EXCELLENT LOCATION within walking distance to retail stores, restaurants, and parks. This remodeled second-floor unit offers lake access, a pool, and includes water in the rent. Flexible deposit option available—can be split over the first three months.

  1500 Gay Rd Unit 1D, Winter Park, FL 32789
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  $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 $262,699

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 9B, Winter Park, FL 32789
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  Est $631,040 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

  • 7% Above List Price
  • $332/SF
  • 5 Days On Market

  • Last Sold Price $589,000
  • May 22, 2023

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES
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  $995,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 3 Baths
  • 3,057 Sq Ft

  1453 Via Sangro Place, Winter Park, FL 32792

  Welcome to refined Florida living in the highly sought-after gated community of Lakeside Estates, one of Winter Park’s most exclusive neighborhoods, where homes rarely come to market. With only 39 residences, this intimate lakefront community offers a level of privacy, prestige, and curb appeal that is increasingly difficult to find. From the moment you pass through the impressive gated entrance

  Brian Diaz KELLER WILLIAMS ADVANTAGE REALTY

  1453 Via Sangro Place, Winter Park, FL 32792
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  /17

  $1,400 Per Month

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

  1695 Lee Rd Unit D213, Winter Park, FL 32789

  Adorable and cozy second floor condo, conveniently located off Lee Road in Orlando, minutes from SR I-4. This 2-bedroom 1 full bath condo is located in the quiet community or Waterfall Cove. Water is included with a community pool and playground for tenants to enjoy. Open floor plan with carpet and laminate in kitchen and bath. Fresh paint throughout. Balcony just outside the sliders in living

  Rachel DeCamp RLL Real Estate Group

  1695 Lee Rd Unit D213, Winter Park, FL 32789
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  $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 $466,549

  Last Listing Agent Elena Sanchez BALDWIN PARK REALTY LLC

  3319 Ellwood Ct, Winter Park, FL 32792
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  Not Listed For Sale

  3000 George Mason Ave Unit 1, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,108 Sq Ft
  • Built 1974

  3000 George Mason Ave Unit 1, Winter Park, FL 32792

  Last Sold Summary

  • $81/SF
  • 58 Days On Market

  • Last Sold Price $90,250
  • Apr 14, 2025

  Last Listing Agent Nathalie Charles PREMIUM PROPERTIES R.E SERVICE
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  /29

  $220,000

  • 2 Beds
  • 1 Bath
  • 854 Sq Ft

  2400 Dominica Run, Winter Park, FL 32792

  CHARMING 2/1 MOVE IN READY TOWNHOME in highly sought-after Windward Square community of Winter Park! NEWER Roof 2025! Spacious floor plan with soaring ceilings! Inviting entertainment space with dining/living combo off kitchen. Ample natural light fills this home with double glass sliders and multiple skylights all in living area! Relaxing views of back park like green space! Convenient location

  Laura Toppin FLORIDA HOME TEAM REALTY LLC

  2400 Dominica Run, Winter Park, FL 32792
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  $1,850

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Condo for Rent

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

  Two-bedroom, two-bath walk-up condo off Lake Killarney in Winter Park, Florida. Spacious rooms, custom upgrades, quiet, and well maintained. Located in the Chateaux du Lac community at 1500 GayRoad. Within walking distance of Winter Park Village, Traders Joe's, restaurants and more. Minutes from AdventHealth Orlando, Park Avenue, Rollins College, and I-4.Pet free unit. Ideally seeking

  1500 Gay Rd Unit 9D, Winter Park, FL 32789
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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 $253,849

  Last Listing Agent Matt Merdian MERDIAN REALTY LLC

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789
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  Est $284,329 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

  • 4% Below List Price
  • $235/SF
  • 19 Days On Market

  • Last Sold Price $295,000
  • Feb 07, 2025

  Last Listing Agent Dawn Romance FANNIE HILLMAN & ASSOCIATES
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  /46

  $714,900

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  1108 Fairway Dr, Winter Park, FL 32792

  Offering WELL BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C,

  Rene Droz, III CHARLES RUTENBERG REALTY ORLANDO

  1108 Fairway Dr, Winter Park, FL 32792
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  /25

  $1,725 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft
  • Townhouse for Rent

  3283 Oak Lake Place Unit 127, Winter Park, FL 32792

  Beautiful freshly painted and cleaned property in Winter park. This is a townhouse style condo (no neighbors above and only on one side)- end unit with rear patio and storage closet. The first floor is a large living space, kitchen, a half bath and laundry with a dining nook. While there are 3 bedrooms upstairs with 2 full baths. The first floor is fully tiled and the upstairs bedrooms have

  Kyle Petteway EXIT REAL ESTATE RESULTS

  3283 Oak Lake Place Unit 127, Winter Park, FL 32792
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  $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 $753,538

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

  1570 Grove Terrace, Winter Park, FL 32789
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  Est $310,744 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

  • 6% Below List Price
  • $684/SF
  • 3 Days On Market

  • Last Sold Price $329,900
  • Jan 30, 2025

  Last Listing Agent Susan Logan LOGAN LAND & HOMES, INC.
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  /26

  $249,900 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  3254 Oak Lake Place Unit 137, Winter Park, FL 32792

  Under contract-accepting backup offers. THIS GORGEOUS 2 BED/2.5BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NEWLY REMODELED AND NESSELED IN WINTER PARK COMMUNITY OF HIDDEN OAKS. THIS ELEGANT HOME FEATURES 1,031 SQ. FT. OF LIVING SPACE, A MODERN SWEDISH KITCHEN FEATURING CRYSTAL COUNTER TOPS WITH FUNCTIONAL DRAWERS, PORCELEN TILE FLOORS. STAINLESS STEELE APPLIANCES

  Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

  3254 Oak Lake Place Unit 137, Winter Park, FL 32792
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  $3,350

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • Townhouse for Rent

  1886 Demetree Dr, Winter Park, FL 32789

  Beautifully Remodeled Ground-Floor Townhome — Available Now in Winter Park Welcome 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

  1886 Demetree Dr, Winter Park, FL 32789
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  $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 $1,261,078

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
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  Est $315,703 Not Listed For Sale

  3251 Crown Jewel Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft
  • Built 2019

  3251 Crown Jewel Ct, Winter Park, FL 32792

  Last Sold Summary

  • 9% Below List Price
  • $247/SF
  • 6 Days On Market

  • Last Sold Price $348,000
  • Jan 15, 2025

  Last Listing Agent Erin Fang FLORIDA REALTY INVESTMENTS

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