Winter Park, FL Homes

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  $949,900 New Construction

  • 3 Beds
  • 3 Baths
  • 1,875 Sq Ft

  870 Carver St, Winter Park, FL 32789

  Welcome to 870 Carver Street, a versatile three-bedroom, three-bath residence offering privacy, thoughtful design, and two distinct living experiences in the heart of Winter Park. With 1,875 square feet under air, the property includes a 1,209-square-foot, two-bedroom, two-bath main home and a 666-square-foot, one-bedroom, one-bath garage apartment, ideal for multigenerational living, rental

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  870 Carver St, Winter Park, FL 32789
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  $1,777 - $2,691 per month

  Rosalia Winter Park 55+ Active Adult Community

  1 - 2 Beds

  3045 Aloma Ave, Winter Park, FL 32792

  Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar-all with an attentive team at your

  3045 Aloma Ave, Winter Park, FL 32792
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  $3,485,000 Sold Oct 17, 2025

  2171 Forrest Rd, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,565 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $763/SF
  • 134 Days On Market

  Current Estimated Value $3,427,716

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2171 Forrest Rd, Winter Park, FL 32789
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  Est $1,365,912 Not Listed For Sale

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,734 Sq Ft
  • Built 2009

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  Last Sold Summary

  • 6% Below List Price
  • $530/SF
  • 3 Days On Market

  Last Sold Price $1,450,000

  Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC
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  $1,095,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,770 Sq Ft

  2607 Lafayette Ave, Winter Park, FL 32789

  Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining.Step inside to discover an open-concept layout that seamlessly connects the kitchen,

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  2607 Lafayette Ave, Winter Park, FL 32789
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  /15

  $2,650 per month

  • 4 Beds
  • 2 Baths
  • 1,858 Sq Ft
  • House for Rent

  1813 E Cheryl Dr, Winter Park, FL 32792

  Lovely 4 bed, 2 bath one story home in desirable Winter Park! Attached 2 car garage, GRANITE countertops in kitchen, walk in closet in primary bedroom. Patio has ceramic tile flooring, overlooking the FENCED backyard! This home features a spacious layout! Location is PERFECT! Convenient to shopping, dining, highways & more!

  Harry Kazarian STRONG FOUNDATION REALTY LLC

  1813 E Cheryl Dr, Winter Park, FL 32792
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  $520,000 Sold Mar 31, 2025

  1810 Taylor Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft
  • Built 1977

  Last Sold Summary

  • 1% Below List Price
  • $372/SF
  • 0 Days On Market

  Current Estimated Value $568,307

  Last Listing Agent Julia Dalessandro FANNIE HILLMAN & ASSOCIATES

  1810 Taylor Ave, Winter Park, FL 32789
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  Est $948,060 Not Listed For Sale

  1245 Wisconsin Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,610 Sq Ft
  • Built 2013

  1245 Wisconsin Ave, Winter Park, FL 32789

  Last Sold Summary

  • 13% Above List Price
  • $322/SF
  • 51 Days On Market

  Last Sold Price $840,000

  Last Listing Agent Emily Bearden COMPASS FLORIDA LLC
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  $725,000 Pending

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

  1108 Fairway Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. 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, and water heater. Step inside to a Sun-filled sanctuary featuring

  Rene Droz, III CHARLES RUTENBERG REALTY ORLANDO

  1108 Fairway Dr, Winter Park, FL 32792
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  $1,365 - $2,100 per month

  Westmount at Winter Park

  Studio - 3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

  1701 Lee Rd, Winter Park, FL 32789
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  $1,645,000 Sold May 20, 2025

  681 Balmoral Rd, Winter Park, FL 32789

  • Land
  • 1.14 Acres
  • $1,442,982 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 55 Days On Market

  Current Estimated Value $1,606,227

  Last Listing Agent Chris Burden EPIC REAL ESTATE ADVISORS LLC

  681 Balmoral Rd, Winter Park, FL 32789
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  Est $184,256 Not Listed For Sale

  2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Built 1984

  2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792

  Last Sold Summary

  • 13% Below List Price
  • $209/SF
  • 6 Days On Market

  Last Sold Price $213,000

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC
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  $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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  $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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  $335,000 Sold Sep 23, 2025

  5144 N Orange Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1976

  Last Sold Summary

  • 16% Below List Price
  • $263/SF
  • 128 Days On Market

  Current Estimated Value $333,143

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  5144 N Orange Ave, Winter Park, FL 32792
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  Est $142,936 Not Listed For Sale

  289 Lewfield Cir, Winter Park, FL 32792

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

  289 Lewfield Cir, Winter Park, FL 32792

  Last Sold Summary

  • $211/SF
  • 58 Days On Market

  Last Sold Price $143,000

  Last Listing Agent Christopher Courtney DENIZ REALTY PARTNERS LLC
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  $730,000

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft

  744 Cornwall Rd, Winter Park, FL 32792

  Charming 4-Bedroom Home in Desirable Winter Park PinesWelcome to your new home in the heart of Winter Park Pines! This beautifully maintained 4-bedroom, 2-bath residence offers a perfect blend of classic charm and modern comfort, situated in one of Central Florida’s most sought-after neighborhoods.Step inside to find warm hardwood floors that flow throughout the spacious living areas,

  Tammy Cuddy VERSALIS REALTY POWERED BY SELLSTATE

  744 Cornwall Rd, Winter Park, FL 32792
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  $1,310 - $2,645 per month

  Signal Pointe

  1 - 3 Beds

  2500 Howell Branch Rd, Winter Park, FL 32792

  Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

  2500 Howell Branch Rd, Winter Park, FL 32792
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  $397,000 Sold Jul 01, 2025

  1109 Denton Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $321/SF
  • 83 Days On Market

  Current Estimated Value $392,907

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1109 Denton Rd, Winter Park, FL 32792
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  Est $225,067 Not Listed For Sale

  220 Lewfield Cir, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Built 1973

  220 Lewfield Cir, Winter Park, FL 32792

  Last Sold Summary

  • 10% Below List Price
  • $192/SF
  • 109 Days On Market

  Last Sold Price $249,900

  Last Listing Agent Alex Galitsky TOP ORLANDO REALTY
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  $2,800,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,553 Sq Ft

  541 W Canton Ave, Winter Park, FL 32789

  Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood

  Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

  541 W Canton Ave, Winter Park, FL 32789
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  $3,475 per month

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft
  • House for Rent

  1850 Whitehall Dr, Winter Park, FL 32789

  This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1850 Whitehall Dr, Winter Park, FL 32789
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  $3,200,000 Sold Apr 30, 2025

  1833 Loch Berry Rd, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,770 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $671/SF
  • 5 Days On Market

  Current Estimated Value $3,024,879

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1833 Loch Berry Rd, Winter Park, FL 32789
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  Not Listed For Sale

  7340 Daniel Webster Dr Unit A, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 1974

  7340 Daniel Webster Dr Unit A, Winter Park, FL 32792

  Last Sold Summary

  • $115/SF
  • 81 Days On Market

  Last Sold Price $145,500

  Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY
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  $566,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 1,885 Sq Ft

  1459 Nottingham Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. Discover this completely renovated 4-bedroom pool home plus office with custom built-ins (could be a 5th bedroom) tucked away in the quiet, highly sought-after Winter Woods neighborhood. Backing up directly to the gorgeous Interlachen Golf Course, this property offers no rear neighbors—a rare opportunity in such a prime location. Extensively updated in

  Shirley Jones COLDWELL BANKER REALTY

  1459 Nottingham Dr, Winter Park, FL 32792
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  $1,236 - $2,425 per month

  Village Park Senior

  1 - 3 Beds

  550 W Denning Dr, Winter Park, FL 32789

  WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

  550 W Denning Dr, Winter Park, FL 32789
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  $145,000 Sold Aug 13, 2025

  7352 Swallow Run, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 802 Sq Ft
  • Built 1983

  Last Sold Summary

  • 39% Below List Price
  • $181/SF
  • 68 Days On Market

  Current Estimated Value $138,637

  Last Listing Agent Ashley Quandt LEERDAM PROPERTIES INC.

  7352 Swallow Run, Winter Park, FL 32792
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  Est $187,774 Not Listed For Sale

  200 Saint Andrews Blvd Unit 2210, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 2210, Winter Park, FL 32792

  Last Sold Summary

  • 25% Below List Price
  • $253/SF
  • 0 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Kelsey Taylor EXP REALTY LLC
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  $824,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,930 Sq Ft

  737 N Capen Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to this stunning Mid-century style 3 bedroom, 2 bath, 1930 sq ft home with a 2 car garage, where sleek modern design meets functionality. Step into the open-concept living space and be captivated by the abundance of natural light streaming through the large windows, creating a warm and inviting atmosphere. The centerpiece of this home is the gourmet

  Jenn Carlisle LPT REALTY, LLC

  737 N Capen Ave, Winter Park, FL 32789
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  $2,730 per month

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

  1611 Little Wren Ln, Winter Park, FL 32792

  This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Hawks Crest along the southern shores of beautiful Lake Howell, this ideal location provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Avenue and Winter Park Village. The home has an open floor plan with tile flooring throughout the downstairs living

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  1611 Little Wren Ln, Winter Park, FL 32792
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  $228,000 Sold Jun 27, 2025

  1979 Staunton Ave, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Built 1948

  Last Sold Summary

  • 24% Below List Price
  • $310/SF
  • 16 Days On Market

  Current Estimated Value $229,618

  Last Listing Agent Michael Kara CORBELO LLC

  1979 Staunton Ave, Winter Park, FL 32789
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  Est $1,541,213 Not Listed For Sale

  101 S New York Ave Unit 303, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,174 Sq Ft
  • Built 2009

  101 S New York Ave Unit 303, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $496/SF
  • 129 Days On Market

  Last Sold Price $1,575,000

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
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  $650,000 Pending

  • 5 Beds
  • 3 Baths
  • 1,917 Sq Ft

  352 Cambridge Blvd, Winter Park, FL 32789

  Under contract-accepting backup offers. This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from three separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a

  Karen Jacobs COLDWELL BANKER REALTY

  352 Cambridge Blvd, Winter Park, FL 32789
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  $976 - $1,373 per month

  Golden Oaks

  2 - 3 Beds

  7701 Acorn Woods Cir, Winter Park, FL 32792

  Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,

  7701 Acorn Woods Cir, Winter Park, FL 32792
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  $385,000 Sold Apr 03, 2025

  1873 Poinciana Rd, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 1,904 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Above List Price
  • $202/SF
  • 2 Days On Market

  Current Estimated Value $397,046

  Last Listing Agent Benondre Cerezo COLDWELL BANKER REALTY

  1873 Poinciana Rd, Winter Park, FL 32792
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  Est $3,020,668 Not Listed For Sale

  140 E Morse Blvd Unit G, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,367 Sq Ft
  • Built 2008

  140 E Morse Blvd Unit G, Winter Park, FL 32789

  Last Sold Summary

  • 6% Below List Price
  • $950/SF
  • 3 Days On Market

  Last Sold Price $3,200,000

  Last Listing Agent Andrea Sider, PA KELLER WILLIAMS WINTER PARK
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  $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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  $5,995 per month

  • 3 Beds
  • 2.5 Baths
  • 2,069 Sq Ft
  • Condo for Rent

  1130 Washington Ave Unit 11C, Winter Park, FL 32789

  Unbeatable Location! Don't miss this very rare and exquisite 3 bedroom, 2.5 bath, two-story Executive-Style condo in Winter Park-ideally located just around the corner from N. Orange Avenue, Park Avenue and Rollins College. Nestled in a prime, tucked-away setting, this home has been extensively remodeled with all new plumbing, electrical, duct work, flooring, appliances, and a natural gas line.

  Keith Race FUSILIER MANAGEMENT GROUP

  1130 Washington Ave Unit 11C, Winter Park, FL 32789
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  $399,900 Sold Oct 08, 2025

  7553 Laurel Springs Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1973

  Last Sold Summary

  • $338/SF
  • 20 Days On Market

  Current Estimated Value $392,348

  Last Listing Agent Yamila Lopez EMPIRE NETWORK REALTY

  7553 Laurel Springs Dr, Winter Park, FL 32792
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  Est $1,462,460 Not Listed For Sale

  311 E Morse Blvd Unit 1-1, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 1-1, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $749/SF
  • 0 Days On Market

  Last Sold Price $1,547,500

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

Showing Results 241 - 280, Page 7 of 18