Winter Park, FL Homes

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  /38

  $424,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  633 Lander Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. LOCATION, LOCATION, LOCATION! Welcome to this charming 3-bedroom, 2-bathroom home nestled in the heart of Winter Park!As you enter the home, you'll notice the living room and dining area flow seamlessly together, leading you into the kitchen featuring solid surface countertops and solid wood cabinetry. The

  Raymond Lopez KELLER WILLIAMS ADVANTAGE 2 REALTY

  633 Lander Rd, Winter Park, FL 32792
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  /50

  $1,094 - $1,955 per month

  Winter Park Woods Apartments

  1 - 3 Beds

  349 Scottsdale Square, Winter Park, FL 32792

  This community boasts a prime location that effortlessly combines charm with convenience. Nestled in a well established neighborhood, it offers residents easy access to an array of amenities, including local shops, cafes, and restaurants, all just a short stroll away. The mature landscaping creates a tranquil atmosphere, inviting residents to take leisurely walks and enjoy the scenery.

  349 Scottsdale Square, Winter Park, FL 32792
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  /2

  $223,000 Sold Oct 30, 2025

  1378 Chilean Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1960

  Last Sold Summary

  • $168/SF

  Current Estimated Value $350,528

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

  1378 Chilean Ln, Winter Park, FL 32792
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  /2

  Not Listed For Sale

  5101 N Orange Ave, Winter Park, FL 32792

  • 6 Beds
  • 2 Baths
  • 1,922 Sq Ft
  • Built 1956

  5101 N Orange Ave, Winter Park, FL 32792

  Last Sold Summary

  • $265/SF
  • 198 Days On Market

  Last Sold Price $510,000

  Last Listing Agent Sonia Reyes INVESTOR'S HOME REALTY
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  /45

  $499,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,627 Sq Ft

  2809 Casa Aloma Way, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 2809 Casa Aloma — a beautifully updated 3-bedroom, 2-bath charming home located on a quiet cul-de-sac in desirable Winter Park. Originally one of the subdivision’s model homes "Monaco", this property blends French Provincial design with extensive modern upgrades. Major improvements include a 2021

  Curt Marksbury WATSON REALTY CORP., REALTORS

  2809 Casa Aloma Way, Winter Park, FL 32792
• 

  

  /37

  $5,900 per month

  • 4 Beds
  • 3 Baths
  • 2,741 Sq Ft
  • House for Rent

  220 W Reading Way, Winter Park, FL 32789

  Welcome to your dream home! This recently renovated gem in the highly coveted Forrest Hills area of Winter Park is now available for rent. Surrounded by enchanting brick streets and majestic trees, this charming residence has been thoughtfully upgraded by the new owner, offering a perfect blend of modern amenities and classic charm. As you step onto the inviting front covered porch, you'll be

  Thomas Hewitt HEWITT RESIDENTIAL, LLC

  220 W Reading Way, Winter Park, FL 32789
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  /2

  $1,575,000 Sold Aug 14, 2025

  1394 Grove Terrace, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,958 Sq Ft
  • Built 2002

  Last Sold Summary

  • $532/SF
  • 5 Days On Market

  Current Estimated Value $1,577,588

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1394 Grove Terrace, Winter Park, FL 32789
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  /31

  Est $268,311 Not Listed For Sale

  2419 Gallery View Dr Unit 10, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1985

  2419 Gallery View Dr Unit 10, Winter Park, FL 32792

  Last Sold Summary

  • 9% Below List Price
  • $288/SF
  • 3 Days On Market

  Last Sold Price $295,000

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES
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  /71

  $699,900

  • 4 Beds
  • 3 Baths
  • 2,702 Sq Ft

  3114 Heartleaf Place, Winter Park, FL 32792

  Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive,

  Nadia Kurakin CHAMPION HOMES

  3114 Heartleaf Place, Winter Park, FL 32792
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  /35

  $1,312 - $2,492 per month

  Summerlin at Winter Park Apartments

  1 - 3 Beds

  3207 Rosebud Ln, Winter Park, FL 32792

  These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

  3207 Rosebud Ln, Winter Park, FL 32792
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  /2

  $625,000 Sold Sep 29, 2025

  3759 Kinsley Place, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,251 Sq Ft
  • Built 1988

  Last Sold Summary

  • 11% Below List Price
  • $278/SF
  • 50 Days On Market

  Current Estimated Value $623,389

  Last Listing Agent Drew Belani COMPASS FLORIDA LLC

  3759 Kinsley Place, Winter Park, FL 32792
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  /42

  Est $1,581,353 Not Listed For Sale

  1805 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,052 Sq Ft
  • Built 2014

  1805 Harland Park Dr, Winter Park, FL 32789

  Last Sold Summary

  • 7% Above List Price
  • $483/SF
  • 12 Days On Market

  Last Sold Price $1,475,000

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
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  /39

  $195,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft

  2924 Antique Oaks Cir Unit 46, Winter Park, FL 32792

  Discover a charming 2nd-story condo nestled in the desirable Parkview Village community of Winter Park. This spacious home features two bedrooms and two bathrooms across 1,105 square feet of thoughtfully designed living space. The interior boasts large rooms, providing ample space for comfort and versatility. Admire the vaulted ceilings that enhance the open and airy atmosphere, while the

  Donna Layton CENTURY 21 EDGE

  2924 Antique Oaks Cir Unit 46, Winter Park, FL 32792
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  /90

  $13,500 per month

  • 8 Beds
  • 6 Baths
  • 7,000 Sq Ft
  • House for Rent

  1860 Via Contessa, Winter Park, FL 32789

  Exceptional Lease Opportunity | The Vias, Winter Park$13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available NowRarely does a home of this caliber come to market for lease. Set on a quiet cul-de-sac in one of Winter Park's most prestigious enclaves — the coveted Vias neighborhood — this magnificent 7,000 SF residence delivers an unmatched

  Kelly Price KELLY PRICE & COMPANY LLC

  1860 Via Contessa, Winter Park, FL 32789
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  /2

  $285,000 Sold Sep 24, 2025

  7777 Fernbrook Way, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Above List Price
  • $261/SF
  • 3 Days On Market

  Current Estimated Value $278,208

  Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  7777 Fernbrook Way, Winter Park, FL 32792
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  /26

  Est $467,074 Not Listed For Sale

  2469 Firstlight Way, Winter Park, FL 32792

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

  2469 Firstlight Way, Winter Park, FL 32792

  Last Sold Summary

  • 1% Above List Price
  • $200/SF
  • 58 Days On Market

  Last Sold Price $462,500

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC
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  /34

  $579,999

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft

  330 Elkhorn Ct, Winter Park, FL 32792

  330 Elkhorn Ct is a beautifully renovated, move-in-ready home located in the highly desired Winter Park Pines community. Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and

  Neil Chetram LA ROSA REALTY CW PROPERTIES L

  330 Elkhorn Ct, Winter Park, FL 32792
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  /39

  $910 - $1,544 per month

  San Jose Apartments

  1 - 3 Beds

  2353 Winter Woods Blvd, Winter Park, FL 32792

  Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

  2353 Winter Woods Blvd, Winter Park, FL 32792
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  /2

  $675,000 Sold Mar 16, 2026

  620 Darcey Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,075 Sq Ft
  • Built 1967

  Last Sold Summary

  • 9% Below List Price
  • $325/SF
  • 14 Days On Market

  Current Estimated Value $709,827

  Last Listing Agent Jason Asa LPT REALTY, LLC

  620 Darcey Dr, Winter Park, FL 32792
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  /47

  Est $1,125,358 Not Listed For Sale

  1939 Woodcrest Dr, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft
  • Built 2020

  1939 Woodcrest Dr, Winter Park, FL 32792

  Last Sold Summary

  • 4% Below List Price
  • $454/SF
  • 2 Days On Market

  Last Sold Price $1,170,000

  Last Listing Agent Angela McCloskey KELLER WILLIAMS REALTY AT THE PARKS
• 

  

  /22

  $474,900

  • 3 Beds
  • 2 Baths
  • 1,715 Sq Ft

  2020 Cocos Ct, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Beautifully renovated pool home in the highly desirable Eastbrook community of Winter Park, featuring major recent upgrades including a new AC system, windows, doors, and flooring throughout the home. This move-in ready 3-bedroom, 2-bath residence sits on an oversized 0.30-acre corner lot in a quiet cul-de-sac with no HOA. The home offers a bright

  Julimar Barreiro Pastrana SERHANT

  2020 Cocos Ct, Winter Park, FL 32792
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  /7

  $1,500 per month

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft
  • Condo for Rent

  7326 Swallow Run Unit 7326, Winter Park, FL 32792

  Bright and freshly updated ground-floor 2-suite condo in a peaceful, well-kept community. This move-in-ready home features new interior paint, new water heater, granite countertops, and durable vinyl plank flooring throughout. The split-suite layout offers privacy and flexibility for roommates or professionals. Zoned for Cheney Elementary, with convenient access to A-rated middle and high

  Jiny Lee NOBSKA REAL ESTATE LLC

  7326 Swallow Run Unit 7326, Winter Park, FL 32792
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  /2

  $315,000 Sold Jan 01, 2026

  615 Warrenton Rd, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Below List Price
  • $258/SF
  • 50 Days On Market

  Current Estimated Value $312,189

  Last Listing Agent Bryan Burns RE/MAX DOWNTOWN

  615 Warrenton Rd, Winter Park, FL 32792
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  /2

  Est $369,441 Not Listed For Sale

  7604 Aloma Pines Ct, Winter Park, FL 32792

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

  7604 Aloma Pines Ct, Winter Park, FL 32792

  Last Sold Summary

  • 2% Above List Price
  • $194/SF
  • 326 Days On Market

  Last Sold Price $362,500

  Last Listing Agent Nakarid Melean INTERINVESTMENTS REALTY, INC.
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  /48

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,291 Sq Ft

  1873 Casselwood St, Winter Park, FL 32792

  Welcome to this enchanting 3-Bedroom, 2-Bathroom townhouse in Winter Park! Walk into an open floor plan giving you comfort and that homey feeling with a modern touch. A gorgeous kitchen area with a granite countertop, that flows with the home and is perfect for hosting. Tile flooring throughout, this home is move in ready!! Coming with a one car garage that was converted into a bonus space that

  Devin Costley ERA GRIZZARD REAL ESTATE

  1873 Casselwood St, Winter Park, FL 32792
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  /26

  $1,170 - $1,975 per month

  Central Place At Winter Park

  1 - 3 Beds

  7000 University Blvd, Winter Park, FL 32792

  Central Place at Winter Park, where contemporary living meets convenience in a vibrant locale in Winter Park, FL. Our one, two, and three-bedroom apartment community offers a prime location on University Blvd. near Full Sail University and just moments away from the charming downtown Winter Park area. Experience the essence of modern living in our thoughtfully designed residences, featuring

  7000 University Blvd, Winter Park, FL 32792
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  /2

  $325,000 Sold Dec 30, 2025

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

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $280/SF
  • 6 Days On Market

  Current Estimated Value $323,555

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
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  /2

  Est $436,076 Not Listed For Sale

  1761 Indiana Ave Unit F, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,598 Sq Ft
  • Built 2008

  1761 Indiana Ave Unit F, Winter Park, FL 32789

  Last Sold Summary

  • 6% Above List Price
  • $258/SF

  Last Sold Price $413,000

  Last Listing Agent Brock Stocksett HOMEVEST REALTY
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  /66

  $1,350,000

  • 6 Beds
  • 4 Baths
  • 4,214 Sq Ft

  3711 Vinsetta Ct, Winter Park, FL 32792

  Elevate your lifestyle in the prestigious Lakeside Estates, a private gated Winter Park community anchored by Garden Lake. In a quiet cul-de-sac, on a wrapping corner lot on over 1/3 of an acre and only a short distance to the playground making it easy. A six-bedroom, four-bath home sprawls over 4,200 square feet with back of the house opening to a covered porch with a generously sized saltwater

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  3711 Vinsetta Ct, Winter Park, FL 32792
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  /14

  $5,895 per month

  • 4 Beds
  • 3 Baths
  • 2,207 Sq Ft
  • House for Rent

  1235 Via Estrella, Winter Park, FL 32789

  Rare opportunity to lease a spacious 4-bedroom, 3-bath home in one of Winter Park's most coveted enclaves — The Vias. Spanning 2,207 SF, this sun-drenched residence sits just a short stroll from the prestigious Winter Park Racquet Club. Flooded with natural light, the open-concept living spaces feature beautiful bamboo wood floors, a well-appointed kitchen with white cabinetry and a large island,

  Kelly Price KELLY PRICE & COMPANY LLC

  1235 Via Estrella, Winter Park, FL 32789
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  /2

  $790,000 Sold Jun 05, 2025

  600 Brechin Dr, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,360 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Below List Price
  • $335/SF
  • 12 Days On Market

  Current Estimated Value $781,081

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  600 Brechin Dr, Winter Park, FL 32792
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  /2

  Est $244,382 Not Listed For Sale

  7148 Swallow Run Unit E1, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,565 Sq Ft
  • Built 2008

  7148 Swallow Run Unit E1, Winter Park, FL 32792

  Last Sold Summary

  • 11% Below List Price
  • $175/SF
  • 21 Days On Market

  Last Sold Price $274,500

  Last Listing Agent Rich Lemon CHARLES RUTENBERG REALTY ORLANDO
• 

  

  /23

  $250,000 Open Sat 10AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7707 Country Place Unit 4, Winter Park, FL 32792

  Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

  Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

  7707 Country Place Unit 4, Winter Park, FL 32792
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  /19

  $1,250 - $1,350 per month

  Eastbrook Apartments

  1 - 2 Beds

  2610-2617 Eastbrook Blvd, Winter Park, FL 32792

  Nestled within the serene and picturesque neighborhood of Lake Howell, Eastbrook Apartments offers a peaceful lakeside living experience with all the conveniences of a big city. This charming community in the Winter Park area is ideal for those seeking a blend of tranquility and accessibility. With 29 exclusive units, Eastbrook provides an intimate living environment with spacious and

  2610-2617 Eastbrook Blvd, Winter Park, FL 32792
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  $517,000 Sold Nov 07, 2025

  1628 Lawndale Cir, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 1984

  Last Sold Summary

  • 6% Below List Price
  • $301/SF
  • 6 Days On Market

  Current Estimated Value $520,042

  Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

  1628 Lawndale Cir, Winter Park, FL 32792
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  /2

  Est $269,156 Not Listed For Sale

  222 Balfour Dr Unit 14, Winter Park, FL 32792

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

  222 Balfour Dr Unit 14, Winter Park, FL 32792

  Last Sold Summary

  • 10% Below List Price
  • $238/SF
  • 206 Days On Market

  Last Sold Price $299,000

  Last Listing Agent Tricia Ramsby BHHS FLORIDA REALTY
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  /54

  $1,974,000

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  2614 Parkland Dr, Winter Park, FL 32789

  Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of

  Ryan Gaston JW GASTON LLC

  2614 Parkland Dr, Winter Park, FL 32789
• 

  

  /23

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft
  • Condo for Rent

  200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792

  Cozy and well-maintained 2-bedroom, 2-bath condo, washer and dryer inside, located in the desirable Winter Park area. This spacious unit features an open and comfortable layout with abundant natural light, a functional kitchen, and a small patio perfect for relaxing. The community offers great amenities including a pool, tennis courts, shuffleboard, clubhouse and beautifully maintained grounds.

  Nohora Gomez COLDWELL BANKER REALTY

  200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
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  /2

  $690,000 Sold May 08, 2025

  1806 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,016 Sq Ft
  • Built 2018

  Last Sold Summary

  • 1% Below List Price
  • $342/SF
  • 61 Days On Market

  Current Estimated Value $708,223

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1806 Mondrian Cir, Winter Park, FL 32789
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  /2

  Est $2,919,257 Not Listed For Sale

  1618 Holts Grove Cir, Winter Park, FL 32789

  • 5 Beds
  • 8 Baths
  • 4,807 Sq Ft
  • Built 2014

  1618 Holts Grove Cir, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $603/SF
  • 173 Days On Market

  Last Sold Price $2,900,000

  Last Listing Agent Shirley Jones COLDWELL BANKER REALTY

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