Newest Homes for Sale in Winter Park, FL

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  /25

  $299,000

  $90K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789

  Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue!Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
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  /26

  $148,500

  $27K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792

  What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real

  Kelly Flores COLDWELL BANKER REALTY

  3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
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  /65

  $3,995,000

  $655K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,181 Sq Ft

  1161 Valencia Ave, Winter Park, FL 32789

  Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Meticulously maintained with great inspection. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an

  Lisa Mahjoub THE REAL ESTATE COLLECTION LLC

  1161 Valencia Ave, Winter Park, FL 32789
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  /32

  $479,900

  $70K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,718 Sq Ft

  240 Orange Terrace Dr, Winter Park, FL 32789

  LOOK NO FURTHER - RECENTLY INSTALLED FENCED IN YARD - NO HOA, PRIME WINTER PARK LOCATION, CLOSE TO I-4! Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and style. Just minutes from Fairbanks and I-4, you’ll enjoy quick access to top shopping, dining, and all that Winter Park has to

  Susan Pinnock A+ REALTY PROFESSIONALS, INC

  240 Orange Terrace Dr, Winter Park, FL 32789
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  /27

  $425,000

  $30K PRICE DROP

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

  1849 Viburnum Ln, Winter Park, FL 32792

  This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor

  Lesly Hijar REAL BROKER, LLC

  1849 Viburnum Ln, Winter Park, FL 32792
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  /60

  $764,900

  $34K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,192 Sq Ft

  2222 Marsh Sedge Ln, Winter Park, FL 32792

  Welcome to your dream Home! This stunning and elegant single-story home, built by Meritage Homes in the gated community of Hawk's Crest in Winter Park, includes numerous upgrades. This is the Pomelo model, equipped with an upgraded kitchen package that includes built-in double ovens and a stainless steel range hood. Beautiful quartz countertops feature an oversized kitchen island with excellent

  Carmen Molina LA ROSA REALTY LLC

  2222 Marsh Sedge Ln, Winter Park, FL 32792
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  /59

  $695,000

  $55K PRICE DROP

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

  744 Cornwall Rd, Winter Park, FL 32792

  Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing

  Tammy Cuddy VERSALIS REALTY POWERED BY SELLSTATE

  744 Cornwall Rd, Winter Park, FL 32792
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  /12

  $4,500,000

  $499K PRICE DROP

  • Land
  • 20,908 Sq Ft
  • $9,375,000 per Acre

  503 N Interlachen Ave, Winter Park, FL 32789

  JUST LISTED - RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,999,000!!! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed

  Kelly Price KELLY PRICE & COMPANY LLC

  503 N Interlachen Ave, Winter Park, FL 32789
• 

  

  /20

  $308,000

  • 3 Beds
  • 2 Baths
  • 1,076 Sq Ft

  1074 Hamlet Dr, Maitland, FL 32751

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  1074 Hamlet Dr, Maitland, FL 32751
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  /37

  $598,000

  $51K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,539 Sq Ft

  2758 Banchory Rd, Winter Park, FL 32792

  Charming Pool Home in Prime Winter Park Location Welcome to 2758 Banchory Road — a true gem nestled in the heart of the desirable Winter Park Pines community. This beautifully maintained 3-bedroom, 2-bath ranch-style home offers the ideal combination of comfort, privacy, and location. With a private swimming pool, lush landscaping, and no direct front neighbors on a quiet cul-de-sac street, this

  Erwin Vargas MR VARGAS PROPERTY MANAGEMENT LLC

  2758 Banchory Rd, Winter Park, FL 32792
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  /26

  $315,000

  $55K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfect blend of privacy, style, and unbeatable location. Just one block from Winter Park Village and only a mile from Park Avenue, you’ll enjoy walkable access to some of the area’s best dining, shopping, and entertainment. Located on the first floor, this beautifully renovated 2-bed, 2-bath home features an open

  Brandon Geers COMPASS FLORIDA LLC

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789
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  /59

  $1,390,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,253 Sq Ft

  501 Lakeview Ave, Winter Park, FL 32789

  MOVE-IN READY! Construction Completed! Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 1⁄2 baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that

  Marie Ledbetter COLDWELL BANKER REALTY

  501 Lakeview Ave, Winter Park, FL 32789
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  /41

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,263 Sq Ft

  5331 Oak Ct, Winter Park, FL 32792

  Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

  Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

  5331 Oak Ct, Winter Park, FL 32792
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  /26

  $185,000

  $25K PRICE DROP

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

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792

  Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. No rear neighbors. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own

  Qing Lin SPRINGHILL PROPERTIES LLC

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
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  /40

  $359,000

  $70K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789

  Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park! This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and Structural Integrity Reserve Study

  Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789
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  /62

  $4,195,000

  New Construction Open Tue 12PM - 2PM $555K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 3,850 Sq Ft

  1150 Via Salerno, Winter Park, FL 32789

  In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered at a newly adjusted price, the home presents a compelling opportunity to experience design-forward new construction in the Vias neighborhood. Developed and designed by Steve & Jodie Warrick Konold of Scout & Co., the 3,850-sf

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1150 Via Salerno, Winter Park, FL 32789
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  /99

  $5,250,000

  $930K PRICE DROP

  • 5 Beds
  • 6.5 Baths
  • 7,278 Sq Ft

  2211 Azalea Place, Winter Park, FL 32789

  Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  2211 Azalea Place, Winter Park, FL 32789
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  /53

  $1,479,000

  New Construction $96K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,895 Sq Ft

  1473 Berkshire Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Limited-time incentive: Seller offering a $20,000 buyer credit for qualified buyers. Brand-New 2025 Mediterranean Luxury in Historic Winter Park. Introducing 1473 Berkshire Avenue — a just-completed luxury residence nestled on one of Winter Park’s most peaceful, tree-lined, and century-old streets. This two-story Mediterranean masterpiece delivers

  Milena Fernandes GOLDEN GROUP REALTY LLC

  1473 Berkshire Ave, Winter Park, FL 32789
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  /33

  $220,000

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  225 Lewfield Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 237-3113

  225 Lewfield Cir, Winter Park, FL 32792
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  /54

  $1,924,450

  $371K PRICE DROP

  • 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
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  /49

  $175,000

  $55K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 208, Winter Park, FL 32789

  This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents

  Debbie Fussell KELLER WILLIAMS REALTY AT THE PARKS

  2500 Lee Rd Unit 208, Winter Park, FL 32789
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  /19

  $89,900

  $10K PRICE DROP

  • Studio
  • 1 Bath
  • 549 Sq Ft

  3071 George Mason Ave Unit 5, Winter Park, FL 32792

  NEW PRICE!!! Charming Studio Condo Near UCF & Full Sail – Ideal Investment or Cozy Retreat!Welcome to this well-maintained ground-floor studio condo, offering 549 square feet of comfortable living space in a prime location near UCF and Full Sail University. Perfect for a student, professional, or investor, this move-in-ready unit features tile flooring throughout, making it clean and easy to

  Katherine Bordelon CASTLE & COTTAGE REALTY LLC

  3071 George Mason Ave Unit 5, Winter Park, FL 32792
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  /2

  $205,000

  $5K PRICE DROP

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

  1695 Lee Rd Unit C202, Winter Park, FL 32789

  This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This

  Hoover Yap PRIMESTATE REALTY, INC.

  1695 Lee Rd Unit C202, Winter Park, FL 32789
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  /22

  $184,999

  $45K PRICE DROP

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

  2923 Antique Oaks Cir Unit 39, Winter Park, FL 32792

  PRICE REDUCED, Seller motivated. Condo in Winter Park, FL Welcome to 2923 Antique Oaks Cir, Unit 39 — a beautifully updated 1,105 sq. ft. first-floor condo offering 2 bedrooms, 2 bathrooms, and modern upgrades throughout. Located in the highly sought-after Winter Park School District, this property combines comfort, style, and convenience. Property Highlights: Size & Layout: Spacious 1,105 square

  Michell Carrasquero GLOBALWIDE REALTY LLC

  2923 Antique Oaks Cir Unit 39, Winter Park, FL 32792
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  /52

  $224,999

  $35K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 202, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool &

  Alison Maltby THE ANDERSON GROUP & CO PL

  2500 Lee Rd Unit 202, Winter Park, FL 32789
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  /31

  $425,000

  $60K PRICE DROP

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

  1354 Tierra Cir, Winter Park, FL 32792

  Located in the highly sought-after Casa Aloma community, this charming 1960s home offers the perfect blend of comfort, style, and convenience. Situated within a one-mile radius of all that Winter Park has to offer, this well-maintained home truly stands out in terms of location, location, location! The open floor plan is ideal for entertaining, with a spacious living room providing ample space

  Carl Mataushek REAL ESTATE FIRM OF ORLANDO

  1354 Tierra Cir, Winter Park, FL 32792
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  /26

  $465,000

  $115K PRICE DROP

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

  2774 Bright Bird Ln, Winter Park, FL 32792

  Motivated seller! Brand new townhouse professionally decorated, and available today! Built in 2024, this property offers a great floorplan: with a lot of natural light and coziness. Fall in love with the modern and spacious house located in a prestigious area! Close to shops and markets this is an amazing opportunity for those looking for a quiet neighborhood but close to everything at the same

  Priscilla Triska FLORIDA CONNEXION PROPERTIES

  2774 Bright Bird Ln, Winter Park, FL 32792
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  /7

  $178,900

  $49K PRICE DROP

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

  2923 Antique Oaks Cir Unit 37, Winter Park, FL 32792

  Attention Students & Parents! Updated First-Floor Corner Condo directly across the street from the Full Sail campus! Why rent when you can buy!2 Bed | 2 Bath | 1,105 Sq. Ft., an updated first-floor northwest corner condo. -Brand-New Kitchen Appliances: Convection oven, refrigerator, dishwasher, and microwave -Interior Laundry Room with new LG stackable washer & dryer -New Air Conditioning

  Cliff Glansen FLATFEE.COM

  2923 Antique Oaks Cir Unit 37, Winter Park, FL 32792
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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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  /25

  $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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  /26

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,283 Sq Ft

  780 Baffie Ave, Winter Park, FL 32789

  Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

  Melissa Woodman FANNIE HILLMAN & ASSOCIATES

  780 Baffie Ave, Winter Park, FL 32789
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  /11

  $198,000

  $2K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3060 George Mason Ave Unit 12, Winter Park, FL 32792

  Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

  Adriana Sanchez AROD PARTNERS REALTY

  3060 George Mason Ave Unit 12, Winter Park, FL 32792
• 

  

  /19

  $510,000

  $89K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,805 Sq Ft

  2627 Ambergate Rd, Winter Park, FL 32792

  Price Reduced !! This beautiful and remodeled home is turnkey and ready to move in!Investors -- You will love the cash flow upside with this property.Updated Roof, AC, Exterior Paint, Patio, Garage, Driveway, Fence, Sprinkler System, Lighting, Flooring, Kitchen, and much more.You will enjoy entertaining your guests with this large saltwater pool with cabana, as well as yard space for

  Ryan Minadie COLDWELL BANKER REALTY

  2627 Ambergate Rd, Winter Park, FL 32792
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  /27

  $700,000

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft

  865 S Pennsylvania Ave, Winter Park, FL 32789

  LOCATION, LOCATION, LOCATION...Desirable Winter Park "College Quarter" Historic District...Come take a tour of this wonderfully updated Bungalow with lots of windows for natural light, original hardwood floors, beautiful crown molding, and high ceilings. Did I mention the location, Walk to Park Ave, Rollins College, Hannibal Square, Mead Gardens, and Lake Virginia. Looking to "House Hack" then

  Jose Vega LPT REALTY, LLC

  865 S Pennsylvania Ave, Winter Park, FL 32789
• 

  /2

  $2,450,000

  • 5 Beds
  • 5.5 Baths
  • 4,010 Sq Ft

  1771 Taylor Ave, Winter Park, FL 32789

  Custom Winter Park home completed in 2019 by FG Schaub Custom Home Builder. Contemporary Florida living awaits in this newly built home, boasting a spacious open floor plan spanning over 4,000 square feet with five bedrooms and five-and-a-half baths. Delight in the stunning gourmet kitchen, gas cooktop, oversized island and an extended walk-in pantry with cabinets. Distinctive features include

  Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

  1771 Taylor Ave, Winter Park, FL 32789

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