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Winter Park Homes for Sale

Winter Park, FL is a family friendly, upscale suburban community. The city is located just seven miles northeast of Orlando. Park Avenue has a variety of upscale shops, restaurants, and art galleries. Winter Park Village offers outdoor shopping and restaurants. Popular nightlife attractions include Luma, Prato, Cocina 214, and Boca. Central Park has beautiful fountains, a rose garden, and seasonal events. Homes in Winter Park include condos, townhomes, and single family homes. The city is home to Rollins College, a private coed liberal arts school founded in 1885.

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Explore all properties for sale in Winter Park, FL in the greater Orlando area listed below. As you search through listings please be sure to contact us with any questions or to schedule a viewing.

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1245 W Fairbanks Avenue Winter Park FL 32789

MLS Number O5898942

  • CommercialSale
  • Property SubType Office
  • Subdivision Killarney Estates
  • Square Feet 20,384
  • Acreage 1.05

Winter Park, FL Iconic, Landmark, Trophy Property. Fully leased with long term credit tenant history. High Visibility Prime Corner location at Fairbanks Avenue and 17-92 (Orlando Avenue) in Affluent Winter Park, an affluent sub-market of the Orlando Florida area. Extremely stable investment with minimal landlord responsibilities. Recently Modernized Elevators, Each Elevator opens directly to each full floor office suite. Recent Fire System Devices replaced throughout the building. Recent lobby and bathroom renovations. Truly a unique investment and 1031 Exchange opportunity for investment. Ample Surface Parking. Free Standing 3 lane Bank Drive Through. Full Financials are available upon request to a qualified buyer investor. 1031 Exchange Opportunity. Thank you for looking.

Listing Courtesy of FLORIDA PREMIER REALTY GROUP

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Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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570 Seminole Drive Winter Park FL 32789

Winter Park, FL570 Seminole Drive

Price$6,500,000

Est. Mortgage: $/month

MLS Number O5439246

  • Land
  • Area Winter Park
  • Mls Status Active
  • Acreage 2.25
  • Subdivision Winter Park Old Town

WALK TO FAMED PARK AVENUE FROM THIS EPIC WINTER PARK ESTATE LOT!! This 2.25 acre lake front crown jewel is a once-in-a-lifetime offering of one of Old Winter Park's most sought after waterfront lots. Situated high above expansive Lake Osceola and only a short walk from famed Park Avenue, this lot, with its prevailing breezes, towering cypress trees and breathtaking eastern facing lake view will inspire visions of the most elegant of estate homes. Located down a long private driveway, just off of quiet brick paved Seminole Drive, this future showcase home site provides the ultimate in secluded privacy in the heart of Old Winter Park. World renowned for its beauty, charm, history and family friendliness, Winter Park's vast canopy of oak trees along its brick roads and stately homes make it among Central Florida's most luxurious communities. Experience Winter Park's shopping, dining and cultural gem - boasting more than 140 boutiques, sidewalk cafes, and museums. In addition to stylish shops, diverse gourmet dining choices and many unique offerings, you can enjoy special events that include seasonal art shows, concerts, exotic car shows, fashion events and holiday festivities. Build anything that you can imagine at this impressive address...there is simply nothing else like it!

Listing Courtesy of STOCKWORTH REALTY GROUP

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$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1731 Pinetree Road Winter Park FL 32789

Winter Park, FL1731 Pinetree Road

Price$4,695,000

Est. Mortgage: $/month

Pending

MLS Number O5889106

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 7,654
  • Year Built 2014

With approximately 120+ feet of waterfront on the most coveted stretch of Lake Maitland in the Winter Park Chain of Lakes, this timeless custom home offers over 7,600 thoughtfully designed square feet with an equally captivating lakeside entertaining area and saltwater pool with spa. Built in 2014 by master custom builder, Beau Einheit, this architecturally stunning home includes 6 bedrooms and 8.5 bathrooms. The ground floor owner's suite boasts a detailed tray ceiling and feature wall, private lake-view terrace, spa-style bath with soaking tub, steam shower and walk-in dressing room that connects to the gym. The gourmet chef's kitchen offers natural limestone countertops, 13' center island, professional appliances and a casual dining area overlooking the great room with 22' ceilings and polished cypress beam detail. The relaxed media room with herringbone inlay hardwood floors has sliding doors that connect the entertaining space seamlessly to the outdoor kitchen. The office, formal dining, wine bar with storage, mudroom, downstairs laundry room and oversized caterer's pantry complete the ground floor. Upstairs offers 4 bedrooms, all with en-suite bathrooms, and an additional laundry room. The separate in-law suite above the 4-car garage can be reached by elevator or an additional staircase. This home also includes a boathouse with a full bath, automatic retractable screens, entertaining space and lifts for watercraft so you can enjoy the Winter Park lake lifestyle and stunning sunsets for years to come.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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433 E New England Avenue Winter Park FL 32789

MLS Number O5809404

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 8,325
  • Year Built 1905

A unique offering to say the least. Originally built in 1920, the woodwork highlights the best of lost skills retained in the massive renovation done in 2009. Sitting on over 1/2 acre this home is a short walk to park Ave and city hall. The library with an office highlights the skills of the craftsman society. You must see the wonderful flow throughout this home featuring 10 bedrooms and 2 luxurious Owners suites. Nothing was lost with formal dining, several living areas and an unbelievably well done kitchen renovation. The photos are only a glimpse of the elegance found throughout this home. One of a kind property that has to be seen to be truly appreciated 10 bed room 12 bath downtown Winter Park estate home completely renovated & expanded in 2009 just steps from Park Avenue. The elegance of the natural gas light fixtures blended w/ the LED lighting is just the beginning of this 1920/current day experience.

Listing Courtesy of TREE REALTY

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$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1128 Preserve Point Drive Winter Park FL 32789

MLS Number O5830109

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 6,179
  • Year Built 2012

Welcome to this gorgeous, one-of-a-kind, contemporary-style home with over 150' on the shores of Lake Berry. Custom built and architecturally stunning, this 5 bedroom, 4.5 bath home is pure perfection inside and out. Set on an oversized 2-acre lot, on a quiet cul-de-sac in the highly-desirable Windsong community, this estate home features a gated entry, home office (optional 5th bedroom), personal fitness center, 3-car garage, salt-water lap pool, and interior finishes by Interiors by Steven G of Miami. This sprawling, single-story home offers luxury at every turn, and not to mention fantastic pool and water views throughout. As you enter the home and step into the formal living spaces your attention is immediately drawn to the sophisticated interior and glass walls that open to reveal a seamless indoor/outdoor entertainment area. The gourmet, chef's kitchen includes only the best appliances, hardware free cabinetry, and is open to the gathering room and side patio. Master bedroom sits at the back of the home taking full advantage of the lake views and is complete with his and her dressing closets, a spa bath, and access to the pool and lanai. Three oversized guest suites each allowing a certain degree of privacy. The outdoor living space wraps around the 82x12 lap pool and offering several covered areas for entertaining. Built for someone who appreciates the most luxurious accommodations, this home is a must see. Additional information on amenities and features are available up on request.

Listing Courtesy of KELLY PRICE & COMPANY LLC

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$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1830 Gipson Green Ln Winter Park FL 32789

Winter Park, FL1830 Gipson Green Ln

Price$4,195,000

Est. Mortgage: $/month

MLS Number O5902307

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 6,444
  • Year Built 1999

Luxury and elegance abound in this private, gated Winter Park Chain of Lakes estate, nestled on almost an acre at the end of a secluded cul-de-sac, with elevated views of beautiful Lake Maitland. Remodeled by award-winning interior designer, Betsy Godfrey, and designed with entertaining in mind, the rooms are large, timeless and sophisticated. Entry foyer has 14' custom doors, Onyx and Italian marble floors, and opens onto living room and dining room with floor to ceiling windows with lake views. Gourmet kitchen with Caesarstone counters, Sub Zero refrigerator & freezer, refrigerator drawers, Wolf gas stovetop, double ovens & dishwashers, and Miele built-in microwave, steamer, and coffee maker. Floorplan is fantastic with kitchen open to family room with gas fireplace and a wall of folding glass doors, spacious “Museum Room” & wet bar, climate-controlled wine room with brick floors, 2 offices, huge upstairs bonus, and 3-way split bedroom plan with downstairs master and downstairs guest suite. Master suite has 2 oversized walk-in closets and one of the most luxurious marble clad bathrooms of all time centered on a glass shower with 2 rain showers & high velocity water massager, plus jacuzzi tub, towel warmer, and endless storage. Upstairs houses 3 bedroom suites and bonus room. Features include Venetian plaster walls, Oak hardwood floors, plantation shutters, remote controlled blinds, designer wallpaper, intricate millwork, 3 car garage. The back has multiple patios - the summer kitchen, the central patio, and the fireplace area off of master bedroom, all overlooking the gorgeous black bottom pool and travertine deck. Boat house with 2 lifts for jet ski & boat. Perfect Winter Park location, close to Park Avenue and all that downtown has to offer.

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

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$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2403 Euston Road Winter Park FL 32789

Winter Park, FL2403 Euston Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number O5887686

  • Land
  • Area Winter Park
  • Mls Status Active
  • Acreage 8.34
  • Subdivision Glencoe Sub

Bring your seaplane and build your lakefront masterpiece. Situated among million-dollar properties, this is prime waterfront with approximately 432 feet on a private peninsula of spring-fed & pristine Lake Killarney. This is actually two lots (total of 1.514 buildable acreage). Seaplanes land at local favorite Hillstone for lunch and by the evening, the fire pits are lit to watch daylight fade and the stars awaken. This hidden gem is located within proximity to Winter Park's exclusive shopping and dining. Residents can work, play and take advantage of all the nearby cultural offerings. Lake Killarney spans 234 acres & is known for nature watching, scenic strolls, paddleboarding, watersports, waterplanes, elegant waterfront dining at nearby venues and much more. Lake levels are properly maintained with 2 drainage wells. Centrally located - near Winter Park Village, Rollins College, Park Ave Shopping District, Farmers Market, Whole Foods and more. Lake Killarney offers true privacy, with no public access. This property offers land, lifestyle and location. *Sale includes 2 lots: 2401 & 2403 Euston.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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668 W Morse Boulevard Winter Park FL 32789

Winter Park, FL668 W Morse Boulevard

Price$3,485,000

Est. Mortgage: $/month

MLS Number O5815144

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 5,819
  • Year Built 2020

Under Construction. Introducing Phil Kean's latest project - The Morse + Pennsylvania Townhomes. A private enclave of high-end urban lock + leave residences comprised of 3 single family homes and 4 shared-wall townhomes. This Phil Kean Designs 3-story home has 5819 heated SF of gorgeous, breath-taking living, along with a private yard, refreshing cocktail pool, summer kitchen, multiple outdoor lanais and terraces, and a three-car attached garage! A private elevator gives you access to all three floors, from the chef's kitchen and living areas on the first floor, the master suite with loft and office on the second floor, and three additional ensuite bedrooms plus a 22x15 loft and a covered lanai and open terrace on the third floor. Interiors done by Phil Kean Interiors using high-end finishes, a designer lighting and plumbing package, a Wolf/Subzero appliance package, an all marble master bath, hardwood floors, and much more. Sliding glass walls and tons of windows give this home plenty of natural light. Ten foot ceilings and a 2-story family room elevate this home's wow factor! Centrally located in Winter Park's downtown corridor, you can walk to Park Avenue, Hannibal Square, the Farmer's Market, Hillstone's and more! Easy access to I-4, Advent Hospital and downtown Orlando. Call today for more information. Five of the seven total residences are already under contract with building 5 selected to be 2021's New American Home.

Listing Courtesy of PHIL KEAN REAL ESTATE LLC

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$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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639 N Park Avenue Winter Park FL 32789

Winter Park, FL639 N Park Avenue

Price$3,465,000

Est. Mortgage: $/month

MLS Number V4912283

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,244
  • Year Built 2018

WINTER PARK: EXCLUSIVE LEGACY TOWNHOUSE | DOWNTOWN PARK AVENUE | A STROLL TO RESTAURANTS AND SHOPS | HIGH END FINISHES: Built in 2019 by Hill Gray Steven LLC, this stunning property sets the bar for high-end townhouses. Located on the renowned Park Ave in downtown Winter Park steps away from culinary experiences and exclusive shops. This townhouse, which has never been lived in, features tumbled handmade Old Carolina Brick, Soundproof hollow core floors, a Slate Mansard roof and copper gutters. Natural light floods the rooms on all 3 Levels through floor to ceilings windows-11" on the 1st floor, 9" on the 2nd & 3rd floor. The high end double paned windows are energy efficient and the window shades are I-Pad controlled. 8" core-hollow concrete separating floors which gives both stability and minimizes sound. Additional features are Oak flooring throughout, crown molding, coffered ceilings, built in cabinets, lights and smart home technology. The Gourmet kitchen boasts custom Busby Cabinets, Stone counters, Wolf's SUB-ZERO appliances, Italian made Rohl faucets and plumbing fixtures and large wine fridge. The 2nd Story holds 2 bedrooms, 2 Full bathrooms and bonus room w/balcony while the entire 3rd floor is dedicated to the Master Suite with private roof top terrace, fireplace and outside bar. All 3 levels have separate temperature controls. Private elevator, 2 car garage w/AC and smart car Charger. Perfect location, easy to lock & leave...become part of Winter Park's legacy of Excellence.

Listing Courtesy of BEE REALTY CORP

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$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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650 Clay Street Winter Park FL 32789

MLS Number O5852283

  • CommercialSale
  • Property SubType Office
  • Subdivision Lawndale Annex
  • Square Feet 12,287
  • Acreage 0.17

List Price includes 3 parcels: This listing includes two other Parcels that are all being sold together. Parcel 12-22-29-5000-04-040, which is a parking lot that serves as this parcel's parking lot. Parcel 12-22-29-5000-04-011, is a one-story building also owned by the seller. See MLS Listing #o5852270 for further details of the additional property. Both buildings and parking lot comprise the SE corner of Fairbanks and Clay.

Listing Courtesy of WEICHERT REALTORS HALLMARK PROPERTIES

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$
%
$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1788 W Fairbanks Avenue Winter Park FL 32789

MLS Number O5852270

  • CommercialSale
  • Property SubType Office
  • Subdivision Lawndale Annex
  • Square Feet 12,287
  • Acreage 0.44

List Price is for 3 Parcels: This listing includes two other Parcels that are all being sold together. Parcel 12-22-29-5000-04-040, which is a parking lot that serves as this parcel's parking lot. Parcel 12-22-29-5000-04-050, is a two-story building also owned by the seller. See MLS Listing#O5852283 for further details. Both buildings are ADA compliant.

Listing Courtesy of WEICHERT REALTORS HALLMARK PROPERTIES

$
$
%
$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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125 S Interlachen Avenue Winter Park FL 32789

MLS Number O5863273

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,160
  • Year Built 2020

South Interlachen Place offers private, separate, luxurious townhome living in downtown Winter Park. The newly constructed residences are built to a standard rarely seen, even in Winter Park. The location is discrete and yet is just blocks from Park Avenue shopping, restaurants, museums and entertainment. Only six families will be able to enjoy living at South Interlachen Place, assuring generous and exclusive zones for each owner. Every residence has a private outdoor terraced front entrance, its own individual garage, and the ultimate luxury of an exclusive roof top terrace overlooking the city - with a powder room, fireplace, media walls and a covered dining area next to the summer kitchen. Each floor of the townhomes is accessible with a private elevator, from the garage to the rooftop terrace. Master suites comprise the whole second floor of each townhome, steps away from the first floor main living area. These beautiful residences incorporate a number of age in place features that allow for adapting living spaces to lifestyle changes. Finally, all of the residences at South Interlachen Place are prewired with smart technology for entertainment, security, lighting and energy management. Only two townhomes remain available.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.71% last updated on Dec 3, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Based on information submitted to MFRMLS as of December 5, 2020 . All data is obtained from various sources and has not been, and will not be, verified by broker or MFRMLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.