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Winter Park, FL Real Estate — Homes For Sale in Winter Park, FL

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Winter Park Real Estate Overview

Originally founded as a resort destination by affluent New Englanders in the late 1880s, Winter Park is today known for its majestic trees, beautiful parks, brick-lined streets, stunning homes, a private liberal arts college, educational museums, sparkling lakes, and amazing shops. Winter Park is located just 15 minutes from the...
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$594,900
$2,204/mo
Monthly Payment:
$2,204
Principal & Interest:
$2,204
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $118,980 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,559sq ft $232 / sq ft SFR
Lot Size13,000sq ft Built1967 On Site23days
Location, Location, Location!!! You can walk to Park Avenue from this beautiful Spanish style home in sought after Park North still at an affordable price it is also within... more
Location, Location, Location!!! You can walk to Park Avenue from this beautiful Spanish style home in sought after Park North still at an affordable price it is also within short distance to Winter Park Village area and all the Restaurants and shops. This home has great character and many features including 4 bedrooms 3 baths, formal living room with wood burning fireplace, formal dining room and oversized family room, inside laundry room and two master suites. You will enjoy having your friends and family over on the beautiful backyard with new sod, matured landscape and a pool with salt water system. The potential is unlimited on this well located home that you can mold to your taste and needs. Call today to schedule your appointment to view this great home. less
Listing Provided Courtesy of Re/max Properties Sw Inc.
Popularity
We show you every available listing. Here's how
$324,400
$1,201/mo
Monthly Payment:
$1,201
Principal & Interest:
$1,201
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $64,880 down)
Winter Park, FL 32792
Orange County School District
4bed 3bath 1,800sq ft $180 / sq ft SFR
Lot Size10,357sq ft Built1964 On Site23days
Move right in!! Beautiful lead glass front door & friendly foyer welcome you to this light & bright 4 bedroom 3 bath split plan home! Living room with gleaming hardwood floors &... more
Move right in!! Beautiful lead glass front door & friendly foyer welcome you to this light & bright 4 bedroom 3 bath split plan home! Living room with gleaming hardwood floors & tiled, wood-burning fireplace opens to your updated kitchen with granite counter tops, maple cabinets & breakfast bar. Large fenced yard boasts a sparkling swimming pool & plenty of room for a swingset! Extras include: updated windows, new carpet in bedrooms, 6 panel doors, extra large shed & 2 car garage! Centrally located near full sail, ucf, rollins college and a short drive to orlando international airport or downtown winter park's park avenue! Bonus!...This home is located on a quiet cul-de-sac with no through traffic!! Welcome home! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$179,900
$666/mo
Monthly Payment:
$666
Principal & Interest:
$666
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $35,980 down)
Winter Park, FL 32792
Goldenrod Orange County School District
3bed 2bath 1,200sq ft $150 / sq ft SFR
Lot Size7,773sq ft Built1965 On Site23days
3/2, Single Family - Pool Home, Living Room, Dining Room, Inside Utility Room with Washer & Dryer Hookups, Carpet & Tile Throughout Home, Fenced Yard, Open Pool, Screened Patio... more
3/2, Single Family - Pool Home, Living Room, Dining Room, Inside Utility Room with Washer & Dryer Hookups, Carpet & Tile Throughout Home, Fenced Yard, Open Pool, Screened Patio - Lease Expires 8/31/2016 less
Listing Provided Courtesy of Legends Realty
Popularity
$175,000
$686/mo
Monthly Payment:
$686
Principal & Interest:
$648
HOA Dues:
$38
(Based on a 30 year fixed loan at 3.75% with $35,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,565sq ft $112 / sq ft SFR
Lot Size4,767sq ft Built1984 On Site23days
Winter Park - Country Lane! Beautiful 3 Bdrm / 2 BT home. Superb Great Room with wood burning Fireplace. Light and Bright with Vaulted Ceilings. Spacious Kitchen with Eat in... more
Winter Park - Country Lane! Beautiful 3 Bdrm / 2 BT home. Superb Great Room with wood burning Fireplace. Light and Bright with Vaulted Ceilings. Spacious Kitchen with Eat in Area. Brand NEW carpet. Fresh Paint in and out! New Doors. Spacious Master Suite adjoins a Bonus Room. Fenced Yard! Community playground, tennis, and Lake Access! Great Schools! Hurry! Won't Last!!! less
Listing Provided Courtesy of Keller Williams Heritage Rlty
Popularity
$129,900
$481/mo
Monthly Payment:
$481
Principal & Interest:
$481
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $25,980 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 956sq ft $136 / sq ft CND
Lot Size2,114sq ft Built1969 On Site24days
Enjoy your Beautiful High End 2 bedroom 2 bathroom property in Winter Park for sale now!!! This property features brand new interior painting, new molding as well as porcelain... more
Enjoy your Beautiful High End 2 bedroom 2 bathroom property in Winter Park for sale now!!! This property features brand new interior painting, new molding as well as porcelain tile flooring throughout the entire property. This home also features a large spacious kitchen with upgraded cabinets, stainless steel appliances, granite marble counter tops, which you will see in all the bathrooms as well. Enjoy your private spacious balcony, great for entertaining family and friends. Property is in new mint condition and ready to go!!! This property also features access to your own private lake with dock for your boat and community swimming pool with clubhouse. Your home is minutes from Park Ave, Rollins College, Downtown Orlando and Interstate 4. less
Listing Provided Courtesy of Triple S Realty
Popularity
$850,000
$3,306/mo
Monthly Payment:
$3,306
Principal & Interest:
$3,149
HOA Dues:
$157
(Based on a 30 year fixed loan at 3.75% with $170,000 down)
Winter Park, FL 32792
5bed 5bath 4,218sq ft $202 / sq ft SFR
Lot Size17,783sq ft Built2006 On Site24days
Elegant Mediterranean style home with barrel tile roof in private Talman Mews community. Split bedroom plan gives everyone privacy! You will love this gourmet kitchen. Sized for... more
Elegant Mediterranean style home with barrel tile roof in private Talman Mews community. Split bedroom plan gives everyone privacy! You will love this gourmet kitchen. Sized for entertaining. Brazilian granite counters in kitchen, wood cabinets, crown moldings, stainless steel appliances, huge walk-in pantry and built in eat in space with solid marble table. Open kitchen/family room floorplan, so that everyone is part of the action. Equally spacious family room with coffered ceilings that can house large furniture. Lots of light with wall to wall sliders and great views to backyard and screened porch. Each bedroom has its own wing. Master suite is very luxurious and the master bathroom is well appointed with soaking Jacuzzi tub, large walk-in shower, dual vanities. One of the extra bedrooms is perfectly situated for home gym. There is also a dedicated office. Soaring ceilings and quarry stone floors in main areas and wide plank wood floors in bedrooms. Gas stove and fireplace, solid designer doors, AC zones, 6 cameras, covered patio with pavers and many citrus trees in the back yard including lemon, lime and red orange trees. Very private backyard. Circular paved driveway. Meticulously maintained. Secluded right side with pond and no neighbors. Minutes away from downtown Winter Park, shopping, schools. Great walking, biking and running. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$164,900
$610/mo
Monthly Payment:
$610
Principal & Interest:
$610
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $32,980 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,539sq ft $107 / sq ft SFR
Lot Size8,069sq ft Built1968 On Site24days
2 Bedroom, 2 Bath, plus a bonus/office, which could easily be converted to a 3rd Bedroom. Large family room, newer carpet, fresh paint, and Priced Right!! Large master has its... more
2 Bedroom, 2 Bath, plus a bonus/office, which could easily be converted to a 3rd Bedroom. Large family room, newer carpet, fresh paint, and Priced Right!! Large master has its own shower, Extra large utility room. AC, wiring, and plumbing redone in 2010. Oak trees provide plenty of shade for the large yard. Central location, convenient to both downtown Winter Park, and Orlando. less
Listing Provided Courtesy of Loveland Properties
Popularity
$799,000
$2,960/mo
Monthly Payment:
$2,960
Principal & Interest:
$2,960
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $159,800 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
4bed 3bath 3,969sq ft $201 / sq ft SFR
Lot Size2.2acre Built1951 On Site24days
Beautifully Updated Home in Desirable Winter Park. This 4BR/3BA home was built in 1951 & has been completely renovated with careful attention to detail and craftsmanship... more
Beautifully Updated Home in Desirable Winter Park. This 4BR/3BA home was built in 1951 & has been completely renovated with careful attention to detail and craftsmanship throughout. Features include expansive main living area with plantation shutters, new wood flooring throughout, high ceilings & glass Pella doors offering breathtaking views of Little Lake Fairview. The Large kitchen boasts new SS appliances, granite countertops, stacked stone backsplashes, and built-in wine rack with a separate dining room featuring dynamic lake views. The Spacious Master Bedroom overlooks the lake and has a large bathroom with soaking tub, walk-in shower, stacked stone feature wall, and granite countertop. A separate guest suite equipped with a private entranceway with its own bathroom and living room. Two additional bedrooms and a newly remodeled 3rd bathroom . Outside is a detached 2-car garage and large driveway. This expansive lakefront home includes a covered boat dock with boat slip and power lift. The outdoor gazebo and bar with flagstone flooring is the perfect outdoor spot for gatherings and conversation. The beautiful grounds incorporate beauty and function with mature cypress trees set among a backdrop of colorful landscaping with a winding path leading from the house down to the lake. With this type of resort-like living, you will never want to leave the comfort and beauty of this truly unique home. SELLER REQUESTS 24-HOUR SHOWING NOTICE & PRE-QUALIFIED BUYERS. less
Listing Provided Courtesy of Listwithfreedom.com Inc
Popularity
$565,000
$2,093/mo
Monthly Payment:
$2,093
Principal & Interest:
$2,093
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $113,000 down)
Winter Park, FL 32789
Orange County School District
3,435sq ft $164 / sq ft MFR
Lot Size21,000sq ft Built1926 On Site25days
Residential Compound! Winter Park historic Home with separate Office suite and private Apartment to the rear of the property, great for rental income or multi-family. This... more
Residential Compound! Winter Park historic Home with separate Office suite and private Apartment to the rear of the property, great for rental income or multi-family. This Spanish villa style Main house was built in 1926 and is 2 bed/ 2 bath. Enter into history… large Living room with original hand cut wood floors, chic crystal accent lighting and gas fireplace. Delightful Dining room with designer wall sconces and chandelier. Large remodeled Kitchen is light and bright and opens to the Family room – perfect for family gatherings. Also on main level is a secondary Bedroom with a full bath. Master Bedroom is on the second floor and features built-in wardrobe cabinets and a fireplace. The Master features a romantic window lined turret, perfect for sitting area or desk. The separate Office is attached to the Guest House and has a full bath, tall ceilings, French doors & accent lighting. The complete Guest House in the rear has Mexican tile floors and is a 2 bed/ 2 bath with living room, dining area, full kitchen and own laundry. All sits on a triple lot measuring 140 x 150 with circular drive, 3 car carport & plenty of room for additional parking. Plenty of room to expand, add a pool and/or a 3 car garage. The east third of the property is like a park with zoysia grass and is completely fenced & gated. Great multi-family situation. This property has been a wonderful rental investment property and less
Listing Provided Courtesy of Parkland International Realty
Popularity
$529,000
$1,959/mo
Monthly Payment:
$1,959
Principal & Interest:
$1,959
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $105,800 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,640sq ft $200 / sq ft SFR
Lot Size2.9acre Built1980 On Site25days
Lakefront paradise! Spacious four beds, three baths 2,640 sq. ft. home in a desirable, quiet neighborhood overlooking spring fed Lake Ann. Take your canoe out and enjoy fishing... more
Lakefront paradise! Spacious four beds, three baths 2,640 sq. ft. home in a desirable, quiet neighborhood overlooking spring fed Lake Ann. Take your canoe out and enjoy fishing for bass! Sit dockside to experience stunning sunsets and sunrises. This house is perfect for entertaining, with gorgeous views of the lake from almost every part of the home. The home features built in bookcases in three of the rooms, crown molding, plantation shutters throughout and vaulted ceilings. A fireplace is in the family room along with a separate living room. French doors lead to a large screened in porch, perfect for an inside/outside sitting area. Double pane vinyl clad windows help keep the house on a year round temperate setting. The home also has an Electric Energy Miser and gets credits from Duke Energy back monthly. This home has a very large backyard with an oversized patio that has plenty of room for a pool, mature landscaping and a beautiful weeping willow tree. The property features a solid 1 acre of land, a storage shed and a lake fed sprinkler irrigation system. The garage has room for plenty of storage with a closet and also a workbench with built in cabinets. The house has been inspected for termites in August 2015 and has passed all annual termite inspections. The property also has a new 1.5 horsepower irrigation pump was added in 8/2015. Close to Interlachen Country Club, several shopping and retail area & Howell Branch Park. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$1,525,000
$5,871/mo
Monthly Payment:
$5,871
Principal & Interest:
$5,650
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $305,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,400sq ft $347 / sq ft SFR
Lot Size14,906sq ft Built2005 On Site25days
A truly magnificent French Provincial on the N. side of the prestigious Windsong community in olde Winter Park... Extensive use of detailed ceilings & moldings, solid walnut... more
A truly magnificent French Provincial on the N. side of the prestigious Windsong community in olde Winter Park... Extensive use of detailed ceilings & moldings, solid walnut hardwood & Italian travertine floors, 3 fireplaces, French doors, plantation shutters, and true craftsmanship throughout that we have come to expect in a "Carlos Posada" signature custom home... Elegant 2-story entrance foyer opening to formal dining & living rooms each with their own personalized beautiful masonry fireplaces... Exquisite designer lighting with crystal & iron chandeliers, built-ins, shelving, quality cabinetry, exotic granite & stone counters... Wonderful 1st floor master retreat with private courtyard, his/her closets & spa like bath, chef's island kitchen with commercial appliances open to family room with stunning high beamed ceiling, additional downstairs bedroom or study & mud room... Upstairs includes 3 or 4 bedrooms plus a bonus/media room along with a main front and rear stairway access... Outdoor lifestyle includes multiple covered areas including a lanai sitting area with tv, detached cabana w/ masonry fireplace, classic over sized lap pool with fountain feature, iron fencing, motor court with 3 garages & lush professional landscaping... A must see stunning home convenient to club style community pool, park, playground & lake access... less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$270,000
$1,001/mo
Monthly Payment:
$1,001
Principal & Interest:
$1,000
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.75% with $54,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,627sq ft $166 / sq ft SFR
Lot Size8,400sq ft Built1971 On Site25days
Recently Reduced $10,000. Beautifully Renovated Winter Park Home. This home is Energy Efficient - Since June 2015 there are energy efficient Double Pain windows throughout the... more
Recently Reduced $10,000. Beautifully Renovated Winter Park Home. This home is Energy Efficient - Since June 2015 there are energy efficient Double Pain windows throughout the house, a new A/C and extra insulation added to the attic. New Hot Water Heater 7 months old.This 3 Bedroom 2 Bath split plan has a Formal Living and Dining Combination with a spacious Family Room for a second Gathering Area and a Wood Burning Fireplace. The kitchen is graced with Solid Wood WATERMARK Cabinets with Glass Doors and GRANITE Counter Tops Soft Close Drawers and Doors. Recessed Lighting in the Kitchen total New Stainless Steel Appliance Package. Extra Large MASTER Bedroom with Master Bath Completely Remodeled. An inside Super Sized Laundry with a Wash Tub and the List goes on. ROOF 4.5 YEARS OLD. ALL flooring Tile or Laminate. French Doors Lead you outside to enjoy a SUPER LARGE PATIO with an INGROUND newly Refinished SPA. All this opens to an outside BRICK PATIO with FIREPIT- the Ultimate for Entertaining. Beautiful Landscaping Plentiful Fruit Trees. This HOME backs up to Interlachen Golf Course CONSERVATION area. NOTHING LACKING HERE EXCEPT YOU. COME OUT and See this SPECIAL HOME. Don't Miss out on this Winter Park Beauty... Low Seminole County taxes and Seminole County Schools how can you beat that.. The owners' loss is your Gain... The owners just finished this terrific renovation and have decided to move out of state. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$299,900
$1,111/mo
Monthly Payment:
$1,111
Principal & Interest:
$1,111
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,980 down)
Winter Park, FL 32792
Seminole County School District
4bed 2bath 2,100sq ft $143 / sq ft SFR
Lot Size13,256sq ft Built1986 On Site26days
Wonderful Winter Park home with A+ rated Seminole County schools. VIEW VIRTUAL TOUR for over 70 pictures! Desirable Quail Run! Lovingly maintained with fresh interior paint and... more
Wonderful Winter Park home with A+ rated Seminole County schools. VIEW VIRTUAL TOUR for over 70 pictures! Desirable Quail Run! Lovingly maintained with fresh interior paint and new architectural 20 year roof in 2014. Great split bedroom plan. Very spacious kitchen, with large eat in space, which opens on to the inviting family room with brick trimmed wood burning fireplace. Vaulted ceilings in many of the rooms adds to the overall spacious feeling. Large master bedroom retreat that opens on to the large covered/screened back porch. Bath has a large Jacuzzi tub and separate shower. This porch is the perfect place to start your day with a cup of coffee or just relax at the end of a long day. Solid wood doors and trim throughout are very high quality. Oak kitchen with newer appliances with a window access to the porch for entertaining. Large Corner lot with nice landscaping. Pool planned for the future if you want to build your own design. Great location, easy access to the Cady Way Trail for recreation and a short distance to the SR417 to ease your commute. Come see all this home has to offer you will not be disappointed! Pride of ownership shows through. less
Listing Provided Courtesy of Charles Rutenberg Realty
Popularity
$700,000
$2,593/mo
Monthly Payment:
$2,593
Principal & Interest:
$2,593
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $140,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,304sq ft $304 / sq ft SFR
Lot Size11,996sq ft Built1950 On Site27days
Enjoy Florida's outdoor lifestyle in the heart of Winter Park. The split-level layout of this 2300+ sq ft 3-bedroom 2.5-bath is flooded with natural light. Multiple outdoor... more
Enjoy Florida's outdoor lifestyle in the heart of Winter Park. The split-level layout of this 2300+ sq ft 3-bedroom 2.5-bath is flooded with natural light. Multiple outdoor living spaces including gated courtyard, balcony facing Lake Sue Ave, open porch under pergola, and large screened porch overlooking heated salt water pool and lush back yard, bringing the outdoors into every room. The open floor plan combinines living room, dining and sitting rooms. Travertine tile throughout the first floor, and solid oak floors upstairs. Kitchen features gas range, black granite, solid wood cabinets, breakfast bar and large eat-in area. Generous utility room with sink and extra storage. Reverse osmosis water filtration and tankless hot water. Spacious 2-car garage. Less than 1 mile to Park Ave, East End Market and lots of convenient shopping and dining. Excellent Winter Park schools. Circular drive for easy access. Deeded access to Winter Park Chain of Lakes completes the package. Let this home be your refuge from the maddening world! YOU MUST SEE THIS BEAUTIFUL HOME TO APPRECIATE IT. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
$450,000
$1,667/mo
Monthly Payment:
$1,667
Principal & Interest:
$1,667
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $90,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,868sq ft $241 / sq ft SFR
Lot Size12,002sq ft Built1955 On Site27days
Great opportunity to purchase a 0.28 acre lot in one of Winter Park’s most desirable areas. Set back behind the Park Grove community this 145x80’ parcel is located... more
Great opportunity to purchase a 0.28 acre lot in one of Winter Park’s most desirable areas. Set back behind the Park Grove community this 145x80’ parcel is located on a quiet cul-de-sac, surrounded by mature oaks and a mix of charming, remodeled ranch homes and new construction. Existing three bedroom, two bath home has recently undergone some renovations; new tile floors throughout the living and den areas, as well as updated countertops and stainless steel appliances in the kitchen. Two-car garage has been converted into an extra storage room, with wall mounted air conditioning; however it could easily be converted back into a garage. Covered patio and screened in pool are in great shape! Move in, tear down, or renovate – the choice is up to you. Zoned for A-rated Winter Park schools and within close proximity to Park Avenue, Hannibal Square and the Winter Park Golf Course. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
2 3 4 5 6 7 8 9 10 ... 15 25
ZipRealty helps you find current homes for sale in Winter Park, FL. We show up to 30% more MLS listings than other websites, including new homes for sale, condos for sale, townhomes for sale, foreclosed homes for sale and land for sale. Set up your unique Winter Park real estate search criteria to see results that match what you're looking for. Explore maps, photos, schools and more to get an idea of what your life would be like in a new neighborhood. Find a local Winter Park real estate agent to work with by reading realtor reviews left by buyers and sellers like you. If you want to know what your home is worth, you can instantly view home values for any address by visiting our Seller Center. If you're planning to sell your home, you can also see how much similar homes are selling for in Winter Park to get an idea of how to price your home.
Local real estate services provided by:
Coldwell Banker Residential Real Estate
Coldwell Banker Residential Real Estate
5951 Cattleridge Ave
Sarasota, FL 34232

844.662.5638
Website provided and owned by Coldwell Banker Residential Real Estate.
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The information being provided by Mid-Florida Regional Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Mid-Florida Regional Multiple Listing Service. Coldwell Banker Residential Real Estate is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Residential Real Estate, a broker participant of Mid-Florida Regional Multiple Listing Service. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.

The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Mid-Florida Regional Multiple Listing Service and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

Copyright 2015 Mid-Florida Regional Multiple Listing Service. All rights reserved.

Data last updated: Saturday, September 5, 2015 at 4:44 AM. Properties in listings may have been sold or may no longer be available.