Call your local brokerage at 844-662-5638

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

403 Properties Found [ Edit Search ]
Save This Search
Receive Email Alerts

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...
Show all »
First page 12 of 27 Last
$1,295,000
$4,797/mo
Monthly Payment:
$4,797
Principal & Interest:
$4,797
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $259,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,510sq ft $287 / sq ft SFR
Lot Size15,749sq ft Built1926 On Site72days
1920's Modern Mediterranean in premier setting on oversized corner lot overlooking Lake Chelton and surrounded by majestic oaks and beautiful brick streets! This elegant 4... more
1920's Modern Mediterranean in premier setting on oversized corner lot overlooking Lake Chelton and surrounded by majestic oaks and beautiful brick streets! This elegant 4 bedroom home is bright & open sitting up high overlooking Lake Chelton wonderfully remodeled & preserved to maintain its historic charm and character! Original hardwood floors and Italian tile enhance the downstairs living areas, including the formal living and dining rooms, and breakfast nook. Designer island kitchen with gas appliances, custom cabinetry, and granite counter tops open to large family room with French doors to lanai... Also a fabulous sunroom with floor to ceiling glass arc windows offering panoramic views of the lake and a peaceful environment to relax in... Separate, outdoor screened patio is an extension of the indoor living space and continues the arc window design and Mexican tile flooring and great character... Upstairs master bedroom is oversized with sitting area, and French doors that open onto a walk-out terrace. Master bathroom is adorned with marble vanities and a marble Jacuzzi tub, walk-in shower, and expansive closet. Two additional guest suites, each with their own bath, and generous 4th bedroom suite/bonus room with wood burning fireplace complete the upstairs. Lastly, there is a detached two garage with covered walkway and a unique "hard to find" unfinished 2nd floor that could easily be converted into a guest apartment with full bath. Located in one of Winter Park's most picturesque neighborhoods. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
We show you every available listing. Here's how
$1,895,000
$7,020/mo
Monthly Payment:
$7,020
Principal & Interest:
$7,020
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $379,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 4,872sq ft $389 / sq ft SFR
Lot Size18,088sq ft Built1994 On Site72days
Custom built, original-owner canal home on Alabama Drive, one of the most beautiful tree lined streets in downtown Winter Park. Hand crafted by Peatross & Huber, the floor plan,... more
Custom built, original-owner canal home on Alabama Drive, one of the most beautiful tree lined streets in downtown Winter Park. Hand crafted by Peatross & Huber, the floor plan, amenities and attention to detail are timeless. Enter into grand foyer with vaulted ceilings and marble floors, flanked by elegant dining room with built in niches, and living room with double-sided gas fireplace. The downstairs boasts a luxurious master suite with pool view, a separate guest suite, and an office with wood beams, wood floors, and a magnificent set of etched glass French doors. Kitchen opens onto family room and has double ovens, Subzero refrigerator, an island, and butler’s pantry. There is also an indoor sunporch, as well as an outdoor screened porch with brick walls that feels like the best of coastal living! 3 Bedrooms + 3 baths upstairs plus bonus area. Features include crown molding, French doors, tray ceilings, hardwood floors, custom built-ins, and abundant storage. Pool area is lovely with outdoor grill and pergola, and home sits on almost a half-acre. Boat house included in sale but sold AS IS. The best location in town, easy walk to Park Avenue, and “A” rated Winter Park schools. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$250,000
$926/mo
Monthly Payment:
$926
Principal & Interest:
$926
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $50,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,398sq ft $179 / sq ft SFR
Lot Size9,360sq ft Built1970 On Site72days
Home in excellent condition with both bathrooms recently renovated. This is a great location with excellent high rated schools, convenient to major roads, downtown Winter Park,... more
Home in excellent condition with both bathrooms recently renovated. This is a great location with excellent high rated schools, convenient to major roads, downtown Winter Park, shopping, dining, UCF, Rollins College & Full Sail. Call today for an appointment to see this lovely home! less
Listing Provided Courtesy of Keller Williams Classic Ii
Popularity
$275,000
$1,019/mo
Monthly Payment:
$1,019
Principal & Interest:
$1,018
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.75% with $55,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 3bath 1,776sq ft $155 / sq ft SFR
Lot Size9,030sq ft Built1969 On Site74days
Fully renovated! Just move in and enjoy! All new appliances, granite counter tops throughout. Tile and wood flooring. All bedrooms are on the second floor. This is a great... more
Fully renovated! Just move in and enjoy! All new appliances, granite counter tops throughout. Tile and wood flooring. All bedrooms are on the second floor. This is a great location with excellent high rated schools, convenient to major roads, downtown winter park, shopping, dining, ucf, rollins college & full sail. Call today for an appointment to see this lovely home! less
Listing Provided Courtesy of Keller Williams Classic Ii
Popularity
$72,140
$495/mo
Monthly Payment:
$495
Principal & Interest:
$267
HOA Dues:
$228
(Based on a 30 year fixed loan at 3.75% with $14,428 down)
Winter Park, FL 32792
2bed 2bath 1,058sq ft $68 / sq ft CND
Lot Size12,549sq ft Built1973 On Site75days
Upgraded Kitchen & Bath in beautiful condo community of Wrenwood of Winter Park. Screened in Patio faces the courtyard and grounds are nicely maintained. Enjoy the lifestyle,... more
Upgraded Kitchen & Bath in beautiful condo community of Wrenwood of Winter Park. Screened in Patio faces the courtyard and grounds are nicely maintained. Enjoy the lifestyle, Community has a pool and fitness center for their residents. BANK OWNED PROPERTY SOLD "AS IS" WITHOUT REPAIR OR WARRANTY. LISTING AGENT HAS NO KNOWLEDGE OF PROPERTY HISTORY, NO DISCLOSURES OR ASSOCIATION DOCS SUPPLIED. BUYER/BUYER'S AGENT IS RESPONSIBLE FOR VERIFYING HOA INFO & FEES, IF ANY, COMMUNITY RULES, SQ FT, LOT SIZE, ROOM DIMENSIONS AND TAXES. THIS PROPERTY IS UNDER AUCTION TERMS. AT CLOSING, IT IS SUBJECT TO A WEB TECH FEE AND MAY ALSO BE SUBJECT TO A BUYER'S PREMIUM PURSUANT TO THE TERMS & CONDITIONS.SELLER WILL NOT ALLOW WATER TO BE ACTIVATED/TURNED ON FOR ANY REASON. BUYER IS RESPONSIBLE FOR ACTIVATING/TURNING ON OTHER UTILITIES. less
Listing Provided Courtesy of Carrington Real Estate Service
Popularity
$375,000
$1,389/mo
Monthly Payment:
$1,389
Principal & Interest:
$1,389
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $75,000 down)
Winter Park, FL 32789
Orange County School District
2bed 1bath 1,148sq ft $327 / sq ft SFR
Lot Size6,248sq ft Built1925 On Site75days
**traditional sale**charming spanish mission style home in historical winter park**corner lot**fenced**open floor plan with arches & 9 ft ceilings**original wood floors**new... more
**traditional sale**charming spanish mission style home in historical winter park**corner lot**fenced**open floor plan with arches & 9 ft ceilings**original wood floors**new plumbing fixtures 2013**new hot water heater 2011**new electrical panel & a/c 2010**pella wood clad windows**remodeled kitchen boasts crown molding, granite, custom tile backsplash, 42" cabinets & gas stove**breakfast nook with sliders to deck - plumbed for a gas grill**dining room with decorative chair rail/wainscot accent**living space features wood burning fireplace and access to screened covered porch**master bedroom features crown molding & french doors to outdoor living space**brick paver walks and driveway**awnings over all doors**detached garage**mature landscaping, oak trees, and brick paver streets surround this beautiful home within walking distance to winter park's famed park ave and rollins college.**tv & surround sound convey** less
Listing Provided Courtesy of Keller Williams Advantage 2
Popularity
$169,900
$629/mo
Monthly Payment:
$629
Principal & Interest:
$629
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $33,980 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,312sq ft $129 / sq ft SFR
Lot Size8,400sq ft Built1969 On Site75days
Location, location, location. Fantastic opportunity to own in Seminole County. Property has scores of potential but needs electrical, plumbing and a new roof. In-ground, working... more
Location, location, location. Fantastic opportunity to own in Seminole County. Property has scores of potential but needs electrical, plumbing and a new roof. In-ground, working pool home is centrally located with easy access to major roads, shopping & dining. Desirable Seminole County Public Schools. Property is Sold AS-IS with no warranties and no repairs. Buyer to verify HOA, taxes, lot sizes, room dimensions, construction type. **Pool in process of being maintained** *Open permit from 2000 for the a/c. Seller will not address, buyer must sign a hold harmless.* less
Listing Provided Courtesy of The Devinney Real Estate Group
Popularity
$849,900
$3,148/mo
Monthly Payment:
$3,148
Principal & Interest:
$3,148
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $169,980 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 3bath 2,744sq ft $310 / sq ft SFR
Lot Size27,500sq ft Built1996 On Site75days
Living the Lakefront dream on Lake Killarney! Welcome home to a one story ideal home with a fabulous floor plan and lake views from almost every room (but one). This home... more
Living the Lakefront dream on Lake Killarney! Welcome home to a one story ideal home with a fabulous floor plan and lake views from almost every room (but one). This home includes 2 large master suites, both with views of the lake, an additional 3rd bedroom with a guest bath and a professional office. Home is located on a quiet cul-de-sac with an oversized 3 car garage and storage galore! The kitchen includes tons of corian counter space with an eat-in bar, island, gas range, and a large dinette area with additional cabinets and buffet counter. The spacious living room includes 13 foot valued ceilings, with canned lights, a gas fireplace, built-ins and large glass sliding doors to help bring the outside living in. Open Dining room is wrapped in custom bookshelves to make a versatile room. The covered patio is perfect for dining and entertaining that overlooks the screened pool with a stone waterfall. Store your boat on your large dock with a covered roof and lift. Ride your boat over to Hillstone for dinner! The propane gas goes to the following: stove, hot water heater, fireplace and dryer. Every window and door has hurricane shutters for protection. 1 large AC system with 3 separate AC zones for comfort. Home sits on over ½ acre of high and dry property! This is fabulous WP Lakefront living! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$2,599,000
$9,629/mo
Monthly Payment:
$9,629
Principal & Interest:
$9,629
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $519,800 down)
Winter Park, FL 32792
Seminole County School District
N/Asq ft N/A / sq ft LND
Lot Size14.2acre BuiltN/A On Site75days
7.5 usable Acre Lakefront Winter Park Equestrian Estate Located in the heart of the city. Ideal for Assisted Living Facility, School, Church or community center under current... more
7.5 usable Acre Lakefront Winter Park Equestrian Estate Located in the heart of the city. Ideal for Assisted Living Facility, School, Church or community center under current zoning. Can be rezoned to fit Approx. 30 Single Family residential home sites. Classic 1960's custom 3br/2.5 bath 2,672 square foot Florida pool home Separate Lakefront Mother-in-Law E Expansive and Extremely Private Lake View under Grandfather Oaks 330' Frontage on Crystal Clear, Spring Fed Lake Florence w/private boat ramp White Sand Beach Horse Swimming Area 5 minutes from Trinity Prep, 10 minutes from Park Maitland On-going agricultural operations uniquely qualify this income producing Winter Park estate for taxes of only $2,200 annually. Subdivide into 4 estate home sites without rezoning or into 30 +/- residential lots by rezoning. less
Listing Provided Courtesy of Stirling Sotheby's Int'l Rlty
Popularity
$275,000
$1,019/mo
Monthly Payment:
$1,019
Principal & Interest:
$1,018
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.75% with $55,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 2bath 1,754sq ft $157 / sq ft SFR
Lot Size9,462sq ft Built1970 On Site76days
Recently upgraded!!! 4 bedroom 2 bedroom house situated on a cul-de-sac. Features a spectacular updated kitchen with stainless steel appliances with 2 breakfast bars. Kitchen... more
Recently upgraded!!! 4 bedroom 2 bedroom house situated on a cul-de-sac. Features a spectacular updated kitchen with stainless steel appliances with 2 breakfast bars. Kitchen opens up to family room and large dining area. Great inside laundry room with plenty of space. Split bedroom floor plan, large master suite with french doors leading out to florida room and pool view. The lot is oversized, and has a large gated fence opening for boat or rv parking. Private fenced backyard includes an in-ground pool, large shed ,& plenty of room to garden and entertain! Conveniently located just 10 minutes from downtown orlando and 35 minutes from the disney attractions, convenient to the 417 toll road, downtown winter park, shopping, and dining. less
Listing Provided Courtesy of Keller Williams Classic Ii
Popularity
$1,100,000
$4,175/mo
Monthly Payment:
$4,175
Principal & Interest:
$4,075
HOA Dues:
$100
(Based on a 30 year fixed loan at 3.75% with $220,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,333sq ft $330 / sq ft SFR
Lot Size12,324sq ft Built2005 On Site76days
This beautiful Mediterranean home is set in the very sought after subdivision of Pennsylvania Place. As soon as you drive into this quaint Winter Park neighborhood you know... more
This beautiful Mediterranean home is set in the very sought after subdivision of Pennsylvania Place. As soon as you drive into this quaint Winter Park neighborhood you know there is no place like home. The home itself boasts a turnkey lifestyle while many luxury features exist as you walk in the front entry. Engineered wood flooring, crown moulding, butlers pantry, a separate bar area for entertaining your friendly neighbors. The spacious downstairs master bedroom includes a sitting area, 2 walk-in closets and oversized ensuite bath. If location and features weren't enough, knowing that the home has been meticulously maintained should give a great deal of comfort. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$800,000
$2,963/mo
Monthly Payment:
$2,963
Principal & Interest:
$2,963
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $160,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size19,059sq ft BuiltN/A On Site76days
Big 150'x130 (approx) building lot (s), serene lake view setting, viewed from the front porch of your new custom home. 15 new homes under construction within 1/2 mile of this... more
Big 150'x130 (approx) building lot (s), serene lake view setting, viewed from the front porch of your new custom home. 15 new homes under construction within 1/2 mile of this location, up to $1.5M. Approved Winter Park City lot split into two 75x130 (approx) lots. See attachment for approval letter. City of Winter Park Building Codes apply. Value is in the land for one large or two separate building lots. Winter Park City maintained Lake Wilbar. less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$2,795,000
$10,355/mo
Monthly Payment:
$10,355
Principal & Interest:
$10,355
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $559,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 6,285sq ft $445 / sq ft SFR
Lot Size32,129sq ft Built2011 On Site77days
Magnificent estate home & unique oversized property in the heart of the Via's... premier location on triple lot (3/4 acre) on quiet street... This home was custom built in 2011... more
Magnificent estate home & unique oversized property in the heart of the Via's... premier location on triple lot (3/4 acre) on quiet street... This home was custom built in 2011 with Hal George at Parkland Homes, top quality craftsmanship & exquisite trim / moldings thru-out, bright-open floor plan, high detailed ceilings, generous room sizes, designer lighting, lots of great windows & french doors... Fabulous 1st floor master retreat with lavish bath along with his & her baths/dressing areas... Wonderful huge gourmet island kitchen with commercial appliances & extensive cabinetry, elegant "club room" with full bar & paneled walls, large beautiful formal dining & living rooms with windows/french doors both sides, and a library downstairs... Upstairs includes 4 bedroom suites, game room & bonus room... The outdoor living is nothing short of spectacular with tremendous grounds, expansive covered lanai (invisible remote retractable screens), classic pool area & walled in private yard... Enjoy the Winter Park Racquet Club, tennis courts, & access to Lake Maitland "chain of lakes" next door... A perfect entertaining home & property!! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$275,000
$1,018/mo
Monthly Payment:
$1,018
Principal & Interest:
$1,018
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $55,000 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,592sq ft $173 / sq ft SFR
Lot Size9,542sq ft Built1965 On Site77days
Winter Park Pines Beautiful home with multiple upgrades including newer roof, AC, stucco, gutters, electrical, paint. Tiled, sprinkler well and timer, fenced backyard, screened... more
Winter Park Pines Beautiful home with multiple upgrades including newer roof, AC, stucco, gutters, electrical, paint. Tiled, sprinkler well and timer, fenced backyard, screened porch, back deck and on a corner Lot. New Windows and Updated Baths. Mature Oak Trees and landscaping. A - Rated Winter Park Schools!! less
Listing Provided Courtesy of Florida Home Realty & Invest
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 32789
Baldwin Park Orange County School District
4bed 2bath 1,548sq ft $116 / sq ft SFR
Lot Size7,508sq ft Built1959 On Site77days
Short Sale! Home needs TLC, great for a redo! Winter Park School District. Located adjacent to Baldwin Park. Great sought after location.
Short Sale! Home needs TLC, great for a redo! Winter Park School District. Located adjacent to Baldwin Park. Great sought after location. less
Listing Provided Courtesy of Palm Properties Of Cf, Inc.
Popularity
8 9 10 11 12 13 14 15 16 ... 21
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
Content provided and owned by Coldwell Banker Residential Real Estate.
Loading....
Loading
The information being provided by Mid Florida Regional MLS 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 MLS. 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 MLS. 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 MLS 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 MLS. All rights reserved.

Data last updated: Tuesday, January 27, 2015 at 9:50 PM