Winter Park, FL Homes under $400,000

One or more photo(s) has been virtually staged. PRICED TO SELL! NEW ROOF, UPDATED PANEL BOX, UPDATED KITCHEN. Welcome Home!! This comfortable 3 Bedroom, 2 Bathroom Winter Park home sits on an oversized lot with no HOA, offering the perfect blend of privacy and freedom to make it your own. Zoned for Seminole County Schools! Step inside to FRESH PAINT (2024), NEW CARPET (2024), A BRAND-NEW ROOF

Jennifer Wemert WEMERT GROUP REALTY LLC

PRICED TO SELL!!!! FIRE DAMAGED HOUSE - LOTS OF POTENTIAL IN THIS WINTER PARK POOL HOME. This is an exciting opportunity for investors or buyers looking for a project! This home offers a blank canvas for renovation. The property is situated in a quiet, family-friendly neighborhood, making it an ideal candidate for full restoration. With required renovations - this blank canvas will become a

Andrey Bustamante BUSTAMANTE REAL ESTATE INC

Here it is! A great Single-Family Home in Winter Park HS district. Check out this beautiful freshly painted interior single story 3 bedroom 2 1/2 bath home with bonus room. When you walk in the front door turn left to enter the Great Room that includes the open concept kitchen, dining and family rooms. The kitchen includes all appliances and offers a propane gas range. From the family room

Lori Hutchinson THE WILKINS WAY LLC

**This property qualifies for a closing cost credit up to $6,100 through the Seller’s preferred lender.**Look no further than this charming 3-bedroom, 2-bathroom pool home located in the highly desirable Winter Park community of Winter Park Estates. Sitting on ¼ of an acre with no HOA, this home is just what you’ve been searching for! Head inside to find the beautifully updated kitchen featuring

Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

2022 Tesla Solar Panels (PAID OFF)Welcome to this charming updated 3-bedroom, 2-bathroom single-family home, located in the highly sought-after city of Winter Park, Florida. Known for its top-rated schools and vibrant community, Winter Park offers an unbeatable lifestyle with close proximity to the iconic Park Avenue, renowned for its boutique shopping and dining, as well as a quick drive to the

Alistair Baxter EXP REALTY LLC

One or more photo(s) has been virtually staged. Incredible Value! Priced to sell under market value! This is your opportunity to get in at a price that won’t last long. Act fast before it's gone! Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the desirable Goldenrod area with no HOA! Fully upgraded luxury home with a large fenced in backyard. Brand new high end upgrades

Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

Welcome to your next home located at 3131 Ash Park Loop in the serene Hyde Park community. This inviting 2-bedroom, 2-bathroom house offers a clean, open split floor plan that’s perfect for both living and entertaining. Move-in ready, this home also presents a unique chance for creative renovations, making it a blank canvas for your personal touch.The property boasts a large screened-in

Amanda Binns STRICKLAND REALTY GROUP INC

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

Unmissable opportunity in Winter Park! Beautiful house for sale with 3 bedrooms and 3 bathrooms, perfect for those seeking comfort, convenience and quality of life.Located in one of the most sought-after areas of Winter Park, with an excellent location, close to schools, shops, restaurants, parks and much more!The community offers a complete infrastructure with a swimming pool, playground,

Marcus Freire de Araujo WRA BUSINESS & REAL ESTATE

Welcome to 264 Balfour Drive — an exclusive residence within a private enclave of just 13 elegant townhomes in the heart of Winter Park designed by architect Nils Schweizer. a student of Frank Lloyd Wright. Offering an attached two-car garage and a premier location, this home blends sophistication with comfort in every detail.Step into a grand living room where soaring ceilings and expansive

Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

Welcome to this delightful 3-bedroom, 2-bathroom home nestled in the heart of sought-after Winter Park! Bursting with character and charm, this property features original hardwood floors that add warmth and timeless appeal, along with a cozy antique wood-burning stove that brings a touch of rustic elegance to the living space. Plus, an updated bathroom is perfect for visitors.Set on a large lot

Jonathan Cole KELLER WILLIAMS WINTER PARK

Build your dream home in the City of Winter Park! This deep 56x157 lot is Winter Park’s best kept secret, located in a quiet pocket of 32789, with beautiful trees and no HOA. This property is centrally located, less than 10 minutes to Park Ave, and zoned for Orange County schools: Dommerich Elementary, Maitland Middle and Winter Park High School. A custom home just went up around the corner in

Kristen Hamilton LOMBARDO TEAM REAL ESTATE LLC

Welcome home to this beautifully maintained 3-bedroom, 2.5-bath residence in the highly desirable Winter Park Oaks community, featuring 1,500 sq. ft. of inviting living space ideal for both comfort and entertaining. The thoughtfully designed two-story layout includes an open-concept main level with a spacious kitchen flowing effortlessly into a bright family room, convenient downstairs half bath,

Serge Osaulenko EVERLANE REALTY LLC

Discover this beautifully renovated 2-bedroom, .5 -bathroom villa in the heart of Winter Park! Nestled on a private cul-de-sac lot with no HOA, this home has been completely upgraded to offer modern comfort and style. Step inside to luxury vinyl flooring throughout, an open-concept living space, and a sleek kitchen with stainless steel appliances. The high-end bathroom remodel adds a spa-like

Renee Anthony WATSON REALTY CORP.

One or more photo(s) has been virtually staged. Welcome you to your charming 3-bedroom, 2-bathroom condo right in the heart of historic Winter Park! This spacious end unit spans 1,322 square feet and features beautiful designer touches that create a cozy and inviting atmosphere. Enjoy the stylish kitchen and baths along with a large primary bedroom that boasts an ensuite bathroom and a

Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just over an acre, lot in coveted Winter Park. Nestled on the end of a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level

Gwendolen Flynn COLDWELL BANKER RESIDENTIAL RE

MOTIVATED SELLER! Beautifully maintained Townhome in desirable gated community of Vistas at Lake Howell. This spacious 3 bedroom 2 and 1 half bath home is ready for its new owner. With new carpet, paint and appliances it's in move-in condition. Large kitchen overlooks the expansive dinning living room combination with sliding doors leading out to the screened-in patio. Upstairs you will find the

Jeffrey Friedman FANNIE HILLMAN & ASSOCIATES

Priced to sell!! Motivated Seller. Outstanding structural integrity, no big assessments ahead! Whispering Waters passed its structural integrity inspection and reserves study with flying colors—earning compliments for the quality and care of the buildings. This is a very well-managed community, and the $1,054 monthly HOA covers nearly everything, including electricity! The only exception is cable

Maria Van Warner FANNIE HILLMAN & ASSOCIATES

LOCATION, LOCATION, LOCATION with partial Lake View! Experience the perfect blend of modern upgrades, prime location, and lakefront living in this beautifully renovated Winter Park condominium. Nestled along Lake Killarney, this two-bedroom, one-bathroom residence offers an ideal mix of comfort, investment potential, and exclusive community amenities. Thoughtfully updated in 2018, the home

Justin Adams EXP REALTY LLC

Tucked away on a quiet street yet just minutes from downtown Winter Park, College Park, and downtown Orlando, this beautifully updated 1955 ranch offers the perfect blend of peaceful living and urban convenience. With 2 bedrooms, 2 baths, and 1,262 square feet of thoughtfully renovated space, this home is move-in ready and full of character. As you enter, you’re greeted by a large, open living

Carol van den Berg FLORIDA ONE REAL ESTATE LLC

Welcome to Harbour Ridge in Winter Park with ••No HOA. This home is situated on a spacious 1/3-acre fully fenced lot offering plenty of room for outdoor activities, gardening, or relaxing and there is an extra-large shed for storage or workshop potential. Inside, you'll find improvements such as a •brand-new kitchen, •luxury vinyl flooring in the primary bedroom and an •updated primary

Barbara Mills COLDWELL BANKER REALTY

Welcome to 690 Osceola Avenue, a lakefront complex in the heart of Winter Park. This sleek, modern residence offers the perfect blend of contemporary design and convenient urban living, just minutes (less than a mile) from the charming shops, restaurants and cultural attractions of Winter Park's renowned Park Avenue. This two-bedroom, two-bath condominium has a private screened balcony with

Sara Cambron PREMIER SOTHEBY'S INTL. REALTY

Who wouldn’t want to live on a street called LOTAFUN? This is your opportunity to build your dream home on a quiet street with convenient access to Winter Park, Maitland and Orlando as well as Interstate 4 either from Lee Road or Fairbanks Avenue. This beautiful vacant lot has 75-feet of frontage and is 100-feet deep. This has a Winter Park address but is located in Orange County. An

Johnny Hurlburt COLDWELL BANKER RESIDENTIAL RE

Presenting a gorgeous, completely renovated condo with a townhome feel, available in highly desirable Winter Park. This two-story home boasts new everything...beautiful hardwood and ceramic tile downstairs and in the bathrooms, new carpet upstairs, fresh paint, brand new countertops throughout, remodeled bathrooms, new stainless steel appliances, and high end fixtures and faucets! There's a large

Moe Mossa SAVVY AVENUE, LLC

One or more photo(s) has been virtually staged. SOLAR PANELS WILL BE PAID OFF AT CLOSING!! Welcome to this move-in ready Winter Park pool home, tucked away in a peaceful cul-de-sac! This gem has been thoughtfully updated with significant renovations, including a composition shingle roof (2019), custom gutters with in-ground drain lines (2019), a Trane HVAC with hurricane slab foundation (2019),

Chelsea Feinberg EXP REALTY LLC

Welcome to this adorable 3-bedroom, 2-bathroom cottage-style home, perfectly situated in a prime location with no HOA! Immaculate and move-in ready, this charming property features a cozy front porch that invites you to sit back and relax. Step inside to find bright, comfortable living spaces with easy-to-maintain laminate and tile flooring throughout. The kitchen offers a warm, inviting

Vanessa Scotland, PA SERHANT

PRICE IMPROVEMENT – Motivated Sellers!Step into this beautifully updated 2-bedroom, 2-bath condo located in the highly desirable Winter Park Gardens community. This move-in-ready unit has been thoughtfully upgraded with modern features, including brand-new plumbing, a tankless water heater, resealed windows, recessed lighting, and ceiling fans throughout. The entire home boasts stylish wood-look

Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

Welcome to your dream home in beautiful Winter Park, Florida! This charming 3-bedroom, 2-bathroom CORNER UNIT is perfectly situated within half a mile to Casselberry Commons Shopping Mall, providing convenience at your doorstep.This home featuring a BRAND NEW ROOF (2023), along with a new thermostat and fan installed in 2024. Enjoy optimal comfort with newly installed AC ducts and insulation

Yvette Hernandez THE REALTY EXPERIENCE POWERED BY LRR

FULL LAKE FRONT VIEW, ONE OUT OF 6 UNITS WITH BEST VIEW IN LAKE KILLARNEY CONDO! Amazing location in Winter Park! Full LAKEFRONT view, fully renovated end unit condo on spring fed, navigable, & private Lake Killarney. Sunset views every evening from your living, kitchen, dining, and master bedroom! . Lakefront pool and private boat dock with ~14 slips (see management for availability).

Adriana Montes MBA ? FLORIDA DREAMS REALTY GRP INC

BACK ON THE MARKET! PRICE DROP! SELLER WILLING TO GIVE CONCESSIONS FOR DOWN PAYMENT ASSISTANCE! Welcome to your dream home in the heart of Winter Park! This charming bungalow has been fully renovated and completely upgraded from top to bottom, blending modern amenities with classic charm. Located between College Park and Winter Park, this home offers convenience, comfort, and style. The

Austin Drawdy LPT REALTY, LLC

One or more photo(s) has been virtually staged. Check out this stunner! This home has New Roof, Fresh Interior Paint. Windows create a light filled interior with well placed neutral accents. Step into the kitchen, complete with an eye catching stylish backsplash. Relax in your primary suite with a walk in closet included. The primary bathroom features plenty of under sink storage waiting for

GREGORY BLACKALL OPENDOOR BROKERAGE LLC

One or more photo(s) has been virtually staged. Welcome to this stunning property with a natural color palette that creates a soothing ambiance throughout. The kitchen boasts a nice backsplash, adding a touch of elegance to this functional space. The master bedroom offers a spacious walk-in closet, providing ample storage for your wardrobe. With additional rooms for flexible living space, the

GREGORY BLACKALL OPENDOOR BROKERAGE LLC

This beautifully maintained three-bedroom, two-bath residence features an inviting open floor plan, perfect for both entertaining and everyday living. Recently painted with a fresh interior, the home radiates warmth and brightness throughout. Enjoy modern comforts with a brand-new air conditioning system installed just six months ago, ensuring a cool and comfortable atmosphere year-round. The

Bianca Botelho RE/MAX ASSURED

Welcome to 1073 Hamlet Drive—an updated 3-bedroom, 2-bathroom block home with over 1,000 square feet of comfortable living space, a 1-car garage, and a prime location in the highly sought-after community of Hamlet at Maitland. From the moment you step inside, you'll be greeted by vaulted ceilings, an abundance of natural light, and an open floor plan that’s ideal for entertaining. The spacious

Wendy Jane MacAnthony ELEGANT REALTY LLC