Homes Under $500K in Winter Park, CO

3 beds

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20 of 40 Listings

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Homes Under $500K in Winter Park, CO

20 of 40 Listings

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Steve Merritt

Realty.com

Lic. #ER.100044960

Call Steve

34Active
$354,900
1 bd · 1 ba · 349 sqft
411 Hi Country Drive 4-12, Winter Park, CO
Skylar Marshall · Real Estate of Winter Park
38Active
$469,000
2 bd · 1 ba · 605.9 sqft
507 Hi Country Drive #11-127, Winter Park, CO
Sheila Bailey · Keller Williams Advantage Realty, LLC
26Active
$425,000
2 bd · 2 ba · 860 sqft
490 Kings Crossing Rd 634, Winter Park, CO
Brian MacMillan

Listing data & MLS disclosures

Grand County Board of REALTORS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listing information ©2026 Grand County Board of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-09-02 06:30:35 UTC
IRES MLS: Information and Real Estate Services, LLC. Provided for limited non-commercial use only under IRES Rules. Copyright © IRES. Broker Reciprocity is the current compilation of active listings of all Broker Reciprocity subscribers except those listings where the seller or the seller's agency has opted out of Internet publication by so indicating on the listing contract or by written notice to the Multiple Listing Service. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user, Information deemed reliable but not Guaranteed. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright ©2026 Information and Real Estate Services, LLC. All rights reserved.
REcolorado: The content relating to real estate for sale in this Web site comes in part from the Internet Data eXchange (“IDX”) program of METROLIST, INC., DBA RECOLORADO® Real estate listings held by brokers other than Realty.com are marked with the IDX Logo. This information is being provided for the consumers’ personal, non-commercial use and may not be used for any other purpose. All information subject to change and should be independently verified. This publication is designed to provide information with regard to the subject matter covered. It is displayed with the understanding that the publisher and authors are not engaged in rendering real estate, legal, accounting, tax, or other professional services and that the publisher and authors are not offering such advice in this publication. If real estate, legal, or other expert assistance is required, the services of a competent, professional person should be sought. The information contained in this publication is subject to change without notice. METROLIST, INC., DBA RECOLORADO MAKES NO WARRANTY OF ANY KIND WITH REGARD TO THIS MATERIAL, INCLUDING, BUT NOT LIMITED TO, THE IMPLIED WARRANTIES OF MERCHANTABILITY AND FITNESS FOR A PARTICULAR PURPOSE. METROLIST, INC., DBA RECOLORADO SHALL NOT BE LIABLE FOR ERRORS CONTAINED HEREIN OR FOR ANY DAMAGES IN CONNECTION WITH THE FURNISHING, PERFORMANCE, OR USE OF THIS MATERIAL. PUBLISHER'S NOTICE: All real estate advertised herein is subject to the Federal Fair Housing Act and the Colorado Fair Housing Act, which Acts make it illegal to make or publish any advertisement that indicates any preference, limitation, or discrimination based on race, color, religion, sex, handicap, familial status, or national origin. METROLIST, INC., DBA RECOLORADO will not knowingly accept any advertising for real estate that is in violation of the law. All persons are hereby informed that all dwellings advertised are available on an equal opportunity basis.

Winter Park housing market

August 2026 · This period is still settling

Selling at 98.8% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Aug 28, 2026

Homes that sold · County records, as of Aug 18, 2026

Median sale price: $1,130,000$672,000–$1,522,500 typical range
Price per sq. ft.: $709
Sales: 15
Paid in cash: 40.0%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $985,000
Homes for sale: 167

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -30.7%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,498 sq. ft.

Winter Park, CO community profile

Population: 1,066
Median income: $72,015
Housing units: 1,726
People per sq. mi.: 15
Area: 71.3 sq. mi.

Source: HJN community data

Explore Winter Park homes

Listing data & MLS disclosures

Grand County Board of REALTORS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listing information ©2026 Grand County Board of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-09-02 06:30:35 UTC
IRES MLS: Information and Real Estate Services, LLC. Provided for limited non-commercial use only under IRES Rules. Copyright © IRES. Broker Reciprocity is the current compilation of active listings of all Broker Reciprocity subscribers except those listings where the seller or the seller's agency has opted out of Internet publication by so indicating on the listing contract or by written notice to the Multiple Listing Service. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user, Information deemed reliable but not Guaranteed. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright ©2026 Information and Real Estate Services, LLC. All rights reserved.
REcolorado: The content relating to real estate for sale in this Web site comes in part from the Internet Data eXchange (“IDX”) program of METROLIST, INC., DBA RECOLORADO® Real estate listings held by brokers other than Realty.com are marked with the IDX Logo. This information is being provided for the consumers’ personal, non-commercial use and may not be used for any other purpose. All information subject to change and should be independently verified. This publication is designed to provide information with regard to the subject matter covered. It is displayed with the understanding that the publisher and authors are not engaged in rendering real estate, legal, accounting, tax, or other professional services and that the publisher and authors are not offering such advice in this publication. If real estate, legal, or other expert assistance is required, the services of a competent, professional person should be sought. The information contained in this publication is subject to change without notice. METROLIST, INC., DBA RECOLORADO MAKES NO WARRANTY OF ANY KIND WITH REGARD TO THIS MATERIAL, INCLUDING, BUT NOT LIMITED TO, THE IMPLIED WARRANTIES OF MERCHANTABILITY AND FITNESS FOR A PARTICULAR PURPOSE. METROLIST, INC., DBA RECOLORADO SHALL NOT BE LIABLE FOR ERRORS CONTAINED HEREIN OR FOR ANY DAMAGES IN CONNECTION WITH THE FURNISHING, PERFORMANCE, OR USE OF THIS MATERIAL. PUBLISHER'S NOTICE: All real estate advertised herein is subject to the Federal Fair Housing Act and the Colorado Fair Housing Act, which Acts make it illegal to make or publish any advertisement that indicates any preference, limitation, or discrimination based on race, color, religion, sex, handicap, familial status, or national origin. METROLIST, INC., DBA RECOLORADO will not knowingly accept any advertising for real estate that is in violation of the law. All persons are hereby informed that all dwellings advertised are available on an equal opportunity basis.

Winter Park, CO community profile

Population: 1,066
Median income: $72,015
Housing units: 1,726
People per sq. mi.: 15
Area: 71.3 sq. mi.

Source: HJN community data

Winter Park housing market

August 2026 · This period is still settling

Selling at 98.8% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Aug 28, 2026

Homes that sold · County records, as of Aug 18, 2026

Median sale price: $1,130,000$672,000–$1,522,500 typical range
Price per sq. ft.: $709
Sales: 15
Paid in cash: 40.0%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $985,000
Homes for sale: 167

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -30.7%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,498 sq. ft.

Your local brokerage

Steve Merritt

Realty.com

Lic. #ER.100044960

Call Steve

Your local brokerage

Steve Merritt

Realty.com

Lic. #ER.100044960

Call Steve

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Listing data & MLS disclosures

Winter Park housing market

Homes that sold · County records, as of Aug 18, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Winter Park, CO community profile

Explore Winter Park homes

Listing data & MLS disclosures

Winter Park, CO community profile

Winter Park housing market

Homes that sold · County records, as of Aug 18, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Your local brokerage

Your local brokerage